Episode 007

Lead Yourself First

with Mike Erwin

Artwork by Tommy Ingberg

Yes, leadership is built on developing relationships with other people. But there are several key character strengths of leadership that we hone in solitude, including creativity, self-regulation and bravery. And leaders throughout history have made difficult decisions and designed creative solutions in solitude.

In the digital age, however, solitude is a lot harder for leaders to come by.

How can we discipline ourselves to put away the smartphone and be with our thoughts long enough to think through difficult decisions, stay on purpose, and create innovative solutions?

Today, Jeffrey sits down with Mike Erwin, the CEO of the Character & Leadership Center and President of The Positivity Project to discuss the leadership qualities he demonstrated in kindergarten and his long history of curiosity around leading people in a positive way. Mike shares the inspiration for his book, Lead Yourself First, explaining how it evolved to become a study of how great leaders practiced solitude during meaningful times. He speaks to the virtues of leadership honed by productive solitude and the difference between a brilliant creative idea and a foolish one. Listen in to understand how the appreciation of beauty can lift you out of adversity and learn to embrace productive solitude in your own life!

Our Guests:


Mike Erwin

Mike Erwin is the CEO of the Character & Leadership Center—and the Founder & President of The Positivity Project, a non-profit organization with the mission to help America’s youth build stronger relationships by recognizing the character strengths in themselves and others. He recently co-authored LEAD YOURSELF FIRST – Inspiring Leadership Through Solitude (Bloomsbury Press), which focuses on how solitude strengthens people’s character—and their ability to lead with conviction, clarity and balance.

» CharacterLeadership.Center

Twitter: @ErwinRWB

Key Takeaways

[2:29] Mike’s young genius

  • ‘Going to be leader’ on kindergarten report card
  • Desire to engage, bring best out of others

[4:55] The mentors who influenced Mike growing up

  • Little League baseball coach/veteran
  • HS baseball coach (character over skill)

[9:24] Mike’s curiosity around leading people in a positive way

  • Formal study of leadership, positive psychology
  • Look for good and positive vs. shortcomings and flaws

[12:22] What Mike learned as a leader in the military

  • Not about you, but people you lead (selfless service)
  • Served as intelligence officer in Iraq, Afghanistan
  • Real consequences if predictions incorrect

[16:40] The inspiration for Lead Yourself First

  • Talk, article by William Deresiewicz article
  • Jim Collins suggested study of great leaders
  • Practice of solitude in meaningful times

[22:43] The cultural conversation around a need for solitude

  • Reflect on relationship with technology
  • Need time to step back and think for self

[28:21] The pros and cons of digital communication

  • Working remotely can facilitate deep work
  • Temptation to call meetings
  • Burnout caused by always being ‘on’

[37:34] The virtues of leadership honed by productive solitude

  • Creativity, self-regulation and courage

[42:19] Mike’s favorite example of creativity in leadership

  • Ulysses S. Grant and the Battle of Vicksburg

[49:11] The difference between reckless and brilliant ideas

  • Creative ideas easier than execution
  • Must have character to see idea through

[53:00] Mike’s ability to appreciate beauty amidst adversity

  • Sunset in desert during deployment
  • Lifts out of hardship, difficulty of moment

[56:43] Mike’s insight on embracing productive solitude

  • Deliberately schedule time
  • Take advantage of pockets of opportunity

[1:01:01] What Mike is questing for moving forward

  • Continue to grow The Positivity Project
  • Promote mindset that ‘other people matter’


Each week brings you in-depth conversations with leaders, stories from change-makers, and provocative ideas from artists and scientists – all designed to inspire you to shape your best work with more possibility, impact, and – yes – wonder.