I’m a new kid on the block here: I’m writing this one week after leaving Double Fine Productions. I feel lucky to have a strong platform from which to make the big leap, so here are the conditions that convinced me I wouldn’t get a better shot:

• Existing freelance business. My wife is already the sole proprietor of Animal Ocean Design, and has more work than she can handle. Her clients are asking for more and more technical work. This provides me with a huge boost in business development, and there’s already a backlog of paying work for me to start on. And of course, she’s already dealt with a lot of freelancer headaches, and can spot a number of mistakes before I make them.
• In-house (literally) artist and web designer. In addition to my contract work, I’m developing my own game 2-3 days a week. My wife can not only handle the visuals, but also the game’s site design, search engine optimization, and more. We’ve worked well together before, and now both of our businesses will rarely need to contract out for additional expertise.
• Low costs (for San Francisco). The mortgage is a bit of a beast. On the other hand, health insurance costs will never be lower for me. I have no kids. I neither have nor need a car. With some restraint, my non-mortgage costs have become very low. (Next item to tackle: all those recurring phone, TV, Tivo, DSL costs: there has to be a way to bring those way down!)
• Between projects. We finished up Psychonauts, learned our lessons, and kicked off the next project. It’s cranking along smoothly. Now’s the best time to leave Double Fine without leaving anyone in the lurch.
• Incredibly helpful people. I don’t know if this is different from other industries, but people in the game industry have been unbelievably friendly and forthcoming. Thanks to everyone who’s contacted me to offer help or congratulations (and I promise I’m working on this networking thing, so that I’ll tag you first next time!). The amount of support out there is a huge confidence builder. Special thanks, of course, to Brian Hook for putting this site together and letting me hang my shingle.
• Got the itch. Intuitively, it just felt like it was time to take the plunge. When I thought about what I wanted to be doing with my days, going independent was the clear winner. Spencer’s and Brian’s introductions sum up a lot of the allure it’s held for me over the past 6 months or so: chiefly, variety and self-determination.

So, there’s my starting point. For the foreseeable future, I’ll be splitting my time between web development, game-related contracting, and independent game development. I’m really excited about all of it, and I’m dedicated to making it work.