Olly Headey

Journal of Olly Headey. Co-founder of FreeAgent. 37signals alumni. Photographer.
More at headey.net.
May 9, 2024

What Ifs

I’ve been solving some funsmallproblems for a little while. I’ve enjoyed it, but lately I’ve been feeling like I need a fun BIG problem to solve. Something big enough to need another like-minded soul (or two) to work with, but not flying cars big IYKWIM. The thing is, before you even get started on solving the big enough thing, you fir...
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April 16, 2024

Tripping the like fantastic

Since I’m fasting on Twitter and generally of weak mind, I found myself endlessly scrolling through the algorithmic “For You” feed on Threads with my best vacant zombie-face on. You know Threads, it’s that banal and lifeless version of The Social Media App Formerly Known As Twitter (SMAFKAT – the .com is available, you’re welcome). If ...
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March 11, 2024

Technical interviews in 2024

Technical interviews have long been a hot topic of conversation/head-scratching in tech circles, but candidates now have technology at their fingertips that was unimaginable a few years ago. Apparently, things are out of control. I’ve done hundreds of interviews over the years and my approach has always been fairly simple: a CV screen,...
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February 9, 2024

Bye bye bros and bots

I last joined Twitter in February 2007. I first joined when it launched in summer 2006, but I decided to delete my account soon after because I didn't understand it. I rejoined a few months later when other people were actually on there, and I've not left since. My first tweet from an old archive I discovered on my Mac. Not exactly ear...
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January 30, 2024

On Photography

I have too many blogs. This blog is for when I'm writing with my work hat on. I had another blog that I used to write on before I got HEY World, but it's sorta defunct. It's an archive of stuff that maybe I'll just turn off one day soon, given that we have the Wayback Machine if people really felt the need to dredge the bottom of my bl...
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January 16, 2024

An old fashioned approach to employee wellbeing

Does your company run a “wellbeing week”? Do you run in-house relaxation classes, resilience training, or offer staff a free subscription to mindfulness apps? Save your time. And your money. A new study from William J. Fleming at the University of Oxford’s Wellbeing Research Centre has found little evidence that support any of these be...
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December 27, 2023

2023 and all that

Another year gone. I’m not going to bore you to death with a dreary list of accomplishments. No, instead I’m going to bore you to death with lists of music and films and culture stuff that I liked in 2023. Music I love albums. Long players. The Spotify robots confirmed this. There have been some great ones. I speed-listened to lots of ...
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December 22, 2023

Simple thinking

Here’s a novel take away. A week of deletion. Subtraction. Simplification. Most companies get more complicated over time. This is why they slow down and start to fear change. This is how they lose their best people and why customers end up going elsewhere. Complexity is exhausting. Downing tools for a “Delete Week” is a good start, but...
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December 12, 2023

Carpe diem (ad carpe futurum)

I’ve been in observation mode recently, refining my social networks. Scrolling the feeds, pulling the weeds. My Twitter (f’u X) and LinkedIn feeds are worky, and I’m connected to lots of founder types, both the VC hunter gatherers and the indie bootstrappers. From this perspective 2023 seems to have been all about the grind, with less ...
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November 7, 2023

Rails is niche. Good!

Is Rails dead? Is it on death’s door, terminally ill or being slowly asphyxiated by Python? No. It’s just niche. Rails is not cool, it’s not the zeitgeist. Not at the moment. Maybe never again. Rails had its moment back in the noughts when it was fresh and an undeniable game-changer. It was the platform that someenormouscompanies were ...
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October 24, 2023

Have high expectations

The most common complaint I hear from founders/leaders in business is the number of people problems they have on their plate. It’s draining, distracting and demotivating. We invest so much time and energy trying to turn these situations around, yet they’re often only resolved when somebody leaves either by choice or by, er, strong enco...
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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...
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October 3, 2023

Building apps for fun or (probably not) profit

If I think back all those years (decades 😳) when we were building the first beta of FreeAgent, foggy memory-bank notwithstanding, there was a lot to get excited about in the day-to-day. Writing code and building the product was great fun for the most part, setting up infrastructure a bit less so (weak *nix skillz) but super-rewarding w...
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August 22, 2023

Building something new

It's been over three months since I left 37signals on a bit of a whim. When I left I had an emerging plan with someone to build something new, but as it turned out I had nagging doubts and couldn't get excited enough about the opportunity so it quickly fizzled. A bit of a shame, but them's the breaks. I decided to take the summer off i...
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August 14, 2023

Ruby on Rails as a career choice in 2023

““Gasping but somehow still alive” — The Smiths, Well I Wonder” Occasionally someone gets in touch with me asking for work advice. I had one recently where the questioner was rather taken with Rails but asked, “Do you think Ruby on Rails lacks enough jobs? I’m concerned about the future.” It’s a good question, and while my gut reaction...
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June 9, 2023

How hybrid can work

The gloves are off. The work experts are at war. Officista VCs are proclaiming that remote doesn’t work and the media seem to be buying it. AI-generated CEOs are calling it a mistake or, worse, morally wrong. On the flipside, remoterinos continue to disagree. As for a hybrid arrangement, that’s a total clusterfuck. The funny thing is t...
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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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