I posted a comment on the Hacker News thread “Ask HN: How do I stop comparing myself to others?.”
Society didn’t offer “Start a geek-centric Web service, then spend years quietly building it profitably, and do so while living in a dozen different cities” as a viable journey, let alone a valuable goal.
Here’s the comment:
Find a goal or even a yardstick that’s more meaningful to you than to anyone else. Ideally, also find a path to it that’s uniquely appealing to you.
It’s way harder to think about what you want than to hop on to society’s defaults (schools, work prestige, wealth, looks, ..). http://www.paulgraham.com/love.html touches on this (“if you admire two kinds of work equally, [choose the less prestigious]”).
When no one else is trying to accomplish the same thing in the same way, only absolute measurements matter: how close did you get? How much did you enjoy the ride?