~12 years of professional experience: 3 as a translator/researcher, 3 as a salaryman, 5 (full-time) as a bootstrapped solo software entrepreneur, 1 as CEO of St

~12 years of professional experience: 3 as a translator/researcher, 3 as a salaryman, 5 (full-time) as a bootstrapped solo software entrepreneur, 1 as CEO of Starfighter (current gig). I go back and forth on this one, as I know why I did it, but: I burned way, way too many years on two jobs which were dead-end and not teaching me at sufficient velocity to justify the use of time. In hindsight, it would have been a better use of my time to be in a different organization for those 6 years. At the time I felt like I was optimizing for personal growth and figuring out this adulthood thing but in the clarity of hindsight I'm pretty sure I could have found that out while not being miserable for 90 hours a week. I should have aggressively applied for jobs early in my career, including jobs I felt were likely to turn me down, rather than constraining my own choices to places I thought I was reasonably well-qualified for. (Specifically, I should probably have applied to Google, and AppAmaGooFaceSoft for that matter, immediately out of college and regularly afterwards.) I was happy and pretty fulfilled with running my own software company, but I would have been happier, more fulfilled, and more successful with a better choice of projects for my 2nd major SaaS. In particular, rather than doing "a good business which I know that I will not be terribly interested in", I should have taken Peldi's advice and done something which both pinged my interests and made use of the various forms of capital I had built up prior to then. (Perhaps email marketing software or something else targeting the software industry, rather than something which helps you if you're the office manager at a dentist's office.) With regards to Starfighter: we decided to bite off two very ambitious development projects then run a boutique recruiting firm. We should have run a boutique recruiting firm for 3 months, then done one not-very-ambitious development project, folded it into the recruiting firm, and then ramped up recruiting and development in parallel. Things I'm generally happy about: Skipping grad school. Choosing to write down what I was learning while I was learning it: A++, would write 3 million words again. If I have a regret here, it is not writing more the last ~2 years. Side projects: lifechanging for me. Getting exposed to a variety of people, companies, and problems by doing consulting, while also getting paid handsomely to do it: great decision. (Probably should have banked more while doing it rather than assuming I would always have a consistent income level and choosing to overspend on some things.) Bonus round: Definitely, definitely say yes if Thomas Ptacek invites you out to coffee. (We met for the first time in late 2009. That conversation altered my trajectory to consulting. A similar conversation in late 2014 resulted in Starfighter.)