The Way of Adventure
An Unconventional Online Course for Young People


Coming up with dream jobs is easy. Turning them into reality is the hard part.

In 2001, four recent college graduates realized that they were about to enter the adult world—and they had no idea what kind of work would make them happy.

Instead of just taking the “best job” available to them, they crafted an adventure. Buying an old RV and painting it green, they planned a 15,000-mile roadtrip around the United States to interview people who were doing personally meaningful work. What resulted was Roadtrip Nation: first a set of interviews, and then a book, and then a TV show that sent hundreds of college students out on their own exploratory road trips.

Roadtrip Nation symbolizes the smart (and adventurous) approach to finding a job or career path. Instead of waiting for an incredible job to fall into their laps—something that almost never happens—these young people went out into the world, found people doing interesting work, and interviewed them about their paths. By doing this, they better understood the strange, winding, and challenging paths that people with unique careers always take.

Your challenge is to do something similar: find one person who’s doing work that you’d love to do, and interview them about their path.

Luckily, you’ve already done a good amount of prep work.

I’m not offering much more guidance on this challenge. If you’ve done all the other challenges so far, then you’re ready to tackle this one.

Meet the person in real life, interview them over Skype, or interview them over email. No matter how you do it, ask genuine questions about how this person got started in their chosen field, what their path was like, and any advice they have for others seeking to take a similar route.

Publish the interview in text, audio, or video format in your portfolio. Choose whichever medium feels most comfortable to you—and make sure that your interviewee approves of it before posting publicly.

Some tools that might help:

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