The other day, while lying in bed, my wife asked if I knew then what I know now, would I do it all over again (with her)? Besides the fact that that is a completely loaded question with only one 'right' answer in that situation, it's still a good question. Personally, I'm not one to rue past decisions, but I know if I knew then what I know now...
- I would have met and 'succeeded' with more girls when I was younger.
- I wouldn't have feared committing to the one I was with to see where it went.
- I would have traveled even more than I did.
- I would have capitalized on more work opportunities, to make the most of them.
- I would have worked harder in identify life passions at an earlier age.
- I would have started playing poker at a younger age, not to become a pro, but to have better used my superior focus back then.
It's usually not a positive step to second guess your life decisions too much because they shaped who you are today. Sure, your life could have gone in different directions, but there is no guarantee it would have been better. Obstacles and unexpected diversions exist on whatever path you take. Your energy is better spent evaluating your choices now and where and why to shift course now.
Over the last couple years, I've talked to several high stakes cash game players who used to kill the highest online games back in the day. Somewhere along the line they got off the fast track. Sure, they could look back with regret on that decision, as they've likely missed out on making tons of money, but they changed course to introduce other aspects into their lives. They changed course to create more balance in their life. They changed course to reduce their stress and variance. They changed course to try new challenges. Once you get off the fast track, it's awfully difficult to recapture that momentum, bankroll and confidence. The old saying is often true, "you can never go back".
It can be a fun exercise to wonder how things might have been different if you knew then what you know now. I know I've had countless dreams where I revisit high school and college years with that knowledge and experience. But you do a better service to yourself focusing on where to go now with what you know.
And if you were wondering, I said "without a doubt I would do it again. These have been the best years of my life!"