Thanks for these advices, it's a great way to organize your thoughts and take risks in a responsible way. :)
I guess this story is not much different than story of my first solo trip. It was almost the very beginning of my freelancing (and any) career, and sometimes I was earning money, sometimes not. But I felt like my life sitting at home and working is so pointless and that if I am freelancer I should travel, so I could say to myself not socializing in a company and having stable income can pay off (if this makes sense :D). So I spent the last money I had to the one-way ticket and made plans for the whole 20-day trip as I already had all the money, and planned the budget, and just stayed with it feeling excited about what is coming in a month. And then, like magically, I started getting best projects untill that time, without even applying for jobs - clients were just coming to me with the offers, and I couldn't believe it! Eventually I earned all the money for the trip in only two weeks, and it was way much more than I have ever earned before.
And what was the risk of my decision? The only risk was that I would not earn enough so that my flight would be cancelled and I would lose some money. And money can be earned again. So, nothing much. :D