Olly Headey

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 "hustle" about. I’m not really sure what this means. Maybe it’s just words, or maybe people are having to, like, work for their dollaroonies now.

One observation is seeing the same sentiments shared and the same questions being asked, over and again. "How do I manage people?", "How do I build a high performing team?", "Why you should give people feedback", "5 hacks to achieve super-productivity". The answers do evolve, but they’re still kinda just the same. It’s all just a little bit of history repeating.

I was totally in grind mode for years, maybe a decade. I was on a steep learning curve for scaling up teams, how to be less of a shit manager, how to wrangle multiple scores of engineers. I'd spend my days focusing on how to keep everyone, but generally not myself, happy. I took these things seriously while being acutely aware of the need to avoid the corporate process sinkhole. I believed in all this through and through, and why not because it’s not so bad and it all kinda works, right? But on what level? Does it actually work for you?

I can look back through the reflective lens of hindsight. Having gone full circle from helping build a chunky tech scale up, to working for the SaaS O.G, to hurtling back to Obscurity Street, Nowheresville, all on my lonesome, I’ve finally understood a few things about what gets me up in the morning and what gets my goat. Here’s a few. Take what you like and if you make it to the end, thanks for listening.


Building a thing for the sake of building a thing is fun but it’s no way to build a thing. You have to really need or absolutely love that thing you’re building or the problem it’s trying to solve. Without that, your purpose and self-worth is flaccid at best, surely? There will be people out there who are deeply passionate about all things, say, MarTech and they genuinely believe they’re not ruiners of all things good with their latest ephemeral content astroturfing app. But they’re misguided.

Purpose is paramount.

The VC-backed rocket ship concept isn’t for me, not any more. It definitely was once and I have no regrets. In fact the dreamer in me still kinda likes the whole charade of it all – the apparent glamour, the jetsetting, making all those big calls with the big boys for those big bucks. Of course, like most things online, the reality is quite the opposite. A few token rocket ship cashtronauts will hit the jackpot but everyone else will end up lost, swathed in endless meetings and performance reviews and wellbeing weeks, and it will suck the creative life out of them to the point where they’ve forgotten how to dream. Caveat emptor, for real.

Creating is paramount.

Some people say “always be shipping” and there’s truth in that, but you could be shipping crates of mince. Create something beautiful or meaningful, don't crate offal.

Advanced AI in the wrong hands is a catastrophe waiting to happen, but right now, in tech, whether you’re standing on the shoulders of giants to push the boundaries of what’s possible with tech-based products, or using it to 10x your day-to-day productivity, AI is your best friend. If a problem shared with a human is a problem halved, a problem shared with an LLM is a problem decimated. This is how we progress.

I’ve found days spent coding without distraction, with a sense of purpose and with reasonable urgency (not maniacal, Elmo) to be immensely fulfilling. Long expanses of focus and solitude can produce the best work. I have become more aware of my tendency to be slightly obsessive when trying to solve the tricker problems though, deep in the darkest depths of the zone. This can be quite suffocating and I’m trying to learn how to come up for air sooner. Breathe, dammit! I think I used to be better at this, but my memory is sketchier these days so maybe I wasn’t.

Truth be told I’ve had a love/hate relationship with coding over the 28 (!) years since I started my first proper job, for far too many reasons to dwell on here, but I’ve ended up in a happy place. Much of this has to do with Ruby, Rails and their communities. They're the most wonderful of gifts (you should watch Ruby on Rails: The Documentary by the way, to help understand). Further to this, obstinately focusing on mastering these tools and ignoring virtually everything else has been immensely satisfying. For me, ignoring the hype and doing one thing well is the real secret sauce to programming contentment and productivity.

The modernists believed less is more and Picasso said art is the elimination of the unnecessary. I’d go further and say contentment is the elimination of the unnecessary. Unnecessary worry, unnecessary stuff, unnecessary technologies, unnecessary distractions, unnecessary opinions.


My ongoing detachment from the grind and the hustle started off being difficult (turns out it requires the patience I tend to lack) but has ended up being cathartic. Rediscovering the joy of creating, finding something to create that you believe in (however small and insignificant), working with people who have talents that inspire you, applying skills you’ve spent decades learning and finally learned to enjoy using. The thrill of ideas. That warm sense of anticipation for what could be, the challenge of putting something into practice, and that warm glow of satisfaction that comes from accomplishment even though it's rarely easy to get there. All of this, it's wonderful thing.

Keep thinking. Stay creative. 

Photos ©️ me

About Olly Headey

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