Ask HN: What's Your Biggest Regret?

My list of messing around:

- Back in high school, I read a biography of Bill Gates and found it cool to learn some programming. Back then we were taught FOXBASE but I taught myself FOXPRO because it is more pretty with all those Windows UI. I asked my parents if I could do some work for their university (they worked as professors back then) but didn't get any reply. I messed around for a bit longer but then my bad grades caught up so I never did any programming for a long while

- In university I got fancied by level design (big thing in late 90s/early 2000s), again only learned a few tools and made some samples. Never drove myself deep enough and gradually lost interest after a couple of years

- Fast forward maybe 10 years, finally mustered enough courage to teach myself C++ as game programming seems to be fun. Learned a lot and made a few simple games including half of a Ultima spin-off in 3 months. Life was a bit hard at the time so had to focus on getting a job and working as a salesman (really hate it).

- Worked hard to squeeze into IT as I still like programming. Wasted a few years on that sales job but eventually landed a BA job. After a couple of hops I managed to land an IT job (current one). In the middle married my wife and got a baby, but never truly found the focus/passion of life. Actually, the closer to my target IT job, the less passionate I'm. I still pick up hobbies nowadays (am reading binary analysis today) but don't really think I can drill deep in any of them.

In retrospect I was obviously depressed, but I took me nearly 10 years to understand why. My relationships with my parents and peers earlier in life had been so fraught that I became convinced I could never have a healthy relationship with someone. I had so little exposure to people whose relationships were healthy that the possibility hardly occurred to me. It’s difficult to describe what believing this for an extended period can do to a person.

I ultimately realized my mistake and set myself towards bringing more people into my life. However, in trying to correct this I made another mistake. I started taking finasteride in an effort to maintain my appearance, as I believed early baldness would negatively affect people’s initial impressions of me (particularly in romantic contexts). As it turns out, I’m one of the unfortunate few who have severe adverse reactions to this drug. Now, in addition to being socially and romantically inexperienced and out of shape, I’m also constantly fatigued, sexually impotent, and ironically still balding.

I again find it very difficult to imagine anyone, particularly a woman, would want anything to do with me. I see others my own age with families of their own now, while I have done nothing. It’s hard to manage the despair.