Ask HN: What's Your Biggest Regret?

Going to grad school. Took on a bunch of debt, which would have been fine if I'd been able to pursue my original career choice. I got MS my last semester and am now stuck in the limbo of 'able to work so I can't get my loans discharged' but 'not able to do work that would PAY ENOUGH TO PAY OFF MY LOANS and not able to do the work I trained for'.

Possibly undergrad as well.

I think I would have done much better in the trades, honestly, but that was not an accepted/encouraged option in the early 00s. Especially for girls. My parents are still giving me guff for having left an office job.

I have been writing fiction for as long as I could hold a pen and always wanted to be a writer. But then computers happened and getting an interesting job was as easy for me as snapping my fingers.

In my early thirties I realized that unless I did something drastic, I was never going to be a writer. So I enrolled in a four year creative writing course. (Creative writing is not routinely taught in college here.) The place had a tough selection policy and was run by established writers with editors and publishers. It is probably the best place in my country to build a network and get noticed.

I did get indeed noticed and published a few short stories in a reputable magazine. Then the publisher (which is one of the most prestigious in the country) had a sit-down with me and told me they really liked my work but they wanted to see something more substantial, which is thinly veiled code for a novel. It was a come-on as big as they come in the literary world. And I fucked it up. I never took them up on their offer. I did not even try and write that book.

After a while my contacts dried up and the window of opportunity closed. Nowadays when I send something to that particular publisher it ends up in the slush pile of uninvited manuscripts (of which they receive over a thousand yearly). I don't blame them, but I do regret it.

Going to try and repost this comment because from what I can tell it was shadow banned, maybe for use of a word that triggered a filter?

Most of these I have made peace with and addressed in my life now, but historically, these have been my biggest regrets:

Becoming addicted to prngrfy and mstrbtion in my early teens and staying addicted throughout my 20s. I have been sober for years now, and for me, it was only possible through working the SLAA[1] program. I never actually knew it existed until a therapist suggested it to me; I wish it had been easier to find, but unfortunately whenever I would search for resources in overcoming prngrphy addiction, I would only ever really find places like the big sub with "astronauts".

On the one hand, I have spent more than half of my life addicted to prngrfy. On the other hand, I now have the gift of potentially being able to spend more than half of my time on this earth sober. The glass is definitely half full for me on this one.

Not learning how to dance until my 30s. I was once made fun of for dancing at a party as a young child (Being a lousy big brother to my one younger brother. This one probably hurts me the most and I still have not been able to forgive myself for it. Funnily enough, my younger brother loves me very much and we have a good relationship now, but when I think about all the ways I failed him when we were younger I just lose it emotionally. Working on this in therapy currently.

Not taking care of my body in my teenage years and 20s, and especially wasting all that free extra T[3] when I was going through puberty. I wish I could go back in time and drag myself to the gym when I first hit puberty! I do a wide range of physical activities now including lifting and I have a body and the kind of mass I never would have dreamed of before, but sometimes I like to imagine what I would have looked like now if I had started 20 years ago. Oh well, I can always see what I look like in 20 years' time!

[1]: My stubborn younger self would have written this due to the vaguely religious overtones of the 12 steps, but I'm glad that as a still-non-religious adult I was able to get out of my own way on this one and just focus on doing what I needed to do to get better

[2]: This is also how I found probably my most important adult friend group after the age of 30!

[3]: I will probably hop on TRT when I'm older and my T levels go down, so maybe I will get to experience something like that later in my life after all

Not getting a CS/engineering degree is my biggest regret. I would go back and get an engineering degree. I have 20 years of experience and I am a CTO. But even today CTO level openings need a CS/engineering degree from a brand name school. My resume won't make it past automated filters at top companies. When people say education and degrees don't matter, it just fills me with rage and regret.

I never felt real acceptance from my parents. Which made the first woman I fell in love with, who was very beautiful and sweet and totally accepting of me, nearly impossible to get away from once I realized that she was unsuitable for me to make a permanent (and sole) life partner. Cue many years spent seeing her on and off while trying to reclaim the same spark elsewhere and fucking up other perfectly-good (if never quite the same, and certainly less intense) relationships.

Unfortunately it seems that a lot of my… sexuality (this word seems like a vast oversimplification in this case) got tied up with her and is basically now gone, and I’m still processing this years later.

I did retain the self-confidence she gave me though, but the cost…