portfolio career? freelance? something in between?
what happens when you leave the job title behind
When I decided to step away from full-time work - at a brand I loved, from a position (and salary) I’d worked hard for - I wasn’t thinking: yes, it’s time to build a portfolio career. I was thinking: I’m ready for something new. I’d love to work across more varied brands. I want more flexibility. I want to live in a new city. I want more time with my son. I want to chase some of the ideas I’d been saving for “one day.”
I also wanted to do it (whatever it is) properly. So I spent months preparing after returning from mat leave - while still working full-time. In the evenings I was drafting LinkedIn posts - slowly getting over the cringe, testing content (TikTok, it turns out, wasn’t for me), creating a website and having these (I think cute) graphics commissioned, preparing for podcast interviews and panels, all while quietly building my personal brand, speaking to people already doing it, and mapping out what my version could look like. But really, it felt like dreaming. In reality for me there was no properly because even with the “prep” I couldn’t fully understand what my life might look like or create a nice neat roadmap - I was just going off a feeling, that feeling of being “ready”.
It wasn’t until I started reading
’s work (here + here + here + a million other articles in her newsletter) that I realised: oh, this thing I’m trying to build? It might actually have a name. And that name might be portfolio career. Others I’ve since discovered writing about this include & The Portfolio Careerist whose newsletters have also inspired me.Still, I’m not sure I fully relate to the term. Is it a portfolio career if most of my income comes from consulting? Or is it freelance with dreams attached? Or is it just… me, building a career with lots of edges - part brand strategist, part writer, part board member, part mum?
Whatever it is, it’s working. So far.
Image: the graphic I had designed that I haven’t used!
I’ve landed a mix of retainer clients and some project-based work with brands I love. I have space to experiment and try new things - Substack has been a particular joy and something I’ve wanted to do for ages (I first registered 3 years ago…!). I’ve had more time with my toddler, during a chapter of his life I know I won’t get back. And while I haven’t yet “diversified” in the way some might define it - there’s no Patreon-supported podcast, no workshops (yet), no print magazine (my ultimate dream!) - I have big dreams sitting quietly in my notebook, waiting for the right moment and it feels like there is the potential to build them which feels really exciting.
When I first left full-time work, I was afraid that stepping away from the security of a job title would make me irrelevant. How much of ourselves is defined by the brands we work for and the titles we have? But in a twist I didn’t expect, it’s actually connected me to more people. More conversations, more like-minded thinkers, more opportunities, more messages - even after moving across the world. (If you don’t know me: I quit my Head of Brand role to move to Sydney from London. You can read more here.)
I also work less. Most of the time. Then I work furiously. Then I rest. And repeat. My rhythm is seasonal - varying week to week, inconsistent and imperfect - and honestly, it feels closer to life than anything I’ve done before.
But with flexibility comes uncertainty. I’m hugely (massively) privileged to have a partner and income to soften the jump. That doesn’t make the fear go away. But it does make the trying possible - and I feel like this isn’t captured in the conversation very often. I have worries - about the future, about whether we’ll (ever) get to buy our own home, if this has the potential to be long term, how to balance childcare - I could go on. But for now, it feels incredibly worth it.
I’m writing this from the terrace. It’s autumn here (in Sydney), but feels like summer. My son’s paddling pool is next to my feet, ready for when he wakes up from his nap - when I’ll close my laptop and won’t pick it up again until he’s gone to bed.
And maybe that’s the point. Maybe success isn’t just about diversifying your income streams, or mastering five revenue channels. Maybe it’s about designing a life that feels spacious enough to try. To make things. To parent. To work with people you like. Support brands you want to be on the journey with. To be inspired. To take risks. To rest. To move cities. To change your mind.
I’m not saying this is forever. But for right now - it’s working. And I feel proud that it is.
Things I’ve Learned (So Far)
Prepare before you leap but don’t overengineer – I spent time building my personal brand (posting on LinkedIn, appearing on podcasts, networking) and connecting with people who were already doing it. That made the transition feel intentional, not reactive.
You don’t need a neat label – freelance, portfolio, just consulting… I’m not sure what to call it. And honestly, I don’t think I need to.
Working across different verticals is a superpower – it keeps me creatively energised and has introduced me to more people, not fewer. It also makes your work better—you bring more context.
Leaving your job title doesn’t mean leaving your relevance – if anything, I’ve had more opportunities (and better conversations) since leaving full-time work - even while moving across the world.
Your rhythm might change – I work less, then furiously, then rest. It’s not 9–5, and it’s definitely not consistent. But it works for where I am right now.
Privilege and pressure can coexist – I’m lucky to have a partner and buffer while figuring this out. That doesn’t make the uncertainty disappear - it just makes it possible to try.
Just start – you don’t need to have it all figured out to begin. If you’re waiting until you’ve set up the perfect business structure, found an accountant, or tested ten different ideas - my advice? Just try. You’ll figure out the shape of it as you go. I still am.
Give yourself permission (if time/resource money) allows to try things without financial goals attached - start the marketing book club, host a download & drinks networking events, make a moodboard, film a TikTok. Moving forward with anything gives energy and momentum to the other areas.
Don’t try to do it all at once – doing too many things at once is tough! Moving countries, changing careers, settling a toddler in a new place, finding a home, submitting a visa, finding clients, writing a Substack - it's been a lot the last few months. It’s been overwhelming at times if I were to do it again I’d launch my portfolio (or freelance?!) career in silo - that way, you can give it the attention it deserves without burning out.
Thanks for reading. If you’re in the middle of your own shift - away from a role, a title, or a way of working - I’d love to hear what you’re learning too.
And, if you're a brand thinking about your strategy, community, partnerships, new audiences, or new markets - or just want to chat about what's possible - my inbox is always open.
This is so awesome to read, and very inspirational. Cheers!
Love love love this Holly 💛💛💛