Wayfinding for the Weary Entrepreneur, with E. Keller Fitzsimmons

Life + Leadership

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:

• Watch our conversation with Kelly on the Life & Leadership YouTube Channel
• Learn more about Kelly’s work at Lost in Startuplandia
• Connect with Kelly on LinkedIn or Instagram
• Get your copy of Lost in Startuplandia: Wayfinding for the Weary Entrepreneur
• Explore Now, Discover Your Strengths or Strengths Finder 2.0
• Discover the Center for Authentic Leadership
• Reframe your inner critic with Katie’s Hidden Brilliance + Elizabeth Gilbert’s Big Magic
• Listen to Chip Conley’s interview on Sounds True
• Find out more about the Modern Elder Academy
• Explore Daniel Kahneman’s work on cognitive biases
• Read about decision-making in Annie Duke’s Thinking in Bets

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