Olly

Writing

I typically write about leadership, management and productivity. Running-a-business kinda stuff. Occasionally I’ll write about music, or life in general.

You can subscribe to receive new posts by email via my HEY World blog or browse the full archive.

Latest Post

Why I love the Fujifilm X-S10 for street photography - a review
17th Jan 2024
The Fujifilm X-S10 is an almost perfect camera for street photography. In this blog post I explain why.

Favourites

An old fashioned approach to employee wellbeing
16th Jan 2024
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.
Simple Thinking
22nd Dec 2023
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.
Carpe diem (ad carpe futurum)
12th Dec 2023
I’ve finally understood a few things about what gets me up in the morning and what gets my goat. Here’s a few.
Rails is niche. Good!
7th Nov 2023
Is Rails dead? Is it on death’s door, terminally ill or being slowly asphyxiated by Python? No. It’s just niche.
Lost at sea
5th Oct 2023
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.
Building apps for fun or (probably not) profit
3rd Oct 2023
With side projects, after a certain period of time lethargy creeps in. You get bored, become distracted, then you wonder why you’re wasting your limited and valuable time on such a fruitless task. If you manage to avoid chucking everything away at this point, you’ll need to make a decision...
Building something new
22nd Aug 2023
Around June time I had a vague idea for something I could build that was small and fun, so I just started building it. No plan, little thought about where it would or could go, just build and see where it lands. Maybe this is bad advice, but I think...
Ruby on Rails as a career choice in 2023
15th Aug 2023
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 was “of...
How hybrid can work
9th Jun 2023
Hybrid requires someone at the top to be the remote champion, reinforcing all the time why we need to work a certain way, correcting behaviours and listening to remote staff to make sure the environment is working for them. If the people at the top have a fixed in-office mindset,...
Stop hiring too many people
31st May 2023
Only hire when it hurts. Bide your time until you’re really feeling the pain. Know what you need to do before you hire people to do it. Resist that urge to splurge.
Why your business needs a progression framework
14th Mar 2023
I’ll be the first to admit that some progression frameworks are lacking in substance, often speaking in banal generics and lacking tangible examples. I know this because I’ve written plenty of regrettable howlers. Without a progression framework, or at the very least a list of expectations for a given role,...
Your company can make ‘remote’ work, it's just choosing not to
18th Nov 2022
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...
It's not your job anymore
13th Sep 2022
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...
Convention over configuration to avoid contraptions
22nd Aug 2022
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 …...
You can’t have peaks without troughs
12th Jun 2022
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...
Think about it
6th Jun 2022
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...
A Startup Story: The FreeAgent Years, 2007-2021
19th Nov 2021
I recently announced my decision to leave FreeAgent, the company I co-founded in 2007. It's been a difficult decision to make as I love FreeAgent dearly – I’m part of the furniture almost – but it’s the right time for me to hang up my well-worn CTO boots. I wanted...
The problem with acronyms
10th Dec 2020
Reducing the use of unnecessary acronyms in your business will increase productivity and employee happiness, and reduce cynicism as you grow. Here’s how. Confusing vernacular isn’t a new thing to me, but I’ve noticed that an acronym[1] population steadily increases as projects, or entire companies, expand. I can sort of...