I’ve been thinking about retirement lately. I’m not retired, at least I don’t think I am, though moving on from The Recount has left me uncertain about how to answer the inevitable “so what do you do” questions – the ones that anchor nearly every social gathering I attend:

Person I Just Met: So what do you do besides hang out at dinner parties? 

Me: I’ve been trying to come up with a good answer for that one.

Person I Just Met: So, you’re retired? 

Well no, in fact, I’m not retired. Why does everyone jump to that term? The word has always bothered me. It lands poorly, evoking decay and senescence. Its cousin “retiring” conjures a person who wishes to disengage from the world, and its root is, well, tired. I mean, who wants to be tired, much less, thanks to the prefix “re” – tired over and over again?

I know there are tens of millions of proudly retired folk, people who embrace the term as an achievement. Fine, but I’m not joining that team. To me, it signals that you’re done adding anything productive to the world in terms of your career. You’re on the penultimate leg of life, and the only meaningful stop left is a long dirt nap.

So maybe it’s time to retire the word’s first definition: “to leave one’s job and cease to work, typically upon reaching the normal age for leaving employment.” It’s such an industrial framing.

I suppose I am technically leaving one aspect of my life, a core narrative that’s driven me for more than thirty years: That of a founding executive in a startup. But I’ve always had a number of projects that ran alongside those companies – conferences like Signal and Web 2.0, board positions on private, public, and non-profit corporations, writing, investing, speaking, consulting – all of which are happily expanding to fill my days just as work with The Recount subsides. And yes, I’m thinking about taking on or starting any number of new projects – but I’ve a new rule for them: They can’t be venture-backed companies with me as the founding CEO. That era is over.

But none of this fixes that problem above: What the hell do I say to the question about what I’m doing with myself these days? Given I have stopped doing the one thing that nearly everyone understands as “having a job,” I need a better answer. Any founder can tell you, being in charge of millions of dollars of invested capital and scores of trusting employees is exhausting. Having done it over the course of seven different startups, then stopping cold turkey earlier this year, I can tell you one thing for certain: I’ve never felt less tired than I do right now. I’m finally not tired, in fact, I’m refreshed, invigorated, and getting more gassed up each and every week that passes.  Is there a word for that? If you’ve got one, please do share. For now, I think I’ll just claim I’m unretired, and see how that goes…

You can follow whatever I’m doing next by signing up for my site newsletter here. Thanks for reading.


6 thoughts on “Unretirement”

  1. John,
    Love this. And consider us ‘brothers in arms’ on how to redefine this amazing moment as founders where you suddenly have new found freedom. Really enjoying the newsletter, keep ’em coming. And , hey, who is the dialogue with and what dinner party were you at! 😉
    Best, C

  2. John, I’m in the same boat as you’re in – after 36 years in my primary career. I’m begiining to call myself an “ActIIvist” in other words someone working on Act II – a different sort of career. In my case, wriitng about & influencing public policy along with angel investing; mentoring. As you say I’m very excited about this new phase!
    I’ll ‘see’ you at Signal – will be aclling in for a few sessions from Singapore!

  3. Congrats on your new phase! I’ve got plenty ideas that I’d be happy to pitch for new projects.

Leave a Reply

Your email address will not be published. Required fields are marked *