Box of Crayons Blog


Jessica Hagy, How to Be Interesting

JessicaHagySo if any of you were kind enough to buy End Malaria, the book I produced a year or so ago to raise money for Malaria No More, you’ll know that every section of the book starts with a cool, edgy, insightful little cartoon. Those cartoons were drawn by Jessica Hagy, whom I’m lucky enough to be speaking with today.

Jessica has a new book coming up called How To Be Interesting.  It’s inspired by a Forbes article she wrote awhile back, and I’m hoping that our chat about the book will inspire me to be more interesting, because it’s been pointed out that I lack that quality.

In this interview, Jessica and I discuss:

  • The importance of curiosity, exploration and saying “yes” to opportunities
  • Why it pays to connect with others and reach beyond one’s own thoughts
  • The value of embracing risk
  • Harnessing the courage to be different
  • How to engage others by talking/writing about your ideas rather than your accomplishments
  • The value of letting go and sharing ideas rather than trying to protect them from being “stolen”

(Scroll down for more in-depth podcast notes.)

Listen to my interview with Jessica Hagy.

0:00:00: Michael and Jessica touch on the 10 principles she’s outlines in her book, How To Be Interesting. She says that “Go Exploring” is the central principle, and goes on to talk with Michael about the importance of being curious, connecting with others and saying “yes.”

0:05:07: Jessica and Michael discuss the “dark” side of exploration, and agree that there’s value in taking risks and acquiring scars – both physical and emotional. As Michael notes, “Wisdom enters through the wound.” This train of thought leads the two to talk about harnessing the bravery within to dare to be different.

0:08:16: Michael asks Jessica about the major crossroads in her life, and she reflects on the year she lived overseas with her husband, and her subsequent decision to keep “doodling” rather than return to her advertising career. Michael adds that “Every choice you make has punishments and prizes.”

0:10:00: Michael and Jessica talk about embracing one’s “innate weirdness,” and note that being memorable is a good thing – particularly when writing or drawing for the Internet.

0:15:14: Jessica and Michael explore what makes someone worth following on the Internet, and concur that people are more interesting when they write about their ideas rather than their accomplishments. The conversation leads them to discuss the merits of sharing ideas rather than trying to protect them from being stolen or copied.

0:19:31: Michael concludes by directing people to Jessica’s blog,, for her latest cartoons and insights.

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