Most days, I sit across from a highly capable person in the disorienting stages of a career transition. I know the terrain well because I spent four years lost in it myself. This is the story of how I uncoupled from a professional identity I’d spent nine years building.

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.

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.

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.

Maybe you're carrying a version of this too. The unspoken duty to make your life look worth what someone else gave up for it. I know that weight. When you put that aside for a moment, what does your version of a life worth living actually look like?

About Work Worth Doing

Work Worth Doing is a space for people who’ve outgrown a professional career they’ve spent years building, and aren’t sure about what comes next. You’ll find essays on identity, purpose and finding fulfilment outside of work too.

I work 1:1 with people transitioning from a professional career into meaningful work. To learn more about how coaching can support you, book a consultation or learn more below.