Rather than regret minimization, I prefer to focus on try maximization. IE try as many new things as you can.
Obviously there are some things that you should never try. Things that you find morally objectionable. Things that have too high a risk of death or permanent disability. Things that will keep you from fulfilling your responsibilities (wife and kids will slow you down). You have to do your own maths on those, but beyond that you should try as many new things as you can manage.
You will fail. You will fail a lot. That's part of the fun.
As a 50 year old man, with four grown kids, in the middle of a divorce after 25 years of marriage, sitting at home with a leg I broke skateboarding last month I can honestly say that I have very few regrets so far. I travelled through a lot of Europe and most of the US before marriage, I've had interesting work, and I've learned how to do a lot of things just by being willing to try.
Remember, failure is always an option and is the expected outcome at least 50% of the time. If you're not failing, then you're probably not trying anything new.
I love this mindset and it sounds like you've lived quite the life so far. It sounds like you have a lot of stories to tell, and I think story-maximization is another good life strategy.
Your thoughts on failure remind me of a twitter thread I read yesterday by a new parent watching their baby try and learn to walk. I haven't had that experience yet myself, but it sounds like you might have. Babies are extremely determined and have absolutely no fear of failure during that phase. It's too bad so many people forget that attitude later in life.
Obviously there are some things that you should never try. Things that you find morally objectionable. Things that have too high a risk of death or permanent disability. Things that will keep you from fulfilling your responsibilities (wife and kids will slow you down). You have to do your own maths on those, but beyond that you should try as many new things as you can manage.
You will fail. You will fail a lot. That's part of the fun.
As a 50 year old man, with four grown kids, in the middle of a divorce after 25 years of marriage, sitting at home with a leg I broke skateboarding last month I can honestly say that I have very few regrets so far. I travelled through a lot of Europe and most of the US before marriage, I've had interesting work, and I've learned how to do a lot of things just by being willing to try.
Remember, failure is always an option and is the expected outcome at least 50% of the time. If you're not failing, then you're probably not trying anything new.