In February this year, I let go of my last design client.

The design work had been a way of maintaining financially stability while I built two businesses on the side. Letting go of that work was an acknowledgement that the bridge had done its job and I no longer needed it to hold me up.

At its most honest, the portfolio career is a stepping stone for people who are psychologically mid-exit from employment. It’s the structure you build when you need the something to hold you up while you figure out what you’re moving towards. There’s nothing wrong with that, but let’s be real about what it actually is.

When I left my career in tech, I had a clear vision for myself. I knew that I never wanted to be an employee again. I saw myself owning multiple businesses, each with various income streams, that I could eventually step back from. I hadn’t really contemplated what ownership entailed, or what it would take to build something with structural independence, or how easy it is to inadvertently create another job for yourself while believing you're building a business. That vision is still very much a work in progress.

Labels played an important role during that transition period, because language can be stabilising. The portfolio career gave me something to call myself while I was still becoming something else. Having a credible answer to “What do you do?” seems to matter more than most people would like to admit.

My interests are shifting. The work I do has always been about identity shifts – intentionally changing the way you see yourself and your beliefs about who you are. That hasn’t changed. What's changed is the context. I'm less interested in the moment a person leaves employment and more interested in what comes after. The growth that happens when you build something of your own has little to do with skills and everything to do with who you become in the process.

The future of work, I believe, is entrepreneurship.

Which is why I've been thinking carefully about definitions. The language we use to describe what we do reflects how we see ourselves and what we believe is possible.

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Why the portfolio career is so seductive

Leaving a stable career is terrifying.

Most people who do it have spent years building a life calibrated to the comforts of a reliable (and usually high-paying) income. The all-in attitude of the founder narrative can feel reckless in that context, because you’re not a 22-year-old with nothing to lose. The portfolio career presents itself as the answer to that tension.

It attracts accomplished professionals who’ve arrived at the understanding, sometimes through burnout, that the traditional structure of work no longer fits the life they actually want. The arguments are genuinely compelling:

Build multiple income streams. Diversification is security. Assemble a career around your skills, passions and the life you want to live.

It’s been described as a new wave of entrepreneurship. In my opinion, that reframe feels quite generous for a transitionary model.

The portfolio career borrows a lot of language from entrepreneurship – building, ownership, autonomy, agency, financial freedom, creating your own opportunities. These words carry weight in the entrepreneurial world. They describe a specific relationship to risk, equity and structural independence. In the portfolio career discourse, these words are used to describe what is, in most cases, a more flexible and self-directed form of employment.

What does building actually mean? Are you building an asset that generates value without you? Or are you building a client list that depends entirely on your continued presence?

What does ownership actually entail? Ownership means equity. Something with value that could exist, be sold or transferred independently of you.

What does autonomy actually look like? If your income stops the moment you stop working, your autonomy is conditional on your continued output. That’s not really independence. That’s a more sophisticated form of employment.

Flattering language obscures reality and makes it harder to clearly see what you’re actually building, and whether the structure you’re operating inside is designed to get you there.

What the four types are actually optimising for

The Portfolio Collective describes portfolio careers as “notoriously difficult to define, mostly because there’s no set rule book you need to follow” which I find weak as far as definitions go. Their taxonomy includes four types:

1. The side hustler maintains a primary income while generating an income from a side project. Their identity is primarily anchored to their main job. Their side project is aspirational but not yet load-bearing.

2. The freelancer is self-employed and exchanges time for money usually across multiple clients. Their identity is usually craft-based: I’m a designer, I’m an engineer, I’m a copywriter. Their income stops when they do.

3. The multi-hyphenate mixes a range of diverse projects at the same time. Their primary identity position is: I contain multitudes.

4. The focused expert monetises deep expertise in multiple ways and charge top rates for it. Their identity position is authority-based: I am the person who knows more about this than anyone else.

Someone monetising deep expertise through multiple income streams is very different to someone with a part-time marketing role who moonlights as a yoga teacher. Conflating the four types under one label is imprecise at best.

A friend of mine built a successful financial advisory for high net worth women and has spent the last couple of years actively working to remove herself from it. She’s hired advisors, trained them on her method and tested a franchise model. Her destination has always been a business that runs without her in the room.

A few years ago, when we were both at earlier stages, she was freelancing in marketing while building her advisory on the side. I was freelancing in product design. She told me she wanted to build a real business, not a ‘fake’ freelancing one.

I was mildly offended.

Wasn’t I finding and securing my own clients? Wasn’t I building something? Wasn’t that what a business owner did?

Now I understand what she meant. The difference is whether you’re building something that has structural independence from your presence. Something that could, in time, exist without you. Freelancing, however well-paid or self-directed, is still you exchanging your time for money. The moment you stop, it stops.

So let’s be clear about what entrepreneurship actually is.

An entrepreneur builds toward something with structural independence from their daily presence that generates value beyond their direct time input. They take on genuine financial risk. They’re oriented toward innovation, growth, scale and creating value that didn’t exist before. The goal is ownership of an asset, not the exchange of time for money.

None of the four types of portfolio careers describe that. So why are all the portfolio careerists borrowing language from entrepreneurship?

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Focus compounds, fragmentation doesn’t

The focused expert is the closest to building a business through reputation, a body of work and a depth of authority.

Notice it’s called the focused expert, not the multi-skilled expert. Focus compounds in a way that fragmentation won’t.

The people who build the kind of reputation that creates real leverage tend to have spent years going deep in one direction. Expertise develops through sustained, concentrated exposure. The market also tends to reward depth over breadth, particularly at the high end.

I know this about myself. I’m at my best when I can immerse myself fully in one thing – following threads, building connections, bringing influences from different places into a single domain. Splitting my attention between unrelated projects doesn’t just divide my time, it divides my thinking.

While I was in my portfolio career phase, I found myself split between product design, coaching and community building simultaneously. Individually, I loved all three. Together, I hated them. I couldn’t go deep enough into any of them to do the work I actually wanted to do. The decision to let go of the design work was much more about cognitive coherence.

Keeping multiple things alive also meant I never had to fully bet on one of them. There’s psychological safety in that. The people who build something significant usually had a period of uncomfortable, clarifying commitment where the fallback wasn’t available.

Becoming more fully yourself is not a business model

Commitment is hard for practical and psychological reasons. For many people leaving employment, their portfolio career serves as evidence that they're finally living as a whole person and they didn’t just trade one cage for another.

Corporate environments have a way of demanding one role, one identity, one dimension of yourself presented consistently to the organisation. The parts of you that don’t fit get systematically suppressed – your creative interests, your intellectual curiosity and the projects that don’t have a business case. After years of that, the promise of a working life that expresses more than one dimension of who you are is refreshing. The portfolio career speaks directly to that hunger.

That hunger is worth examining. What most people are actually reaching for isn’t the expression of multiple interests through multiple income streams. It’s the experience of becoming more fully themselves. Those are related but not the same thing. One is a business structure. The other is a lifelong project that an elaborate work arrangement cannot fulfil.

The assumption underneath the multi-passionate argument is that self-expression through work is the primary measure of satisfaction. Not every dimension or interest of a person needs to be monetised to be expressed. Some things stay sacred when they’re kept outside the market entirely.

Here’s a question worth sitting with: if the thing you’re building on the side were already generating enough to live on, would you still be doing the fractional, freelance or part-time role?

I’d bet that most people would say no.

Which means the portfolio career isn't the destination. It's the thing you're doing while you're not yet ready to fully own the thing you actually want to build.

Unless, of course, you’re closer to the focused expert, but then the question changes: if you're monetising deep expertise across multiple income streams is that still a (portfolio) career or is it a business?

My own structure has evolved like this: full-time employee → freelancer → portfolio career → solopreneur. I’m currently somewhere between solopreneur and business owner. Updating the label I use is already changing the questions I ask and the decisions I make.

When I hold the business owner lens, I think less about delivering and more about building. Less about the next client and more about the system that means I don't need to be the one serving every client. I think about products rather than services. I think about how technology can be integrated into what I deliver. About what an ecosystem looks like rather than a practice. I’m thinking about how to build something that generates value when I’m not the one in the room. It’s changing my relationship to time and what I put my energy into.

The way you see yourself changes the questions you ask. The questions you ask change the decisions you make, and the decisions you make change what you build.

Maybe you’re mid-transition, processing the weight of it all and finding comfort in the portfolio career narrative. I've been there too. When you're ready to put that label down for a moment, what would change in your work if you started seeing yourself as a business owner instead?

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Kasia has the kind of warmth that makes you feel she’d smile at you on the street and strike up an easy and genuine conversation. Outgoing, warm and open, she’s originally from Poland and now lives in East Sussex.

She describes herself as a creative practitioner. It’s a fitting title that captures the many ways Kasia expresses her artistry and curiosity. For over 13 years, her professional roots were in design, creating interactive, narrative-driven spaces before moving into teaching at the University of the Arts London. Today, that same spirit of creative experimentation runs through her work as a retreat chef, yoga teacher, and textile artist — each one a different medium for exploring creativity, connection, and wellbeing.

The call to adventure came in 2020, when Kasia accepted a role to teach design in Vietnam. After more than a decade in the design industry, she had begun to feel its constraints. “People romanticise the idea of design,” she told me. “It’s an amazing industry, but after a while the work becomes repetitive…I wasn’t able to be as creative as I wanted to be and it wasn’t providing creative satisfaction anymore.”

Teaching had always been the most energising part of her work, and the opportunity to do it in a new country felt like a fresh start and a way to trade the hustle of five different freelance jobs for one meaningful adventure.

Vietnam opened doors she hadn’t expected. Immersed in a new culture and slower rhythm of life, she began experimenting with textiles and exploring this new form of creativity. She describes that period as being “gifted a lot” — a time rich with discovery and connection.

But it was also the beginning of a more difficult chapter.

During those same years, her husband was diagnosed with advanced cancer. What began as an adventure soon became a profound initiation into loss, resilience, and the reweaving her life.

Losing someone you love doesn’t just leave a gap where they once were. It rearranges everything — the way you see yourself, the way you move through the world, even the rhythms of daily life. Grief has a way of gripping us so tightly that it turns everything upside down. Suddenly, you’re not only mourning the person, but also the version of yourself that only existed in relation to them.

It wasn’t just the loss of the person she loved. It was the loss of a shared identity as a couple, a creative collaborator, and the life they had been building together. “You’re not just dealing with loss of someone you love,” she told me. “Your whole identity shifts. You’re no longer meeting people as a couple. Even your professional life changes. I was his primary caretaker while he was ill.”

Grief invited Kasia to explore the role of creativity in healing. Yoga, which had once been a quiet part of her life, became an anchor that helped her reconnect with herself when everything around her was changing. When life feels uncertain, the practice has a way of gathering the scattered pieces of you. It offers moments of stillness when everything else is shifting, and quiet strength when words and logic can’t reach the places that ache.

Her commitment to yoga opened a new door into Ayurveda, holistic living, and the connection between nourishment and wellbeing. Cooking plant-based food became both an act of care and creative expression, a way to nurture herself and others. What began as personal rituals of healing, slowly evolved into a new chapter of her creative practice, one rooted in embodiment, community, and the art of living well.

Today, Kasia is discovering how to weave together these different parts of herself into her own unique professional tapestry. She describes this time as “seeding”: planting ideas in different places and seeing which ones take root. Sometimes it’s a workshop that draws a handful of people. Sometimes it’s a casual conversation at yoga, offering sweet treats and “feeding random people,” that blossoms into something new. Some seeds grow quickly, others take time.

For her, teaching is the common thread that runs through it all. “At the core of my being, I am a teacher, an educator that uses different tools to provide different experiences.”

She resists the pressure to define herself as one thing or to subscribe to narrow definitions of success.“I find measuring success tricky sometimes. Monetising a new career is one way, I guess, but I feel it’s not really always the best measure of success. Taking a first step to make a change, embracing the unknown and reframing challenges as opportunities for growth is already a success. Allowing my intuition to guide me and taking mindful actions is my personal success.”

What I admire most about Kasia is the way she is allowing her process to unfold. She has opened herself to up to new people and conversations, guided by curiosity rather than certainty. She is experimenting with what feels alive, saying yes to new opportunities, and, most importantly, learning to trust herself.

Kasia’s story reminds me that reinvention doesn’t always begin with a vision. Sometimes it begins with loss, with grief, with a life that has been rearranged without your consent. The work, then, isn’t to narrow yourself into a single new identity. It’s to learn how to hold the different parts of yourself, the ones that were there before and the ones grief has revealed, and let them become a life that feels whole.

I think this is what’s hardest to communicate about transitions like hers. There is no neat after. There is only the slow, patient practice of seeding, and the willingness to keep going when you can’t yet see what will grow.

If Kasia's story resonated, you can find her work at kasiahamilton.com. She's an interior designer, lecturer, retreat chef, textile maker and yoga teacher, weaving together food, design and community through workshops, retreats and seasonal events.

The cleanest version of my story goes like this: I burned out, quit and found my calling.

The real story is considerably less coherent. I didn’t wake up one day thinking that I needed to make a career change, and I certainly didn’t know what I’d be transitioning into. The realisation crept up on me over a few years, growing louder and louder until it became too unbearable to ignore. I took a career break hoping that the answers would materialise and I became disillusioned when they didn’t.

The literature suggests that major career transitions unfold over three to five years. I didn’t know this until I was well past the peak of my transition. During that time, I carried a lot of shame about why I hadn’t figured it all out after multiple attempts at breaking free. I knew I was capable. What I couldn’t understand was why my next step refused to come into focus. I genuinely feared that I’d become lazy, broke and adrift.

Most of what I’ve shared in previous pieces has been about the moment I first burned out. I wrote about the slow unravelling of the self in A letter to myself about what comes next. It covers the years from Google through Deloitte, to the first time I took a career break. This piece goes back to where the pattern started, and forward through the four years it took to transition out of a career in tech.

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The foundation I didn’t have

It all begins with my ethnicity. I come from a bi-racial family and grew up in Australia. My mum is Chinese-Indonesian and my dad is Ecuadorian.

Ethnicity tends to be the earliest inherited identity. It’s the category that determines which language(s) you hear, the foods you eat and the stories you’re told about who you are. It’s also the category other people reach for when they want to place you, a quick read that stands in for the longer work of getting to know someone.

Most people inherit an identity solid enough to stand on without ever examining it. Mixed heritage denies you that. You feel the pressure to pick a side or to prove you’re enough of any one thing, and when you can’t, you learn to adapt like a chameleon instead. I spent many years doing that. What I didn’t understand then, was that I’d been handed the central task of life quite early on. Everyone, eventually, has to decide which parts of their inherited identity are actually theirs.

My Jungian therapist, who is Chinese by heritage but grew up in Portugal once said to me: “It’s common for people like you. The soul tends to be a little shaky.”

I really felt that.

The debt I tried to repay with grades

Like many children of immigrants, I grew up watching my parents work hard in menial jobs to create a better future for my siblings and I. The opportunities I was handed, a comfortable start and a degree, were created through sacrifices I could never fully repay. It felt like it was my duty to make something of myself to justify the cost.

There’s a term for this. It’s called immigrant guilt.

It describes the persistent, low-level sense that the comforts, choices and freedoms of your life aren’t quite deserved, because of what was sacrificed to make it possible. The guilt happens when one uses those options in ways the sacrifice didn’t anticipate. You’re given a wider life and now you want to spend it on something that looks like a luxury or a betrayal: leaving a stable profession, marrying outside the culture, moving away, choosing meaning over security.

The guilt is often unearned and the debt unspoken. There’s an inherited dimension too. It can sometimes be about carrying a family’s whole relationship to scarcity, risk, gratitude and loyalty. The success the sacrifice was meant to produce becomes the very thing that triggers the guilt. The more freely you live, the wider the gap between your life and the lives of your parents who paid for it.

A child can’t repay that kind of debt, but a child can bring home good grades. Good grades look like proof the sacrifice had been worth it.

I was an A-grade student from a very young age. On school report cards, my teachers consistently described me as: “responsible and conscientious.” In my final high school exams I graduated top of my year while also being a school captain.

The formula of high grades equals high worth continued into my career. My first job out of university was at Google. People spend their whole career trying to get there. I walked in with very little experience and was admitted into a world of brilliant people. The brand did something to how people saw me, and how I saw myself.

Somewhere along the way, work became the way I defined myself.

Leaving and returning

Five years into my career, I burned out. We understand burnout to mean long hours, high stress and a person who has given too much for too long. All of that was true for me, but there was more to it — an emptiness underneath an otherwise enviable life. Calling it burnout let me believe the problem was the workload and that rest would fix it.

What followed was four years of leaving and returning. I quit my career three times, but I also went back three times. I tried to make it work in different configurations – smaller companies, freelance, remote, portfolio, four-day work week – before finally admitting that no version of that life was going to fit anymore.

