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[quote=Anonymous]OP here. 
I think what bothers me is that we sacrificed a lot (in money and time) for his schooling.  I sacrificed my own schooling opportunities because we were stuck in a particular city for his. 
Then his school classmates (he's now 10 years out) and our friends, neighbors and associates in DC are all so ambitious.  He just is not.  It bugs me.

He's been handed advancements in his job because he came in way over qualified and over time became indispensable to a wide array of people (just by being who he is).  He's smart and this comes out over years and when there's an opening people have said, 'well XX would be good for this, he's been doing this job anyway for the past year".  But looking back I'm just maddened by him.  He could have (and still could) be so much more.  We're sort of on the hamster wheel.  We both work long hours and will never get ahead of our mortgage or be able to pay for private school or anything beyond a pretty-bare-bones existence.  A good life but  sort of "government cogs in a wheel" sort of life.  
He is brilliant but has zero ambition.

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