[nickler]

He's stuck in the success trap. You've detailed a list that has very little actual correlation to fulfillment. Those are all issues related to security, comfort, and a lifelong desire to one day avoid work.

I wrote a couple pieces on this at startupathlete.com.

Protip: millions of $ =/= success. Ask any millionaire what they would wish for and it's not another million $.

That being said, one of the best questions to ask when someone is in a rut is, 'if money was no object, if you had millions in the bank, what would you be doing'. The follow up, 'why aren't you doing that', will always have some excuse about money, which is bullshit. It's about fear, security, and risk tolerance.

The happiest people I know have the stones to risk their pride, lose all their stuff, and live with mistakes. The saddest people I know spend their later lives regretting the risks they never took.

Wish you both the best of luck.