Great stuff Tim - I have taken the off-ramp in my career and left safe jobs to pursue dreams. I have experienced both the elation of building something successful from scratch, and the fear and emptiness of waking up with no income, no money, a failed company and a bleak future, feeling that people are laughing at me.
Things to remember: 1) it doesn't matter who is laughing at me, because who still believes in me is what matters; 2) success is an accumulation of failures, and the lessons they bring; 3) and you said it in your article: it's better to have tried than to live with the regret of not trying.