Your cost structure

One of the things you have to figure out before you take a leap (quitting your job, starting a new business, travel the world…) is to figure out your cost structure. Before you do that, though, you have to know what it is you want.
When I was living in South America I was deadly broke. Seriously, I ate rice and beans, twice a day, for three months — all of that while living in a friend’s apartment. Did I have to do that? Well, it depends. My number one priority was to make certain change happen. A change that in the form I wanted it, required me to be an entrepreneur, which meant that I couldn’t take a job and focus on my project at the same time. So I had to figure out a way to stay alive as long as possible without having a paycheck. (Today is the same though.)
That means, cooking your own food every day, cutting some social expenses and don’t buy stuff. And when you’re a month away (or several if it scares the heck out of you) you look for some freelance gigs.
I did that until poverty kicked in, so I had to take some freelance gigs in order to stay alive a little longer and make the change I seek.
Do you have to do this? It depends. On two things: (1) What it is you want, and (2) How bad do you want it.
If your goal is to live in NYC for its own sake, then you’re going to have big fixed costs, so you’d need a regular paycheck — a fat one.
On the other hand, if you want to build your own business, then you have to figure out your expenses and think about how many months you can stay alive. And the goal here is to stretch your resources as much as possible. If you’re not willing to eat rice and beans, so to speak, then you have to rethink what it is you want.
Sometimes this is not an easy road, but if you want it bad enough, you can sacrifice some short-term gratifications for a long-term purpose. If you have some savings this might look like a bit far away in the future, but the time to plan for money is when you don’t need it, otherwise it’ll too late. Hence, the only way to keep playing is to figure out your cost structure and make the proper changes in your lifestyle.