Did I underachieve in life?

100%!

Also be weary of the potential (IMO) misleading hope that further degrees are useful after a certain age / point of your career.

As a general rule, the “younger” you do this in your career (i.e. the shorter your career), the better your potential benefit, especially if you change jobs. Just simply because recruiters and potential hiring managers will use your degrees to judge your capabilities instead of evaluating your actual capabilties - it’s just easier for them to do so.

Additional degrees after a certain age are not detrimental, but after having reviewed probably thousands of CVs I would look at these exactly as @Burningstone decribes them: not helping you much careerwise, but perhaps interesting to you personally. At best, the hiring manager would conclude that it’s perhaps a good sign that the applicant is interested in further educating themselves, even if it’s not for an immediate career advantage.

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What made you feel so guilty?

I was the top 1% of students at the university but that was because I was so poor that I wouldn’t be able to afford to study without the tuition, and with 30% unemployment rate back then in Elbonia, and a general poverty in the country, that was my to be or not to be. I was feeling guilty of pursuing the easiest faculty instead of the one I was really interested in and self-studying. It took me something about 20 years to finally realize that university didn’t matter at all, for me it was just low paying job (but stable) allowing me to study for the career I wanted.

Speaking about career… I felt into the trap of “things going fine” in Elbonia, where I got a job paying enough not to worry about basic things, and since I was still relatively young, I wanted to enjoy my life finally… so I wasted another 10 years only to migrate to Switzerland with something like 20k CHF wealth in the age of 36. I don’t regret the move at all, but I also don’t regret any more that I’ve spent so much time in Elbonia whilst I could have started a living in The West so much earlier.

It takes time but with age things starts looking different. We have highs and lows, it doesn’t really matter from the perspective.