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New interview: Crafting the life you want

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A friend of mine has 4 college interns working for her, and last week she asked me to speak to them about business and psychology.

When I got there, they’d prepared questions about writing and productivity and marketing, but we spent the most time talking about how to deal with the pressure of parents’ expectations. I noticed this because one of them said, “I want to major in X, but I’ll probably be a computer-science major because of my Dad.”

How do we deal with all the expectations people have from us?

  • “You’re doing WHAT? That’s crazy.”
  • “You should do X job…there’s a lot of demand for it”
  • “How do you know that will work? You should just be happy to have a job at all in this economy.”

I shared the story of how I ended up being an author and entrepreneur…even though my mom still asks if I want to be a doctor.

So how do you set big goals and deal with the pressure of what other people expect? Especially when you don’t even know if you’re making the right decision?

For me to learn how to do this, I spent a lot of time studying unconventional people doing unconventional things. One of the best people doing interesting things is my friend Chris Guillebeau.

He’s the founder of the Art of Nonconformity blog, which originally started off talking about traveling, and now covers everything from tackling personal barriers to living an unconventional life.

A few years ago, he set a public goal of visiting every country — and he just finished!

And he created a conference called WDS — World Domination Summit — which just hosted 3,000 people, effectively shutting down Portland while people from all over the world attended.

On the surface, we have a lot of similarities: We both run blogs, we’ve both written books, and we both live unconventional lifestyles.

But dig deeper and there are big differences:

  • I’m outspoken. He’s much quieter
  • I love testing and analytics. He doesn’t really care
  • I’ve focused on building my team, while he’s done it on his own
  • He’s mastered the art of events and connecting people in real life. I’m pretty new to events

I bring this up to show you how you could live an unconventional life, no matter what your personality or style is.

That’s why I was so excited to invite him into my studio to study how he does it. This is another interview in my “Ramit’s Brain Trust” series, and here’s a sneak peek:

In this interview, you’ll learn:

  • How to conquer the fear of setting BIG goals
  • How to start a business, build a loyal community and become a public figure…even as an introvert
  • Why “forced accountability” can help you achieve your goals
  • How to use blogging to find and crystalize your voice
  • The value of habit vs. outcomes
  • Chris’ strategy for dealing with criticism, both emotionally and tactically
  • Chris’ biggest surprise from running his own business and traveling to every country in the world
  • How to create an Annual Review for your life (and how it became one of his most helpful tools)
  • And more

This interview is part of my “Brain Trust” program, where each month I unveil a new interview with my personal mentors, advisors, and confidants each month. Each month, you get access to these private interviews.

This program is closed right now. If you’re interested in getting on the wait list, you can add yourself here:



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