Having feelings of regret on things that clearly went wrong, whether in trading or other matters of life can be powerful instigators for self-reform.
The first step is to accept the factors that led to feelings of regret, but then it's important to realize that:
1) some things are just out of your control, and
2) it's possible to find fault or envision a more ideal outcome at just about everything the more you go looking for it.
Instead of dwelling on factors out of your control, such as an unexpected piece of news that moves the market against your positions, or stressing out over the fact that you could have made a killing using another trading approach, it's best to take a forward-looking approach to matters.
There are in fact a myriad of outcomes in both your financial life and general life (some of which are of course intermingled), and it's easy to second-guess yourself based on observed outcomes. For example, a person who joins a large company might be the envy of startup employees for the work-life balance that they enjoy, only to flip the script if their startup does well while the large company simultaneously undergoes a round of "right-sizing" (i.e. "layoffs" in laymen terms).
Moving on...
The process of evolution doesn't involve an active analysis of past factors or a conscious effort to correct past wrongs, but rather involves actively adapting to factors that one faces in the course of one's survival. Taking a cue from biological systems, in light of today's constantly changing financial markets, we too must actively adapt to the realities of our immediate surrounding conditions and data. That isn't to say that we should erase our memories of past lessons and failures, but rather simply accept present conditions for what they are and pave a course of action accordingly. Remember that since present-day conditions did not originate from a vacuum and are in fact dependent on past events and conditions, we are indirectly still impacted by past decisions.
If you missed your chance to try out for American Idol when you were 25 a decade ago, it's simply too late to do that now, but it's not too late to try out for Broadway! If you didn't hold onto that Apple stock from 2004, there's nothing you can do about it now aside from hope to learn from it in your next investment decisions.
Regret Minimization
This brings us to an interesting juncture in how to deal with feelings of regret. In deciding whether to pursue his big idea that would become Amazon, Jeff Bezos is said to have thought to himself something to the extent of "how will I look back at my life at the age of 80?" This article from Inc.com describes his thought process, dubbed "regret minimization." Note that his words are not necessarily a call to action to follow his particular path in life (i.e. entrepreneurship), but more of a general suggestion to reflect upon what will "ultimately" make you happy when looking back at things later.
The idea of projected happiness at a "destination" point in time makes me a bit uneasy though, as if to say that your present-day happiness is overridden by sentiments you formulate when you're 80 years old. For example, if someone who had an early interest in chemistry decides to pursue social work and leads a fulfilling life helping and meeting others, only to realize at 80 years old that they maybe should have tried to pursue a career in biochemistry, does that make that person's life any less fulfilling? What if the inverse were to happen, i.e. a person who thought they were leading an unfulfilling life their whole life suddenly realizes it was all worth it at the end - does that life of constant hardship suddenly become worthwhile?
I think the answer to both of these questions is "no." What matters most is the quality of one's daily life, which is a function of both present and past conditions. If one is able to reap the benefits of hardship on a short-term basis, maybe that life is indeed worthwhile, but should not be deemed worthwhile based on some realization many years down the road.
The best way to avoid regret is to therefore lead a life that's consistent with your beliefs and aspirations, where you can confidently place one foot in front of the other without being stifled by fear or overrun by aimless zeal. As they say, it isn't the end that matters the most, but the journey. I would contend that the same goes for careers, relationships, and even personal finance. On this last point, consider two scenarios:
1) You live hand-to-mouth for most of your life but win the lottery near the end of your life
2) You live with few material worries for most of your life but aren't guaranteed to have enough to be care-free near the end of your life
I'll leave this one up to you --which one is tragic, 1) or 2)? Your answer should help you decide on how to live your life.
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