This was originally posted on 4/7/2013.
Six weeks ago I handed my employer my formal resignation. Two weeks ago I waved goodbye and left the office to begin work on my second startup.
At this stage in my life I have no children, no mortgage, a small passive income from my first startup, two rock solid technical cofounders, a working prototype for our idea, a monetization strategy, and enough cash saved up to bankroll some small business expenses. In short, there was very little risk to quitting. Yet I still struggled with the decision and on that Thursday as I walked into the chilly North Carolina air, I couldn't help but wonder if I was making the right decision.
Quitting is hard for social reasons. I worked at a small Django consultancy with an excellent group of folks who I respect and admire. But even there, among independent-minded, intelligent, professional, driven peers, most were confused why I would want to quit an excellent job. One coworker was frustrated that I was helping perpetuate the Silicon Valley brain drain, "don't move out there and be one of those guys," he told me during my last week. But by far the most common reaction to my news was "why?" accompanied by what I perceived to be quiet pity. "Oh dear, he thinks he's going to start the next Facebook."
To everyone yearning to quit their job and pursue their startup dreams, do your homework, then quit now. I'm not sure I would be capable of quitting my job with $100k in a home loan, 2 children, and a car payment. Quitting gets more difficult the longer you wait, so brace yourself and jump soon.