Olly Headey

October 5, 2023

Lost at sea

You know where you came from
You know where you're going
And you know where you belong

— The Smiths, These Things Take Time

Leaving FreeAgent was a natural progression. The company was stable, I’d done a good job and I didn’t feel there was much left for me to achieve. Great people with youth and energy were eager to move on up. Time to go.

I got recruited by 37signals soon after leaving FreeAgent so I didn’t have time to dwell. I had a big new challenge and I dove right in. There was a lot to learn, and I gave it pretty much everything I had, full gas. I think I did pretty good. I got positive feedback from above and below. Then I decided to call it a day, abruptly and somewhat impulsively which isn’t really like me, truth be told. Looking back it seems rather rash, but the planned company/team growth that I was there to help with didn’t really materialise and I was increasingly feeling like a spare part as I ticked things off my list while sufficient new challenges were not being added to it. It’s a damn shame as it’s the best company I’ve ever worked for. Other than my own, which was better, obvs 😆

I’ve done a lot of dwelling over the past few months and I’ve been up and down and back around several times. It’s odd, all these peaks and troughs, the what ifs and what nexts. It’s hard to explain, but I'm game.

Imagine you’ve been navigating your sturdy boat for years with a band of trusted sailors. You’ve become a team with hardened sea legs. You’ve hit choppy waters, sprung leaks, faced shark attacks, but it’s ok – you work it, figure it out between you, and end up in calmer waters, a lot more experienced and confident to face the next stormy whitewater. Then you decide to leave that steady ship on an exciting transfer to someone else’s superyacht. You’re no longer an executive officer, probably not even a first officer, but somewhere above a deckhand. Maybe a second officer, if that’s a thing. You enjoy your time, learn a tonne, make lovely new friends, but before you get too used to those all-expenses-paid trips to glamorous destinations around the world you make a snap decision to jump ship.

It’s a thrill, but when you’re deep in the drink starting to feel a shiver, you realise that the azure water ain’t quite as inviting as it looked from the deck. Then you find yourself lost at sea.

You’re fortunate and unlikely to drown, so do you try and risk a goliath swim ashore that you know will be exhausting, or do you twinkle-smile and wave at passing ships to see if one will pull you aboard? A tempting and easy(ish) option perhaps, but potentially unfulfilling. If you don’t do either, chances are you’ll end up flapping and splashing around, rudderless, waiting for some kind soul to drag you out and slap you about the face with a big trout until you come to your senses.

That's what it's like. You get the feeling I’m overthinking this? 😅

I don’t know many founders who’ve worn similar shoes as me, so maybe this flux is normal. Or maybe it’s late onset of a mid-life crisis? Or both! Not many people write about these experiences (post-acquisition founder exploits, not mid-life crises) which is a shame as it would be really therapeutic to read. Instead I resort to getting therapy from writing nonsense like this. Sorry, internet.

At the end of the day, things just take time. Patience is required (damn). It’s just another “problem” that you’ve gotta work like you did in those choppy waters back in the day. You'll get there. It was never going to be easy, but I’m quickly coming to the conclusion that navigating the seas is a whole lot better with shipmates than it is on a solo crossing. 

Anyone got a trout?


About Olly Headey

Journal of Olly Headey. Co-founder of FreeAgent. 37signals alumni. Photographer.
More at headey.net.