Almost every time I’ve made a major decision about how to spend my time, I’ve later thought to myself, “Man, if I had done my homework better on this decision, I would probably have made a better call.” Not that I think most of my decisions were bad—I think many of them were probably a good call anyway—just that they would have been improved (in expectation) by more thoroughly trying to learn things like:
- what sorts of options I had
- what were my main uncertainties about their goodness
- information that would resolve those uncertainties
This phenomenon has persisted despite me being aware of, and trying to correct, this tendency not to do enough homework. For instance:
When deciding which colleges I wanted to go to, I ruled some out (notably tech schools, e.g. MIT and Caltech) based on the general principle that I wanted to have classmates with more diverse interests. I think I probably ruled them out based on insufficient evidence.
When I decided to go to Harvard, it was mainly on the basis of getting much more financial aid there than I did elsewhere. I didn’t go to the revisit weekends for any of the other places I got in. I think Harvard worked out extremely well for me, but that again I could have done a lot more evidence-gathering. I also didn’t sufficiently consider the option of taking a gap year.
When picking classes at Harvard, I browsed the course catalog a lot, but I didn’t make much of an effort to seek out older students with similar interests/background to me and get their opinions. I think this led to me missing out on a bunch of interesting classes (mostly humanities) and taking a few classes that were too easy or superficial (freshman math and computer science, lots of “general education” courses).
When I was applying for summer internships during my freshman year, I only applied to two (Fog Creek and Khan Academy) based on things randomly being salient to me. I should have been way more systematic about this.
I got an offer from Fog Creek midway through interviewing with Khan Academy and accepted largely on the basis that Khan was taking a long time to move me through the interview process and wasn’t asking me very many technical questions, so I inferred that Fog Creek would teach me more technical stuff. This inference was pretty clearly unsupported; Khan seems like a great place to go to learn technical stuff.
In college I tried to become a research assistant for a couple professors. Both times I got offered relatively boring projects and ended up either flatly turning them down or not doing very much on them. Again, I picked these professors based on not-very-strong reasoning like who I was aware of at the time; I should have made much more of an effort to find people doing interesting work.
During my sophomore year I was part of a team that won some money in an entrepreneurship competition at Harvard. I decided to spend my summer working on our project. This didn’t go very well because (a) nobody else from our team was working on it full-time; (b) we didn’t have a very good idea of what we were building; (c) two of the team members didn’t see themselves working on it full-time essentially ever; (d) we didn’t have any users to give us feedback. All of these things were trivially foreseeable if I had tried to spend some time thinking about why startups tend to fail.
Many of my decisions at Harvard were guided by my “academic taste:” what kinds of skills I thought would end up being important, what kinds of research projects I thought would be interesting, etc. Unfortunately my taste changed a lot, and I wasn’t usually very sure about it. I think if I had tried harder to develop strong views about what kind of things were important to work on, it would have improved a number of my academic decisions.
Again, most of these things worked out pretty well in the end. But in each case I think there would have been pretty high returns to getting more information about my options and doing more to resolve my uncertainty about them.
Comments
As a contrary point of view, there often is a point of diminishing returns when evaluating fine differences in colleges. Once you get to a certain degree of quality—it’s clear that some colleges are obviously holistically better than others, but when it’s time to compare within a quality band—the experiences of a typical high school student simply don’t prepare you to make a real and informed decision or even to ask the right questions.
By analogy, during my university’s fraternity recruitment, all the fraternities tried to sell themselves on the quality of their brotherhood. However, that is something whose value is only understood after you’ve picked your fraternity and experienced it for yourself: most incoming freshman do not have analogous experience we could appeal to. Instead, there’s a reason why fraternities compete on who has the hottest women and best booze: those are metrics you know your audience understands.