Fragments and identity

My winding path to a portfolio career

Last time I wrote about Slow Creation as a strategic choice, but maybe it’s a survival strategy.

Sometimes I knowingly create a version of reality for myself and others where things are working out, so I have the resilience to stay the course. In darker times I reflect on the decisions I’ve made - those sliding doors moments - where life could have been different.

Fragments of a career

Burning out working in community development trying to do everything in a remote Australian town after graduating.

Leaving what should have been a dream job in politics to travel solo through Europe because I didn’t have enough life experience.

Turning down a PhD place because I’d convinced myself I wouldn’t focus on a niche topic long enough to do it justice.

Trading a career in education for a corporate role when I needed financial security to support my family.

Only to walk away from the London life to start my first business.

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Years later, with what now looks like the portfolio career I wanted, I carry a nagging sense that I'm nowhere near where I should be.

Those decisions felt right at the time. Each was meant to be a step towards something more authentic, more me. But taken together, they look like someone who can't stick to anything.

Recently, I’ve heard people describe this as "identity debt" – the accumulating weight of all the versions of ourselves we think we should have become. Every time we pivot, we don't just move forward; we also carry the story of what we left behind.

Meanwhile, there's a more positive force at work – what psychologists call the "actualising tendency". That’s the persistent pull towards becoming who we actually are, rather than who we think we should be.

For me, the friction between the two – the debt of abandoned identities and the drive to become our best self – creates a particular kind of creative paralysis. I want to build something meaningful, but I’m haunted by every time I fell short.

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The performance

I could probably get more attention on social media, if I wanted it.

But that’s the trap for creators like me, because when you're trying to build authority in public whilst carrying private doubts about your credibility, you start performing confidence you don't feel and resort to tactics. You learn to create an 'other' in your writing – the corporate drones, the academic gatekeepers, the hustle bros – to define yourself against.

I’m good at it. I understand how to provoke responses, how to speak to people's frustrations with traditional career paths. I can write hooks that would make recovering corporate types feel seen and understood.

But if I perform the role of "someone who's figured it out," I feel like a fraud. Because most days I don’t. I’m better at describing problems than solving them.

Each time you successfully pretend to have authority you don't feel, the gap between your public persona and private doubts widens. You get better at sounding like an expert, and more sure than ever no-one is falling for it.

Those career fragments I collected? Each one still whispers its own version of inadequacy. "If you'd stuck with research, you'd have real credibility." "If you'd stayed in politics, you'd understand how things actually work." "If you hadn't left teaching, at least you'd be helping people."

Is the portfolio career performance just my latest? Writing about creator economics, performing expertise about the creator path, whilst still figuring it out myself…

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The reckoning

Before this draft I’d started writing about slow creators and "imposter syndrome" before I caught myself. That moment was instructive, because I realised I was writing it to convince myself as much as my audience.

But what if the career fragments above aren't evidence of my inability to commit? What if they served a purpose? What if the actualising tendency that kept pulling me away from perfectly reasonable paths was worth following, even when it looked chaotic from the outside?

My mind tells me I should have this figured it out by now. That other people my age have clear trajectories and impressive credentials. If I'd picked one thing and stuck with it, I'd be further along.

But further along towards what, exactly?

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I'm starting to suspect that the portfolio career many of us are building – this messy combination of writing, consulting, creating, thinking – is what actualising tendency looks like in a world where the traditional careers no longer make sense.

I'm still figuring this out, obviously. Still carrying my baggage, still performing confidence I don't always feel. But I'm interested in what might happen if I stop trying to resolve the tension and start working with it instead.

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What do you think? I'd love to hear your thoughts in the comments - especially if you've experimented something similar or you’re building a portfolio career yourself. I think the most valuable insights come when thoughtful practice is applied in the real world. That's why I'm documenting my own journey of navigating the creator economic, growing a consultancy, and sharing both the successes and the learning moments as they happen.

I help service business founders build functional systems and distinctive positioning through my consultancy, Designing Value. My approach prioritises practical strategy over generic solutions.

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