Predictably (at least, to everyone except myself), I've decided to work full-time at my startup (financial markets applied to Internet), instead of returning to MIT in Fall 2008. I'm going to try to take 1-2 classes per semester at Stanford or UC Berkeley (or possibly online) so as to retain the option of returning to MIT in Spring 2009 (if the startup doesn't go anywhere) or sometime later (if it does). (I can also "thank" MIT's financial aid policies and administration for making this decision a bit more automatic for me...)
While I'd eventually like to get to work on aerospace and nuclear projects, it's possible that getting a successful VC-funded startup completed, plus personal wealth, would put me in a better position to work on those projects than if I just went back to school now. I think it would be nearly impossible to do this startup in Boston or while a full-time undergraduate; while I can probably delegate a lot of the actual software development, the next 6-12 months will require full-time hands-on involvement in product management and business development. Another option I've been considering is just doing a University of Edinburgh MBA (on-site or online or some combination), since that program does NOT require an undergraduate degree, and is well respected (for a European MBA program; it's not HBS or Stanford GSB, especially if done online...). One of my main reasons for trying to complete a degree is "immigration points" in various countries -- while just having money and being an "investor visa" works, having a degree would make a lot of things more automatic, and a graduate/professional degree helps even more. (Although, there is a certain ironic amusement in being not only a college but also technically a high school dropout in social/professional circles full of PhD/MD/MBA holders.)
The nice thing about this particular startup is that it's a "regulatory arbitrage" play, but it's not actively opposed by the regulator; it's just creating new efficiency, and actually expanding the scope of activity in the "regulated" world. I'm learning a lot about financial markets in the process -- I've had a decent layman's understanding of how they work, but some of the technical and implementation details are fairly obscure and interesting. There are also some fun technical problems to solve, but it's really a "market" company vs. a "science" company, another feature I like. It's also something with a substantial "halo effect", in that if successful (or even just visible), everyone likes it, and thinks positively of the people involved, and all the "competitors" can actually overall make more money by adopting the system themselves (lower margins per transaction, vastly higher volume, greater overall profits). It's not a cure for cancer by any means, but still good.
I'll probably post more about this on a company blog (URL added here later in an edit), and on my personal non-MIT blog (http://www.venona.com/blog/) -- this blog will remain for any academic related matters. (distressingly for my view of the sciences and their relative importance, I'm more interested these days by finance and economics than most engineering, science, or math...)
I am going to return to MIT to finish my undergraduate degree (I'm in the top 20 google hits for "MIT dropout" now...). Hopefully, majoring in Course 2-OE (Mechanical with Ocean Engineering) and the fifth year Master of Science in 22 (Nuclear Engineering). Obviously I'll continue to take classes and participate in activities in CS/EE and Management/Entrepreneurship.
I apparently only have a single semester of MIT credit, due to financial issues the first time around!
While it is certainly possible to have a good career without a university degree, I'm increasingly interested in engineering and scientific startups, vs. pure Internet startups, and the stronger technical background will be valuable. Additionally, in raising larger investment rounds for such projects, having credentials from a university like MIT is very helpful.
Several of my friends are going back to school this fall -- mostly into graduate programs, but some are finishing undergraduate. MIT is probably one of the better schools for an adult student -- I remember lots of ~30 year old Israeli freshmen, after their military service. MIT has a large percentage of graduate students and active alumni, and has world-class labs and other resources.
The main negatives for me of returning to school at MIT are:
* Residency in Massachusetts -- this can be avoided as a full-time student, provided you live in dormitory of FSILG housing.
* Financial matters -- the $10/hr UROP wage is a good deal less than I'm used to earning, but there are other opportunities in the area
* Dealing with university structures designed for 18-22 year old students; at MIT this is less of a concern than most schools, but the "in loco parentis" expectation is present even at MIT.
* Boston weather -- luckily, MIT is largely connected by tunnels, and I will have a car.
* Doing "all nighters" at 30 years old is a lot more difficult than at 16 -- hopefully old age and cunning will triumph over youth and skill
I would actually prefer a university system where students spent several years post-secondary working or otherwise doing self-directed activities prior to college; I suppose this is equivalent to rapidly progressing through undergraduate and taking some time off before grad school. Ultimately, I think the structured k-12, 4 years of undergrad, 3-8 years of graduate/professional school system needs to be rethought, and probably compressed in some places and broken up in others.