Midlife MavericksI met Madalena at a conference last week.
She’s from Porto, like me. She’d reached out before the event for us to meet, but by the time I got there I’d completely forgotten who I was supposed to be looking for. Perimenopause brain. Classic.
So I went to the organisers and asked them to introduce us. And there she was.
Four kids. A blog with a serious following. A published book. Regular contributions to several publications. Creative projects on the side that she describes, half-laughing, as “basically therapy.” Full of beans. Within ten minutes we were finishing each other’s sentences. Every presentation we sat through, we were shaking our heads at the same things, nodding at the same things.
Two women, same age, same city, and we’d never met. It took a couple of ladies from Lisbon to introduce two gals who are Northern Portuguese through and through.
At no point in the conversation did Madalena say the words “portfolio career.”
But that’s exactly what she has.
Quote of the Week
Instead of a career, think of a portfolio of activities.
Charles Handy
I hear this all the time. Women who are consulting and mentoring and writing and advising and speaking and volunteering, and when someone asks what they do, they fumble. They list things. They apologise for the length of the list. They say “it’s a bit of everything, really” and then change the subject.
They’re running a portfolio career. They just haven’t given it a name.
And I think the naming problem is part of what keeps people stuck.
Forget the Label. Look at What You’re Actually Doing.
We get so bogged down in naming conventions. Am I a freelancer? Am I a consultant? Am I fractional? Am I a solopreneur? Am I just… doing stuff?
Strip the labels away. A portfolio career is doing a collection of things you’re deeply interested in, that bring you variety and creative freedom, that let you contribute meaningfully, and that, let’s be honest, can also make you serious money.
The people I talk to don’t want less work. They want less of the wrong work. Less time drained by meetings that should have been emails. Less energy wasted on politics that have nothing to do with the actual job. Less of that hollow feeling when you spend a whole day being “busy” and can’t point to a single thing that mattered.
They want to work. They’re excited about work. They know there’s something they’re bloody good at. What they want is the freedom to do that thing, and maybe four other things alongside it, in a pattern that fits their life. A pattern that flows with their energy, their family, their season of life.
For some people, the writing strand is therapy. The speaking strand is adrenaline. The coaching strand is purpose. The consulting strand pays the mortgage. And the volunteering strand is the bit that makes the whole thing feel like it means something.
That’s a portfolio career. Whether you call it that or not.
What It Actually Looks Like
My version: capital introduction and investor advisory for hedge fund managers. Coaching and mentoring. Two newsletters (this one, and one for emerging hedge fund managers). A weekly column for a Portuguese publication. Public speaking. Corporate advisory on AI implementation and adoption. Content across Substack, Threads, and increasingly LinkedIn. Volunteering and mentoring younger women, because sending the elevator back down matters to me.
Seven strands. Some earn money. Some earn energy. Some earn both.
I didn’t plan this on a whiteboard. I started with what I knew, paid attention to what people kept asking me for, and added strands as they made sense. The portfolio wasn’t designed. It was discovered.
The variety is the reason the whole thing works. Each strand feeds the others. The coaching makes me a better writer. The writing makes me more visible for advisory work. The advisory work gives me stories for the coaching. It compounds.
The Part That Scares People
Two fears come up every time.
The first is money. “But my income won’t be predictable.” True. Some months are champagne, some months are questioning every decision since 2019. But a single employer feels stable right up until the restructuring email lands. At least with a portfolio, when one strand dips, another holds.
The second is identity. “But people won’t understand what I do.” Also true. Some won’t. But the people who matter, the clients, the collaborators, the people who actually hire you, they don’t care about your job title. They care about whether you can solve their problem.
OWN IT
If you’re reading this and thinking “that sounds like what I’m building, I just didn’t know it had a name,” good. Now you know.
And if you’re still in corporate, watching someone like Madalena or me from the inside, wondering whether you could do something similar: you can. You already have the skills. You already have people in your network who would pay for what you know.
You don’t need to quit tomorrow. You don’t need seven strands figured out. You need one. One thing someone would pay you for that has nothing to do with your current job title.
Start there.
I wrote a deep dive on portfolio careers this week: what they are, how they differ from freelancing or fractional work, why they’re exploding right now, and how to know if one fits you. Read it here.
Hit reply and tell me: what’s the strand you’d start with? The thing you’re already doing, unpaid or unrecognised, that could be the first piece of your portfolio. I read every reply.
See you next Wednesday,
C
