TO ALL THE LONG TERM TRAVELLERS: How did you do it?

So I'm sitting in my warm comfortable office staring at my computer screen for what feels like the millionth time - and i'm bored and unfulfilled.  :lamer:

I yearn for adventure!

My question to all those of you out there that have dropped their day-jobs, lives, careers and families in order to satisfy their wanderlust: how did you do it?

I constantly read books on adventures, ride reports and follow blogs - but battle to summon up the courage to sell everything and up-and-leave.  I guess one of my worries is that job security in RSA, particularly within the aviation sector, is not guaranteed at the best of times.  Having said that, I owe no money to anyone, have no dependents and am generally free.  I've reached a point within my life where I'm able to do it, and its likely to be one of the few opportunities to do so.  How did you structure your travels so that you had some plan on your return?

Another concern is how do you finance your travels?  I have some money saved, and would probably be able to sustain myself for a while if I travel cheap (I've always done so, shouldn't be a problem).  Society puts so much pressure on us as thirty-something-year-olds to start saving, invest in property and make allowances for retirement.  How do you live for the moment whilst still being responsible for your future?

Family - I know this one isn't easy for anyone.  How do you manage to leave them behind? 

I know each persons circumstances are different, and I know there isn't a hard and fast guide to this.  However I'd appreciate anything you have to contribute.

Thanks in advance for your feedback,

Lim