Just sent my resignation letter and this is my plan.

Hi folks. I've just sent in my resignation letter from my job. Damn you all. ;)

My immediate plan is to plug the most obvious holes in my CS and math education. Being an art school dropout, I have plenty of those, but there are a few that I really want to address now, because otherwise I know they will be nagging me at inopportune times.

I'll also be catching up on the reading recommendations in the Library section of this site. I've read most of them already, but I'm sure many of them will make more sense now.

In parallel to such reading, I'll finish a pet project with no business aspirations, which I want for personal use: a subset/bastardization of the editor part of Jef Raskin's Humane Environment (AKA Archy). I plan to use that as my programming editor from then on. I did a couple prototypes in the past and I know I like it. I don't like Archy itself because of its compromise of using alt keys for leaping; I got myself a thinkpad-like keyboard with buttons under the space bar for this purpose. Again, this is something I had put on hold for too long, and I want to give it a chance before I commit full force to a startup.

I'll timebox 4 months for this although, in good programmer optimism tradition, I hope I'll be done earlier. After that, done or not, I plan to put out a few cheap startup failures fast. This is much in the spirit of the common advice to novice Go players: "lose your first fifty games fast". I'll just brainstorm for projects that I can execute by myself in, say, one month. At the end of the timeboxed period, if the project is not anywhere near shippable state, I shelve it and move to something else. Otherwise, I throw it at people and see what happens. Then follow up on the ones that get a better reaction.

From this I expect to get some basic competence in business (esp. marketing and dealing with users), system administration, and fluency in web programming (my background is in user interface design and programming for a MMOG). I also expect to get something I can show to potential cofounders so they can evaluate my taste and my ability to execute. And who knows, maybe something more ambitious grows out of one of these ideas.

My goal is to be able to apply to YC with a straight face in winter 2008 or summer 2009.

Please let me know what do you think about this. Don't pull any punches; I'm interested in criticism, objections, and alternatives, rather than moral support.

Thanks for reading this far!

That's a big step and it takes courage. Good for you. I like most of your plan, except for one point: Why the 4-month delay? Study and a pet project!!! Doesn't seem like a high priority thing for someone who's betting his career on a startup. It sounds like an excuse to delay starting the hard work of a startup. Plus, I'm guessing that you'll be living off of your savings. If that's the case, then you have a limited time to do the try/fail cycle a few times before you have to get back to a full-time job. I think you should start right away, and you can do your study on the side.

Best of luck.

Good luck!!!

Winter 2008 or summer 2009 is too far out. Work expands to fill time after all. If you aim for Summer 2008 you might be able to do this better.

Sounds like an excellent justification for flaky procrastination. You can follow this plan and hope the things you learn on the way can be applied to your startup. Or you can take your best idea, work hard to build it and learn as you go.