We know good decisions are independent of good outcomes. One makes a good decision with the facts and options available. The outcome is out of one’s control so one must believe the process of repeatedly making good decisions will lead to good outcomes more often than not.

What about regret? If I believed in the process and was fully aware of the fact that ‘this might not work’ then a bad outcome should not dissuade me or make me question the decision. Looking at base rates on starting a business or investing in a stock should make it a clearly difficult endeavour.

Such is theory but in practice, I find feelings of regret often come out from a bad outcome. This regret might be even more prominent from not making a decision I wished to make but opted for the other and suffered a bad outcome. One where what I believed to be the good decision at the time wasn’t followed through with.

The logic being that, at least if I chose the option I thought was right at the time, I may not have regretted a bad outcome. Even if it turns out, the human in me will still toe that line of regret at a bad outcome of what seemed to be a good decision at the time. Fixed environments in games (i.e. chess, tennis) can make it clear relatively quickly if something was a good decision or not but in the wicked environment of career, business, and investing….it seems the passage of time is required to reflect on whether the decision was good or not. Mainly because of how life plays out slower than the seconds and minutes inside a game.

To put it plainly, most life decisions can’t be judged until a significant time has passed and life has played out a bit. This was the thought exercise resulting from discussing past big decisions I made in my life with a few close friends. The decision regarding education.

The first indication of this for me was in my first big decision. Where to attend high school. For most this isn’t a choice when they are 12-14 as it depends on the geography but for me, it was a choice. I choose an all-male private school and I regretted and hated the decision for most of my five years there. It wasn’t until I graduated that I was grateful and glad about my decision. This decision has continued to compound and nearly ten years later and I’ve grown to be extremely grateful I made the decision. I also won’t know what my other choices would have led to but I would never have gotten into powerlifting nor would I have cared so much about human psychology and creating if I hadn’t gone to that high school.

The same can be said about what to study at university. I regretted and lamented my decision for years. The cycle of seeing faults clearer than the good continued. Even years afterward, I regretted the decision to study accounting. It’s only been recent that I started thinking maybe it was a good decision for me to study accounting ten years ago. I don’t know what paths the other options would’ve led me down but I’ve come to realize that even if I had gone on to take that engineering scholarship to be a mechanical engineer, I probably would’ve left it eventually. Whether it was accounting or engineering, I think I would’ve left either profession so that wouldn’t have mattered. But I don’t think I would’ve learned to appreciate investing as much if I had gone into engineering. Others have and I might’ve. But I’ll never know and I don’t need to know. I know that the decision to study accounting led me to discover Buffett in my 4th year and that’s been a major turning point in my life. Though I had left being an accountant seven years ago and felt the time to have been wasted, I now feel they were all crucial for me.

Maybe it’s the side effect of aging year by year but I am starting to think that “time cures everything”. Some say the ‘god' people worship is really time. Time seems to be the unforgiving element that reveals all truth and I wonder if this is the case for decisions as well. Most decisions compound and one needs to look back over a period of 5+ years to get a glimpse of whether it was right or not. Most times, it’s right….but maybe it’s not about whether the decision was right or not but rather if it’s one we should be grateful we made and no longer have to regret. Apparently, one of the things people on their deathbed say is that they regret not doing things they wanted to do but they don’t regret things they did that had a bad outcome. I think time helps with looking back on our decisions.