(In reverse chronological order) 1) Quitting ZenPayroll. Ended up leaving what are now millions of dollars of (paper money and unsellable) shares on the table,

(In reverse chronological order) 1) Quitting ZenPayroll. Ended up leaving what are now millions of dollars of (paper money and unsellable) shares on the table, at a time when the company was clearly taking off. Now building a values-focused, mission driven company the right way and loving every minute of it. 2) Quitting LivingSocial after 11 months when I realized that they weren't what they sold me on. The pitch was building back-office tools for SMBs, but in the end they never did the right thing for SMBs if it wasn't also in their interest. 3) Dropping out of college as a philosophy major, believing I could learn to program. Joined LivingSocial as an aspiring engineer, which turned out to be a great place to start. Great exposure to the Ruby community, experience with hard things (scale, caching, business problems creeping into the product.) As you may notice, my biggest fear is regretting wasted time. While I tried to change each one of those places to be what I knew they could be, until you start your own company you must (rightfully) defer to what others decide is "right". I've realized I have an incredibly high bar for making difficult decisions, which isn't realistic to "manage up."