Ask YC: Four Year Roadmap

One option would be to do what Joshua Schachter did. He built Delicious in his spare time. When he was ready to quit his job, he transformed Delicious from a hobby into a startup by raising money.

If your 4 year tenure is absolutely non-negotiable (or if you're not ready), then fiddle - let your hacker instincts take you places. Learn a scripting language (python ruby etc), write a blog, dissect apps, join an opensource project..

After four years of quality exploration, you'll have built up some formidable experience that isn't easily replicable.

I hadn't really done any web programming before starting tipjoy. With a full time commitment, we went from start to launch in 3 months.

You should certainly be able to do side projects. The best part is that you don't need to try to make money, so you should focus on building something interesting and useful.

If you want to do tiny free projects for tipjoy, let me know :)

Why wait 4 years? Why not join a startup (or technical company) now and start doing the things you want full-time instead of fitting them in around a job you don't value? You can learn a lot getting hands-on at the ground level, and if you want a mix of tech skills and business savvy then why not work at several startups (over time) and help grow them - you may get to do everything and anything from software/service design to marketing and PR. It is probably the best experience you can get if your aim is to start your own startup and will also equip you well for applying to places like Google.

If you really have to stay at the job for some reason, then I'd say in your spare time practice programming and building web apps around what you are interested and that solve problems you face. Launch them and see what happens. You may suck/fail at first, but over time you will definitely learn a lot, and will get better with each iteration you take - you never know one of them may really take off. You can practice business skills in growing your apps and once you have done it a few times, try doing it for other businesses (ideally in other fields too for some diversity to other markets). There are many courses/books that can teach you the skills, but if possible, find someone whose expertise you respect to mentor you.

Many successful businesses were, and still are, started by people in the same boat so please don't let worries about lack of skill/experience stop you from starting.

Make something. The only way to keep your skills current is to use them, and the best way to expand your skills to to build something.

A great video interview appeared here a while ago. It's about how it takes a couple of years to really get good enough at a creative field to produce good work. You go through a period of creating work that's not as good as your ambition would like it to be. Here's the link: http://www.youtube.com/watch?v=-hidvElQ0xE

It's worth the time to go through the process of creating a body of work. After doing it for a couple years, you'll be able to focus far more on doing something wonderful, rather than just doing /something/.

"You can't wait for inspiration. you have to go after it with a club." - Jack London

First of all congratulations for having a long-term plan. You know where you want to end up. That's big. And you're flexible enough that it can be a startup or a prestige company.

Micro-apps. Build something small like a Twitter visualization (twistori.com was built in a day, twittervision.com in 4 hours!), release it, build a blog to record your projects.

And I'd like to suggest broadening your portfolio: If it's all technology, it's all in one basket. Entrepreneurship is about taking on and managing risk. Outside the controlled world of compilers and stack traces, there is opportunity.

Consider taking on activities of varying risk. What are you scared at getting better at? Does it scare you to give a presentation? Join Toastmasters. Or ask a question at the microphone in a public forum (that's p.s.) Does it scare you to mingle in a room of strangers? Get a group of guy friends and go practice. Nothing to lose. Or start by going to a lecture and talking with the person you sit down next to. Does not having control scare you? Mentor or tutor a teenager. Or be the new guy in an interest group.

Startup now!

Why wait? Find others or friends whom you can learn from or work a full time gig while paying a team or offshore developer to build your product.

THough you first need to have an idea. That is when that component of a startup is most vital. Later on not so much...

Who knew you had to be so adaptable. Learning that now being in Philly's incubator! Great learning experience!

Four years is a lifetime! While I'm sure there is a good explanation (jail, military?) I'm having a hard time imagining what you're up to.

As you're apparently captive, I'd recommend making the most out of it. Technologies and trends shift, but your dreams and competencies will stick with you. Do whatever you want, with gusto.

That said, additional formal education is never a bad way to go.

So what is it, then? Military? If so, I'd imagine there are lots of opportunities for a "very good hacker" to use and expand his skill set. Experience is key, so go after it. At this point, the thing I'm most curious about is why you're not giving us a bit more detail on your current situation.