How I accidentally built a portfolio career

A patchwork stitched around my values, created on my own terms.

Jul 10, 2025

I knew something needed to change

By the end of 2023, I was done. Work had become something I poured so much energy into, but the return felt hollow. Like running a marathon on a treadmill: exhausting but you don’t actually get anywhere. I was tired, disillusioned, on the edge of burnout and questioning whether the whole default model of work even made sense anymore.

I couldn’t stop asking questions I didn’t know how to answer: How are we supposed to fit everything into 24 hours: a job, relationships, health, creativity, contribution - all while enjoying it? Honestly, it felt like an unsolvable puzzle.

All I knew was that something had to change. I couldn’t keep pouring all my energy into one direction, the economy, while feeling so detached from what mattered.

A year of experimentation

So in 2024, I jumped headfirst into that change. I quit my job without a plan and that was not because I had some genius career move lined up, but because I couldn’t keep building a life around things that I didn’t want. I needed space to pause, recalibrate, and figure out what feels ‘more me’.

Knowing what you want out of life is the foundation for setting up a strategy what to do next. But if you don’t know, and I didn’t, the only way forward is to explore. That means reflection and experimentation, not just thinking but trying. So I declared 2024 my year of experimentation. And after a much-needed break, I gave myself one clear goal:

🎯 Explore alternative ways of working and financing life.

What I thought work had to look like

What surprised me once I stopped is how limited my thinking about work had been. In my head, there were basically two options on the table: full-time employment or starting my own company. That’s what everyone else seemed to be doing. Pick a lane. Stick to it. Grind.

Neither sounded particularly appealing. I’ve never been great at doing just one thing. I’m a generalist that is multi-passionate, multi-skilled and adaptable. That’s why I’ve generally enjoyed early-stage startups: jumping in wherever needed, wearing multiple hats, making things happen.

So what if this was my strength? What if I stopped trying to find a single perfect job that contained everything I wanted and just broke it all up into smaller pieces that make up my version of work? Could I dedicate some time of my week to making an impact, some to explore my passion, and some to making money? Or could I in the long run even detach making money from how I want to spend my week?

Building without realizing

So I started experimenting with those thoughts. But most importantly, for the first time in my life I let go of rigid planning, started living into each day, and followed my interests to see where they’d lead. Naturally curious, it didn’t take long until I started reflecting, reading, learning, experimenting and talking to people.

Since quitting, I’ve done deep inner work to figure out what I want in life, what I care about, and what I’m good at. I discovered that impact is more important to me than money.

In practice? I learned a new language. I studied climate change. I went deep into Web3 and crypto. Explored how to use AI to build a team of one. I took on a fractional marketing role. I launched some smaller side projects. I started writing on Substack. I began saying yes to some things, a clear no to others.

Somewhere along the way I also got my financials in order, started investing in crypto (because why not hedge against the collapse of everything?), and picked up a 20-hour-a-week creative marketing role to cover the bills.

Without really realising it, I was building a collection of things I love doing, things I’m good at, and things that pay the bills (sometimes those overlap, sometimes not).

Finding language for it

Somewhere along the way, I discovered Anna Mackenzie and her writing on portfolio careers. And suddenly, there was a name for what I was intuitively building.

Anna Mack's Stack

WTF is a portfolio career?

When I made the decision to move on from my former business, my goal was to get a job at a VC firm or as Chief of Staff at a Seed-Series A startup. I wanted stability and security, and if I’m being brutally honest (we’re friends now, right?), I wanted something notable to put on LinkedIn to help allay my fear of becoming irrelevant now that I was no lon…

a year ago · 188 likes · 51 comments · Anna Mackenzie

A portfolio career is defined as having several part-time jobs or multiple income streams rather than one full-time gig. It involves pursuing multiple passions, interests and types of work.

A part time job (eg. working 3 days a week for a company)
A part time business (eg. working 3 days a week for your own company)
A done-for-you service (eg. contracting, consulting)
A done-with-you offer (eg. coaching, mentoring, advising)
A do-it-yourself offer (eg. a digital product, online course)
Creative work (eg. writing, podcasting, Tiktok-ing, playing music)
Giving back (eg. volunteering, pro-bono work)
A mix of any or all of the above

There it was. I got genuinely excited. Even though this was already what I was doing, it was comforting to know what it’s called. (Humans and their love for labels, right?)

I reached out to Anna and ended up doing mentoring with her. Finally, better knowing what I’d like to do, it was time to map out a rough strategy: we designed my short- and long-term plan for this portfolio path, worked on my positioning to close fractional work, and talked a lot about Substack.

But most importantly, she was further along this road than I was and with that, a thought partner to bounce ideas around and help navigate this messy middle. She’d been through the same struggles, had answers to my million questions and it was simply inspiring to see how she’s shaped and reshaped her own portfolio career over the years. Thanks, Anna! 🫶🏻

Portfolio careers are meant to evolve

And while I’m not yet where I want my portfolio career to eventually be, I have to acknowledge: I’ve built one.

A portfolio career is never static and always evolving as priorities shift and interests change. But what matters is that I’m the one shaping it. I’ve created work on my own terms, around my values, choosing who I work with and what I work on. A life where I have the freedom to scale work load up or down as my priorities change.

And I’m proud of that.

Along the way, I’ve learned something important: Sometimes it’s impossible to force a strategy at the beginning. Sometimes you just need to explore, experiment, start building in the middle and connect the dots later.

Some people will tell you that you need it all figured out before you decide to create a new life for yourself. I don’t think that’s true. You’ll figure it out while doing. The important thing is to start.

If you’d like to learn more about portfolio careers 🫶🏻

Subscribe to the newsletter of Anna Mackenzie! Anna also created a six part deep dive into portfolio careers which I can highly recommend:

Saying goodbye to “traditional” work, and why I’m building a portfolio career instead. Read here.
WTF is a portfolio career? This post.
How I’m building my portfolio of clients, projects and income streams. Read here.
Skills you need to run a successful one (wo)man show. Read here.
One thing they don’t tell you about working for yourself. Read here.
To portfolio or not to portfolio, that is the career question. Read here.