The leaving always began as relief. It was easy to believe the job itself was the problem: the workload, the direction, the leadership. But the truth was, I didn't want to spend my time sitting through another meeting discussing the minutiae of something I didn’t really care about. The fear was that my life was slowly being consumed by work that didn’t matter. Quitting felt like coming up for air.

Then came the stretch in between. The first time, I took a three-month break. The break was supposed to fix whatever it was in me that made me unable to cope. The goal and trajectory hadn't changed. I treated the career break as a delay, not a turning point.

The second time was a longer spell of two years. I trained as a yoga teacher, partly because I loved it and partly because I wanted to believe I was building toward something rather than just running away. I did the maths on what it would take to live as a yoga teacher. The maths didn't math. So I started freelancing as a designer. In each of these breaks, I expected clarity to arrive about what I might do next, but it never did. What arrived instead was anxiety about status, money and time.

So I'd go back. The return always felt like maturity, as though I’d finally stopped indulging in a fantasy. I told myself I was being responsible and that the discomfort I felt was just the price everyone pays. The voice underneath it was the same one that had got me the grades, the scholarship and the job at Google. It said I was being weak and going back would prove that I wasn’t a complete failure. I'd tell myself the role would be different, and for a few months it was. Then the emptiness would settle back in. With each return, I withered away faster than the last.

The last time I returned to a job was three years ago. It was a startup that offered a 4-day work week. The promise of a spare day to build something on the side, while maintaining a full-time salary was too enticing to give up. By the third month I was already researching exit strategies. Seven months in, I quit. For the final time.

I told my partner I had no choice but to figure out how to generate my own income. I cornered myself into it, which isn’t what I’d recommend you do. But committing to that decision brought me relief, because it was finally the end of this exhausting cycle of leaving and returning.

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What proximity did

A commitment like that is easier to keep when the people around you make it look ordinary. At the time, I was staying at a coliving space in Tarifa. My partner was six months into building a SaaS product. There was a couple who grew a large following around 3D animation. There was a woman who ran sailing retreats and was about to launch a course. There was a guy who was the owner of an agency. All of them were building something of their own.

Living among them made the alternative less abstract. The people around me were doing it. The question stopped being, “Can this work?” and started being, “What would my version look like?”

At one of the dinners we shared together, I mentioned that I’d quit my job. The natural next question came: “What are you going to do instead?” I admitted that I didn’t know. I said I wanted to do something in personal development, but I didn’t yet know what it would look like.

Nobody diminished it. They started brainstorming with me and they cheered me on as though not-knowing were a perfectly reasonable place to be. I've only had a handful of moments like that in my life, and every one of them has come from someone who has built something of their own. Never from someone who hasn't.

The experiment that wasn’t supposed to be coaching

Figuring out the shape of my work took a few months. I read widely and talked to people working in the space, who pointed me toward more books and more people. One of those conversations led me to a group coaching program, which I joined as a participant. A few months later, I enrolled in a coaching course as an experiment.

On the first day of my course, I told the cohort that I wasn’t there to become a coach. I was considering retraining as a clinical psychologist and didn’t want to commit to six years of university for a career I wasn’t sure I’d enjoy. The coaching course was a way of finding out whether the work was for me.

What I discovered was that coaching is a related but distinct discipline to therapy, and I loved what it asked of me. The quality of attention. The discipline of not rushing in with answers. The privilege of witnessing people in tender moments and small acts of growth.

In my first session with a coach I’d hired for myself, I described being pulled in two different directions. She didn't try to solve it. She slowed it down and asked me to separate the two pulls and look at each on its own.

One part of me wanted to scale the freelance design work into an agency. It was the obvious move, the lucrative one, the one that looked right on paper. The other part of me wanted to find out what coaching could become. This one was harder to justify. I kept reaching for reasons the first option was sensible and the second one wasn’t.

She took the weight off the decision by telling me that I didn't have to choose a life. I only had to choose what mattered most for the next six months. The change of timescale shrank the size of the question in my mind. When she asked me to rank the options, the answer was obvious. It came out with none of the negotiation. What she helped me see was that I’d spent most of my life choosing what looked right from the outside. For once, I wanted to choose the thing that felt right from the inside.

What the sacrifice was for

For most of my life, I had assumed that I was meant to repay my parents’ sacrifice with achievement, status and a salary that continued to climb. I wanted to be able to point to a trophy and say, “Look, all your hard work paid off.” Proof that what they left behind had been worth it.

To understand what my parents left behind, it helps to understand what kind of leaving it was. There is a difference between moving countries because you want to and moving because the economy, politics, or the absence of a future has made the choice for you. There is an additional weight on top of that, which is that not all migrants are received the same way. Some nationalities are welcomed, while others are received as lesser than.

Their sacrifices wouldn’t have been honoured by a daughter who collected every gold star but grew miserable reaching for them. The guilt hasn’t disappeared completely. I don’t think it ever will. It surfaces sharply when I remember that my parents are approaching eighty and I’m a twenty-four-hour flight away. What has changed is my understanding of what their sacrifice was for.

I see it most clearly when I watch my nephews growing up inside the life that my parents made possible. The sacrifice was never a loan made to me. It was the beginning of something that belongs to a whole lineage, and it is still unfolding.

A few months ago, I listened to the story of a Venezuelan woman who left home in her early twenties. She arrived in Ireland with a suitcase, no money and no English, and she took whatever job she could get, to pay her way into a Masters in architecture. She studied ferociously, graduated top of her year and went to work for a prestigious architecture firm. The day she was presented with her citizenship certificate, she broke down in tears. She had worked so hard, for so long, to reach that moment. And standing inside it, she finally understood that none of it was the life she wanted.

Her story touched something tender in me. A few weeks later, I retold it to a client who was in the middle of his own version this story. The story brought him to tears. The recognition of the unlived life cuts deep, because the achievement, the striving and the sacrifices that funded it were all very real. And still, it can lead somewhere that was never yours.

I honour what my parents gave me not with a trophy, but by trying, as fully as I can, to live a life that is actually mine. It turns out that was always the assignment.

If you’re standing at your own threshold, here are two ways to step forward:

• 1:1 Coaching: Inner work for people building something of their own. You’re highly capable, self-aware and you know what you want to create next, but haven’t quite given yourself permission to act on it. Together, we make sense of what’s in the way, so you can be pulled by what actually matters to you, rather than pushed by what you think you should do.

• Luma Circle: Curated experiences for women building their own business. Join our Monday Momentum group in June to connect with similarly ambitious female founders, learn together, and support each other as your business grows and evolves.

It’s been one of the most meaningful things I’ve ever done. Which is why it caught me off guard when I started feeling a strange distance from it all.

I’ve referred a few clients to essays about career change on this platform. I’ve watched them light up with recognition and felt genuinely happy for them, while also noticing some distance in myself. Their story still mattered. It just didn’t feel like mine anymore.

My interests are shifting. I’m curious about what building a business stirs up in the person building it. The fears it surfaces. The relational patterns it reveals. The way entrepreneurship becomes, if you let it, a vehicle for inner work.

It's a familiar impulse – the rush to name what's next. I see it in myself and I see it all around me. There’s a growing community of people who’ve left traditional careers and found real camaraderie in naming themselves differently. Multi-passionate. Portfolio careerist. Squiggly. These terms validate experiences that the old model had no room for, and they give people permission to stop pretending they need to fit neatly into a single box.

What I find myself wondering, though, is whether some of us are trading one form of over-identification for another. You leave a career you’d fused with — The Strategist, The Engineer, The Head of — and then you fuse with the leaving itself. Multi-passionate becomes the new badge. The label changes but the grip stays the same.

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Here I am, three years into a coaching practice, feeling my own centre of gravity shift again. I first started writing about this shift here:

Career change was the window people walked through to find me, and it remains a genuinely difficult emotional threshold to cross.

The first time my professional identity dissolved, I was terrified. I didn’t trust myself. This time, the discomfort is familiar and I know it doesn’t mean something is wrong with me. I know the impulse to grab a new label and hold on tight is an old Part that just needs some compassion and reassurance from the Self. The most honest place to stand is in the space between what you’ve been and the thing you haven’t yet earned the right to name.

These shifts happen in seasons. The first time the rug gets pulled, you think you’ll never find solid ground again. The second time, you recognise the terrain and trust yourself more, because you’ve survived not knowing before.

I remind myself that coach, facilitator, writer, community builder aren’t who I am, they’re just what I’m doing in this season of life. The moment I grip any of them too tightly is the moment I stop being available for whatever wants to come next.

Melyssa Griffin built a wildly successful online business, then shut it down to open a bookstore in Lisbon. I think about that sometimes. To trust that the next thing doesn’t have to justify the last one.

The real skill isn’t reinvention. It’s the willingness to keep loosening your grip on the identity and the story you’ve been telling about yourself, and to stay curious about what remains when you do.

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If you’re standing at your own threshold, here are two ways to step forward:

• 1:1 Coaching: Inner work for people building something of their own. You’re highly capable, self-aware and you know what you want to create next, but haven’t quite given yourself permission to act on it. Together, we make sense of what’s in the way, so you can be pulled by what actually matters to you, rather than pushed by what you think you should do.

• Luma Circle: Curated experiences for women building their own business. Join our Monday Momentum group in May to connect with similarly ambitious female founders, learn together, and support each other as your business grows and evolves.

There are coaches whose primary credential is a dramatic personal story and the transformation they’re selling is their own. Whether it translates to yours is a different question altogether.

There are coaches promising seven-figures in ninety days, or a complete identity overhaul by the end of the program. Human change doesn’t always come with a delivery date and promises like these are designed to speak to desperation rather than possibility.

There are coaches who’ve built their practice on visibility alone, whose authority rests on follower counts and the confidence of their captions. In an attention economy, being loud is easily mistaken for being good.

All of this contributes to confusion about what coaching actually is. Allow me to slice through that confusion.

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The noise problem

I wrote in a previous essay that social media arrived with a genuine promise of connection, creative independence, the proliferation of a variety of perspectives and democratised reach. What followed was the explosion of that promise into an industry. Suddenly, everyone was a brand competing for the same finite resource of human attention.

The coaching industry didn’t cause this, but it has been reshaped by it. The result is the conflation of coaching as a discipline and the influencer coach model. Those two things are not the same.

What gets lost in all of this, is the kind of coaching that has rigour. It’s one of the few spaces that operates in deliberate opposition to the attention economy. It asks you to turn down the volume of other people’s opinions and listen more closely to your own. In an economy that rewards noise, it’s a genuinely countercultural space.

How we got here

These days, you can find a coach for almost anything. The proliferation reflects a growing demand for a particular kind of support: personalised, non-judgmental and focused on the individual. We are more psychological aware, navigating more complex transitions and we expect more from our working and personal lives than previous generations were encouraged to.

Some of what has emerged is genuinely useful. Some of it reflects a market that has grown faster than the standards meant to regulate it. When a market gets crowded, the burden of discernment falls on the consumer, which, my guess, is partly why you're reading this.

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How did the coaching industry become so bloated?

Well, it all started in 1974 when Tim Gallwey published the book, The Inner Game of Tennis. The premise was that every player faces two games simultaneously:

1. The outer game: the physical contest between you and your opponent on the court

2. The inner game: the mental battle against self-doubt, over-thinking and interference from the conscious mind

Gallwey’s insight was that traditional sports instruction amplified the problem, rather than solving it. The more a coach told a player what to do, the louder the internal critic became. The coach’s job was to quiet that interference, allowing the player’s natural ability to surface. He went on to apply the same framework to golf, skiing and music.

Corporate adoption followed soon after, thanks to John Whitmore, who took Gallwey’s principles into the business world and developed the GROW model in the 1980s – it’s one of the most widely taught coaching frameworks. Organisations began embedding coaches into leadership development programs and executive coaching flourished.

Then came the professionalisation of coaching in the 1990s, when Thomas Leonard founded CoachU and the International Coaching Federation. These institutions gave the field training standards, credentialing pathways and a community of practitioners who referred to themselves as coaches.

In 1998, Martin Seligman stood before the American Psychological Association as its incoming president and argued that psychology had spent a century studying what goes wrong with people and almost no time studying what goes right. Together with Mihaly Csikszentmihalyi (the psychologist behind flow theory), he founded positive psychology – the study of human flourishing rather than human dysfunction. The question shifted from "What is broken and how do we fix it?" to "What does a well-lived life actually require?" It built on the work of Carl Rogers (more on him later) and Abraham Maslow, but gave it scientific rigour and institutional legitimacy. The idea that investing in your own development began to take hold outside corporate environments.

The democratisation of content accelerated it further. Podcasts, YouTube channels, blogs and later social media brought personal development to anyone with a phone. Self-help became a genre and an aesthetic. Concepts that had previously lived in psychology textbooks began circulating freely, repackaged for mass consumption. For many people, this was their first encounter with the idea that inner life was worth examining.

Digital platforms like CoachHub and BetterUp then reduced the cost of professional coaching delivery, making it a standard employee benefit for progressive organisations. In 2025, the ICF estimated 123 000 professionally affiliated coaching practitioners worldwide. That number doesn’t include those operating under the coaching label outside any professional framework.

The rapid growth is part of what has created the quality variance problem. Which is how we ended up here.

How I got here

I used to roll my eyes at coaches.

A client recently joked that all the coaches he’d seen online wore hats. “What’s with the hats?” he asked. I laughed, because I knew exactly what he meant.

There’s something about the way certain coaches present themselves that used to make me recoil. What I eventually realised was that I was recoiling from the performance of coaching.

My own path to coaching came via a long detour. For a few years, I followed threads of curiosity into yoga, somatics, trauma theory and adult development. I was interested in human potential and the specific question of what gets in the way of a person becoming who they’re capable of being.

A conversation with a friend gave me the permission I needed to try coaching. I joined a group coaching program as a participant first. What I encountered there sent me looking for more. So, I enrolled in a training program. I announced to my cohort that I wasn’t here to become a coach. The training was merely a career experiment.

What I didn’t anticipate was how much I would learn about myself in the process. The practice asks things of you that professional life trains you out of. In one of our first sessions, we were asked to use silence deliberately. The task was to ask a question and then wait, without rushing to fill in the awkward silence. It was harder than it sounds. Most of us, having arrived from corporate backgrounds, had spent years filling every available space with performed competence.

In the silence, you begin to notice the story running just below the surface of what someone tells you. You start developing an awareness of how much more is communicated outside of the words people use. Sometimes, the words themselves are the last thing to tell you what’s actually happening. The slight hesitation before an answer. The subject that keeps being circled but not named. The moment the energy shifts. The sense that something is being held back. Learning to attend to all of these subtleties changes how you listen and therefore how you respond.

About a year ago, some friends asked me what I’d be doing if I could have any job in the world. I didn’t have to think much. I told them I’d be coaching. Sitting with another person while they find their way back to themselves is one of the most extraordinary things to witness.

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Coaching and its neighbours

Coaching sits adjacent to several other disciplines – consulting, mentoring, therapy and spiritual guidance. The boundaries between them aren’t always clearly drawn. Some practitioners exist on a spectrum between two or more of them. For example, therapists who have trained as coaches and move fluidly between healing and growth work; mentors whose guidance shifts into coaching as the relationship deepens; practitioners who weave contemplative traditions into frameworks grounded in western psychology. These hybrids can be incredibly effective, but it also makes it harder to know what you're signing up for. Better doesn’t necessarily mean more, nor does it mean choosing a pure category. It’s more about knowing what kind of support you actually need.

A consultant is the expert in the room. You are paying for their knowledge and good judgement. A good consultant will diagnose the problem and make clear recommendations about what the solution should be. A mentor draws on their own experience to guide you. They have been where you are trying to go. The value that a consultant or mentor offers is directional and advice-led: this is what I did, this is what I learned, this is how I would approach your situation.

A therapist works primarily with what has already happened. The focus is on understanding how earlier experiences have shaped present patterns, processing what has not been processed and building the psychological foundation needed to live well. Therapy is clinical work, which requires a specific type of training, ethical framework and relationship with the client.

Spiritual guides, teachers, gurus, shamans, energy healers, wisdom keepers draw from a wide range of ancient and contemporary traditions. Their role is to help people access meaning, transcendence and a sense of connection to something larger than themselves. There can be real value in that. The challenge is that spiritual communities tend to attract people at their most vulnerable: unmoored, searching, open to almost anything that might give them solid ground.

A coach, in the humanistic tradition, brings a quality of attention that allows another person’s own intelligence to surface. Carl Rogers was the psychologist who founded person-centred therapy in the 1950s. His ideas have become the philosophical backbone of modern coaching. The premise is that human beings have an innate drive toward growth, what he called the actualising tendency, and that this drive needs the right conditions (unconditional positive regard, empathy and congruence) to emerge. Those conditions are not techniques so much as a quality of presence.

