I stood at a fork in the road: aeronautical engineering or fashion design.

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.

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.

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.

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.

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.