Back in the 1990s people were just starting to apply mathematical models and computer power to finance. Because it was new, simple techniques could make lots of money. Now many of those techniques have been largely arbitraged out of the market.
If I could go back to the 1990s I’d apply what modern quantitative techniques and make piles of money. Move over David Shaw!
These are fun exercises. It's fun to think about the different paths that could have taken. What is worth considering is that if you like where you are now, there is no other path to this point. All of the events and decisions, large and small, lead you to this point.
If we did go back and change something, especially something major, our lives would be different, perhaps very different. For example, if I really had been a finance quant back in the 1990s, my life would have followed a very different course. There is no way to know whether my life would have been better or worse.