I think there's a corollary to this - if it turns out you don't always wish you did, it probably wasn't that great. The question then becomes, how certain are you this is something you will always regret having not done?

This is one of the best quotes I've read on HN. Very true!

I have also seen much crazier things. A friend of mine from college who is a stand up comedian, decided to hitchhike his way from NYC to LA to "find Tom" of MySpace. He filmed his entire journey and shared it on the web. Additionally, he also crashed with all his MySpace friends the whole way so his cost is practically 0 (besides the bus tickets).

It's definitely doable on an even smaller budget :) Good luck and let me know when you arrive at the valley!

You sound like you have nothing holding you down and a great trip ahead of you. Once the job and bills start rolling in it becomes more difficult to break away and do it. Not impossible, just more difficult.

Just do it! I'd recommend doing the west coast bit if you leaning that way.

My way would be Chicago -> Seattle -> San Fran.If time and money and/or your desire permit then swing down the south for Austin -> New Orleans -> NY -> Boston.