2025 Year in Review: The Engineering Skill I Had to Unlearn
On uncertainty, and learning too late how progress actually works
2025 was the year I realised an attitude which had carried me through my career had been silently failing me.
Eleven years of working as a software engineer had taught me to be incredibly careful. I’d never start a project without knowing exactly what I needed to do, and how long it would take. If there was anything I wasn’t sure about? The first priority would be: come hell or high water, find out everything you need.
Often, the question of the day would be, “How can we derisk it?”
It turns out, I had a propensity for this thinking, too. Things needed to “click” in my head or I wouldn’t believe I understood it, even if I had no idea what the missing piece was.
Most of all, I’d always need a plan where I could clearly see the link between action and result. If it wasn’t obvious exactly how my input would create the intended outcome, I wouldn’t want to even start.
After all, who likes fumbling around with the unknown? We’ve got features to deliver!
It was a skill—or, perhaps, a habit—that I trusted more than anything.
But 2025 was the year it fell apart.
The mentality that had once made me effective became the thing that was slowing everything else down.
When preparedness becomes overplanning
Here’s a horror story from my engineering career which I still tell.
I was put in charge of a new feature: a “mega-menu”. I was to take an existing menu on our product’s user interface and add a hierarchy to it; that is, one of the options needed a set of sub-options. Sounds easy enough…
Anyway, I’ll leave out the jargon. We spent a few days planning the work and estimated it would take 2 weeks. And about 2.5 months later, I completed the feature, but not before I’d:
Added about 2000 lines of code across 40 different files
Introduced a whole new system for displaying the interface components in the project
Rewritten an open-source software repository which we needed in a different programming language
In the post-mortem, we came to a simple conclusion: we hadn’t planned this work carefully enough. The answer was thus…more planning.
MORE. PLANNING.
I might grouse about it now. But the reality was that they were very much correct! We massively overshot the deadline and underestimated how complex the feature would be because we hadn’t done enough work derisking it before we started.
And yes, like surgery and space exploration, software engineering is one of those fields where it pays to know more rather than less. The risks are more knowable in advance, and the cost of getting things wrong is huge.
In entrepreneurship? There’s no way to know what will happen until you try.
I made the choice to become an entrepreneur in late 2024. I just refused to take action until things “clicked” and I felt like I had a clear path to inevitable business success. This approach was doomed to failure from the start.
The problem wasn’t that my “engineering skill” had failed.
The problem was the constant promise of everything suddenly feeling much easier if I just waited a bit longer. Just a tiny bit more prep; just a tiny bit more knowledge.
And strangely, it’s not the first time I’ve been taught this lesson. The first time goes way back…
A story from my days at university
My degree was in chemistry.
I vividly remember sitting through a module on sustainable chemistry. Our lecturer would often break from the subject and tell us about his research group. As one story went, they experimented a lot with that most environmentally friendly of all solvents: water. Had they discovered anything groundbreaking? No, not yet. So why were they researching it?
Because they found it interesting.
In the professor’s words…maybe one day they’d discover something great. But researching something just because it was pretty cool was underrated. Sometimes, the best course of action is to go down that path just to see what happens.
And you know what? Some of the world’s biggest discoveries (penicillin, microwave cooking…even viagra) were an accident.
It doesn’t matter if you were researching something for a specific result, or if you just felt like finding out. “Not knowing in advance” is part and parcel of the whole thing.
“Knowing exactly what to expect” is a fine reason to venture into the unknown. It’s just a luxury that won’t exist in many fields.
Often, it’s even better to take on the discomfort of, “I have no idea what will happen when I try this…but finding out is the most exciting thing.”
It wasn’t going to work until I unlearned this
To make entrepreneurship work, I’d need to completely abandon the safety of knowing how anything will play out.
Taking extra time to plan things works in software engineering. In fact, going forth without it is reckless.
But as an entrepreneur, you’ll usually have to just move fast and figure out the rest later.
Said differently, this is the mentality I’m resolving to take into 2026:
Clarity should come FROM action, not as a prerequisite to it.
Assume I understand more than I think. Even things I don’t understand can come later. After all, risk is the best part of the whole venture.
The analogy between research and taking a punt on ourselves is so strong because they both mean pushing the frontier of what we know to be true.
Millions of people have started businesses, so it’s not quite like discovering antibiotics for the first time. But it’s the same in that no one knows how any one person will handle it, least of all themselves.
When I head into the unknown, I’m still at the cutting edge of my own knowledge and experience. And there’s no other way to figure out what will happen without taking that step anyway.
We should always try to push the boundary
So why do we so often shy away from the things we want to achieve?
Often, we can be so tightly coupled to a framework that we stop even noticing it. The idea that there are other ways to live life feels totally alien.
Even if we do consider:
Breaking away from the career ladder
Building a skill or habit which forces you to show up differently (e.g. singing, going to the gym, entrepreneurship)
Moving to a new city or country
…we might immediately dismiss it as, “It’s not who I am.”
But if it’s something we’d always wanted to do, then…well, why not?
I always wanted to be a skilled singer. Somewhere in my mind, I had the idea that “singing lessons” were for failures. If you weren’t naturally talented, there was no hope.
But a few years ago, I got over myself enough to take some lessons, and I’ve loved it ever since. I’m not the greatest singer in the world. But I’m more able to put myself out there, and now I don’t have to sweat bullets should I ever find myself in a karaoke bar.
It could be business, music or tech…
…but for anyone who dreams of a different life, however that may be, they owe it to themselves to give it an honest go.
I want to be a skilled singer. I want to be a science/tech YouTuber. I want to be a self-sufficient entrepreneur.
It sounds terrifying. I might fail. In fact, most of what I do probably will. But finding out is the exciting part. Certainty is overrated; more of it comes from observing first-hand what doesn’t work rather than trying to figure it out in advance.
I’m not going to stop being careful.
But I’m done waiting for certainty to give me permission to begin.
To all who are reading: I hope you’ve had an incredible 2025. Here’s to a truly fantastic new year, and to an epic 2026.
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Sometimes you don't know what you're looking for until you find it