I have found that I can't actually plan with much certainty, and, quite often, the very worst thing that can happen, is that Everything Goes As Planned.

I have found utility in "overengineering" my life. Not just the tech I do, but in most things, and creating small, robust, high-Quality, and adaptable structures. Things that can be rearranged, and repurposed, when (not "if") the context/paradigm changes.

I started maxing out my retirement in 1990, and that's a good thing, because, in 2017, when I finally started looking for work, I was surprised (and disgusted) to find that no one wants to hire us olds. I wasn't planning to retire, but I wasn't consulted by Reality.

In my work, I have found utility in writing in modular fashion, and making every module as high-Quality as possible. I've had to toss quite a few, and had to do substantial refactoring on some, but, for the most part, they have served me very well, and continue to do so, to this day.

In a similar fashion, I try to address all sorts of corner cases in my code, to the point of being called obsessive by some colleagues - but it definitely helped a few times with really stubborn and obscure bugs.

An extra log line here or there, or an e-mail sent to the admin in weird situations, goes a long way - provided that you don't generate many false positives, because no one pays attention to a program that cries "binary wolf" too often.