I don’t think people consciously realize this, but one reason downwind jobs like churning out Java for a bank pay so well is precisely that they are downwind. The market price for that kind of work is higher because it gives you fewer options for the future. A job that lets you work on exciting new stuff will tend to pay less, because part of the compensation is in the form of the new skills you’ll learn.
PG’s essays are usually good, insightful reads, but this blurb just jumped out at me.
His concept of Upwind vs Downwind is about maximizing your potential. If you’re upwind, you have many possible paths forward (since you haven’t specialized yourself into a niche). While you’re downwind, you don’t have as many doors open to you, but you should be making the big bucks.
I find myself in an “other” category, since I don’t consider myself in a high potential upwind or highly compensated downwind position. I’m downwind yet I’m making peanuts. My solution to this is to gradually get upwind by expanding my skills (reading about UXD and RoR) over time.