I was a system administrator for a small services firm. When I started in 1997 there was easily enough work to fill 40 hours per week, but as time went on, I smoothed all the issues out, and the actual workload slowly dropped. Additionally, there were some issues with the in-house database (Smiley) developed by the consultant I replaced.
Since I had quite a bit of free time, I attempted to address those issues with a system wide upgrade, which would have saved quite a bit of time for the accounting department and others... but due to risk-aversion, they didn't adopt the changes... so I tried again later... and by attempt #3, I had a new version running which kept sync with everything in the legacy version.... and they still wouldn't bite.
In the end I was showing up, making sure everyone's computers were working ok, and then waiting for things to break. The 3 attempts to upgrade Smiley took all initiative I had at self-starting, and broke me. It's more than a decade later, and I can't find the self-confidence to stick to any long term projects.
I learned a lot of things, having essentially a decade of free time to pursue any rabbit holes I cared to, back when Google actually worked. But thanks to the anti-incentive with Smiley, and a case of Long Covid and the accompanying brain fog... any progress on personal projects is scatter-shot at best. See my frequent mentions of BitGrid here, for an example.
That's probably the main reason I left what was otherwise my best job. I knew that if I stayed longer, I'd never be employable anywhere else, both because I'd have stopped learning, and because I'd have grown too comfortable/scared to move.
The other problem with an easy job is the boredom. If you are in office or even remote but present, remaining engaged but bored for 8hrs/day is torture.
