Some good responses here, so thank you everyone who took the time.
I certainly do alright for myself, Moo (though big city living and rent prices still make me feel under-compensated at times), but if you've never worked in a similar position as mine you can't imagine how boring life can be. I pull off 80-100 hr weeks on a not-that-unusual basis, and much of that time is spent explaining things to upper management which range from risk analysis to (I kid you not) how to hide cells in Microsoft Excel. The day-to-day grind of answering to people who logically do not have the proper skillsets to deal with today's world of finance but still outweigh you on every level because they were born in a time of low competition and limited technology is quite difficult to deal with. And you kind of have to suck up to these people to advance, because if you don't, you can be assured your colleagues will. This alone makes me yearn for something where my skill and ambition is tied to my results.
The family issue is certainly something I've considered. But at the risk of sounding like one of those whiny "men's rights" activists, I truly believe that millennials are screwed when it comes to marriage, at least in the States and probably most of the Western world. Divorce is laughably easy and statistically probable, women (and often men, to be fair) my age seem lazy and narcissistic, and when children are involved the courts will almost always favor the woman. Plus at my income, it's extremely likely that I'd get hosed financially in a divorce. I honestly can't see marriage as a rational decision for successful men in my generation.
I'm on the shorter side of average, around 5'9/175 cm. I'm really not overly concerned with sleeping in the car. I was dirt poor growing up and slept on the floor of the kitchen until I was around 16. The Avalanche actually sounds pretty comfy, but then again you guys make some good points about the Prius gas millage savings (though I guess that could be partly mitigated through tax deductions when I file as a "pro gambler," yet another headache in this scheme). I'm thinking the gym is a good idea because I'm pretty big into weight training and I don't know how I could get/keep the look I want without weights (that being said, I'm far from creative in terms of working out, so feel free to correct me there). The hiking sounds like a good idea regardless, though.
It was only for a little more than a week, but a road trip I took with my friend where we just slept in his old Honda was one of the best experiences of my life. I could see how it could get old fast, though. I actually kind of like the idea of feeling like a bum. It feels more real than my current lifestyle. Dealing with the security issues/cop hassling is definitely a concern though.
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