I'm 36 too, I have a wife and kid, and I left a boring safe job to work for what I'd describe as a late-stage startup. My wife works a stable job and brings in a better health lan, too. So while I'm not doing something quite as risky as leaving to start my own probject, I do understand the urge to try something a little more thrilling with a higher potential payout.

Truth is, you'd probably be able to get a big boring job again quite easily if you wanted one. The last time I looked for a job, I had two offers within a few weeks and a substantial counteroffer from my (now ex) employer. The market has its ups and downs, sure, but in the end, I doubt it would be all that hard for you to go back to a bigco and blub away if it comes to that. Which I hope it doesn't for you and for me.

It's excellent that you're giving this a try. Good luck. Do you have a blog or anything? Keep us posted!