What happened
Somewhere along the way, I’d started to think of myself as an old bloke slowly winding down towards retirement. Not consciously, and I don’t remember ever making a decision that the difficult career moves were behind me, but I think I had started to assume that was just what happened next.
Then work got messy.
I’d been at a large critical infrastructure company for about two and a half years when the business decided the move towards Agile hadn’t worked the way they wanted. The whole Agile practice was put at risk while they worked out what came next, and that dragged on for months and months.
During that time, I watched some very good people leave. As they went, more work and responsibility landed with the people who remained. The pressure kept increasing at the same time as none of us really knew what our jobs were going to look like — or if we even had jobs.
Eventually we were told the organisation was moving back towards a more traditional waterfall model and that we’d need to apply for jobs in the new structure. The problem was there still wasn’t a clear timetable. We were still “at risk”, still waiting, and still didn’t really know when anything was going to happen.
That was the point where I decided I’d had enough of waiting.
It wasn’t some dramatic flash of inspiration. I just realised I hated feeling as though somebody else was in control of what happened to me next. So I started looking.
Age was definitely part of the calculation. I was 52, and I did wonder whether I was getting close to the point where changing jobs might become harder. I was working for a very large company and, however uncertain things felt internally, there was still something reassuring about the size of the place. Leaving might mean giving that up.
But I also started thinking about the other side of it. Would waiting another year or two actually make me safer, or would I simply be older when I eventually had to make the same move?
Once I decided I was leaving, I felt noticeably calmer. Nothing had actually improved yet. I hadn’t found another job and the uncertainty hadn’t disappeared, but I felt like I’d taken some control back.
Then something else surprised me.
When I started looking at jobs, I found myself being matched against roles that were more senior than the ones I had been doing. I initially rejected these. At this age, I thought, I was supposed to be reducing stress, not signing up for more of it.
But my children were older now. Family life wasn’t as demanding as it had been ten years earlier, and I suddenly had more room to commit to work if I wanted to.
Eventually I stopped rejecting those roles just because they looked bigger than what I was used to, and I accepted a senior role.
To say it was stressful would be an understatement. I was working 14-hour days, reporting daily to the board, CEO, CTO and heads of department, and the pressure was relentless. We achieved what we needed to achieve, but after five months I knew it wasn’t sustainable.
So I decided to move again.
That scared me more than the first time. I’d only just changed jobs and now I was doing it again. I was convinced it would look horrible on a CV.
I went back into the market anyway, and once again I found myself being considered for jobs that were above the level I had thought of as “mine”. I ended up being offered two roles in the same week. Senior management roles. Big jobs. Could I? Should I?
I ended up choosing the one that looked like the bigger mountain to climb.
What changed in how I judged it
And that’s probably where the realisation landed.
The horrible job in the middle had taught me something useful. I hadn’t lost my appetite for challenge. I had lost my tolerance for relentless pressure, chaos and being treated badly. Those are not the same thing.
Challenge still energised me. In fact, I think it energised me more than I expected.
Somewhere along the way I had started to convince myself that I was slowly becoming somebody who should be winding down. I’d had some serious health problems, and somewhere in my head I’d started linking those with getting older and slowing down.
The last year has been one of the most unsettled periods of my career, but it has also moved me forward enormously. My salary has increased by around 25%, and that extra income is one of the things that has made earlier retirement planning possible.
I stopped assuming that getting older automatically meant I should want less challenge. What I actually wanted was a better kind of challenge — something difficult enough to be interesting, without the chaos and pressure becoming destructive.
That distinction turned out to matter far more than I expected.
The question I’d ask myself now
Have I genuinely lost my appetite for challenge, or have I just lost my tolerance for bad pressure?
And maybe another one:
Am I slowing down because that’s what I really want, or because I’ve quietly started telling myself that people my age are supposed to?
The jobs that appeared, the risks I could take and the things that mattered to me were specific to my circumstances. The useful bit is the question, not copying my answer.