CM 030: Chris Guillebeau on Winning the Career Lottery

Blog Post - Chris GuillebeauWe each have work we were born to do, but it can take time and effort to find it. Becoming comfortable with the search is half the battle, because we need to try different kinds of jobs and work environments. With each experience we gain greater insight into the skills and knowledge we have to share, and we find our perfect blend of work, skills and meaning.

In his latest book, Born for This, Chris Guillebeau, bestselling author of The $100 Startup and The Happiness of Pursuit, shares his own experiences and the stories of the many people he has interviewed, to help us navigate this process and choose our own path. Chris is the creator and host of The World Domination Summit, and a successful entrepreneur, speaker, and blogger. After a 10-year personal quest, he has visited every country in the world.

In this episode, we talk about:

  • Why you see yourself as self-employed, even if you work for someone else
  • The joy-flow-money framework for evaluating creative opportunities
  • What it means to bet on yourself
  • The environments that support your best work
  • The skills you most need to learn (and they are not what you think they are)
  • Why giving up is actually a good thing
  • Strategies for hacking new products and services
  • Why curiosity is so important

Selected Links to Topics Mentioned



Born for This by Chris Guillebeau

The $100 Startup by Chris Guillebeau

The Happiness Pursuit by Chris Guillebeau

The World Domination Summit

Steve Jobs

Seth Godin


Shenee Howard

Manifest Destiny

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  1. […] Chris Guillebeau,the bestselling author of The $100 Startup and The Happiness of Pursuit, recently shared some really good experiences and stories from his upcoming book – Born for This. And I’d like to share a few notes I’ve made from an interview he did for a podcast. […]

  2. […] the challenge is time, urgency, or traction, we need a targeted plan to achieve our goals. In a recent conversation with successful entrepreneur, Chris Guillebeau, we talked about his latest book, Born for This. In […]