If you want to see what those conditions look like in practice, watch Carl Rogers counsel Gloria. This session, filmed in 1965, is one of the most extraordinary demonstrations of person-centred work. Rogers doesn’t advise, interpret or lead Gloria toward a conclusion he has already reached. He simply listens with a quality of attention so complete that Gloria begins to hear herself differently. By the end of the session, she arrives at her own answer through a process that Rogers barely directs at all. It is a demonstration of what’s possible when a person is given the conditions to trust themselves.

The premise that connects Gallwey and Rogers is that the person in front of you already has more access to their own answers than they realise. It has just been buried under years of noise, expectation and learned patterns of thinking. The coach’s job is not to provide the answer. It’s to reduce whatever is preventing the person from hearing themselves clearly.

These distinctions are important to grasp because the kind of support you choose shapes the kind of growth that is possible. In short, if what you need is guidance from someone who has walked your path, seek a mentor. If you need to heal what the past has left behind, work with a therapist. If you are searching for meaning through ritual and tradition, a spiritual guide may serve you well. If you want someone to diagnose a problem and tell you what to do, hire a consultant.

If what you are after is the capacity to trust your own judgement, to author your own life rather than live one inherited from expectation, then coaching may be the right container for that work.

The tells

You’ll know you’re in a good coaching relationship because of what it asks of you, not what it gives you.

Good coaching starts with a mirror. A skilled coach reflects you back to yourself with enough accuracy that you can finally see what you’ve been unable to see alone. The quality of the coach’s attention, their questions and their willingness to sit in the discomfort with you begins to change what you’re able to see in the mirror. The mirror starts to become transparent. You stop seeing only your own reflection and you start seeing through it. It becomes less of a surface and more of a threshold.

The best coaching conversations are ones where the client does most of the talking, where the questions are well-placed and where silence is used deliberately rather than filled out of discomfort. A good coach does not arrive in session with frameworks to present or insights to offer. Their curiosity about you sits above their enthusiasm for their own methodology.

A good coach also does their own work. They will have their own coach, and they may be in regular supervision, a practice borrowed from therapy in which coaches reflect on their own work with a more experienced practitioner, to ensure they are not bringing their own unresolved material into the space. Many also have their own therapist. Ongoing personal development is the foundation of doing the work responsibly.

There is one more thing worth saying and it comes from my own experience. My coach, supervisor and therapist have no significant online presence. All three have built their practice on reputation, referral, the quality of the work itself and the relationships that the work produces. The most effective coaches are the ones that people recommend to each other in the privacy of conversations that never make it onto Instagram.

The coaches worth finding are rarely the ones trying to find you.

What to expect

A coaching session is neither a motivational talk nor a therapy session. If you've never experienced one, it can be difficult to know what to expect.

A session usually lasts between fifty to ninety minutes. It begins with the client setting the agenda, not the coach. You arrive with something you want to think about, a decision you're sitting with, a pattern you keep noticing, a conversation you've been avoiding, an emotion that’s present. That becomes the starting point. In the early sessions, the coach may offer more structure to help you find your way in. Over time, you learn to arrive knowing what you need to work on. The shift from being guided into the conversation to initiating it yourself is a sign that something is developing.

From there, the coach’s job is to walk beside you, neither leading nor following. They ask questions, reflect back what they are hearing or feeling. They might offer an observation as a hypothesis to be explored rather than a conclusion to be accepted. The coach tracks not just the content of what you say but the way you say it – where the energy rises, where it flattens, what gets glossed over and what keeps returning. They create space for the thinking to deepen beyond the first and most obvious layer.

For many people, particularly those arriving from professional environments, the experience of being in a coaching session can feel disorienting at first because you’re not being assessed or advised. You’re being listened to with a quality of attention that most of us rarely receive, even in close relationships. That can feel unfamiliar and uncomfortable, but when it's working well, it can also be profound.

A coaching engagement unfolds over several months rather than a handful of sessions. The early sessions are often about establishing trust, understanding the presenting situation and surfacing the story under the story. The middle phase is usually where patterns become visible, assumptions get examined and experiments get designed and tested. The later sessions tend to consolidate what has shifted and prepare the client to continue without the container.

The work doesn’t end when the session does. Most coaches will ask you to take some kind of action between sessions, however small. These between-session commitments are the laboratory in which the insights from the session get tested against real life. The session is the thinking space. What happens between sessions is where the change actually lands.

What the client brings to this process is equally important as what the coach offers. You are expected to be honest, to show up prepared to be uncomfortable and to act on what you discover. A coaching engagement is not something that happens to you. It’s something you actively participate in.

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Are you actually ready?

Coaching isn’t for everyone.

Coachability is a real concept. It refers to the degree to which someone is able to receive, reflect on and act upon what is uncovered by the coaching process. If you’re not yet ready to act on what you discover, the timing might be off. The focus is on growth and understanding what’s getting in the way and building the capacity to move forward. It’s not about intelligence or how much you want things to change. It’s about readiness.

A coachable person is willing to be honest with themselves. This is harder than it sounds. Most of us have spent years constructing a coherent narrative about ourselves, and coaching tends to poke at the seams of that narrative.

The process is one of slowing down enough to understand the actual problem, which is often not the one you arrived with. It requires a person to sit with uncertainty without immediately reaching for a solution. It produces insights which are only useful if they lead to change. Understanding why you do something is not the same as changing it. Change requires repetition – new behaviours practised until they become habitual, new ways of relating to situations, new neural pathways formed through action. A coaching relationship holds you accountable for the gap between what you know and what you actually do.

None of this means you need to have everything figured out before you begin. You just need to be honest about where you are.

A coachable person also has sufficient emotional stability to confront difficult truths. This is where the boundary with therapy becomes important. If you are in acute crisis and you are struggling with your mental health in a way that requires clinical support, coaching is not the right container. Coaches and therapists work different parts of the same terrain. Therapy builds the foundation. Coaching builds on top of it. Therapy asks what happened and how it shaped you. Coaching asks what you want to do with who you are now. Used well, the two are more like consecutive chapters than competing alternatives.

Questions worth sitting with

Coaching is an unregulated profession and there is no legal requirement to hold a qualification or belong to a governing body. Anyone can call themselves a coach, which is exactly why credentials matters.

The three most recognised professional bodies in Europe are the International Coaching Federation (ICF), the European Mentoring and Coaching Council (EMCC) and the Association for Coaching (AC). Membership to each professional body is voluntary, but it signals that a coach has met minimum training hours, demonstrated their practice through assessment, committed to a code of ethics and ongoing professional development. When you’re evaluating a coach, ask which governing body they’re affiliated with and what level of accreditation they hold. It won’t tell you everything, but it tells you they’ve been held accountable to something beyond their own judgement.

Before you begin looking for a coach, it’s worth spending some time with a few questions.

Questions to ask yourself

• What are you hoping coaching will give you?

• How willing are you to do the thinking yourself, rather than being guided toward an answer?

• What is it that you already know (a decision half-made, a direction already forming) that you might be hoping a coach will give you permission to act on?

• What would you need to feel safe enough to be genuinely honest in a coaching relationship?

• How well-resourced do you feel right now, and is there anything that might be better held by a therapist before coaching becomes useful?

Question to ask about the coach

• What training does the coach have and where did they get it?

• Who do they turn to for their own personal development?

• In the discovery call, who did most of the talking?

• How did you feel when you ended the discovery call – heard or sold to?

• How much of their approach tries to fit you into a framework they’ve already decided on, versus how much of their approach accounts for your complexity?

• What do the people who’ve worked with them say?

Coaching is a relational practice which means the relationship itself is the work. The quality of the coach’s attention, their ability to be genuinely present with you, their willingness to sit with your uncertainty without rushing to resolve it – these are the mechanisms through which change happens. The conditions for growth (unconditional positive regard, empathy, coherence), cannot be manufactured through good methodology alone. They require genuine human contact.

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I wrote this piece partly to think clearly about the industry I’m operating in, with all of its contradictions. Practising responsibly means being willing to name what’s wrong with it.

It also means questioning whether I’m doing it well. I bring things to supervision, coaching and therapy. I sit with the uncomfortable questions about whether the things I say or do are in the client’s best interest or mine; about whether I’m the right person for a particular client and whether I’m growing as a human being at the same rate I’m asking my clients to. This is the part of the work I find most alive.

This article will sit as required reading before anyone books a discovery call with me. What I offer is slow and durable, and if you arrive at that call having read this, we can begin from an honest place.

Earlier in my coaching career, I used to buckle in my boots when people asked me what I did. I’d watch their faces for signs of scepticism and compensate by over-explaining or hedging. I don’t do that anymore. I have enough evidence, from the people I’ve worked with and from my own experience of being coached, to know that this is one of the most honest journeys a person can choose to go on.

The best kind of coaching gives you back the ability to trust your own decisions, and that is worth being discerning for.

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If you want to understand what coaching looks like from the other side of the relationship, this account written from the client's perspective makes for a great read. It’s honest about the resistance that came before the results and specific about what actually changed for them.

If you’re standing at your own threshold, here are two ways to step forward:

• 1:1 Facilitation: For high achievers who’ve outgrown the framework they’ve been operating within. We work at the level of identity – uncovering the scripts shaping your career choices, defining your own standards for success and building the confidence to trust your judgement.

• Luma Circle: Curated experiences for women moving from employment into entrepreneurship. Join our monthly dinners to connect with fellow founders, learn together, and support each other as your businesses take shape.

I had just come back from a three week break during which I read three novels. I let the pace of life slow down to something that felt genuinely sustainable and I relished it.

Then the break ended.

The thought of returning to the treadmill of notifications produced a tiredness that arrived before I’d even opened a single tab. It was the weariness of a person who had just remembered what it feels like to be fully present, and was now being coaxed back into fragmentation.

I suspect you know this feeling. A low-grade dread that hums in the background when the stillness of a break meets the chaos of everything waiting.

Three weeks of immersion in novels had reminded me that sustained attention is still possible, and yet we’ve created a world that actively discourages it. We’ve built infrastructure that monetises interruption and the cost of operating inside it, is becoming very expensive for a person like me.

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Neil Postman saw it coming in 1985

In Amusing Ourselves to Death, he argued that the medium through which people receive information fundamentally shapes how they think.

Postman was writing about television. Television’s grammar – fast cuts, emotional imagery, fragmentation, brevity, entertainment value – makes it structurally hostile to serious argument and sustained attention. He warned that the danger is that we will prefer amusement over understanding and lose our appetite for serious thought and complexity.

He couldn’t have imagined that one day, each of us would carry a portable television around in our pocket.

Published in 1985, the book was remarkably prophetic. With the help of social media, algorithmic feeds, infinite scroll and the general collapse of attention, we’ve accelerated the trajectory he diagnosed earlier.

Television’s grammar has infiltrated everything.

Browse any streaming platform and you’ll find thousands of hours of content dressed up as cultural richness, designed to keep you in the room for one more episode, sated, until the night has gone and nothing has been asked of you.

What you will find less of, is the kind of storytelling that leaves you unsettled, demands you sit with a complex idea and refuses to resolve its own tensions into something comfortable by the last episode.

Sustained attention doesn’t vanish overnight. It erodes, and so does agency.

How we got here

This story is much older than television.

Independent journalist, Jonny Harris, recently traced the history of information back centuries. His core argument is that information has always been in a tug of war between the powerful and the masses.

Every time a new medium emerges and briefly democratises the flow of information (the printing press, radio, television, the internet), the powerful move back in. Today, a handful of the world’s wealthiest men are consolidating control over the platforms, studios and the channels through which almost all information travels. The pipes are being bought up. When you own the pipes, you shape the prevailing narrative.

I find myself observing how the world is unfolding around me and the speed at which consequential events are being swallowed by the next big headline. Outrage flares for a news cycle or two, and then it dissolves as the feed moves on to whatever comes next and we forget what’s happened. We move on before we’ve had a chance to digest it all.

The question that I keep coming back to is: If we cannot sustain attention on the things that matter most, what does that mean for our capacity to act on them? That question alone deserves a separate essay to unpack.

Postman called it amusing ourselves to death. What we are doing now might be closer to scrolling ourselves into passivity.

Welcome to the attention economy

Social media arrived with a promise of connection, creative independence, the proliferation of different points of view and democratised reach.

For a while, that promise was real. The idea that anyone could build an audience, reach people they would never otherwise meet and create work that found its own audience was a radical shift in what was possible for an individual.

What followed was the transformation of that promise into an industry. Courses, funnels, engagement strategies and content optimised for reach. Suddenly, everyone was a brand. Everyone had a niche to stake out, a value proposition to articulate and an audience to grow. The crowded marketplace that once existed in the physical world moved online, and the noise it generates is unlike anything that has come before it: billions of people competing for the same finite resource of human attention.

Cory Doctorow has a word for what happens next: enshittification. His argument is that platforms follow a predictable three-stage cycle. First, they begin by offering genuine value: free access, useful services and real connection. Once users are dependent, user data and attention is monetised, ads increase and the experience degrades. Finally, once users are locked in to the platform, value is extracted and transferred upward to executives and shareholders.

You only have to open Instagram Reels to see the end state of that cycle. Everyone is selling something. The feed that once connected you to people you cared about now connects you to people who want you to buy something from them.

Thankfully, social media usage peaked in 2022. By the end of 2024, daily time spent on platforms has dropped nearly 10% in developed countries outside the US. Gen Z is leading the exit, driven by disillusionment, mental health concerns and a recognition that what was once marketed as social has quietly become anti-social.

The attention economy isn’t dying. It’s just increasingly expensive to inhabit, particularly as AI floods every feed with content that is entirely without interiority.

Side bar: I want to be honest about where I sit in all of this. Yes, I will quietly advertise my services at the end of this piece. I am critiquing an ecosystem I am part of, and I think that tension is worth naming rather than hiding.

Writing long-form pieces here on Substack is something I genuinely enjoy. The thinking it requires, the depth it allows, the conversations it opens. What feels like a treadmill is the incessant nudge to stay visible in the small daily ways the platform rewards through Notes. It’s not a reluctance to be seen. It’s a desire to protect a quality of attention and pace that the notification cycle quietly erodes every time I let it back in.

The future belongs to the deeply human

That instinct to protect my attention and resist the pull of the feed in favour of something slower and more deliberate, turns out to be more than a personal preference. It points toward a set of economies that are growing in the shadow of the attention economy. David Shapiro calls them the authenticity axis: a set of economies expanding precisely because AI cannot touch them.

The first is the attention economy, but not as we currently know it. The nature of what earns genuine human attention is shifting. The winners will be those who say something that could only have come from a life actually lived: ideas that have been tested against reality rather than generated by a prompt.

The second is the experience economy. We prefer embodied experiences facilitated by other humans. A live concert is better than a recording because you were in a room with other people, present to the same moment. A dinner where the conversation goes somewhere unexpected and you drive home feeling more alive than when you arrived.

The experiences that cannot be replicated digitally become scarcer and therefore more valuable. We are moving toward a world where people crave physical presence more acutely because they are getting so little of it.

The third is the meaning economy, and it may be the most important of all. As the relationship between labour and income becomes less predictable and AI begins to absorb more of what once defined professional identity, people are asking what matters. That question requires guidance, reflection and the kind of hard-won understanding that only comes from someone who has genuinely grappled with it. This is the economy of therapists, coaches, facilitators, spiritual guides and community builders: roles whose value increases in direct proportion to how much the world around us is automated and accelerated.

Mo Gawdat takes this argument further. He says that the real crisis of AI is not just economic, it’s also existential. Since much of modern identity is constructed around productivity and professional contribution, when that scaffolding is removed, people will face a reckoning. Those best positioned for what is coming are not only the top 1% of technical talent, but those who have cultivated genuine creativity, emotional intelligence, deep relationships and a sense of meaning that does not depend on being productive.

The YouTube thumbnails alone tell you something about the moment we are in.

I’ve written a lot about the attention economy because it’s the water we’re all swimming in.

Understanding its history, mechanics and costs is my way of orientating myself. I don’t believe you can make a considered choice about what you want to create without first understanding the system you’re choosing to work within or against.

The attention economy isn’t where I want to spend my energy, and it’s not where I think the most interesting work is happening. What I do find worthy of my attention is what’s growing in its shadow: the experience economy, and the corner of it I find myself increasingly drawn toward.

If you want to go deeper on the meaning economy and the inner work of decoupling identity from productivity, these earlier essays are the place to start:

• Work Worth Doing

• Performing a Life You’ve Outgrown

• Becoming Who We Are: The Many Deaths of Identity

I didn’t plan any of this

In the past ten years I’ve moved around a lot. My longest stay in one place was around eighteen months. What I hadn’t built anywhere, was the kind of deep and rooted belonging that sustains a person over a long period of time. I was meeting people everywhere, yet feeling like I belonged nowhere.

