Portfolio careers are a stepping stone, not a destination. The label is keeping you small.
Most portfolio careers aren't businesses. They're a more sophisticated form of employment.
Up until recently, I had what others might call a portfolio career. I freelanced as a product designer, supported people through career transitions, and built an audience of female founders.
In February this year, I let go of my last design client.
The design work had been a way of maintaining financial 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 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.
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:
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.
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.
The multi-hyphenate mixes a range of diverse projects at the same time. Their primary identity position is: I contain multitudes.
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?
