I was reading this Ask HN (https://news.ycombinator.com/item?id=1879530) from about 6 years ago and wondered what HNers regret. Not necessarily your views on the concept of regret but actual examples from your life. I mainly regret not taking university seriously half a lifetime ago, but as a result I became a lifelong self-learner.
Suggested related reading on the topic:
"In Praise of Missing Out: Psychoanalyst Adam Phillips on the Paradoxical Value of Our Unlived Lives"
https://www.brainpickings.org/2015/08/17/missing-out-adam-phillips/
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In the Ask HN link above, a guy says he opened an unread email two years late and saw it was from Facebook in 2009 wanting to hire him.
Similarly, perhaps, one of my regrets was having received an early 2014 email that I didn't open, from someone I didn't much feel the need to keep in contact with. In late 2014, I finally read it. It was an offer to be the personal guide to the US team at the World Cup in Brazil...
But there is one thing I can't shake.
I met a girl a little over a decade ago, and fell madly in love. We became a couple, but due to various events our relationship ended. Not least because at one point years ago, I was put on the spot and asked where our relationship was headed, a thinly veiled attempt to get me to commit. I loved the girl – still do – but I wasn't ready to settle down and marry. I wanted to focus on my career and build a business and do all of these other things and I just couldn't commit. Not long thereafter, our relationship ended and I relocated to a different country.
It's cheesy and unoriginal, but it's the one thing I regret: not marrying that woman.
Before anyone comments to that effect: I don't have a particularly hard time dating, and have plenty of experience both before and after this woman. But I've never connected with anyone like that before, and it genuinely feels as though I've lost someone hugely important, like family. It's a very sad feeling and cheesy as it may be, it's my only real regret.