On TechCrunch, James Altucher identifies himself as a screw-up, proudly. If you are trying and doing a lot of things, the odds are you will screw up.
And, in the breakthrough book "The Hypomanic Edge," John D. Gartner hammers that America was founded by a bunch of screw-up Puritans. Misfits in the old world, they had no choice but to try to survive in the new one. The result was the most successful economy ever.
Also, as we all know, if Steve Jobs hadn't been fired, he wouldn't have matured into the kind of thought leader and businessperson he became.
Therefore, it makes no sense for working Baby Boomers to be articulating or losing sleep over regrets. They should have gone to medical school. They should have taken the overseas assignment in China. They should have not made an enemy of so-and-so.
Not only is that a waste of time. After all, it takes mistakes to clarify our options. Living in a world of regret positions us as losers - and boring. No one wants to hear that. What they do want is to understand what you learned from those experiences. Professional survival in the 21st economy is all about learning.