Why generalists are built for portfolio careers

Two peas in a pod, a match made in heaven.

I’ve been a generalist from the moment I exited the womb.

At kinder, I was just as adept at building sandcastles as I was at glueing pieces of uncooked pasta onto a DIY picture frame. I was an all-rounder at school too; an academic student who loved both physics and art history, a rower, a violinist, a theatre kid, and in my later years, a fake-ID flouting party animal.

I loathed the idea of doing one thing and somehow found roles that tolerated my allergic reaction to specialisation. My first job was a graduate role at Uniqlo where I helped launch the brand in Aus, and I was then hired at beauty giant Mecca in a catch-all position supporting the Head of Business Development with anything she needed.

I loved both jobs although I’d be lying if I didn’t say that I felt perpetually out of place. I was creative, but not creative enough to have input in meetings with the Creative Director. I understood the numbers, but not deeply enough to hold my own in conversations with the CFO. I spent weeks in meetings with Mecca’s architects, but my lack of technical understanding meant that lots of it went over my head.

Each morning I trundled to the office in my big girl pants and never shied away, but in every meeting, at every table, on every call, shame was lurking beside me. Telling me I should have more depth. Telling me I should know more.

It wasn’t until I quit my job in 2019 that I realised shame was an unwelcome poltergeist hurling vicious objects of self-doubt from every corner of the room, and that actually, my broad skillset was not a ghost but a superpower. It allowed me to see opportunities, solve problems and get shit done. It allowed me to build my very own portfolio and fall in love with life.

Let’s start with some definitions

A portfolio career involves having multiple income streams, clients, products and projects on the go. It’s both a model of working and approach to life - one that de-centres the system and radically reorients how we deploy our time, energy and skills.

A generalist is someone who:

• Has competence across several fields or activities

• Connects ideas across domains, industries and contexts

• Is agile and experimental

• Excels in ‘wicked environments’ (according to David Epstein, author of Range), which are settings without clear rules or predictable patterns

A match made in heaven

The generalist skillset is *chef’s kiss* when it comes to a portfolio career. To successfully build multiple income streams I believe that one must master four things:

1. The ability to experiment, experiment and experiment some more

Success in a portfolio career comes from trying, again and again, until something sticks. You must put work into the world - a service offering, a piece of content, an ask - knowing full well that it might fail. And then, you must take every flop, every mistake and every misstep, and have the courage to turn it into something new.

I’ve thrown a gazillion strands of spaghetti onto the wall over the last few years. Some have stuck, like this newsletter, and others have completely missed, like the literal hundreds of sales calls that have led absolutely nowhere. But I stick with it, no matter what. I switch it up. I pivot. I move forward.

Generalists are like chameleons and our willingness to try, test and tweak is simply how we operate. We’re born experimenters. We’re not chained to a methodology nor are our expectations tainted by past experience. We’re agile. We never stop until the job’s done.

2. The skill of turning insights into income

Opportunities to add value are everywhere which means opportunities to earn money are too. Every single one of my income streams has come off the back of noticing a gap or problem and figuring out how to make something of it:

• My early paid writing gigs came from relentless pitching, countless rejections and, over time, understanding what editors wanted to see

• All my fractional work has come through conversations with founders, not job boards or recruiters

• My first digital product - the Portfolio Career OS - emerged from an assumption that many self-employed people can’t scale because they lack the systems and structures to support it. I validated my hypothesis, built an MVP, iterated, and turned it into my second biggest income stream

This is what generalists do. We relentlessly look for ways to contribute because we’ve spent our entire careers moving between jobs, industries and contexts, scanning our environments to figure out how to help. We’re never head down. We’re eyes up. Feelers out. Game on.

3. A weird amount of get up and go

In portfolio-career-land there are no hand outs. Nothing is served up on a silver platter, in fact, there are no platters in sight. This is particularly true when you’re starting out - in the early days I hustled for every opportunity, every client and every project. I wrote online for a full year before my first qualified lead landed in the inbox. It’s fair to say that building a portfolio career requires a high level of agency.

It’s a good thing, then, that generalists are born doers. We don’t know it all, so we must figure it out. We’re paid to take a half-baked idea and turn it into something real. While specialists struggle when something is outside their realm of expertise, we take action. We excel.

4. The mindset and flexibility to run your career as a business

When you’re both the CEO and Operator you must do it all - strategy and execution, sales and marketing, product and delivery, finance and admin…the list goes on. You’re working on and in your portfolio career at the same time. You must run the business while simultaneously being the business. It’s a lot.

But generalists are jugglers. We may not be sales gurus, but we can persuade. We may not be marketing experts, but we can tell stories. We may not be coders, but we can build using AI and no-code tools. We take off one hat and put on another, moving fluidly between tasks, timelines and topics. We do it all because we can. Because we’re built this way.

PS. If you’re a generalist trying to build a portfolio career, you need a system that holds everything together - your clients, your offers, your content, your energy. That’s why I created the Portfolio Career Operating System - the exact system I use to run my portfolio business. It’s built for people who do many things and want to do them well. Check it out here.

It’s meant to be

Generalists breathe breadth but the cult of specialisation has been suffocating us slowly.

Until now.

Generalists and portfolio careers are soulmates, two lovers destined to ride off into the sunset as one. We’re drawn to complexity and a portfolio approach is diversified by design. We crave variety and this working model means no two days are the same. We’re eternally curious. Experimenters, lifelong learners and free spirits at heart who want to carve out something that’s uniquely ours.

If you’ve ever felt displaced, boxed in, constrained or alone in a crowded meeting room, then please listen closely and hold my hand. You’re not weird. You’re not the odd one out. You’ve just been trapped in a bad relationship.

But now you’ve found The One.

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🎙️ Work opportunities for generalists are EVERYWHERE, you just need to learn where to look…

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🫶🏼 When you’re ready, here are three ways I can help:

• Free Training: Stabilise, Systemise and Scale Your Portfolio Career in 2025: learn the inbound and outbound acquisition strategies to generate a consistent flow of leads and grow your income, and the workflows to that will help you increase capacity beyond your time.

• The Portfolio Career Operating System: join 200+ portfolio careerists and learn how to structure and run your entire business, so you’re miles and months ahead of everyone else in the market.

• Portfolio Career Mentoring: 1-1 sessions to help you get started and build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.

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