That “funny feeling” of envy / jealousy only exists when the subject of our envy resembles us in some way. I don’t get jealous if Bill Gates has a big success, but I do get jealous if someone close to me in age / race / location does something very similar to what I’m trying to do. I don’t get jealous if a good friend becomes a marvelously successful chef, but I do get somewhat jealous if he becomes marvelously successful (or at least more successful than me) in my field of choice.
People who lead traditional career paths, then, have more people to compare themselves to. A young attorney has thousands of other attorneys around the same age and pursuing the same type of law against whom he can measure himself.
One reason I think envy is less pronounced in entrepreneurship circles is that entrepreneurs tend to lead idiosyncratic lives. It’s hard for a life entrepreneur to find another person whose path overlaps in a major way. Hence, fewer people seem directly competitive.
This has its downsides. Loneliness. You feel like few people can appreciate how you got here and where you’re going. And you lack easy benchmarks on how you’re doing in life relative to peers.
But there are upsides. You more frequently can Bask in Reflected Glory of your friends’ successes. Your drive to soar higher can come from genuine inspiration at others’ success instead of raw jealousy. The latter can incite action, but the former is more pure and sustainable.
Bottom Line: If you carve a unique path in life, fewer people (especially in your friend set) will seem directly comparable / competitive, and this will allow you to genuinely revel in their successes as opposed to being privately consumed by jealously.
(hat tip to Ramit Sethi for helping spark this theory)