The Setup

A friend of mine had good connections to get interviews to work as an investment banker when he graduated from college. He didn’t take advantage because he didn’t want to work 100+ hours a week. Instead he has worked a variety of jobs that he hasn’t been very happy with, and occasionally laments not giving Wall Street a chance.
Today I was pulled into an email discussion about whether or not recent market events should make him happy he chose the path he did. I was alone arguing that even if he was currently losing his fortune and at risk of losing his job he still might be happier had he been an investment banker. The two arguing that he was better off not giving his life to his job at 23 are two of the most career oriented people I know under 30. I pointed out the oddity of our positions, considering I was sitting at a coffee shop by the beach at 11:30 on a monday morning, and had bought my refreshment with student loan money.
The response was that the grass is always greener on the other side. Finally getting me to my point.

The Best Email I Wrote Today

The grass is pretty fucking green where I’m sitting.

A Tangent

Suppose that my friends overall happiness since graduating from college is higher than it would’ve been had he been an investment banker. Let’s also suppose that his overall happiness would have been higher had he been a rich Wall Street type and the financial collapse didn’t happen (so the current path is better soley because of the financial collapse). Did he still make the right choice?
My point being that looking at decisions in retrospect, is it fair to judge them with full hindsight, or should they be judged by what we knew at the time? I would argue the latter.
It’s also a nice example of how the black swan theory can be applied to personal decisions. If you decide to follow road A, imagine some horrible scenarios that the road could take you to (like devoting your life to a job just for money and then losing everything). Then consider the likelihood. Even if the chance is small, if it’s bad enough you might want to take road B. Of course the same considerations should be made about road B.