In early 2024, I had just moved again. This time to Bilbao. I didn’t know a single person.

It started with a Facebook post. I felt ridiculous even writing it: introducing myself in a women’s group, sharing a photo, and asking if anyone wanted to grab a drink. I wasn’t expecting much.

To my surprise, I was overwhelmed with messages and comments. These messages carried a sense of relief that someone else had made the first bold move. It turned out that many other women were feeling exactly the same as I was. So we met up in person.

Shortly after, I was asked to become a local community leader for Girl Gone International. The group grew to 750 members while I was living there. What strikes me now is the quality of the need it revealed. These women were looking for friendships with people who would come to understand the particular texture of their lives. They wanted to be known by people who were genuinely curious about them.

Since then, I’ve hosted at least one in-person gathering nearly every month since March 2024, from casual drinks to more curated gatherings.

When I moved back to Ericeira in early 2025, something had shifted. I wanted to connect with women who were building something of their own and who understood the highs and lows of growing a business. So I started attending the SheSapiens Women of Impact Breakfasts. What began as me covering for the host while she was overseas, eventually turned into a community leader role.

Earlier this year, I launched Luma Circle with my co-founder Marie. We started gathering women business owners around a dinner table centred on a business topic. What I keep hearing is some version of the same thing: I didn’t know how much I needed this.

Modern culture has made commitment feel like a risk. Nobody wants to commit to plans anymore. The RSVP has become a negotiation: maybe means “probably not”, yes means “I'll decide closer to the time” and no means “I'd rather keep my options open”. It’s a response to modern life: everyone is overstimulated, tired and managing invisible workloads. So we all hover at the edge of connection, hoping that connection will arrive fully formed, without effort.

What I’ve discovered in the short time I’ve been doing this work is that going first (making the first move, extending the first invitation) is a rare and valuable skill. Community has rules, and one of them is that someone has to go first.

Curation and facilitation

I spent most of my career in experience design. It’s the umbrella term for visual, interface, user experience, product and spatial design. Experience design is about intentionally shaping an experience, whether digital, physical or augmented. I got into it because I loved beautiful things. Not just aesthetic things, but things that make you feel something deeply human or provoke reflection.

The questions I liked asking were:

What does this experience open up for a person? Where is the friction? Where is the delight? What does the experience of moving through this space actually produce in a person?

I’d been asking those questions about human-computer interactions for a decade. Now, I ask them about human-human interactions, group dynamics and rituals.

I don’t have a settled name for this work yet. The term community builder has become so common that it’s started to lose its meaning, and the word community has been so thoroughly colonised by tech platforms and corporate wellness programmes that it no longer reliably points toward what I’m trying to describe.

What I do sits closer to curation and facilitation: creating conditions for genuine human connection.

You can rent a beautiful venue, invite interesting people and still end up with an evening that feels transactional and hollow. I’ve been in those rooms. I’ve also been in rooms where something different happens, where the conversation goes somewhere nobody planned and people leave less alone than when they arrived. The difference between those two rooms is almost always the person holding the space and how willing they are to go first.

What I’ve learned is that the host sets the tone for everything that follows. When a host shares something real at the start, something with a little vulnerability in it, the room reads that as permission. People stop performing and start connecting.

Empathy, facilitation, the courage to be the first person in the room to say something true, a sensitivity to what a space needs at any given moment: these are developed through practice and through the kind of inner work that makes authenticity possible in the first place. There is a real and growing gap for people who can do this well, and I think it’s one of the most undervalued forms of work in the experience economy.

I don’t have a five-part framework to offer you. That may come in time. What I have right now is a growing body of lived experience and a clearer sense with every gathering of what works and what doesn’t.

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Where the outer work meets the inner work

The work I do in coaching has always been about the inner journey: helping people decouple who they are from the professional identity they’ve built, reconnect with what they actually value and create something that genuinely feels aligned. That work happens in the slow and careful space of a coaching relationship.

What I’m noticing in the gatherings I host is that the same territory comes up. When you put a room full of women who are building businesses together and hold the space well enough that people feel safe to be honest, what surfaces is rarely a question about strategy or growth. It’s almost always something more personal. The fear of being seen. The guilt of charging what you’re worth. The loneliness of making decisions that nobody else fully understands.

Building a business is one of the most reliable vehicles for personal development I’ve encountered. It has a way of surfacing everything you have been avoiding. Every fear, every inherited belief about worth and visibility and what you are allowed to want, eventually finds its way to the surface.

What I’m moving toward is a space where the outer work and the inner work are not treated as separate tracks and where the practical questions of building a business sit alongside the deeper questions of who you are becoming in the process. I don’t know exactly what that looks like yet. I’m learning as I go, which is exactly what I’d tell my clients to do.

It’s only going to get louder

The next decade will be louder than anything we’ve experienced so far. More content, more noise, more AI-generated everything, more people competing for the same finite resource of human attention. More personal brands, more people selling something.

There will be questions worth reckoning with: What kind of work do you want to do? What kind of life do you want to build? What you are willing to protect? What you are willing to let go of?

Let me be clear. This essay is not a blueprint. It’s not a call to action to quit your job, start a business or become a community facilitator. This essay is closer to a series of deliberate choices made by someone who got tired of the noise and started asking what she actually wanted to move toward instead.

Something that gets lost in the conversation about the future of work is that culture is not something that happens to us. It’s shaped, incrementally and quietly, by what individuals choose to create. Every person who decides to gather people in a room rather than perform at them online is making a small cultural choice. Every writer who chooses depth over discoverability. These choices compound.

If the attention economy extracts, the experience economy gathers. If content is infinite, presence becomes rare. If production is automated, meaning becomes the differentiator.

The future, at least the part I want to help create, is deeply human.

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If you’re standing at your own threshold, here are two ways to step forward:

• 1:1 Facilitation: For high achievers who’ve outgrown the framework they’ve been operating within. We work at the level of identity – uncovering the scripts shaping your career choices, defining your own standards for success and building the confidence to trust your judgement.

• Luma Circle: Curated experiences for women moving from employment into entrepreneurship. Join our monthly dinners to connect with fellow founders, learn together, and support each other as your businesses take shape.

It’s a black and white interpretation, but also not entirely wrong. We’ve all experienced the hollow productivity of reports no one reads, meetings that could have been emails, projects designed to justify headcount rather than solve actual problems. (For more on this line of reasoning, read Moral Ambition).

But Work Worth Doing means something more.

When I quit tech, I told myself the work wasn’t meaningful and what I needed was work with more impact and purpose. These were easy answers. Clean explanations that allowed me to avoid the fear associated with what I actually wanted: complete autonomy and agency over my life and livelihood. I wanted to architect my own path, not execute someone else’s vision. Creative freedom on interesting projects wasn’t going to cut it.

Work Worth Doing is about the inner work that career ambivalence invites us into – confronting the unconscious patterns driving our choices and developing our own set of values and principles. It demands the capacity to trust yourself when there’s no external validation to lean on.

Self-authorship is at the centre of this work. It’s the capacity that makes Work Worth Doing possible.

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Why this matters now

We’re living through a strange moment in the history of work. Technology has reshaped work for centuries and each wave of advancement has shifted what humans do for a living. The printing press displaced scribes. The mechanical reaper transformed farming. The sewing machine upended garment production. But each time, new forms of work emerged to absorb the displaced.

Something different is happening now.

We’re hurtling towards what David Shapiro calls a post-labour future, where machines will increasingly handle both physical and cognitive work. Companies are producing more with fewer people. AI and robotics are only accelerating this trend. We’re already living it: mass layoffs in profitable companies, entire departments replaced by software, creative roles absorbed by generative AI.

David Shapiro’s Substack

Understanding Post-Labor Economics in Six Easy Steps

I’ve been working on post-labor economics now for a few years. In fact, my most popular video of all time on YouTube was one of my first public forays into this topic. Back in November 2023, I uploaded “Post AGI Economics” that was inspired by a talk I gave at Clemson University, and the questions the students had…

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a year ago · 69 likes · 22 comments · David Shapiro

If human labour is becoming less necessary for production, then we are being asked, perhaps for the first time in history, to seriously consider what work is actually for. Not just economically, but existentially.

What would you pursue if economic survival wasn’t the only motivation? What contribution feels worth making? What do you want to spend your finite time doing?

These questions feel impossible to answer when you’re trapped in a job that pays the bills. Yet they’re also becoming harder to ignore.

If you’re questioning what you’re doing with your time, you’re not just having a personal crisis. You’re responding to a shift that’s bigger than you. The question of what makes work worth doing isn’t just philosophical anymore. It’s practical and becoming increasingly urgent.

The old social contract is broken – work hard, stay loyal, climb the ladder, retire comfortably – that story no longer holds. People are waking up mid-career and realising the path they’ve been following was never theirs to begin with. When that realisation hits, most people assume they need a new career.

What they actually need is harder to find.

The presenting problem is rarely the actual problem

Last year, I facilitated 80+ hours of coaching with professionals navigating career ambivalence. Most were in their late twenties to mid-thirties. They’re capable, highly-educated, experienced and all have achieved some form of external success.

What they bring to coaching is rarely a practical problem. It’s emotional.

Predictably, these highly capable individuals believe what they need is a plan. Plans feel like control in an uncertain world. If this were a planning problem, they would have already solved it.

What’s actually stopping them isn’t lack of clarity. It’s permission to want what they really want. Tolerance for uncertainty. The courage to act before everything feels resolved. Self-trust.

They come asking: “Which path to take?” “How do I decide?” “What’s the right move?”. These aren’t planning questions. They’re questions about trusting themselves.

One client came to me after landing what she believed was going to be her dream role. Within a year, she felt deeply dissatisfied. Part of the work was untangling what belonged to the environment she was in (subtle dynamics and unspoken expectations) and what belonged to older patterns she’d learned to carry in similar spaces. The question wasn’t, “Is this job good or bad for me?” It was, “What happens when I stop abandoning myself?”

This is where the real work happens. Not in creating a plan, but in asking the right question. The mistake most people make is trying to solve the surface problem without understanding what is actually driving the dissatisfaction.

When you rush through uncertainty because forward momentum feels safer than sitting still, you risk making decisions that recreate the same pattern in a new environment. Different company, same discomfort. Different role, same abandonment of self.

Work Worth Doing demands something different. It invites you to stay with the discomfort long enough to understand what it’s telling you. To grow in directions you didn’t plan for. To act before you’re ready because you’ve learned to trust your own judgement.

This is the work of self-authorship: learning to trust yourself as the one who chooses.

Self-authorship

Self-authorship is the capacity to generate your own values and principles rather than absorbing them from external sources. This isn’t a skill you learn. It’s a developmental transformation you can’t think your way into.

Most people think that being an adult means acquiring more skills and knowledge – getting better at what you already do. Psychologist Robert Kegan’s research shows something different: becoming an adult is about fundamentally transforming how you understand the world.

Kegan’s theory identifies five distinct stages of adult development. Each stage represents a completely different way of understanding yourself, others and reality itself.

Stage 3: Socialised Mind

About 58% of adults operate at Stage 3. At this stage, our sense of self is shaped by external sources: the ideas and beliefs of the people around us and the systems we’re part of. We derive our values from family, culture, society and institutions.

Our sense of self is borrowed from our relationships, our job title, our company’s brand and what is externally validated. We spend an enormous amount of energy trying to avoid disappointing other people. When there’s conflict between important people in our lives, we struggle to answer: “What do I want?”

This is where most people stop developing.

Stage 4: Self-Authoring Mind

About 35% of adults reach this stage. At this stage, we are no longer defined by other people, our relationships or our environment. We understand that we are a person with thoughts, feelings and beliefs that are independent from the standards and expectations imposed upon us. What was once, “I am my relationships and roles” becomes, “I have relationships and roles, but I choose how I engage with them.”

We determine our own standards for success rather than adopting them from external sources. We can distinguish others’ opinions from our own opinions. We recognise that our interpretation of an event creates our emotional experience. We develop an internal sense of direction and the capacity to create and follow our own path, even when it conflicts with what others expect of us.

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The journey between stages

The transition from Stage 3 to Stage 4 is gradual and nonlinear. It typically requires two things: disorientation and time. Something has to shake your existing meaning-making system. A career crisis. A personal tragedy. A relationship breakdown. The realisation that following all the rules didn’t lead where you thought it would. These moments force you to question the external authorities you’ve been using to navigate your life.

This developmental shift doesn’t happen through insight alone. It requires what Kegan calls a subject-object shift: moving what controls us (subject) to something we can control and reflect upon (object). You don’t wake up one morning self-authored. The transition can take years. You build the capacity through repeated acts of self-trust. Small decisions where you choose your own judgement over external approval. It’s practice.

There is no single path to building this capacity. What the paths share is a common feature: they create conditions where you can no longer rely on external structures to tell you who you are or what you're worth.

Some of these conditions are external. A career transition that strips away your professional identity and forces the question: Who am I without it? Building a business tends to surfaces everything you haven’t yet examined: fears around worth, beliefs about capability, inherited stories about who you’re allowed to be and what makes work legitimate. Living across cultures, where the values and norms you grew up with are no longer the default.

Others are internal. Therapy that makes the unconscious patterns driving your choices visible. A contemplative practice (meditation, journaling, time in silence) that creates enough distance between you and your thoughts to examine them. A creative practice that requires you to generate something from your own perspective rather than mimicking someone else's vision. Experiences of grief or loss that dissolve the identity you'd built and ask you to construct a new one.

The outer experiences accelerate the process by removing the scaffolding. The inner practices deepen it by helping you examine what's underneath.

Support structures matter in this liminal space between stages. You need people who can hold complexity with you, who won’t rush you through the discomfort because of their own anxiety. People who won’t hand you their blueprint for how to live.

Professionals trained in developmental work (usually therapists and coaches) understand this distinction. Their role isn’t to provide answers or direction. It’s to help you strengthen your capacity to trust your own judgement, especially when there’s no external validation to lean on. The goal is gradual development of your own internal authority.

Direction that isn’t self-authored doesn’t hold.

What I’m seeing

Most people who come to me aren’t actually looking for a new job. They're responding to something deeper: a growing awareness that the way they've been living no longer fits who they're becoming.

They might call it a career change, reinvention or pivot. What’s really happening is they’re stumbling upon a developmental threshold. They’re being called toward self-authorship.

When you operate at Stage 3, employment feels like the natural answer. Someone else designs the role, sets the standards, tells you what success looks like. You show up, perform well, get validated. The system works…until it doesn’t.

The breakdown happens when you realise you’ve spent years optimising within someone else’s framework. You’ve become excellent at meeting external expectations while slowly losing touch with your own judgement. This is the threshold where most of my clients arrive. The external markers of success are there. The problem is that what they do was authored by someone else.

What happens next follows a pattern. First comes the realisation that the dissatisfaction isn’t about the specific job or company. It’s about operating within constraints you didn’t choose.

Then comes the question: What if I stopped waiting for someone else to design my path?

This question surfaces everything Stage 3 taught them to avoid. What if I fail? What will people think? Who am I to believe I can do this? Buried underneath the fear is curiosity, energy and the first stirrings of agency.

As automation and AI absorb physical, cognitive and creative labour, few of us will be able to rely on our employer to tell us who we are, what we stand for or why our work matters. This is where self-authorship stops being a developmental ideal and becomes a practical necessity.

If your identity is built entirely on your job title and your employer’s brand, what happens when that category of work disappears? If you’re waiting for external structures to tell you what’s valuable and meaningful, what do you do when those structures dissolve?

This is the question career ambivalence is really asking. Not which job to take next, but what work is actually for.

What do you want to spend your finite time creating or contributing to?

That’s not a question you can answer from Stage 3. Your wants are too entangled with others’ expectations to hear your own. Self-authorship is what allows you to know what matters to you and to trust that knowing enough to act on it.

The shift isn’t a change in jobs. It’s a change in how you relate to your own authority.

Where to begin

If you’re standing at this threshold, the most important thing to understand is this: the discomfort you’re feeling isn’t a problem to solve. It’s an invitation to grow.

The people who are most alive are the ones who stopped performing a life that earns approval and started authoring one that feels coherent from the inside.

That shift requires quiet courage, and it’s available to anyone willing to do the work. This is what Work Worth Doing actually means. It’s a commitment to doing the inner work that a meaningful life demands: staying present with discomfort, developing the capacity to author your own path and trusting your own judgement.

That capacity, hard-won and entirely yours, is worth protecting.

