Is there such a thing as too much freedom?

If anybody were to know, Derek might be the guy. Derek quit his last job in 1992 and in 2008 he sold his business, CD Baby, to the tune of $22 million.

Over the years he's been a professional musician, a circus ringleader, an entrepreneur, a world traveler, a popular TED speaker and a book publisher. He writes at www.sivers.org.

We explore with Derek how to move on from an expired identity, what does freedom mean anyway, how to follow what's interesting to you and how we might travel in the future.