While tempted to engage in “if I had only” thinking, I realize that there are problems with it.
First, there is the question of free will. It seems clear that any claims that “I could have chosen __” are based on claims about a version of free will that I just don’t feel exists.
Second, wishing that you had made a different choice is the type of fantasy thinking that is involved in troublesome time-travel ideas. We imagine the world to be exactly as it is/was while only modifying one thing. In other words, we can’t pretend that we can identify the scope of what would be different if we had made another choice. Saying that I wish I had done x is to say that I wish I had done x, but that every other thing that my choosing y had influenced and created would not exist.
Third, we’re just not able to understand the consequences of any decision we make. We can only catch glimpses and pretend that we understand. Did I make a good decision by choosing to do x? It might appear to be a horrible decision. But I have no way of determining what this decision really means.
If my wife decides we really need red peppers for a salad and she asks me to drive to market to get some – and I am killed by a drunk driver who blew a red light, she might spend the rest of her life regretting that decision. “Why?” But how often do we arrive home safely from the market and celebrate that return?
When I failed out of my first attempt at college during my first semester, I beat myself up for many years. But working for two years and eventually getting back to college only to meet my wife-to-be makes it seem that my decision to slack off originally was a “good” thing. But I think these are constructs that have little justification. It’s my mind putting together clean stories that I can use to encourage the concept of agency and make sense of my life.
When I am in a clear state, I like to think of that classic story about the farmer whose horse ran away. When his neighbors found out, they said “how unlucky”. He replied, “maybe”. Soon, his horse returned and was joined by 3 wild horses. The neighbors said, “how luck”. He replied, “maybe”. The next day, his son was thrown while trying to tame one of the horses and broke his leg. The neighbors said, “how unlucky”. The farmer replied, “maybe”. A few days later, soldiers came by to demand that all able-bodied men join the fight in a war. His son with the broken leg was not enlisted. The neighbors said, “how lucky”. The farmer replied, “maybe”.