Leave a comment

If you’re standing at your own threshold, here are two ways to step forward:

• 1:1 Facilitation: For high achievers who’ve outgrown the framework they've been operating within. We work at the level of identity – uncovering the scripts shaping your career choices, defining your own standards for success and building the confidence to trust your judgement.

• Luma Circle: A community and business education space for women moving from employment into entrepreneurship. Join our monthly dinners to connect with fellow founders, learn together, and support each other as your businesses take shape.

Before I took an exam, I knew what grade I would get before sitting it. When I put myself forward for school captain, I knew I would get it. When my high school’s career counsellor advised me to choose subjects that would scale well in my final exams, I chose design anyway. I knew I would score highest in my year.

This certainty followed me into early adulthood.

When I applied for university scholarships, I knew they were mine. When I applied for an internship at a coveted design studio, I knew I’d get it. Three months later, I knew they would offer me a job. I declined their offer because I sensed something better around the corner.

A month later, Google advertised five graduate positions in their Creative Lab. The application had one question with a 150-character limit. I crafted something that was intriguing enough to land me the role. I spent two years as a contractor before they offered me a permanent position.

I turned it down.

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I told my boss at the time, “I care about the person I’m becoming, more than the job that I have.”

I was about 26 when I said that. I don’t think I really understood the magnitude of what had accidentally spilled out from my unconscious. My boss understood what I meant and didn’t try to convince me to stay.

That creative lab was the best possible job I could have hoped for straight out of university. We experimented with technology and culture, played with ideas, pushed boundaries. It was an expansive place to be.

Simultaneously, I taught design in an academic setting and I felt like an idealist working in a creative lab at one of the world’s most desirable tech companies.

Something inside me was calling for experiences beyond an office and beyond Australia.

Deep down, what I really wanted was to move to New York. I wanted to make it in the Big Apple and prove to myself (and others) that all of these strokes of luck weren’t simply because I was a big fish in a small pond. I wanted to know that I could be a big fish in the vast ocean.

I was a year into a new relationship. I’d just moved into a share house. I felt like I needed to get serious about adult life, like I needed “real-world” experience.

So I joined Deloitte.

I thought I was making a smart move. The salary was much more than what they’d offered me at the Creative Lab. There was clear career progression, a formal mentorship structure. Deloitte worked with banks and insurance companies. You know, “real-world” stuff.

What I didn’t anticipate was the toll it would take.

The work itself wasn’t terrible. It was the environment. I had come from a place at Google that nourished play and creativity and I dove head-first into an environment where performative professionalism was the norm. The people at Google were truly brilliant, and well-adjusted – people I looked up to. I didn’t feel that same admiration for anyone at Deloitte.

No one in my family had ever held a corporate job, so I was never taught the unspoken rules of corporate life. I do remember speaking to my sister’s friend who worked at PwC. As a female Malaysian director, she’d hit the jackpot of all glass ceilings amongst the white boys club. As a half-Asian woman myself, I prepared myself for the corporate politicking by putting up my defences and wearing a mask.

I thought I could play that game.

How wrong I was.

Within two years, I didn’t recognise myself. That embodied knowing and surety of self that I’d carried for most of my life began to dissipate. For the first time in my life, I was sliding down the slippery slope of depression.

My therapist even drew it out for me.

I coped with the depression by numbing it with weed. I wondered what had happened to me. I’d forgotten what my hobbies were. I didn’t know what I was curious about. My days were spent commuting, working and sleeping.

If this was what adult life was, I hated it.

One day, on the train commute to work, I downloaded Headspace. I’d heard that it was helpful for stress. I felt more than stressed.

I stuck my headphones in, hit play on a track and closed my eyes.

My eyelids trembled. My eyes darted around behind closed lids. They just wouldn’t relax. I found it difficult and pointless. I was expecting it to cure the tragic state of my life and make the dullness go away.

I kept doing these short meditations on my daily commute, yet I still arrived at work over-caffeinated, irritated and anxious.

Everything came to a head when I felt squashed by the demands of a particular director. In hindsight, I can see that the director wasn’t the problem. I was the problem. My nervous system had been in a chronic state of dysregulation. My tank was empty and there was nothing left to give.

So I quit.

I didn’t know what would come next, but deep down I knew I couldn’t stay. Briefly, a flicker of that embodied knowing returned.

I’m 34 now. It’s been a six-year journey of uncoupling who I am from the professional identity I spent ten years building. I’ve been learning to trust in my choices again and regaining confidence in my ability to reinvent myself.

That embodied knowing hasn’t quite come back in full force. On some days, it’s more logical than visceral.

Three distinct moments from my twenties have been echoing in my mind lately.

First, whilst I was studying fashion design, I worked as a sales assistant in an independent boutique. One of the owners invited me to lunch and asked how fashion school was going. She told me, “When I look at you and Magdalena (fashion designer), I see different people. Magdalena is a designer. You are an artist, Jennifer.”

Second, at my graduate exhibition for visual communication, I exhibited bacteria cultures laser-engraved with the Genesis story from the Bible, a critique on the materials we use to produce design artefacts. I was introduced to the Danish founders of a boutique graphic design studio in Sydney. Of my work, they remarked, “This is not design. This is art.”

Third, in the closing days of a UX cohort I taught at General Assembly, each student was invited to write messages of gratitude for one another. Next to my name, a student wrote, “There is a hidden depth in you.”

In the past few months, I’ve been working with a brilliant coach, Dina Maccabee, who is also a composer, violinist and vocalist. She came into my world at a moment of self-reorientation. Who better to help me than an artist herself.

Through our conversations, it’s becoming clear I’m orienting towards self-expression.

I started publishing my writing on Substack back in July. I intended it to be a resource collection and marketing tool for my coaching practice, where I talk about career change and identity shifts. Around the same time, I joined a Toastmasters club to improve my public speaking and communication skills. Though it’s become something else entirely.

The act of writing and arranging my inner world on a page has awakened something in me. The value of writing comes from the work put into the piece before it’s published. Once it’s published, it feels like cartharsis.

In the book, The Shadow of the Wind, Zafón makes references to the power of reading and writing as a tool for healing and discovering oneself. One passage has stayed with me:

Julián had once told me that a story is a letter the author writes to himself, to tell himself things that he would be unable to discover otherwise.

That’s what this Substack is becoming for me. A space to write letters to myself.

I’ll continue writing about identity shifts and career change because that work matters to me deeply. Yet this space will also hold the stories that are yearning to climb out of me.

My coaching practice is evolving too, away from career and in the direction of identity work and depth psychology. I’m interested in meaning-making, self-integration and authentic relating.

Simultaneously, I find myself occupying the space between community building, speaking and facilitation with Luma Circle.

I’m taking the next few weeks to write privately about these evolving directions, to clarify who I want to support and how. I’m trusting that embodied knowing that’s steadily returning.

It feels like the natural evolution for someone who spent a decade building a professional identity, then six years uncoupling from it, and is now stepping further into something that feels true.

I don’t have it all figured out yet. (Writing that feels like I’m breaking the fourth wall of coaching).

What I have is the permission and grace to evolve and be something other than what I thought I should be.

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If you’re standing at your own threshold

If you find yourself between chapters, not quite who you were, not yet who you’re becoming, this is the work I do. I work with people at two different stages of expansion. Both are about expanding possibilities, just with different focuses.

→ 1:1 facilitation: Identity shifts that show up as career change

A three- or six-month coaching partnership for high achievers ready to move beyond productivity-as-worth and step into work that actually fits who they’re becoming. We combine deep self-inquiry (meeting the parts of yourself driving overachievement) with grounded action. This isn’t tactical career advice. It’s identity work.

Learn more

→ Luma Circle: For women building something of their own

Luma Circle is a business education platform and community for aspiring female founders. We’re in early stage, currently hosting in-person gatherings that create space for conversation, clarity, and courage. Over time, we’ll grow into a community offering coaching, business education, and support to move from employment to entrepreneurship.

Learn more

“Hey! Want to grab a coffee?”

I felt the conflict: the pull of wanting to connect, but knowing that I wouldn’t actually enjoy spending time with this person.

I didn’t want to go.

I knew exactly how it would play out. I’d sit in a cafe listening to the latest drama with her boyfriend, over a drink I don’t even drink. I’d listen to her complaints about not finding a higher-paying job, even though she had no interest in improving her skills, or her dream of finding someone to provide for her so she wouldn’t have to work.

I’d heard it all before.

But I typed back anyway: “Hey! Yes, sure. Let’s do it.”

And so, there I was again. Sitting across from her, asking myself, “Why am I here again?”

I knew the answer.

Loneliness. Limited choices. People-pleasing dressed up as friendship. The discomfort of saying no.

Later that evening, I said to my boyfriend: “I don’t want to be around her. I don’t know why I keep saying yes.”

He looked at me gently, “Then why do you?”

I didn’t have a good answer.

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The inheritance we don’t question

Maybe you’ve been here too. Saying yes when you really mean no. Giving your time to people who want you to carry their problems, rather than own their choices.

This is what happens when we settle for whoever is around. We accept the friends from school who stuck around, the colleagues who became our social circle because they were there.

It’s not that these people are wrong. It’s that they were never really chosen. They were just available and convenient.

Looking back, I see the pattern so clearly. Not just in friendships or community, but in every aspect of life. My relationships were built on proximity, not values. I was maintaining the familiar simply because it was familiar.

The thing about defaulting to the people who’ve always been there, is that you don’t have to admit that you’ve outgrown them. You don’t have to put yourself out there.

But comfort has a cost. It keeps you surrounded by people who reinforce the identity you’re trying to leave behind.

Starting from nothing

When I arrived in Lisbon almost 6 years ago, I didn’t know a single person.

I moved into an apartment with six bedrooms and eight people living there. These people became my closest friends because we were locked in the same space together during COVID.

My work colleagues were nice enough, but I never really saw them as friends. I’d go out for drinks after work because it seemed like good form to connect with your colleagues.

So by default, I had two communities: housemates and colleagues.

People I didn’t choose, but that someone else had haphazardly chosen for me based on an interview. I was building a community around whoever happened to be available.

When I left my job and took a sabbatical, everything started to shift. Suddenly, I had no structure. No routine. No professional identity. The future felt completely uncertain.

I’d grown up believing that financial security was what one must aim for in life. My parents never had it growing up, so they taught me not to take risks. Leaving a stable job felt like stepping off a cliff.

What I didn’t know then was that this sabbatical year would become the single most powerful thing to happen to me in the past six years.

It forced me to re-evaluate everything: who I was, what I wanted, how I was living. And for the first time, who I was choosing to spend time with.

Finding people through intention

During that sabbatical year, ashtanga yoga increasingly became an important part of my life and I felt a calling to practice more, go deeper, learn more.

I started meeting people through this practice. We were united by more than proximity. We shared interests and these people were asking similar questions as I was. My community started to feel closer to who I was becoming.

There’s something about the ashtanga practice which weeds out the faint of heart. It’s a difficult and strict practice. You can tell who is there for spiritual depth and who is there for the ego inflation.

These were people who had chosen this path intentionally, not stumbled into it by default. They were definitely not there because it was convenient. They were there because they’d made a deliberate choice to show up, even when it was hard.

Two years earlier, when I’d left my job at Deloitte, most people looked on my decision with pity. I could see it in their eyes. “So what are you going to do next? What’s your plan?”

Shortly after, I went to a yoga retreat. I remember telling the group why I was there: I had left my job. I didn’t know what I was going to do next. But I knew that environment wasn’t for me.

The yoga teacher congratulated me.

For the first time in my life, someone didn’t look down on this counterintuitive decision. She actually celebrated it.

That’s when I started to understand the difference between communities built on proximity and communities built on values.

Creating spaces for connection

Fast forward a year, I moved to Ericeira. For a brief moment, this place felt like it could be home.

I was starting to understand what an intentional community felt like. I knew what I was searching for. Which made the reality of Ericeira more frustrating.

Ericeira is the Byron Bay of Europe. The surf and yoga lifestyle is undeniably beautiful. But beneath the surface, something felt off.

There are two types of yoga people here. The first group charges crystals under full moons, while the second group treats yoga like a performance. These weren’t the kind of people I’d connected with during my sabbatical.

Then there was the transience. I’d meet people, start to feel like I belonged. Then they’d move on. Ericeira felt transient in a way that left me constantly starting over. I was tired of building friendships that had expiration dates.

I started to resent this place because I couldn’t find my people: the ones with ambition but not on the treadmill of achievement. The ones who are intentional but not untethered and performatively spiritual.

My boyfriend and I started travelling, searching for somewhere that might feel right. Eventually, we moved to Bilbao.

I was still looking for the right place. What I didn’t realise was that I needed the right people.

In Bilbao, I started hosting meetups. For a year, I brought women together. I learned that I could create community, that I didn’t have to wait for it to appear.

But I was surrounded by people in conventional careers. None of them were questioning whether the traditional route was even what they wanted. They weren’t expansive in the way I needed the people around me to be.

I had learned to create spaces for connection. I just hadn’t yet found the people I was meant to connect with.

Choosing differently

When I moved back to Ericeira this year, I joined a female founders breakfast.

Walking into that for first time, I felt like I didn’t belong. Everyone else seemed further ahead. I was ashamed about being right at the beginning of my journey. Admitting I was starting from scratch felt exposing.

The format was simple: each woman had a few minutes to share her business journey. The invitation from the hosts was to share vulnerably.

There was something really special about the way the hosts held that space. This wasn’t a place to perform. It was a place to unmask.

Slowly, I started sharing more truthfully about where I was. I realised everyone else had felt the same way I did. We were all figuring it out. We were all learning and growing.

Within a few months of attending those breakfasts, I was given the opportunity to host. I took the leap, even though I felt like total impostor. It grew my confidence. My self-belief. My sense of belonging.

This was connection built on vulnerability and shared values of growth, authenticity and sisterhood.

And I think that’s what the right community does. It doesn’t keep you comfortable. It expands what you think is possible for yourself and invites you into truth-telling.

The people who shape you

The people you surround yourself with either keep you where you are or show you what else is possible.

When we feel stuck, we need new examples of how to live. We need people who’ve walked a similar path and survived. We need to see that the thing we’re terrified of doing is not only possible but worth it.

You can select who those people are. But it requires choosing and not settling for relationships built on convenience or loneliness.

I can say now that I genuinely enjoy the small company I keep. These relationships weren’t handed to me. I sought them out.

This past weekend, I launched a community I’ve been building. A space for women who are creating something of their own, who want to be surrounded by others on a similar path.

I’m excited about the women who will gather. About the conversations we’ll have and the possibilities we’ll open up for each other.

How to find your people

If you’re in the in-between space right now, here are some practical steps for building the community you need:

Audit your current circle

Ask yourself: are these people I chose, or people I settled for? Do they expand my sense of what’s possible, or keep me playing small? This isn’t about cutting people off. It’s about noticing the expanders in your social circle.

Get clear on who you’re becoming

You can’t find your people if you don’t know who you’re looking for. What values matter to you now? What kind of conversations do you crave? What version of yourself do you want to be around others?

Follow your curiosity

Join a class. Attend a workshop. Show up to an event. The people you’re looking for are asking the same questions you are. Go where those questions are being explored.

Make the first move

Post in a group. Reach out to someone whose work resonates. Most people are waiting for someone else to be brave first. Be that person.

Create the space you wish existed

If you can’t find the community you’re looking for, build it. Host a dinner. Start a meetup. Gather people around a shared interest. You don’t need to know what you’re doing. You just need to show up.

Give it time

Deep friendships don’t form overnight. Keep investing in the people who expand you. Consistency builds trust. Trust builds connection.

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Who are you choosing?

The life you’re living right now was shaped by the people around you. The conversations you’ve had. The examples you’ve seen. The possibilities you’ve witnessed.

If you want a different life, you need different people around you. Not because the people in your life are wrong. But because you likely never really chose them in the first place.

The in-between space is uncomfortable. It’s lonely. But it’s also where you get to decide who walks beside you next.

The people you’re looking for are out there. They’re waiting for someone to gather them. That someone could be you.

If you’re standing at your own threshold

If you find yourself between chapters, not quite who you were, not yet who you’re becoming, this is the work I do.

I work with people at two different stages of expansion. Some are in deep identity transition—they know something needs to change but they’re still figuring out who they’re becoming. That’s 1:1 facilitation work. Others have already made the leap and know they want to build something of their own—that’s Luma Circle, where we focus on the practical side of starting and scaling a small business.

Both are about expanding possibilities, just with different focuses.

→ 1:1 facilitation: Identity shifts that show up as career changes

A three- or six-month programme for high achievers ready to move beyond productivity-as-worth and step into work that actually fits who they’re becoming. We combine deep self-inquiry (meeting the parts of yourself driving overachievement) with grounded action (small experiments, narrative building). This isn’t tactical career advice. It’s identity work.

