What worked for me was two things: calculating my number and tracking all of my expenses. I did that listing everything that I wanted that would make me and my

What worked for me was two things: calculating my number and tracking all of my expenses. I did that listing everything that I wanted that would make me and my wife happy, calculating the yearly cost of those things, and dividing that by the average yearly rate of return for a plain old index fund portfolio, which was 4% at the time. When I did this six years ago, my number was $5M. Which is a lot, but is also not very much. I can't find the spreadsheet now, but it included things like: - A $700,000 house in Highland Park, Dallas (houses are >$1M now, which is still a bargain if you're coming from the Bay) - Two cars totaling about $150,000 - $30,000/year in vacations - A large spending budget I knew that short of starting a startup and it getting an exit (and me not getting screwed by my investors or partners), the only way I'd be able to hit this is to get as close to where the money is made as I can and being ruthless about comp negotiation. Tracking all of my expenses has helped me visually see where the lifestyle inflation is happening and determine what things I should invest more into or cut out of my life. It has also made forecasting big future purchases much easier, as I can see how the purchase will impact me with a very high degree of confidence. This somehow makes me attaining that thing more real, which helps drive me towards taking opportunities that will yield more comp. I don't believe in "be happy with what you have." That's what those with say to those without to make them "feel better" that they didn't win the life lottery. I say "always chase more, but know what 'more' is so that you know where to stop!"