Yesterday I chatted with a friend who is navigating a job change. He’s very good at what he does and has several options, which I am hoping will cause a bidding war for his talents. But still, the situation is difficult for him; it’s a big decision and he has lots of different factors to weigh with lots of uncertainty.
This has been a surprising realization to me as I’m now more or less an adult. The most difficult thing is not in getting what you want, but in knowing what you want.
I didn’t realize this as a young person. It felt clear to me in high school that getting good grades was better than getting bad grades1, or scoring goals was better than not scoring goals, and so the difficult thing was studying for the physics test or running sprints on the hot artificial turf. The difficult thing was getting what I wanted.
As I’ve grown up and have a bit more self awareness and a lot more control over the ways I spend my life, I’ve found this has flipped and that understanding what I want, what will actually bring me happiness or fulfillment or whatever it is I’m actually optimizing for, is a much more challenging problem than getting what I want.
This may be because I’m an indecisive person but I expect it’s quite common. Limiting ourselves to careers (although of course this applies to everything in life):
I have many friends who have comfortable lives but are listless and directionless and have a strong yearning for purpose.
I have 1 friend, that I know of, who has a clear, long-term career goal he is working towards. This friend seems much happier in his work life and is making strong progress towards the goal; I have no doubt that he will achieve basically what he set out to do.
A common way I see the difficulty of knowing what you want expressed is an intelligent person who is having a “quarter life crisis.” In deciding what career to pursue, they face a tradeoff between many factors, but two of the most salient seem to be prestige and lifestyle:
Let’s assume they’re (un)fortunate enough to have had the cultural indoctrination to even know what these jobs are and to have a rough sense of this chart in their heads (universities and business schools do a good job of this). They know that investment bankers work a lot but make a lot of money and wear fancy clothes, software engineers make a lot of money and don’t work so much and don’t wear fancy clothes, etc.
They still must choose which one of these suits them best (in economics terms, what their “utility curve” looks like). Do they care a lot about prestige, and are thus willing to trade off their lifestyle to be in BigLaw? Or would they rather have a little more balance and be a tech PM, or a lot mellower lifestyle and be a software engineer?
How would they know?
How much do they hate getting work emails at 11pm versus how much do they like flying in business class and meeting CEOs and pronouncing it “fin-ance?”
I suppose there are two different strategies to deal with the difficulty of knowing what you want. The first is to get better at introspection, so that you understand your own preferences better. This is mainly the route I’ve taken, through things like meditation and writing and lots of navel gazing. It’s mostly been helpful and I think I have a better sense of what I care about than I did 5 years ago.
The second strategy is to stop worrying about optimizing and just choose something and commit to it. This strategy implies that the true value comes in investing deeply in something and going all the way with it, no matter what that thing is. I think this view is gaining popularity as a reaction against millennials’ tendency to always choose optionality. I liked the book Four Thousand Weeks which nudged me closer to this viewpoint.
In retrospect I realize this is much less strictly true than I thought it was then.
Thank you, Joe
To continue, getting satisfaction and joy from work involves commitment to it, which means giving up many other kinds of work that might also have brought satisfaction and joy. That is what I used retirement for. But even in retirement choices must be made--to get, one must accept giving up. I regret that trying to have it all results in having very little.