Learn more

→ Luma Circle: For women building something of their own

Luma Circle is a business education platform and community for aspiring female founders. We’re in early stage, currently hosting in-person gatherings that create space for conversation, clarity, and courage. Over time, we’ll grow into a community offering coaching, business education, and support to move from employment to entrepreneurship.

Learn more

I’m grateful I already weathered a major identity shift in my early 30s, when the stakes felt lower. Before a mortgage, marriage or children. Before the weight of caring for ageing parents. I’m grateful I listened to the unease early and chose differently. It means the years ahead feel wide open to create a life that’s truly mine.

The unease started at 28. On paper, I had everything I thought I was supposed to want: the job, the relationship, the money, the clear trajectory. On the inside, small cracks appeared: numbness, disillusionment, a quiet “Is this really all there is?”

Over the next few years, I tried to “solve” it. I changed jobs. I left a relationship. I moved overseas. I signed up for yoga retreats. None of those things solved the problem. What they did do was create opportunities for self-exploration and for reconnection with parts of myself I’d lost along the way.

I didn’t have the language for it then, but I was hearing an early echo of what many don’t encounter until midlife: the summons to ask not just what the world expects, but what the soul is asking now.

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Middle age arrives as a perfect storm

There isn’t a universal definition of middle age, but its characteristics are unmistakable.

Psychologists describe it as the phase when the future no longer feels limitless and existential questions surface with new urgency. Economists mark it as peak working years (roughly 35–54), when financial responsibilities mount. Sociologists define it by roles: juggling career, parenting and caregiving for ageing parents whilst managing a web of social expectations.

What makes midlife so charged is that it’s not just one transition. It’s many, all arriving at once.

The people around me are asking big questions: whether to have children, what it means to raise them, whether to keep climbing the career ladder or walk away from it altogether to create something of their own. Many are carrying multiple roles simultaneously: advancing in careers, raising children, caring for parents. The weight of expectation is everywhere—from partners, families, workplaces and culture at large.

Choices feel heavier now. Their consequences more permanent. Some quietly wonder if it’s too late to change course.

This is why midlife carries such intensity: external responsibilities peak precisely just as the inner voice grows louder. The summons of the soul collides with the pressures of the world. What looks like restlessness or discontent from the outside is often something deeper stirring from within—a growing tension between the life we’ve built and the life we know is ours to claim.

A summons, not a crisis

The term midlife crisis has been co-opted by popular culture as a way to dismiss someone’s distress—clichés about sports cars and affairs that reduce genuine psychological upheaval to punchlines.

The reality is far more complex.

James Hollis, a Jungian psychologist, describes midlife in his book Finding Meaning in the Second Half of Life as a psychological passage when the old scaffolding of identity can no longer hold. What looks like a breakdown is often the psyche breaking through.

By this stage of life, two things have happened: we’ve been separated from our parents long enough to make our own choices, test them and feel both success and collapse. We’ve also developed enough ego strength to reflect, critique and risk new values and directions.

Hollis says that midlife distress often shows up first in intimate relationships, then in careers, and finally as personal symptoms—depression, insomnia, addictions or a restless longing that refuses to quiet down. When we ignore it, it erupts through troubling dreams, intrusive thoughts or self-sabotaging behaviour.

These questions don’t wait for a specific birthday. They surface whenever the life we’ve built on adaptation starts to feel too tight. They confront us with the gap between what we’ve achieved and what we feel in our most honest moments.

Whether at 28 or 48, the summons is the same: to ask not just what the world expects of us, but what the soul is asking now.

This past weekend, I listened to a podcast hosted by The Imperfects. The episode featured psychologist Dr Emily Musgrove discussing Hollis’ work on midlife. For the first 30 minutes, one of the hosts, Josh, was mostly silent whilst the conversation explored the tasks of midlife, the U-curve of happiness, the shift from achieving to meaning-making.

When Josh finally spoke, his voice cracked. He’d just been diagnosed with depression the week before. Despite having what he called “the best job, the best wife, the best kids” — all the external markers of a life well-lived — he felt numb. He described a fear of taking up too much space, of needing to “get out of the way” as his children grew.

The dissonance was striking: everything looked right on paper, yet inside, something fundamental had collapsed.

What Josh was confronting was the very essence of midlife. The moment when external achievement no longer protects us from internal reckoning. This is what Hollis means when he describes midlife as the psyche breaking through. The pain isn’t pathology. It’s information.

The difference between quarter-life and midlife is mostly timing and intensity. At quarter-life, the questions revolve around early career scripts—Am I on the right path? At midlife, they take on deeper existential weight: mortality, legacy and the ache of the unlived life.

The unlived life

The unlived life names the gap between the life we live to please others and the life we know is ours to claim.

It shows up in many forms: the creative impulse you’ve always felt but never pursued. The career path you sacrificed for security, even though it never fit. The conversation you’ve avoided. The relationship you never repaired. The risks you postponed until “later.”

It lingers in envy—that subtle pang when we see someone living a life we’ve denied ourselves. We’ll explore how to decode that envy shortly…

The tragedy of the unlived life is not that we never had the chance. It’s that we turned away from it, again and again, out of fear, duty or habit. We choose adaptation over authenticity. We choose applause over aliveness.

Once you’ve glimpsed the unlived life, you can’t unsee it. You can’t unknow the truth that it’s never too late to begin living it. Which makes the real question not “Is it too late?” but “What is this unease trying to tell me?”

Jung offers insight into what’s really happening.

The unrest isn’t malfunction

Jung described midlife as a fundamental shift from one orientation to another. In the first half of life, we build identity and pursue external goals. In the second half, external achievements lose their lustre, while meaning and authenticity come into focus. The transition brings confrontation with parts of ourselves we’ve long ignored, visceral awareness of mortality and re-evaluation of values.

For women, midlife often coincides with questions about motherhood—whether to have children, navigating the identity shift of becoming a mother, or reconciling professional ambition with caregiving responsibilities. Yet, out of the weight of these changes, something shifts: a growing assertiveness, a reclaiming of personal authority that may have been set aside. The “good girl” who kept everyone comfortable begins to fade. Research shows women’s confidence often peaks around age 60, suggesting that midlife isn’t decline but an opening into something fuller.

I hold this tension myself. Women are gifted the ability to create and hold life, which is undoubtedly a deeply rich and meaningful human experience. Yet I also want the freedom to live for myself, to pursue my goals without setting them aside. It sounds selfish. Perhaps it is. But it’s honest. Balancing these desires isn’t simple, and this question occupies more space in my mind as I move further into this life stage.

For men, midlife often involves a softening. The focus on competition and achievement that defined earlier years gives way to something more collaborative and nurturing. Many men shift from what researchers call vertical ambition to horizontal expansion—from climbing hierarchies to mentoring, teaching and creating legacy. Strength doesn’t disappear, but it makes room for vulnerability.

This questioning is visible everywhere, among both men and women reshaping what work means to them. What looks like people leaving their careers is often something more nuanced: a search for work that aligns with deeper values.

Hollis writes about the distinction between a job and a vocation. A job is what we do to meet external expectations. It gives us structure, stability and identity. A vocation, by contrast, is what we do in response to an inner summons. It may or may not pay well, but it moves the soul.

Some people need their job to be their vocation. Others need the separation. It requires discernment about what your life actually needs. So the question becomes: “What arrangement lets you honour both your material needs and what genuinely matters to you?”

When the scaffolding of career identity starts to feel shaky, most of us interpret the discomfort as burnout or personal failure. We think something is wrong with us. We wonder if we’re being ungrateful, unrealistic or self-indulgent.

The script that says a job must be everything—identity, purpose, security, meaning—is breaking down. A new one is forming, where distinguishing between job and vocation matters. Where work can provide stability without consuming your entire sense of self.

A job may keep the lights on, but vocation is what keeps the fire lit.

Decoding your envy

Envy is one of the most honest teachers we have. We don’t envy everyone—only those who hold something we feel we deserve. Hidden in that discomfort is information about our unlived potential.

The mistake we make is envying people in their entirety, when actually it’s only a small part of what they have or do that resonates with us. The School of Life offers a useful exercise in The Career Workbook to help decode what your envy is really pointing toward.

Take out a notebook and create four columns:

1. People I envy

   List four names. Two might be people in public life or media. Two might be people you know directly—well or casually. Don’t overthink it. You might envy your sister, someone you met briefly at an event or your former colleague.

2. What they’re known for

   Write down their most obvious achievements or what they’re recognised for.

3. The positive bits I don’t actually want

   Even when we envy someone, we don’t want everything about their life. Focus not on the downsides (the long hours, the travel, the scrutiny) but on the positive aspects that don’t appeal to you.

   Maybe you envy a wealthy entrepreneur, but when you look closely, you realise you don’t actually want the wealth—you want the autonomy. Maybe you envy a creative person, but it’s not their art you want—it’s their ability to structure their own time.

4. The positive bits I do want

   This is where the insight lives. Extract from these specific lives a few things that genuinely interest you. What moves are these people making that lie at the root of your discomfort and painful longing? These are the breadcrumbs pointing toward your unlived life.

Your envy isn’t random. It’s showing you something important. The question is: are you willing to listen?

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Swimming in deeper waters

Middle age isn’t defined by a number. What I’m experiencing today—the quiet questioning, the reorientation—feels best described by its characteristics rather than the milestone itself. It’s a period when the waters of life begin to move with a stronger current. We’re no longer wading in the shallows. We’re learning to swim in deeper water.

It’s also about discernment—separating what’s truly mine from what’s conditioning. I feel this most acutely when I think about whether to have children. The question occupies space in my mind, but it doesn’t feel like confusion. It feels more like an invitation to clarity.

The term midlife crisis needs a rebrand. It’s not something to be mocked or pathologised. It’s a call to wake up to what’s real, to notice what no longer fits and to listen for what wants to be born through us next. Beneath the clichés of sports cars and affairs lies something deeply human: the longing to live a life that is truly our own.

The summons is here. The question is whether you’re ready to listen.

Navigating what’s next

If you’re standing at your own threshold, somewhere between who you were and who you’re becoming, this is the work I do.

I support professionals navigating midlife transitions: people who sense something deeper calling but aren’t sure how to translate that into meaningful next steps.

Here’s how we can work together:

→ 1:1 Coaching: Navigating career and identity shifts

A three- or six-month journey combining deep self-inquiry with grounded action. Together we clarify what’s calling you forward, decode what your unease is telling you, and design small experiments that move you closer to alignment.

Book a consultation

→ Luma: For women building something of their own

Luma creates spaces for conversation, clarity and courage through in-person gatherings. Over time, we’ll grow into a network of mentors offering the guidance women need to move from employment to self-employment.

Join the waitlist

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There is beauty and depth in Ceylan’s name alone. In Turkish, Ceylan means gazelle — a symbol of gracefulness, gentleness and beauty. This feels true of her as a person. Her presence is grounding, and she has a gift for communicating in elegant phrases. Her website reads:

“No one finds lasting fulfilment by becoming who they believe they’re expected to be.”

Originally from Turkey, Ceylan spent twelve years at a top-tier American law firm, eventually working her way to partnership before stepping away in 2019. Her career in law was thriving, yet she describes the closing of that chapter simply: “The journey felt complete.” The work that had once felt alive now resembled a marriage that had become merely functional.

Ceylan’s story doesn’t begin when she left law. It begins much earlier. She grew up in a spiritual household, reading holy books from the age of 13, exploring shamanic constellations at 17, and diving into esoteric studies in her twenties. For years she taught meditation alongside her legal career, while also training in somatic psychotherapy for four years. These practices were never meant to become her career.

And yet, slowly, almost imperceptibly, they began to pull her in that direction.

The crack widened after a six-week initiation journey in New Zealand. Coming home, she stood at what she describes as a fork in the road. The idea of continuing on her current path as a lawyer was impossible. It wasn’t a rational decision weighed on a list of pros and cons. It was, as she says, a “choiceless choice.”

What helped most was the work she had already been doing. Years of therapy, trauma healing, and depth work, supported by a strong community, gave her the resilience to stay the course. She emphasises that “the work happens before you quit.” Without that inner foundation, she says, it’s easy to be pulled back into old identities or make reactive choices.

Her transition was also gradual and intentional. At 34, she didn’t have a mortgage or children, and she had enough savings to give herself time to explore. She took an eighteen-month sabbatical and spent the next six years living nomadically, offering herself the space to reflect, rebuild, and slowly find her way forward.

She resisted the urge to monetise quickly, experimenting instead from a place of aliveness rather than financial necessity. “I wasn’t experimenting from the place of ‘I need this to pay rent,’ but from the place of ‘this is where I come alive.’”

Seven years on, Ceylan has built a thriving practice at the intersection of somatic therapy and depth work, helping individuals and groups navigate intimacy and embody their deepest sense of purpose. She pairs the pragmatism of her legal background with the depth of her spiritual path. What I admire most is her refusal to give easy advice. Instead, she points people back to themselves: “do your inner work, don’t leap reactively, and make sure your decision comes from a clean place”.

Ceylan’s story isn’t one of burnout or disillusionment. It’s the story of someone being called into a deeper expression of herself. It was a call that could no longer be ignored. Her decision to leave law wasn’t an escape but a movement toward integrity, love, and spiritual freedom, even when it meant letting go of certainty, prestige, and a clearly defined identity.

What I keep returning to in Ceylan’s story is her refusal to make it sound easier than it was. She did the work, for years, before the work was visible from the outside as anything at all.

The work happens before you quit, she told me. Without it, she said, it’s too easy to be pulled back into old identities, to make reactive choices, to mistake escape for calling. I think this is the line that separates the transitions that hold from the ones that don’t. The outer move is the visible part. But what makes it possible, and what makes it last, is everything that happened in the quiet years before.

James Hollis writes that to engage with the summons of our souls is to step into the deepest ocean, uncertain whether we’ll be able to swim to some new, distant shore. For some the entry is gradual. Others are pushed suddenly into deep waters. Ceylan, I think, walked in slowly. Year by year. Until the shore behind her was no longer where she lived.

If Ceylan's story resonated, you can find her at ceylankara.com. She's a facilitator of depth-oriented transformation, trained in complex developmental trauma as a Master NARM Practitioner and in somatic psychotherapy. She works with individuals and groups arriving at fulfilment in relationships, work and life.

The question was: “If you had a shot of courage, what career would you choose?” He thought carefully, then said: “I’d work on my app.”

It was an idea he’d been carrying for years, but he quickly shut it down. “But I haven’t started on it because I feel stuck in my current job. Trapped by the salary.”

His fear of public speaking was loud, but the shame of being trapped by a pay check was louder.

It was heartbreaking and familiar.

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The elephant in the room

Finances are the number one concern when it comes to making a career change or starting a business. Understandably so, when the job market is brutal. Mass layoffs, shrinking industries, and precarious contracts are leaving people clinging to their jobs for dear life. Even those in “safe” corporate roles can feel the ground shifting beneath them.

As Rosie Spinks reflects in her piece, Everyone I know is worried about work, there’s a widening gap between the work people expected and the work they’re actually living. Jobs and companies that were meant to provide both meaning and security haven’t held up their end of the bargain…

What Do We Do Now That We're Here?

Everyone I know is worried about work

Almost everyone I know is worried about work: finding a job, keeping the one they have, or what will happen when the work they do no longer exists…

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a year ago · 1462 likes · 103 comments · Rosie Spinks

…Or perhaps we were naïve to think they ever could.

This disconnect isn’t limited to freelancers or creatives. It’s everywhere.

We put all our stock in the idea that specializing in one field, industry, or competency — one that almost always occurs within the confines of a screen — in exchange for a steadily-increasing paycheck was the smart move to make. We accepted that we better get really, really good at it if we wanted to command the kinds of salaries that keep us afloat in this system, so we worked until the point of burnout to deliver to companies we thought would love us back. Or at the very least, not fire us the very moment there was a marginally cheaper way of doing things.

And so, people find themselves in a bind.

It isn’t only about the money. It’s about the status a job carries, the identity it gives you, and the sense of belonging to a certain peer group. It’s about retirement contributions, health insurance, school fees and the mortgage. These aren’t trivial concerns. They’re the scaffolding of modern life.

The problem is, many people assume the choice is binary: cling to their career (and all the security it provides) or start over from scratch. This kind of black-and-white thinking is exactly what keeps them stuck.

A true shot of courage is often found in the grey: in the experiments, the gradual shifts and the creative solutions that allow you to move forward without losing everything you’ve built.

There are practical ways to support yourself as you transition into meaningful work. It takes planning and a clear-eyed view of the risks you’re willing to tolerate. And of course, everyone’s circumstances will be different.

Here are some of the most common strategies people use to fund a career change—without blowing up their lives. My hope is that this cracks open a sliver of possibility for you.

