The portfolio career is coming for your retirement too

Dear Friends —

New here? Each week I write about identity, longevity, and designing a next chapter with the same intention you brought to your career. Glad you came.

I fell into a TikTok rabbit hole yesterday. The video that started it was a woman in her late twenties explaining her "portfolio career" — a marketing job four days a week, a yoga certification she was finishing on the side, and a small candle business she ran on weekends. The comments were full of people her age describing their own versions. A nurse learning to code. A teacher who does voiceover work. Nobody treated this as remarkable. It was just how they assumed a working life now gets built.

I kept watching longer than I'd like to admit. Not because the candle business interested me, but because the underlying logic did.

These are people who looked at the single-track career — one employer, one skill, one ladder — and decided it was too fragile to bet a whole life on. And they're not wrong to think so. AI is dismantling the assumption that one well-developed skill carries you for forty years. When the ground under any single role can shift in eighteen months, a spread of roles isn't a lack of focus. It's insurance. They're building portfolios for the same reason a careful investor does: because concentration is risk.

Here's what struck me, though. They're being forced to do at 28 what most people in my world never do at all.

Because the single-track career has a retirement equivalent, and it's just as fragile. We call it golf and grandkids.

I want to be careful here. There is nothing wrong with golf, and grandchildren are one of the genuine joys of this stage of life. But as a plan — as the whole answer to the question of what the next chapter is for — golf and grandkids is a single-track bet. It concentrates your entire sense of purpose into one or two activities and assumes they'll carry the weight for decades. They won't. The grandkids grow up. The body that golfs four times a week at 65 does not necessarily golf four times a week at 80. And you are, statistically, looking at twenty, thirty, possibly forty years on the other side of your career.

I've written before about the arithmetic of longevity — that we inherited a retirement frame built for maybe a decade of life after work, and we're now living three or four times that. The math doesn't just stretch the old plan. It breaks it. A concentration that works for ten years fails over thirty.

So the same logic those younger workers reached for applies, with more force, to anyone designing a next chapter. Not a single grand replacement for the career you left. A portfolio.

I worked with someone last year — I'll composite the details, because the pattern matters more than the person — who arrived at exactly this problem. He'd sold the company he spent two decades building. The financial side was handled cleanly. And ten months later he was awake at 6 a.m. scrolling listings of businesses for sale. Not because he wanted to run another company. Because he didn't know what else to do with the part of himself that had run the last one. The single track had ended, and he'd been handed golf and grandkids as the alternative, and every cell in him knew it wasn't enough.

What he actually needed wasn't one new thing. It was a portfolio of several, sized correctly. A paid role with real stakes — but smaller stakes than running a company. A way to channel two decades of operating wisdom into something that mattered to him now. A learning project with no purpose except that he'd been curious about it before work crowded it out. And a body he could count on for the thirty-year horizon, not just the next physical. No single one of those carried the weight the company used to. That was the point. The weight got distributed, the way a portfolio distributes risk, so that no one disappointment or ending could take the whole structure down.

This is, in large part, the work I do one-on-one with clients.

It's worth being precise about what that work actually is, because "design a portfolio next chapter" can sound like a worksheet exercise, and it isn't. It starts with signals — clarity of direction, how fused your identity still is to the role you left, vitality, the intentionality of your connections, how aligned your life feels with what matters to you now. Those signals tell us where you're actually standing, which is often not where you assume. From there the work organizes into a handful of strategic focus areas: the identity work of loosening grip on who you were; the roles that give the builder in you somewhere legitimate to go; the relationships that used to come free with work and now have to be built deliberately; the physical foundation underneath all of it. The areas are sequenced, not scheduled — built in the order that actually works, at a pace that's yours.

And the recommendations inside it are roles and practices, not hobbies. There's a real difference. A hobby fills time. A role has stakes — it expects something of you, and it gives you something back that matters. The whole point of a portfolio next chapter is that you get to have several of those again, chosen for fit, none of them required to be the one big answer.

The younger workers on my TikTok feed figured out the structure under economic pressure. You get to design it on purpose, with more resources and more clarity than they have, and a great deal more reason to get it right.

You built your career deliberately. The next chapter deserves the same kind of intention — and a great deal more than golf.

Onward.

— Cara

This is the work at the center of what I do. If you're sitting with the question yourself, here's where I write about how I think about it.