Olly Headey

May 11, 2023

Venturing into the unknown. Again.

It only seems like yesterday when I started a new role at 37signals but time hurtles by when you're having a wild adventure (even more so when you're pushing 50 😳). And just as all the best adventures must come to an end, so it is that after an intense 14-month journey I've decided it's time for something new. 

Things are afoot and it's bittersweet. 

I'm sat here, a couple of hours after saying goodbye, trying to write something lasting and meaningful but words are failing me. I've got so much I want to say, but it's not coming out. Not today. I hadn't anticipated this, but it's all a bit much so, what the hell, in true 37signals fashion I figured I should just publish the full announcement I made to the company yesterday verbatim and leave it at that 🥹
Sorry to spring a surprise but I wanted to let you know that tomorrow will be my last day at 37signals 😱

I absolutely love 37signals, all you great people, our awesome products, this high-trust environment, and all the excitement that's happening around the new products. I feel honoured, truly, to have had the opportunity to be part of the 37s journey for the past 14 months and it's been a wild ride. Truth be told, I feel like the job I came here to do is reasonably complete, so it's the right time for me to go and build something new again. I miss being part of the action!

I'm leaving with things in good shape, but I'll be spending today and tomorrow tying up a few loose ends and handing things over, so please ping me if you need anything. Hopefully I won't be leaving anyone in the lurch 😬 but I'm only an email away. 

Making this decision was tough, a real gut wrench, but l'm a believer in following your heart. 37signals really is a remarkable company full of remarkable people. One of the greats. I leave with only good things to say about the company, the people and the culture. I will miss you all enormously, but I'II be taking many wonderful memories and new found friendships away with me.

Thanks for everything 🙏❤️

The happiest of times with some of the best people you could hope to meet at the Hotel Monteleone cocktail bar, French Quarter, New Orleans, April 2023 ❤️

About Olly Headey

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