Fletch wrote: Sometimes though, when those things get combined it takes the fun out of the thing you like to do...
Yep. Makin a career out of your passion or hobby can kill the joy for sure. Once you bring money and profit into it, as needs be done with all business (and all work is business nowadays) then jobs can tend to flatten out into the same thing. ie. sell yourself, keep costs down, get more clients, don't get fired, etc etc.
Staying in a sucky but high paying desk job and using the cash to expedite your weekend adventures is fine, so long as you do get out on those adventures and don't spend your free time needing to recover from the work week, or shopping at Ikea. The more demanding your job, the more you actually need to work at prioritising and making happen the fun stuff you're slaving away to pay for in the first place. As we get older it's easier to slack off.
The one thing that's really different now from 20 years ago, when I started climbing, is that a lot more people work on contracts, rather than permanent full-time, stay-til-you-die type jobs with only two weeks off a year. This is more insecure for your income and family, but can give you more free time, and time in blocks to do stuff you otherwise couldn't. Engineers, doctors, IT people are benefitting from this particularly well (Radson, bastard!). So if you're good at your white-collar desk job, look down the track to see if you can do it in a contract or consulting form, rather than full-time. That type of thing really needs to be set up in advance, maybe years in advance, often surreptitiously, by making and maintaining certain contacts, specialising in things others hate, doing courses etc. 'Create a market for yourself', as Arnold Schwarzenegger said (seriously).
But whatever you do, however you do it, if your wife is on your side with it (and you on hers for her stuff) it will come down to foreseeing the compromises, putting up with them if they still (mostly) lead to what you want, and not being afraid to change if they don't.