If you were able to split time and replicate yourself, where would your paths take you?
I would probably have taken the risk of starting my own firm two years ago. This would be instead of taking the safe path with a great paycheck and minimal risk, but with a lower upside and less freedom. It would be hard to envision a life without the kids, so this would be the most obvious "fork" I could've taken in my life and one that I most think about.
If you were to sit down with the much older and different yous, what might you discover?
Older/future Joe would probably just tell me to run with it. I have slowly learned this as I've grown older. You can't do everything you want to, but if you are happy more times than not, you're doing well. Make the most of what you have, improve on what you can, and learn to let go of regret as you wouldn't be where you're at today without all of the decisions you've made.
I agree. As long as you're happy more often than not, you're doing well. Ups and downs are natural in everything and you can't appreciate the ups as much without the downs.
you wouldn't be where you're at today without all of the decisions you've made
You make an excellent point. Regret can certainly eat you alive. If we are able to objectively observe our own past, we can uncover hidden lessons from these regrets. There was some reason for this "wrong" choice, and like you said, every single decision you've ever made is what defines you and your current place in time.