25Y Male making over $250K+ annually. Still stuck. Help?

Two thoughts on this:

1) True, if it had been his own firm, he would have been a millionaire. But would he have known enough about his business at age 23 to create that same firm? I'm betting he has learned a huge amount in the last two years -- that he's much wiser and more savvy now than he was before he started this process. That wisdom will make him much better positioned to someday build his own empire than he would have been had he jumped the gun and started building without it. That's an advantage that very few 25-year-olds have.

2) OK, so his boss is a millionaire and he isn't. But what he will find as he earns more money is that there is no amount of money that is "enough." Say he goes out on his own and makes as much as his current boss does. Now he's a millionaire, but now he finds himself envious of multi-millionaires. And what he doesn't realize is that those multi-millionaires are envious of people who have hundreds of millions, and the people with hundreds of millions are envious of the people with billions... and on and on. It never ends. There is never enough.

Or as one of my favorite reads, Stephen Mitchell's translation of the Tao Te Ching (http://acc6.its.brooklyn.cuny.edu/~phalsall/texts/taote-v3.h...), puts it:

   Fill your bowl to the brim
   and it will spill.
   Keep sharpening your knife
   and it will blunt.
   Chase after money and security
   and your heart will never unclench.
   Care about people's approval
   and you will be their prisoner.
   
   Do your work, then step back.
   The only path to serenity.

Stop reading startup sites every day.

It might take a while to find a good therapist- so some support there with encouragement to keep trying if the first one doesn't work out can be helpful.

Focusing on mindfulness, and also healthy habits like regular exercise also might help. To aid with getting into a meditation practice, I ended up going to a workshop at a local Zen center, but Yoga works also. There are also an increasing number of meditation groups that are based on mindfulness meditation that's not based on any traditional practice, but rather based on the recent understanding we've arrived at with how meditation actually effects the body- look for "mindfulness based stress reduction".

I don't have nearly that sort of income but have been fighting a similar battle for a long time. It can take a little while to get through. At least the subject hasn't been completely paralyzed by lack of fulfillment, and made things work in the mean time.

I know this doesn't need saying ... But I can guarantee you that there are ~25 year old bankers at the investment bank who are making more a lot more than $100k. Technology roles are discounted at investment banks, since they perceive technology as a cost centre, not a profit centre. But at Google/Apple/etc, it's the opposite - technology is a profit centre, and finance roles are a cost centre.

I think we agree in the large part. The part about relying on a third-party professional was assumed.

I'm reminded of a relative's teeth: they might have been born with exceptional enamel, preventing all manner of early cavities, but now they lack the oral hygiene habits they need going forward.

Along those same lines: to what degree are you uncommonly well-adjusted, versus born to circumstances in which many of your foibles don't cause problems to _you_ because of the consequence buffer provided by fortuitous race, sex, orientation, class, etc.? I know I can get away with under-developed stress processing because I'm white and male and date women, for example.