Stay put, build on the side

One of the safest ways to begin is to keep your full-time job while experimenting with something new on the side. It’s the old adage: use your 9-5 to fund your 5-9.

This path isn’t without challenges. It often means giving up evenings or weekends, and sacrificing free time. In return, you give yourself the chance to learn, make new connections, build confidence and even start earning, without letting go of the security of your salary.

In his essay, The Death of the Corporate Job, Alex McCann argues that traditional jobs are no longer forever homes. Instead, they’ve become funding mechanisms—a way for people to maintain a corporate persona while quietly building their escape route.

They're using the corporate infrastructure—the steady salary, the laptop, the stability—as a platform for building something real. The corporate role hasn't died; it's become a funding mechanism for actual work.

Still Wandering

The death of the corporate job.

Last week, I had coffee with someone who works at a big consulting firm. She spent twenty minutes explaining her role to me. Not because it was complex, but because she was trying to convince herself it existed. "I facilitate stakeholder alignment across cross-functional workstreams," she said. Then laughed. "I genuinely don't know what that means anymo…

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9 months ago · 4655 likes · 744 comments · Alex

I’ve seen this play out in clients and friends of mine who’ve kept one foot in the corporate world while carving out space to build their own thing. It’s not about splitting your energy forever; it’s about creating a bridge until your new path can stand on its own.

And yet, I personally found this strategy difficult. I tried to treat my job as “just a job,” but it’s not in me to coast. My free time has always been sacred. By the end of the workday, I needed space to decompress. Staring at a computer for 12+ hours didn’t energise me and switching gears into my own project after work wasn’t sustainable.

So while this is the safest route, and perhaps the most ideal on paper, it doesn’t work for everyone.

Re-negotiate your hours

A second, often overlooked option, is to re-negotiate your hours. Most people assume their employer would never agree to fewer days or flexible hours, so they don’t even ask. But in reality, this strategy is often more accessible than it seems.

Reducing your hours, even by a single day a week, can free up headspace and energy for exploration, networking, or building your business, while still keeping income flowing. Some choose to go part-time. Others compress their hours, working four longer days instead of five.

One of my clients was a global brand director at a multinational company. Her role was demanding: back-to-back meetings, no time to think and by the end of the day, she was depleted. Outside of work, she was training as a coach and longed to give more time to it. But her reality was complicated: bills to pay, little savings and even a company-provided car. Walking away from her salary would have been reckless.

Together, we explored her options: moving to another department, becoming an independent consultant, finding a new job, or reducing her hours.

Her top choice was a four-day week. The idea of asking filled her with anxiety. She caught herself thinking: “I don’t want to know, in case it’s a no.” We prepared by clarifying her boss’s likely concerns, identifying compromises, and building the courage to have the conversation.

In the end, her boss said yes without hesitation, and that one shot of courage gave her the breathing room she needed to build her coaching practice, while still holding onto stability.

The lesson? The fear of asking is often bigger than the reality.

Save for a rainy day

This isn’t just a strategy for career change. It’s basic financial hygiene.

Without savings, every setback feels like a crisis. With a buffer, you can approach the transition with calm and focus instead of panic.

If you’re serious about a career change, give yourself a buffer that’s bigger than you think you’ll need. Especially if you’re building a business, it will take time before income is consistent. The runway you create can be the difference between giving up too early and seeing your new path through.

Small, creative income streams can help you top up savings too: renting out a spare room, selling unused items, or freelancing. They may not replace your salary overnight, but together they add days, weeks or maybe even months to your runway.

Streamline

As our salaries increase, so too does our spending. It’s almost automatic: the nicer apartment, the gym membership we rarely use, the extra streaming subscriptions, the daily coffees, the expensive holidays to recover from the stress of the job.

Some of this spending is intentional, but sometimes, it’s a coping mechanism for a reality we don’t love. When the workweek feels draining, we justify the €25 lunches, the €300 outfits for a job we secretly hate, or the wine that takes the edge off.

The problem is, these habits quietly raise the bar on the lifestyle we feel we “need” to maintain. Which makes stepping away from a steady salary feel impossible.

Streamlining is about breaking that cycle. Go through your outgoings with a fine-tooth comb and ask: Do I really need this, or am I spending to soothe myself?

By lowering your baseline expenses, you create freedom. Every euro not spent on coping can be redirected into savings that support your transition. The sooner you do it, the less dependent you become on keeping a salary that no longer serves you.

Downsize

If trimming small luxuries isn’t enough, bigger shifts may be necessary. Housing is often the biggest lever: moving to a more affordable home, taking in a flatmate, or even going home for a while.

Most of us accumulate more than we actually need. I’ve downsized multiple times. I left a relationship and moved back in with my parents. Later, I sold most of what I owned to move overseas. In Lisbon, I sold everything again when I decided to take a year-long sabbatical. Downsizing wasn’t deprivation. It was an investment in buying myself time and space.

Every time I let go, I felt closer to the life I wanted.

Re-engineer

Sometimes the money is already there, you just need to restructure it. Refinancing a mortgage, transferring high-interest debt to a 0% card, or renegotiating big bills can free up cash. That extra breathing room can fund classes, childcare, or tide you over during a slower income period.

I’ve seen friends make bold moves by unlocking assets, such as selling a shared apartment with an ex, which gave them the peace of mind to start fresh.

Not everyone will have the same financial flexibility. If you’re living paycheck to paycheck, the road is harder. But even then, resourcefulness can create a buffer, whether through salary negotiations, side income, or restructuring expenses.

Career change is not easy, but saving, streamlining, downsizing, and re-engineering your finances are all levers you can pull. Together, they buy you the most precious resource of all: time.

Ask for support

For many, the idea of asking for help feels uncomfortable. We don’t want to be a burden, or admit we can’t do it all on our own. But no one makes a big transition without support. Sometimes the most overlooked resource in a career change isn’t money. It’s people.

Support can take many forms:

Financial

Changing the breadwinner dynamics, reaching out to family or arranging temporary living situations. Even short-term help can create enough breathing room to make choices from a place of calm rather than desperation.

As with most things in career change, starting small helps. For example, if your partner is open to it, you might experiment with living on one salary for a set period of time. That way, when the time comes to step into something new, it doesn’t feel so drastic.

Practical

Support doesn’t always involve money, but it can be a game-changer. It’s about redesigning how you live and with whom. Examples include:

• Childcare swaps with friends

• Batch-cooking circles to free up time and energy

• Sharing a car, splitting groceries, or rotating school pick-ups

Though not directly related to career change, I love the idea of mommunes: shared living arrangements where single mothers (or mothers who crave more community) live together under one roof. They pool resources, share childcare, and offer one another the emotional scaffolding often missing in isolated, nuclear-family living.

While not for everyone, mommunes show what becomes possible when people decide they don’t have to “go it alone.” These models aren’t just cost-saving, they’re life-giving. They create space for single mothers to pursue study, work, or entrepreneurial projects they might otherwise have shelved.

Emotional

When you’re in the middle of a career change, you’ll inevitably hit moments of doubt:

What if I fail?
What if this was a terrible idea?
Maybe I should just go back to what I know.

Those are the moments when who you have in your corner matters most. You need people who remind you of your vision when you lose sight of it. People who cheer for you on the hard days and celebrate the tiny wins.

Surround yourself with expanders: people who’ve successfully made bold changes themselves. Their stories make your own feel possible and you can borrow courage from their path until you find your own footing.

Be discerning about who you share your goals with. Not everyone will understand why you’re stepping off the beaten path, and some will project their own fears onto you. Find the people who pull you up, not the ones who quietly tug you down.

Even the best financial plan can crumble under the weight of self-doubt. That’s why people in transition often seek out niche communities and group coaching to feel less alone, and to keep going when things get hard.

Institutional

Depending on where you live, government benefits, retraining grants, or business incubator programmes can all act as a temporary bridge.

Some organisations go further: On Purpose runs year-long associate programs in purpose-driven companies, providing training, coaching and a modest salary. ivee helps women return to work after a career break, with flexible roles, upskilling and community support. These kind of programs give you community and a softer landing as you transition.

Proof that you don’t always have to bootstrap your way through change completely on your own.

Build bridges, don’t burn boats

The truth is, there isn’t a single best way to fund a career change. The most resilient path usually combines several of these strategies.

What matters is that you don’t leave your job as an emotional reaction. As one person I interviewed wisely put it:

“Don’t leave your job. It’s tempting, but it’s also destabilising. Career change isn’t an easy threshold to cross. You want to be sober when you make that decision. Make sure it’s coming from the right place. A clean place.”

Of course, sometimes staying isn’t possible. I know that feeling too. There was a point when I couldn’t force myself to stay any longer. I needed space and time away to figure out what I wanted.

I was fortunate: I asked for support from family when I moved back home. I downsized my life. I took a four-day-a-week job, then I freelanced for a few years. I had enough savings to carry me for years. Piece by piece, I stitched together different strategies. And almost by accident, I ended up with what I now call a portfolio career.

Why portfolio careers matter

The new model of security is about diversification. Instead of putting all your security into one employer, one paycheck, one identity, a portfolio career blends multiple streams of income. It creates resilience. If one piece falls away, you still have others.

Think of a portfolio career as having one foot in what you already know, and one foot in the future you want to create. It’s the bridge that offers the stability of a regular salary while you experiment, learn and take measured risks.

In practice, it might look like:

• Consulting two days a week in your old field while you develop your coaching practice

• Taking a fractional role with a startup while you work on your book

• Freelancing with former employers while building a new skill set

But here’s the catch: a portfolio career relies on people knowing who you are and what you offer. Opportunities don’t appear out of thin air, they come through reputation, relationships, and visibility.

That’s why your personal brand matters: the act of being recognisable for your ideas, skills and perspective. Visibility isn’t vanity. It’s leverage. It’s what allows opportunities, collaborations, and clients to find you. A personal brand is your body of work (essays, talks, projects, collaborations) that signal: this is what I do, this is what I stand for and this is the value I create.

My hope here is simply to open the door: to show you that something more fulfilling is available beyond the confines of a full-time 9–5 job.

When you step into this liminal space between employment and entrepreneurship, you begin picking up invaluable skills that no one can take away from you: how to create an offer, how to market yourself, how to sell, how to communicate.

I can’t tell you how many times I’ve met professionals who’ve held director or VP-level roles and, when they finally decide to start their own business, realise they have no idea where to begin. Even seasoned marketing executives often stumble when it comes to marketing themselves.

That’s the hidden gift of a portfolio career: it teaches you how to stand on your own two feet, develop skills that travel with you, and build a body of work that belongs to you, not to an employer.

Maybe this is what a true shot of courage looks like. Not blowing up your life overnight, but daring to take one step into the grey space, where security and possibility can coexist. You can value financial security and still take bold steps.

Portfolio careers may be the answer to the transition problem. For many of us, this is the grey space we’ve been looking for. Not clinging to the old model, not leaping recklessly into the unknown, but building a career that’s flexible and truly our own.

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Navigating what’s next

Over the last year, I’ve built an ecosystem of support for professionals in transition. Wherever you are in your journey, here’s how we can work together:

→ I want to make a career change

I offer 3 and 6 month 1:1 coaching programs that follow a clear arc: discovery, career experimentation, and professional narrative building. If you’re ready to move into a role (or a business) you love, without starting from scratch, you can book a consultation here.

→ I want to start my own business

Through Luma, we help women turn ambition into action. Our curated, cohort-based program and in-person retreat support you to take the leap into entrepreneurship with confidence. Join the waitlist here.

→ I’m a female founder

I’m also a community leader for SheSapiens — a network of female founders across Europe and online. We host accountability groups, in-person events and expert masterclasses. I lead the Ericeira community, where I co-host our monthly female founder breakfast. Explore the membership here.

From the outside, everything looked fine. Big 4. Decent salary. A clear path. But I was grinding my teeth in my sleep, over-caffeinated and uninspired.

The most invigorating part of my day was weaving my motorcycle through traffic on the way to work. That short moment of freedom before I locked myself back into autopilot. I didn’t know it then, but that unraveling was the beginning of a slow return to myself.

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We like to imagine career change as a neat before-and-after. You quit the job. Update the CV. Take the leap. But real change is rarely a single moment. It’s a series of wake-up calls and brave decisions.

When I finally walked away, there was no lightning bolt of clarity. No big breakthrough. Just a slow, uncertain peeling back of all the layers I’d built up to survive. And honestly? It was hard, and it was confusing. Four years of experimentation, missteps, detours and insights.

If I could go back, I’d give myself one thing: someone to walk beside me. To help me listen and stay with the discomfort and to remind me that it was okay not to know. When you’re inside the fog, you can’t see the way out.

When you’re burned out, overwhelmed, or quietly numb, the mind looks for external solutions:

• A better job

• A new manager

• A company with values that actually match yours

But deep change often starts with discomfort and the moment you realise that checking the boxes doesn’t quiet the discontent. It feels like the version of yourself you’ve been performing feels too small to keep living in.

So you stay. You convince yourself the problem is you.

But what if that tension you feel is a wake-up call?

When I finally left, I started small. Practising yoga at home. Going on a retreat. Speaking out loud for the first time: “I’m unhappy and I don’t know what’s next.”

That honesty cracked something open.

Slowly, I found people who reflected parts of myself I’d forgotten. It didn’t make sense all at once, but it felt like the beginning of something real. That’s why spaces that offer support matter so much—containers where you can unravel safely, be witnessed without judgment and slowly remember who you are beneath all the performing.

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Your brain will talk you out of it

Your cognitive biases are doing their job: trying to keep you safe. During periods of change, they can also keep you stuck.

Knowing these biases exist doesn’t make them go away, but it does help you move through them with more awareness and self-compassion. Here are a few that show up often during a career change:

Loss aversion

We tend to fear loss more than we value gain.

“If I leave, I’ll lose my salary, my stability, my title, my professional identity…”

Even if your current role is draining you, your brain overestimates what you’re giving up and underestimates what’s possible on the other side. You stay because the idea of losing status, benefits, or credibility feels unbearable.

Instead, ask yourself:

“What am I already losing by staying where I am? Time? Joy? Energy? Growth?”

Sunk cost fallacy

We believe that because we’ve invested time, energy, or money into something, we must continue, otherwise it’s all wasted.

“But I studied for this.”
“I’ve spent 10 years in this field.”
“I can’t throw it all away now.”

So many people stay on paths that no longer fit, not because they want to, but because walking away feels like admitting failure. Staying in a life you’ve outgrown doesn’t make that past investment more valuable. It just deepens the cost.

Reframe it: That time taught you something. The skills, relationships, and experiences still belong to you, even if your next step looks different.

Status quo bias

We prefer things to stay the same, even if the current situation isn’t ideal.

“This job isn’t great, but it’s fine.”
“Maybe things will improve if I just wait a bit longer…”

Change (even change we want) can feel threatening. So we rationalise staying where we are as the safer bet. You might even start to minimise how bad things are just to justify not moving. The devil you know feels safer than the possibility of freedom.

Ask yourself:

“If nothing changes, what will my life look like a year from now? Five years from now?"

Confirmation bias

We seek out information that confirms what we already believe and ignore anything that challenges it.

How it shows up:

• You pay more attention to stories of people who failed after leaving their jobs.

• You dismiss examples of success as lucky or not applicable to you.

• You tune in to fear-based advice and tune out the part of you that’s dreaming of something more.

This bias strengthens the stories your fear wants to tell: that change is too risky, that you’re not ready, that you’ll fail.

Reframe it: Actively seek out stories of people who’ve made brave shifts and observe how they handled uncertainty, not just success.

Endowment effect

We place more value on things simply because we already own them.

How it shows up:

“At least I know what I’m doing here.”
“My job might not be great, but I know the system.”
“I don’t want to start from scratch.”

Even if your job isn’t aligned anymore, it feels more valuable because it’s yours and because it’s familiar. You may find yourself clinging to routines, relationships, or roles that don’t actually feel good, simply because they’re part of your current reality.

Reframe it: What if your future self had something better but you had to let go of the familiar to receive it?

These biases are normal and they’re very human. The key is to notice when they’re running the show, and to choose differently from a place of self-trust.

The most dangerous place to be isn’t in a toxic job you desperately need to escape. It’s in a comfortable one you can tolerate. You’re not miserable, but you’re not satisfied either. And because you could put up with it for another year or two, you do.

Until a year becomes five. And five becomes your entire career. I’ve worked with professionals in their 50s, who tell me, “I can’t believe it’s taken me this long to leave.”

If your job is “fine”, it’s easy to convince yourself that now isn’t the right time. That you should wait until you have more clarity, more money and more confidence. The danger is: the longer you wait, the more normal the numbness feels.

