In today’s TAWRedux you said, "Here was where it started to feel like my software career suicide at least had not been a terrible mistake." This is the first time I’ve seen you use the word "suicide" to describe the end of your software career, and it makes me wonder about whether there was a breaking point where you sort of snapped and said "fuck this, I’m working full time on the music" and quit soon after. Did it happen like that or did you undertake Thing a Week after a careful planning period? Did you try to keep bridges intact, and how much did you think about the possibility of returning to the ranks of the code monkeys?
Even when I started the software job I told myself it was only temporary, and that I was soon going to leave and do music full time. Nine years later I was still telling myself that. If there was a single moment, it came at the end of my time at home after my daughter was born. I took three weeks off and was just at home with my new family. When it was time to go back to work I had a real resistance to it – not just wah wah I don’t want to go back to work, because truthfully it was kind of awful at home with the sleep deprivation and the standard new parent insanity. It was deeper than that. I remember thinking how it just didn’t make sense: here was this new person and I had three weeks with her and then zip zap, I was going to go back to the office EVERY DAY FOR THE REST OF MY LIFE? This is OK with everyone, this is how we do things?
Of course I did it, but I had already started planning. My entry to music was not a complete free fall. At this point I was having some success in writing and performing for audiences, tagging along with Hodgman on his Fame Adventure. I felt talented, I was pretty sure that if I worked at it I could make SOMETHING happen eventually, figure out some way to make money from music. At the very least I knew we wouldn’t starve. My wife went back to work full time eventually, and I figured worst case scenario I’d bum around for a year and then just go out and get another software job. On the day that I left I still felt like that was a distinct possibility, and really I LIKED writing software and querying databases. I was hopeful that I would find another way, but I was certainly open to the idea that Thing a Week would ultimately become a brief interruption in my software career.