Matt Gemmell wrote in Losing Direction:

One of my dreams is of course to do the shareware thing; start a little software company and get some well-focused, beautiful little apps out there, targeting niche markets and filling those needs as perfectly as I can engineer them to.

That’s exactly my dream with Happy Apps and WebnoteHappy, my well-focused (on bookmarking the web), beautiful little app. The trouble is, and I think Matt is trying to come to terms with this, is that this is not easy. Its also not what society wants you to do. And unlike college, your parents (or anyone else for that matter) are not going to pay for it. If you were to start the next wbtwo.oh company, then _maybe_ you would have a slim chance of getting VC money. And health insurance in the US isn’t cheap. So its a big struggle to live out this dream.

At least you have to give it a shot. I watched the movie Dodgeball recently and the main character was in the process of giving up his dream. Then Lance Armstrong, the man who singlehandedly popularized colored wrist bands, shows up and basically tells him “look I was diagnosed with brain, liver and testicular cancer” and says that even with all that he managed to live out his dream and something like “I’m sure you have a good reason for quitting your dream but you’ll probably regret this for the rest of your life.”

So to Matt and others out there, I say go for it. But do some planning first to maximize your chances before you take the leap. Maybe I should write about that more.

If you crash and burn, then try again. Or maybe it just wasn’t meant to be. But you have to try. Otherwise, you’ll never know, probably after a year or two of difficulty in starting up, if you would have succeeded.