Midlife MavericksThe replies last week were different. More of them than usual, all saying the same thing in different words: I know this. I’m living this right now. I feel like a number with an expiry date.
I was ill most of the week. The low-grade, annoying kind that makes everything harder without giving you permission to cancel anything. But I had a long car ride from Porto to Lisbon with one of my best friends. She had just turned 50. I’m not far behind. We were on our way to a 50th birthday party. That car ride turned out to be the most useful thing I did all week.
Somewhere on that drive, I asked her directly: “What are you going to do about it? How are you preparing? You’ve got maybe five years. What do you actually want?”
We weren’t angry. Not panicking. We were in that particular state that arrives when you finally let yourself look at something you’ve been keeping in your peripheral vision. Curious. Trying to map something that isn’t fully formed yet. Asking “what could this look like?” instead of sitting in the dread of what it won’t be.
Quote of the Week
“The future enters into us, in order to transform itself in us, long before it happens.”
Rainer Maria Rilke
Too Old to Hire, Too Young to Retire
The managed exit is rarely dramatic. There’s no confrontation, no sudden ending. There’s a restructure. A package. An offer timed when you’re tired, that costs the company less than keeping you.
It tends to happen around 55. Sometimes earlier.
A 30-year-old with five years of experience costs half what a 52-year-old with 25 years costs. That calculation lands in a spreadsheet before it ever becomes a conversation with you.
OECD data across multiple countries shows that workers over 45 who lose their jobs take twice as long to find another one as workers under 40. Twice. And then there’s the AI screening layer: tools built to make hiring faster are inadvertently filtering out the most experienced candidates. Longer career histories, more varied roles, titles that don’t map cleanly to today’s job categories. The software flags them as poor fits, so the recruiter never sees their CV.
Most of you already knew it felt broken. The data just confirms what you’ve been feeling.
What the Package Doesn’t Factor In
I’ve watched my mum retire. After decades of work that was central to who she was. What I wasn’t prepared to see was how hard the transition was. Not financially. Personally. Because leaving work isn’t just leaving a job. It’s leaving the version of yourself the job has held in place for 25 or 35 years. The daily evidence that you’re useful. The intellectual engagement. The social contact. The thing that keeps the brain moving.
There’s a reason so many women in their 50s and 60s who stay engaged in meaningful work stay sharper for longer. Purpose, connection, and challenge do something for you that disappearing into domesticity does not.
This isn’t an argument against retirement. It’s an argument for choice. People who want to keep working past 55 should be able to. Work, for many of us, is bound up with how we stay sharp, how we stay connected, and who we are. Having that removed on someone else’s timeline is a very different thing from choosing to stop.
The managed exit doesn’t offer that choice. It optimises for cost and calls it a restructure.
OWN IT
I need to tell you something, because I think it matters.
I already have a portfolio career. Right now, I’m actively thinking about what the next five years of it look like. Which strands I decommission. Which ones I invest in fully. What having writing online does for my positioning. What AI changes about the shape of the work that will exist. I don’t know exactly what it will be yet. But I’m building toward it now, while I can still see the options.
This week, I sent two proposals to prospective clients that scared me properly. Outside my usual scope. Outside my comfort zone. Scared the shit out of me, frankly.
Filipa had to talk me back. Remind me that I’m Claudia Quintela and I’ve got this.
I have a portfolio career. I’ve been doing this for years. And I still needed someone to remind me who I am before I hit send.
I’m telling you this because the version of this story where you build a portfolio career and then everything feels certain. That version isn’t real. The fear doesn’t go away. You send the proposal anyway. That’s what building looks like from the inside, at every stage.
If you’re still employed and mapping your next five years, the starting point is practical: what do you know that someone would pay for, what does your contract actually allow, who in your network has a problem you could solve? I’ve written it out step by step in How to Build a Portfolio Career While You’re Still Employed. It covers the skills audit, the contract check, how to find your first client without a pitch deck, and how to scope a first project small enough to run alongside your day job. If you’re in the building phase, that’s the map.
Five years out isn’t early. For most people, it’s barely enough time.
Reply and tell me where you are with this. Already building something on the side? Still figuring out what the offer could be? Just sent something that scared you? I read all of these.
See you next Wednesday,
