I've actually started a side business that does reasonably well. How do I extricate myself from the 9-5?

[SSF Tofudebeast]

I was in a very similar position about 5 years ago. What finally convinced me to take the leap was that my corporate job was doing a round of layoffs. I volunteered, and got laid off with a 4 month severance package.

That helped, but really 4 months isn't that long. We grew the business (my wife and I, we started it together), but still we went into debt around $50k just getting by until the business was strong enough to take up the slack. We are doing better now, and have about half the debt paid down.

I would suggest you look at your business and and put together realistic numbers as to how long it will take to grow it to where you can replace your lost income. Do you have savings to cover the gap? What can you cut out of your household budget to live cheaper? How much money can you save up over the next year to help cover you during the transition? Can you get a business loan to help out? If you get a loan, can you cover the payments even if the economy should weaken again? Look into getting a line of credit (apply now while your income is strong) to cover you when payments are coming in inconsistently. These are some things to keep in mind.

Like Kelly said, health insurance can be a big deal. Find a good agent, and start shopping around. You almost definitely won't be able to afford a policy as good as your current corporate one, but at least arrange it so you can get basic coverage lined up for when you make the big leap.