Olly Headey

Journal of Olly Headey. Co-founder of FreeAgent. 37signals alumni. More at headey.net.
May 31, 2023

Stop hiring too many people

I did a talk out in Portugal to a group of company founders this time last year and I bait-named it “Lose the body fat. Why keeping your company lean makes it more attractive.” I pulled in a reasonable crowd and the talk went down okay, but not as well as I’d hoped, so I buried it in my Keynote graveyard and hoped never to speak of it ...
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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...
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December 26, 2022

My 2022 in culture

2022 almost felt normal, at least in terms of going to the cinema, theatre, gigs. Here’s a quick look back on the things I watched/read/listened to across the year. Music I don’t feel I listened to that much great new music in 2022, or found an album that I just couldn’t stop listening to. There were some good ones, of course, and the ...
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November 18, 2022

Your company can make ‘remote’ work, it's just choosing not to

2020 forced the majority of people in tech to work from home. It happened in days, and for the most part companies managed this upheaval without major issues because they were already using tools to make remote work possible. SaaS has become ubiquitous. Whiteboards were left untouched and there was an early fall of sticky notes on meet...
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November 10, 2022

Products I use to manage work and life admin

To friends and family I’m thought of as a proper techie, but to the real techies I know my tech-fu would be considered rather weak. This is fair. I like using tech to get stuff done and make my life easier, but I don’t really go for nerding out on tech for the sake of nerding out on tech. I manage my work and my increasingly-overflowin...
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September 13, 2022

It's not your job anymore

One of the realities of being a startup founder is having your fingers in all the pies. On the one hand you get to do a job you love, the way you want, day in day out. On the other hand you get the honour of taking on that heap of far less interesting things that need doing. This could be company finances, customer support, sales, mark...
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August 22, 2022

Convention over configuration to avoid contraptions

In the world of software development, taking the convention over configuration approach has many advantages. It’s no coincidence that Ruby on Rails defined this approach and the Rails framework is still unsurpassed in terms of developer productivity. If you get too trigger happy with software configuration, those indulgent experiments ...
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June 12, 2022

You can’t have peaks without troughs

Some days feel productive. For programmers, it’s when you get deep into the zone and come out the other side having pieced together a challenging puzzle. It can be sheer delight. For managers, it’s when you approach the ‘zone horizon’ (you’ll never get deep into the zone like programmers, that’s the deal) and focus on a chunky project ...
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June 6, 2022

Think about it

Listen to your gut. Trust your intuition. Lean on your experience. I think there’s a reasonable amount of truth in this when it comes to making decisions, and I can think of many examples where my initial instinct turned out to be a pretty good choice. Impulsive decisions can often be the best ones. This isn’t the case for reactions. T...
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March 9, 2022

Why do we bother with social media?

Concern and despair about the perils of social media come in waves, and there have been some stormy waters in the circles I inhabit this week. Why do we do this to ourselves? I’ve had a love/hate relationship with social media since it’s incarnation. In fact, I’ve had a love/hate relationship with the social aspect of the internet sinc...
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March 4, 2022

Getting Real with a new job

It’s been six weeks since I officially left FreeAgent and rather longer since my mind started wandering off into the dense forest of 'what next'. After a modest break of trying to do very little (I am very bad at this!) I find myself rolling up my sleeves, ready for something new. But what? Over the years I’ve come to know a lot of fou...
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March 9, 2021

Boosting the signal

I had a day "out of the office" yesterday (not to be confused with the previous 360 consecutive days out of the physical office since March 13, 2020). I just had a day off, which shouldn't be a particularly big deal. If anything urgent happened I would have received a phone call, otherwise I should easily be able to catch up with thing...
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March 4, 2021

Hello new blog that is likely doomed to live an unfulfilled existence

I built a minimal blogging app for fun last year, primarily as a way of applying WD-40 to my long-dormant Rails dev skills. I like it, but I still don’t blog enough. Unless you count unpublished drafts, of which I am a total ninja 🥷. HEY have now launched an even more minimal approach to blogging (with the same ethos, which is nice – v...
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