I actually have been doing similar things, but without the side projects to back me; depending on my mood and the opportunity I:<p>- do some high-end consulting at an above-market rate<p>- enjoy myself at a below-market rate in a start-up<p>- take some time off to spend it with the kids, while I learn about new things<p>This usually happens in streaks of a few weeks/months...<p>Regarding the continuous flow of money to back you: while it is nice to have, it is not exactly a necessity; I build a little pile of cash and am very picky when I spend it. You don't need a continuous flow of money to get started, but you have to prioritize what is important for you.<p>Last year I have been doing high-end consulting for about 5 months, spent 4 months at home learning new things (ElixirLang etc) and enjoying myself with the kids, and the remainder was spent remoting for a start-up where I ended up experimenting with Erlang, GoLang, Haskell and a plethora of tech stacks.<p>In my opinion, people tend to forget why they work (to have a life and enjoy themselves), and end up focusing on getting more and more ... They tend to be afraid of breaking their habits and always predict doom scenarios.<p>I have been doing this for years, and my income fluctuates like hell - I even once posted a graph of about 10 years of income on my blog -, but I enjoy my life and work...<p>I agree that it does induce some stress every once in a while (for example, in January this year, I had just paid a huge amount to social security and taxes, and after a two week break my project was ended), but in the end you always manage.<p>If it had not been for this stressy period, I now would not be working on two start-ups simultaneously: one as a consultant for one or two days per week, and the remainder of it on my own (for which development is being paid for in advance by the first future customer). Maybe that is the post-traumatic growth Nassim Taleb was referring to in it's "anti-fragile: things that gain from disorder".<p>I would suggest everyone to really think about your work/life/fun balance and just take a leap of faith.<p>"If you do not change direction, you may end up where you are heading." - Lao Tzu