I too, form part of the group that would like to give up the day job (IT, yes I know) and go self employed. Work - Life balance is being used a bit too liberally these days, especially by those who understand it the least. Employers\management that is.
One gets to a point in life where one's tolerance for fools diminishes to almost zero. It isn't helped by these fools thinking they can control your working life and some treat it like personal feifdoms. We've all experienced these forms of life in the past. This and the general dis-satisfaction with the rat race, is a large driver for me, and probably for most. There's only so long one can put up with meetings for meetings sake, and management who haven't a clue. Previously going Freelance would have been the solution - until HMG decided to take your pants off, let alone pull them down. [Sorry - rant over!]
Having spent so long in IT and having a skill set that's well paid and in demand, can make leaving IT, more difficult. However, there's only so long one can continue "making the Emperor's new clothes" before the rot sets in.
The hobby side of things is a great deal more rewarding. For me it's a case of trying to make a slow steady transition. For some months - I've been accepting work from friends\aquantancies, and kept track of how long\much it took as opposed to what I thought it would take\cost and thankfully as time goes on - the gap is almost zero. Although it's about the averages.
But then I'm fortunate enough to be multi-skilled - the only thing I'm not really interested in doing for others is roofing. For me, there needs to be multiple income streams - to not only provide a variety of work, but also to stabilise voids, etc. Whilst some of the work may having nothing to do with woodwork - it is unfortunately part of the bargain to pay the bills. Until you are able to pick and choose.
Sometimes, I find myself having to ask about something - it has never bothered me. As a child I was taught "To ask a question, is to suffer but a moments shame, but to remain ignorant is to remain a lifetimes shame." Believe you me that didn't half p*ss off a few teachers\lecturers later in life. The only difference now is that if the person I'm asking doesn't cut the mustard in terms of answer, manner, etc - I'll find someone else.
For me working for someone else would be difficult - I couldn't drop down to sub £10\hr, but it's as Greybeard said
- those who want to or those who have to.
I'm fortunate in falling into the want to camp.
I'm happy enough doing it part time - improving the numbers (time\materials\etc) and if I can make a go of it - will do, or if it doesn't go well, drop it back to a hobby, with the odd bit for a mate. I've found costing to be the hardest part - in the early days I've had jobs go completely loss making, to some jobs swing completely the other way.
It does require a slightly different way of thinking - production techniques, mechanisation, etc. - that has been the harder part, although not hugely difficult.
Tim nailed it on the head for me,
My plan though was to run a business first and that it happened to be in woodworking - I do see quite a few people trying to nail a business plan to a woodworking dream and that seems to me to be a recipe for disaster both emotionally and financially.
Couldn't have said it better myself.
My reasons for switching were simple - bored of corporate clap trap and dancing to others tunes, plus a hankering to combine creative and physical work while running my own business. Clearly you still end up dancing to the customer's tune but its ultimately your decision.
Hope it helps.
Dibs
p.s. Sorry for the rant