In 2021, I stepped away from the traditional path choosing entrepreneurship over another executive role.

No firm. No title to lean on. No guaranteed pipeline.

Just a growing curiosity that there might be a different way of earning a living — taking what started as a side hustle and building it into something more future-proof: a portfolio career.

In March 2026, I hit five years out on my own.

In the spirit of “living my legal life out loud”, here’s five things I’ve learned.

1 — Freedom is earned, not given

Working for yourself looks like freedom from the outside. In reality, it’s a level of responsibility most people never have to carry, or can comprehend.

There’s no one setting direction. No one fixing your pipeline. No one defining what “good” looks like. No regular salary safety net. No parental leave.

You’re the strategist, the operator, and the safety net.

One of the biggest personal stretches for me has been managing the overwhelm when work slows or is delayed, including payment of invoices.

But over time, if you stay in it, something shifts. You build systems, processes, judgment, resilience — and for me, a deeper sense of trust.

That’s when the freedom people talk about actually starts to show up.

2 — Your brand becomes your business model

As a solopreneur, you are the brand.

The standard of your work. The way you think. How you communicate. Whether you follow through. Whether you can sit in the grey and still move things forward.

Over time, that becomes your pipeline.

The work I enjoy most now tends to come through networking, conversations, content, and referrals, not pitches.

And social media has played a real role. It shortens the distance. Cold outreach often feels like a warm introduction.

3 — You have to get comfortable being misunderstood

When you step outside a traditional structure, people don’t quite know where to place you.

A portfolio career — what does that even mean? Are you a lawyer? A GC? A consultant? A content creator? A speaker?

For me, it’s been yes to all of it, at different times, in different proportions.

That ambiguity can feel uncomfortable in a profession that values neat labels and specialisation. We’ve been told for decades that “niche is best”.

That’s never quite worked for me.

My brain values variety. Different problems. Different rooms.

And increasingly, I think that’s the edge a kind of neo-generalist approach in an AI-shaped world.

You don’t need everyone to understand it. You just need the right people to.

4 — Revenue follows clarity, not effort

Early on, I said yes to almost everything. It felt like the right thing to do — build momentum, build security, build confidence. For the first 18 months I didn’t touch a legal matter, wanting to check my passion for practising.

But the biggest commercial shifts didn’t come from doing more.

They came from getting clearer, including on how much time I give away for free, to pay it forward etc, on where I add the most value, the work I want to be known for, and what I don’t do anymore. And getting clear on what fits alongside being a working mama, without frying my nervous system.

That clarity changes everything — how people engage you, how you price, how you scope, how you protect your time.

For the most part, I’m at the stage now where I aim to work less, but be paid more.

That’s not arrogance. It’s years of experience, experimentation and a much sharper understanding of where I’m strongest.

5 — There is no arrival point

I used to think there would be a moment where everything felt settled. Where the model was “done”.

That hasn’t happened yet.

What I’ve built is closer to a portfolio than a single lane — legal advisory, fractional GC work, consulting, speaking, writing.

In the early years, I was focused on out-earning my corporate salary (which I did pre-motherhood).

Now, with two little boys under three, the flexibility I’ve built matters more than anything.

Priorities shift. The mix shifts. The market shifts. Life shifts.

And that’s the beauty of doing it this way.

So, if I had to sum up the last five years in one line: there isn’t a safer path, just more familiar ones.

And what’s next?

More of this. At a pace that allows me to be a present Mama while my kids are young.

And, (not so) quietly in the background — paid Board roles.

Thank you to everyone — past, present and future — who has supported me along the way. I’m beyond grateful.

Best, Anna