I'm about 60. My early life left me with no confidence that I would make it this far, so by the time I was 21 I was getting ready to die.
What it's been like to grow old
* My body's in officially lousy shape, but I don't feel much worse than I did at 21. Sure, arthritis makes music harder, and being fat makes it hard to tie my shoes. For some reason, though I know I should feel worse, I don't really.
* When you literally wake up glad to be alive every day, and I have done so for half a century, minor things like your body betraying you or someone else's political leanings take on much less importance.
* I am never, ever bored. There are so many things I want to learn, so many products I want to create. I have never known a programming language so well that it bored me, because I always used them as vehicles to get something interesting done. They are tools to me. Like any craftsperson, good tools are important but they are always subservient to the product.
* I have been fighting a losing battle with weight for 50+ years. It's terrible. I am ashamed that I'm morbidly obese and dependent on diabetes and high blood pressure pills. Every time I go out I'm embarrassed to be fat. Every thin person I see is a rebuke, unless they're smoking. (To me smokers are honorary fat people.) Don't fucking tell me to eat right and exercise right and sleep right. I fucking know it. It's just hard and I never stop trying.
* I have been a horrible insomniac for 55 years. I figured by now there would be a cure for it. A good night of sleep for me is 3 1/2 hours. A bad night of sleep is 20 minutes. 3 1/2 hours is not enough for me to feel good for most of the day but it's enough to get essential work done.
* After a traumatic brain injury when young, my memory went bad. Consequently I have always been a slow learner. I have probably suffered some cognitive slowdowns but I don't notice them at my age. Learning is hard for me now, but it was hard for me at 21. I just have to work harder than anyone else. Fine with me! I chose work I enjoy.
* I still have absolutely no problem pulling all-nighters when the project interests me.
Things I saw that other people didn't seem to see as much
* By the time I was 14 I had observed that SV-type jobs were cyclical. Even though I wasn't tech-oriented then I realized if I ever got into a tech field I'd have to keep up in order to remain relevant. Decades and many millions of dollars later, I still keep up. I have worked for myself for the last 21 years but I still act as if I may need to get a job at Google tomorrow. I still study every night (in my case, Go, py4web, and database infrastructure).
* Whenever I got a job, I assumed things might get bad so I always stayed within bicycling distance in case there was a gas shortage or something.
* I saw that two-income families often contained two people who came home with a need to share their stress, but also take care of the kids. This results in neither one wanting to listen to the other, and the resulting tension harms family life. So I made a deal with my wife that one of us work, and one stay home. Didn't care which one (turned out that I was the worker, and we both like it that way). Also I married someone who understood that sometimes I have to work hard. We planned to be poorer than our friends, but the opposite happened. I was able to get ahead by studying at night and trying out different ideas.
* From a very early age I saw that some people got hit hard by "unexpected" events like high medical expenses or business failures. I knew I would either have to safe very carefully (like Asians, who make up most of my family) or be a good earner. I ended up being a good earner who doesn't save as carefully as he could. Result: I spent $40K/year on insurance premiums and can easily absorb it. I own several houses outright and have no debt.
* I never had a "special" way of treating women I dated. There was never a me-who-buys-flowers vs. a me-who-ignores-her-once-we-get-married. I always dated women I liked to be with during daily activities, like shopping or doing the laundry. I just never take the people close to me for granted. Of course I buy flowers for my wife after being married 30 years, and it's always because they look like good flowers, not because it's a day merchants tell me to buy them.
* I read history. I understand how long empires last. I love America and its values, but I fear the mob. So I own lots of guns and have always lived in places that felt defensible.
* You know those old movies and stories where the person is given a second chance on life and appreciates people around in a new light? I have always been that way. My wife, not so much. So we see our children differently. To me they are enormous treasures and (not recommending this, it's just me) even though they're all adults I live in abject fear that something bad happens to them.
What would I advise younger people to do? Well, my most successful idea, I think, was to figure out by 25 what my core values were, because everything comes out of that. In my particular case, it went:
* No one cares about your job more than you do. For me this led to the understanding that I should start my own business. You don't have to and, more important, may not want to! But I feel it's less risky than working for someone else. If you don't do that at least save up for a rainy year (below)
* Be a decent citizen
* Treat people different from me with respect
* Try to admit when I'm wrong
* Treat my kids with at least as much respect as I would treat Bill Gates or a cop or a waiter, and be as polite to them as I would be to anyone else
* Do work that wouldn't embarrass my kids if they told their friends about it
* Being rich is good because it helps with independence and safety buffers, but it's always subordinate to taking care of the people I love
* Expect people to be motivated by their base instincts, and by incentives. People are neither natively good or bad, so be ready for them to be bad. That means understanding your core values and sticking to them
* Take logical risks you can afford and be ready to learn from them
* Feel free to cut harmful family members out of your life. I will guess that I went through more than my share of bad stuff when young. This left me with a very simple rule. Family is important, but it's also what others make of it. I would give family members who harmed me an explanation of why I felt bad, then ghost them if nothing changed. Nothing ever changed. Do I feel bad after they died? Do I feel like I should have connected better with the people who raped or beat or neglected or abused me or accused me of horrible things I didn't do? Absolutely not. I have never regretted removing harmful people from my life, family or not
* When you're evaluating doing something big, the more you like it, the more you should try to talk yourself out of it. You should be super honest about both the potential upsides and the potential downsides. Project what would happen to you a year after the worst or the best happened
* Expect bad things to happen. Easy for me to say now? Sure, but I was totally ready for Covid by the year 2000. Completely. So were observant Mormons and many Chinese people
* Avoid debt
* Have at least a year's living expenses saved in case of unemployment, unrest, etc.
Obviously YMMV, but because I wanted nothing more than to escape from my childhood home/school life, by 13 I had read autobiographies of famous achievers and had crystalized these values based on their successes and mistakes. I developed as a way of escaping the present. It was either that or kill myself. I'm very glad I didn't kill myself but I needed some logical reason to have hope.