I took some time to think about this over the long weekend after watching The Matrix and thinking about Neo's choice of which pill to take. I cogitated over choices I made in my life starting in my teen years and how they guided me to the life I live now and the responsibilities I have taken on based on those decisions. They say you regret the things you didn't do, but I cannot say that I agree unless I were a time master and could see the timeline that "would have been" based on the choices I didn't make.
Please feel free to provide a comment with your answer.
If you knew then what you know now about the IT industry (how it would change over the years, and the hours you would dedicate to it over time), would you make the same choices you made and do it all again?