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You don’t need a 10-year plan

You just need a starter idea. That might be:

• Taking a class that sparks your curiosity

• Journaling to reconnect with your own voice

• Reaching out to someone who’s been where you are

So instead of asking, “What job should I do next?” Try asking:

• What’s making me feel most alive lately?

• What version of me am I ready to stop performing?

• What support would help me feel less alone in this?

Today, my life looks radically different. I don’t work to prove anything anymore. I work because I believe in what I’m building and I’m betting on myself. None of this happened in a single leap. It happened step by step. One small act of self-trust at a time.

Navigating what’s next

If you’re in the middle of an identity shift, or standing at the edge of one and you’d like support navigating what comes next, here’s how we can work together:

Coaching Partnership

I work with creative and tech professionals who are outwardly successful, but deep down feel quietly unfulfilled. I help them move into new roles (or a business) they love, without having to start all over again.

→ Book a Consultation

I know because I tried. New company. New country. New title. Each change brought a fresh start. Then the same old anxiety crept back in.

Prove your worth.
Don’t slow down.
Earn your rest.

I told myself the job was the problem. But what I was really running from was me.

Your next job won’t save you if you’re still performing a version of yourself that’s rooted in fear. Those stories will always follow you around, no matter your salary or status.

Career change doesn’t start with a CV re-write. It starts with your nervous system and your willingness to tell a new story.

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Dilt’s logical levels

Many people come to coaching feeling stuck. They’ve switched jobs, updated their CV, maybe even moved countries. But the dissatisfaction lingers. They say, “I thought this next move would feel better.”

Often, they’ve only shifted the surface-level layers of their life. Not the deeper ones.

To understand what I mean, let me introduce you to a model called Dilt’s Logical Levels. It helps map the layers where change can occur:

Environment – Where you are
e.g. You join a remote-first company or move to a new city

Behaviours – What you do
e.g. You update LinkedIn, apply for jobs, attend events

Capabilities – What you’re good at
e.g. You take a course, learn about AI, improve your skills

Beliefs & Values – What matters to you
e.g. You realise you value freedom more than status

Identity – Who you believe you are
e.g. You stop seeing yourself as just a strategist and start seeing yourself as a creative guide

Purpose or Vision – What you're here for
e.g. You feel called to support other women in finding their voice

The lower levels (environment, behaviour, capability) are easier to change. They’re also the most visible, which is why we go there first.

Sometimes, a new job or new skill does help. But if you haven’t addressed what’s happening at the deeper layers (your beliefs, identity, purpose, nervous system), you’ll end up re-enacting the same story in a new setting. A story like:

If you're not producing, you're falling behind.
Money equals safety, so don’t rock the boat.
Your value lies in how much you can handle.

These aren’t just thoughts. They’re survival strategies, rooted in your body and performed for years. No wonder the same patterns show up again, no matter the title, company or salary. You’re not broken. You’re just stuck in a script you haven’t questioned yet.

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Life scripts

Most of us are living out a story we didn’t consciously choose. In Transactional Analysis, these are called life scripts. They’re unconscious patterns and narratives we begin writing in early childhood, shaped by what we see, what gets praised and what helps us feel safe.

• By the age of 4, the essential plot is already forming

• By 7, the key themes and roles are in place

• By adolescence, the story is polished and revised with real-world characters

Then we live it. Not knowingly, but through the choices we make, the risks we avoid, the people we please and the roles we play.

Your life script is like an internal compass. Instead of pointing toward purpose, it points to what once felt safe. Maybe it sounds like:

I must succeed to be loved
It’s dangerous to stand out
I’m only valuable when I’m useful

These stories aren’t inherently bad. They helped you survive. But over time, they become cages. We keep following the script, hoping it will lead somewhere different. But the destination is already baked into the story.

Eric Berne, who created the concept of life scripts, believed every script is unconsciously written with a final scene—a payoff. We build our lives around reaching it. Even if we’re miserable. Even if it no longer fits. Letting go would mean rewriting the story. And that feels risky.

Berne described three categories of life scripts:

1. Winning – The story ends in achievement and fulfilment.

2. Losing – The goal is reached, but it comes at deep personal cost.

3. Banal – No high or low. Just safe, predictable and small.

Berne said you can often tell the difference by asking: “What would you do if this plan didn’t work out?”

• A winner has multiple options.

• A loser bets everything on one.

• A banal script avoids the question entirely.

How do you change the script?

You can’t think your way out of a story you’re performing in your body. These are learned patterns, often created to secure love, safety or attention when we were young. Maybe no one saw you unless you were achieving. Maybe love felt conditional on being good, helpful or successful. The way out is asking yourself:

What did I need back then that I didn’t get?
How can I meet that need now, with all the resources available to me as an adult?

You’re not a child anymore. You get to offer yourself what no one could give you: unconditional love, support without performance and space to just be. That’s what breaks the script and changes your trajectory.

Most of us were cast in a role before we even learned to speak. Maybe you were the golden child. The achiever. The peacemaker. You learned to earn love by being useful, staying small, getting it right. But you're not a child anymore. You get to ask: Is this still the story I want to live?

The path to meaningful work isn’t just about upskilling, networking or rewriting your CV (though, they are important). It’s about becoming aware of the deeper script that’s been driving your choices and gradually, writing a new one.

Curious about your own life script?

Here’s a prompt adapted from TA Today (Ian Stewart & Vann Joines)

Imagine you’re in a theatre. The play about to begin is the story of your life.

What kind of play is it? A comedy? A tragedy?
Is the theatre full or empty?
What’s the mood of the audience? Are they engaged, asleep or walking out?
What’s the title of your life’s play?

Now watch the scenes unfold:

• Scene 1: Your earliest memory as a young child

• Scene 2: You between ages 3–6

• Scene 3: A snapshot of your teenage years

• Scene 4: A scene from your current life

• Scene 5: A glimpse 10 years from now

• Final scene: The closing scene of your life story

Notice what themes, patterns and roles emerge. Is this the story you still want to live?

You don’t need to change everything today. But noticing the story is the first step in rewriting it.

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The work beneath the work

This is the change beneath the career change. Career change doesn’t start with your CV. It starts in your nervous system and in the stories you’re ready to stop performing.

When you begin to move out of your script, the payoff isn’t just a new job. It’s a new relationship with yourself. One where you stop performing and start belonging.

Not someday, when you’ve earned it.

But now.

Navigating What’s Next

If you’re in the middle of an identity shift, or standing at the edge of one and you’d like support navigating what comes next, here’s how we can work together:

Coaching Partnership

I work with creative and tech professionals who are outwardly successful, but deep down feel quietly unfulfilled. I help them move into new roles (or a business) they love, without having to start all over again.

→ Book a Consultation

At 17 years old, the weight of my future landed squarely on my shoulders. Engineering made a lot of sense on paper—I excelled at maths, physics and design. Fashion seemed like the frivolous yet fun choice.

For a long time, I believed there was a right career path. A thing I was meant to find, name and stick to. That belief made every career decision feel high-stakes. Each choice had the power to make or break my future.

Should I move overseas?
Take this job?
Quit that one?
Start from scratch?

All I knew was what I was good at and what others reflected back to me. I hadn’t yet learned how to listen inward. My older sister urged me to take the unexpected path. She reminded me that I was a creative person. So I chose fashion.

It wasn’t the wrong choice. But it was the first in a long series of experiments that would shape the next decade of my career.

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I now know that a career isn’t a single choice. It’s a long string of tiny experiments. Here are some of mine:

I studied fashion, until I realised I didn’t want to work out of my parents’ garage at 30. So I pivoted quickly into visual communication. I spent two fun years at Google, until the novelty of free buffet meals and sleep pods wore off.

I then moved into management consulting where I learned fast and lost myself even faster. A lesson in knowing what’s not right.

I quit everything—my job, my relationship, and even my country. I moved to Portugal and joined an AI startup. Moving countries doesn’t make your baggage disappear, but it does give you space to see yourself differently. This was the moment I finally started listening inward. Yoga and meditation became a way to reconnect with myself.

Later, I took a sabbatical. Freelanced. Taught English to children and yoga to burnt-out employees. Eventually, I thought I was ready to return to my old life. It was a misaligned decision and a full-body no.

Which brings me to the current chapter. Following unexpected threads. Initiating community. Building my own business.

On paper, it might seem chaotic. Looking back, it all makes sense. Each choice was its own experiment. A question asked. A thread followed. Small acts of self-trust.

If I’ve learnt anything over the past decade, it’s that you don’t find your thing by thinking about it. You find it by doing.

I stopped searching for the perfect plan and started trusting that these strange, subtle nudges were taking me somewhere.

Looking back, I can now name what I was doing. But at the time, I didn’t have the vocabulary or the support to make sense of the path I was on. No manager or mentor ever asked me what I was curious about. No one helped me notice what felt alive in me. No one framed my pivots as possibilities. Most people think coaching is about giving advice. Real coaching is about listening for what’s already stirring inside someone, before they’ve found the words for it.

It wasn’t until years later that I stumbled across frameworks that helped me understand what I’d intuitively been doing all along. If you’re in the middle of a shift, or standing at the edge of one, these ideas might help you name what’s unfolding for you.

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Tiny experiments

Ten-year plans don’t hold up in a world that changes this fast. Anne-Laure Le Cunff invites us to treat life as a playground of tiny experiments, modelled on the scientific method.

When you feel stuck or unsure, don’t try to architect the perfect plan. Start with a hypothesis. Run a small, low-risk, curiosity-led experiment. Then, see what happens.

The goal isn’t success, it’s information. Each tiny experiment becomes a data point, with two types of metrics:

• Internal: How did it feel? Energising or draining?

• External: What happened? What outcomes or signals did you get?

Some experiments will succeed. Some will fail. All of them will teach you something. Tiny experiments help you replace fear with curiosity and control with learning.

Portfolio careers

You are not just one thing and your career doesn’t need to be either.

Someone with a portfolio career blends multiple roles and earns income from multiple, diverse sources, rather than a single full-time job.

The term was popularised by author Charles Handy in his book, The Age of Unreason, as a way to navigate an unpredictable economy and evolving sense of purpose.

Today, it’s more relevant than ever:

• Job security is shaky

• Flexibility matters

• People crave meaning, not just money

• Growing desire for flexibility and autonomy

• Remote, gig work continues to rise

In a portfolio career, you can be a consultant and a coach, a designer and a retreat facilitator, a startup operator and an artist.

A portfolio career is less about climbing and more about weaving. It values range, not rank and embraces seasons of change, side projects, sabbaticals and reinvention.

Squiggly careers

Careers are no longer ladders. They’re squiggly, self-authored paths which prioritise growth, learning and fulfilment over the traditional corporate climb.

The most meaningful careers, and the most interesting people, rarely follow a straight line. They loop, zigzag or even backtrack depending on their interests, life stage or goals. A Squiggly Career (Helen Tupper and Sarah Ellis) is built on values, strengths, and curiosity, not job titles or hierarchy.

Born out of their own frustrations with traditional career advice and the rigid ladder mindset, Tupper and Ellis name five key skills that help you thrive in a squiggly career:

1. Know your values – Understand what matters most to you at work.

2. Use your strengths – Identify and use your natural talents.

3. Build confidence – Build self-belief to navigate uncertainty.

4. Nurture your network – Create meaningful connections to open up possibilities.

5. Stay open to possibilities – Stay curious and open to different career options.

In a squiggly career, progress looks more like exploration rather than an ascent.

Tension of opposites

Carl Jung believed that personal growth doesn’t come from choosing one side of a conflict. It comes from holding the tension between two opposing truths.

I want freedom and security.
I crave impact and rest.
I feel lost and I trust myself.

Jung encouraged people to hold the tension, allowing a new, more integrated solution to emerge. He called this process individuation.

In a culture obsessed with quick decisions, clear paths and binary choices (“Should I quit or stay?”), we often try to resolve inner conflict too quickly. Instead of rushing to resolve the tension, you can stay with the questions and explore both sides. Holding tension without forcing a decision allows new possibilities to arise.

A more satisfying career emerges when you honour both parts of yourself. Career pivots you hadn’t considered. Hybrid roles. Creative solutions. Conflicts often show you your deepest value. For example, the desire for independence might highlight a suppressed entrepreneurial self.

If we ignore or suppress one side of the tension, it often resurfaces later through burnout, dissatisfaction, or a sense of being stuck.

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Together, these frameworks helped me reframe my career as a living system, shaped by questions, patterns, nudges and values.

I’ve worked with coaching clients who get stuck because they’re trying to think their way into the perfect next step. They want clarity before they move. Certainty before they try. But that’s not how clarity works.

You don’t think your way into a new career. You experiment your way into it.

Sometimes the experiment is big—quitting a job, moving countries, taking a sabbatical. I’ve done all three. But most of the time, it’s small. You start writing. Take a class. Offer a service to one person. You follow a flicker of curiosity and see where it leads.

And slowly, the path begins to shape itself beneath your feet.

Navigating what’s next

If you’re in the middle of an identity shift, or standing at the edge of one and you’d like support navigating what comes next, here’s how we can work together:

Coaching Partnership

A coaching container for professionals who are ready to do meaningful work on their own terms.

→ Book a Consultation

I blinked in surprise.

“Jamie*, what the hell?”

The last time I’d seen him was about a year and half ago. Back then, he was deeply committed to a spiritual path and followed a strict vegan diet. He didn’t drink, didn’t smoke. It was his way of life. I’d only ever known him as that version of himself. He laughed and said, “I’m allowed to change. There’s no obligation for me to be the same person.”

His words landed deeper than I expected.

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We expect consistency from others and from ourselves, because we like neat stories and tidy identities.

“You’re the ambitious one.”
“You’re the chill one.”
“You’re the reliable one.”

It can feel disorienting when someone shifts out of a version of themselves we’ve come to rely on. But people aren’t fixed. We learn. We outgrow things. We wake up one day and realise what once fit, doesn’t anymore.

Even when we recognise that in others, we struggle to allow it in ourselves. We hold ourselves hostage to who we used to be. Not because the identity still fits, but because it’s earned us approval and belonging. We stay in the job, cling to the title and keep playing the role long after it stops feeling true. Letting go would mean stepping into the unknown.

And that’s terrifying.

If you’re not “the successful one,” or “the go-to problem solver,” then who are you?

This tension between who we’ve been and who we’re becoming is at the heart of developmental psychology. For a long time, psychologists believed that our inner development ended around age 21. We now know that we continue to grow and evolve throughout our entire lives.

In How to Know a Person, David Brooks draws on the work of Erik Erikson and Robert Kegan, to map out a series of life tasks. One of those tasks is career consolidation. This season of life is marked by the drive to prove ourselves through competence, achievement and credibility. For many of us, that pursuit defines our 20s and 30s. We choose degrees, job titles, industries and social circles to make ourselves legible to the world. We become “the marketer,” “the engineer,” “the expert.”

But there’s a cost.

The pressure to perform and succeed can create distance from ourselves and others. For many, career success fails to satisfy. The identity that once gave you something to strive for starts to feel like something to escape. Even if you’re no longer that person anymore, letting go can feel unsettling.

This is why career change often feels so confusing and hard. It’s not just about updating your LinkedIn profile. It’s about outgrowing a version of yourself that once kept you safe and respected. When you stay too long in the version of yourself that’s no longer true, you start to feel it in your body: burnout, restlessness, numbness and even dread. It’s a sign that something new is trying to emerge.

When you loosen your grip on who you’re supposed to be, a different path begins to reveal itself. You begin to follow curiosity. You take steps that don’t always make sense, but feel right. You start building a life that fits who you’re becoming, not who you’ve been. You begin questioning the limits of the identity you’ve constructed.

What takes its place isn’t another title or label, but a deeper desire to serve, to contribute and to live in alignment. It doesn’t happen all at once. But change begins the moment you stop asking for permission, and start giving it to yourself.

You don’t owe the world consistency. You owe yourself truth.

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How to listen for what’s emerging

Here’s a simple framework – Past, Present, Pull – to help you begin that process.

Past: Who You’ve Been

• What labels or roles have you carried for a long time?

• Which of these are no longer true, or no longer serving you?

Present: Who You are Being

• What version of yourself are you still performing, even though it doesn’t feel like you anymore?

• What identity would you let go of, if you didn’t feel you had to explain it to anyone?

Pull: What’s Emerging?

• What are you curious about lately?

• What feels more “you” than what you’re currently doing?

There’s no need to reinvent your whole life overnight. Just see what happens when you give yourself permission to change, even a little.

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Navigating What’s Next

If you’re in the middle of an identity shift, or standing at the edge of one and you’d like support navigating what comes next, here’s how we can work together:

Coaching Partnership

A coaching container for professionals who are ready to do meaningful work on their own terms.

→ Book a Consultation

*Name changed for anonymity