It’s easy for entrepreneurs and leaders to get so caught up in the day-to-day that we fall into a kind of sleepiness. And for many, it takes a dark night of the soul to wake us up to what’s really important. But what if we’d rather not wait for a crisis to find our way? How can we develop the self-awareness to lead with intention and follow our calling?

Today, we’re joined by E. Keller Fitzsimmons, the author of Lost in Startuplandia: Wayfinding for the Weary Entrepreneur. An accomplished tech entrepreneur and artist, she earned the Silvertip PwC Entrepreneurship Award and Speech Technology’s Luminary Award. Kelly’s VR production company, Custom Reality Services, premiered its first two projects at the prestigious Sundance Film Festival, and her work has appeared in Network Computing, InformationWeek and Inc.

Kelly begins by sharing the health crisis that inspired Lost in Startuplandia and helped her step into her role as a creative. She explains how she learned to appreciate her strength of positivity and challenges us to own our strengths—and accept our shadow side. Listen in for Kelly’s insight on why entrepreneurs and leaders need support from a ‘triad of truth tellers’ and learn how to cultivate the self-belief it takes to move through heartbreak and live your purpose.



Themes explored in this week’s episode:

  • How curiosity + creativity serve as the through line in Kelly’s eclectic career
  • The health crisis that inspired Kelly to write Lost in Startuplandia and redirected her to a path more in line with her purpose
  • How Kelly learned to appreciate her strength of positivity and understand how it gave her the fortitude to be an entrepreneur
  • The dark night of the soul that helped Kelly get in touch with her shadow side
  • How we fall down as leaders when we make decisions to make ourselves look good
  • Kelly’s strategies for cultivating self-belief through little acts of courage and turning down our inner critic
  • Knowing when to ‘stay in the game’ and when to take a step back and heal
  • Why we all need to establish a triad of truth tellers who help us make important decisions
  • Kelly’s current work with artists and musicians + how she is leaning into her own creativity


Resources from this episode:


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Quotes from the episode:

“I was using technology and my startups as canvas.”

“I’m just now, facing 50, having the courage to say, ‘I’m an artist.’”

“Who was I if I couldn’t be an entrepreneur? That identity was holding me too tightly.”

“An entrepreneur is someone who is willing to withstand discomfort for unreasonably long periods of time.”

“Making hard decisions? Almost never do we go with the one that makes us look bad. And that’s when we really fall down as leaders.”

“It wouldn’t bother you if it wasn’t something that you just don’t want to acknowledge about who you are.”

“Jealousy, envy—all of these emotions that we’d rather not own up to. They’re right there. And when we don’t own them, they run our lives.”

“We live in a culture that is out to sabotage our self-belief for commercial gain.”

“The only way to cultivate self-belief is through little acts of courage.”

“The cure to the sleepiness that we all fall into is heartbreak. And we don’t hold it as a gift, but it is.”

“You need to be able to see things from multiple perspectives because they’ll catch things that people that are close to us or in our echo chamber just can’t see.”

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