Growing a portfolio career with Anna Mackenzie

Working in seasons and building a creative life layer by layer

Jul 18, 2025

If you’re a solo operator or freelancer you’ve been told to niche down. Define one target persona. Become the go-to in one industry.

But what if the idea of that sends you to sleep because you want to utilise various skills or work within different industries? Photography and writing 📷🖋️? Painting and accountancy 🎨➗? Gardening and consulting 🌷📈?

Luckily Anna Mackenzie entered the chat to shine a light on another way of approaching work: the portfolio career.

When Anna’s post “Saying goodbye to "traditional" work, and why I'm building a portfolio career instead.” took off on Substack last year, she noticed the signal and created more content on the topic across platforms before building out a mentoring service and digital product in response to the clear demand for more support. It’s an absolutely 🔥 example of validating ideas and demand with your community before investing in creating the product or service.

Given that the portfolio career approach rejects traditional notions of success by default, I wanted to speak to Anna about her approach to growth.

Enjoy!

Chat soon

Matilda x

Hello! Please give us an intro to you and your work.

Hey! I’m Anna, a Startup Advisor & Operator, Portfolio Career Mentor and Writer based in Melbourne. I’ve had an ultra squiggly career working across corporate, small business, high growth startups and scale-ups, as the founder of my own brand and now a solo operator with a portfolio of projects, clients and income streams:

I help startups from Pre-Seed to Series A start, grow and scale their businesses globally.
I'm a Portfolio Career Mentor, helping those who aspire to leave the 9-5 (or who already have) build a diversified and sustainable portfolio of work
I write the popular weekly newsletter Anna Mack’s Stack, where I share weekly guidance and practical insights to help others build a portfolio career and life on their own terms
I offer a digital product called the Portfolio Career Operating System.

Many of us pursuing solo or portfolio careers have actively walked away from many traditional ideas of professional success (big team, big office, big title etc.) Why do you think these aspirations have changed?

I started to question my career choices after spending a lot of COVID lockdown stewing in my own thoughts (read: having an existential crisis). At the time I was running my own business that looked very glamorous from the outside, but inside I was deeply unhappy.

I felt constrained pouring everything I had into one pursuit, disconnected from the work, and like I’d lost myself in pursuit of a goal that looked good on paper. At some point the trade offs became too loud to ignore and I made the decision to leave that business and go out on my own.

I think my story is a pretty common one, and many of my mentoring clients have told me that they’ve worked hard and sacrificed a lot to climb up the corporate ladder, only to look around and realise that they hate where they’ve ended up. I think we’re experiencing a collective awakening when it comes to what success looks like, and I’m here for it!

How do you approach balancing the growth of the different streams within your portfolio?

I operate in seasons. Sometimes I’m in launch mode, other times I’m in build mode, and occasionally I’m in rest mode. I also flex my client work up and down depending on what else is happening in my life. I’ve learned the hard way that trying to do everything at once is a recipe for disaster, and so I try to get clear on my quarterly focus and the financial and impact goals I’m trying to hit, and build my life around that.

What’s a common misconception people have about growing a portfolio career?

That you have to do everything at once! People assume that having a portfolio means immediately juggling five million projects and income streams, but most sustainable portfolios are built slowly over time, layer by layer, opportunity by opportunity.

What are you intentionally choosing not to grow or scale in your work right now?

Fractional work with startups. This used to make up the majority of my income but over the last 12 months I’ve grown my revenue from 1-1 mentoring and my digital product, which has allowed me to pull back on more intensive client work. It’s been a hard decision in some ways because I absolutely LOVE getting into the weeds with founders, but I also know that I’m in product development mode and something has got to give.

So much of traditional growth is tied to scale - more clients, more revenue, more visibility. In portfolio work, do you think growth needs a reframe beyond “more”? What could this look like?

In my mind growth relates to “more” but it doesn’t just mean more clients, revenue, visibility or external success. For me, it can mean more time, more reflection and introspection, more rest, more personal growth, more fun, more adventure, more reading, more writing, more hobbies and more fulfilment.

A lot of the time realising more in my personal life means doing less in my professional life, but I am absolutely fine with that trade off because my end goal isn’t to build a massive multimillion dollar business, it’s to build a life that’s creative and fulfilling.

Thanks for reading. You can read Anna’s Substack here or connect with her on LinkedIn or Instagram.

On a planet of finite resources, why are all the brands around us striving for infinite growth? What should you be doing instead? Broken Growth a newsletter about reimagining growth in ways that don’t fuck up people and planet. From big-picture thinking to practical strategies. Written by London based freelance strategist Matilda Lucy.