The Host, Revealed: Skippy’s Journey in His Own Words w/ Jesse Link

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About the Episode: 

Today, in the final episode of our very first season, the tables turn. 

For nearly 30 episodes, I’ve asked the questions, held space for others to open up, and pulled at threads in hopes that you, the audience - leaders and colleges - could find resources and actionable strategies. Now I find myself on the other side of the mic, sitting face to face with my mirror, Jesse Link - (and by chance a literal mirror!) We get into my own journey — my upbringing, my family, the roads I’ve walked, the mistakes I’ve made, the systems I’ve built to stay standing, and the people and relationships that keep me whole. 

Guest Host:

Jesse Link is a strategic partner to agencies and growing businesses, helping CEOs connect the dots between their numbers, their narratives, and themselves. He’s also the lead researcher at Healing Our Politics, and, proudly, a coaching client turned lifelong friend. 

From college athlete, to climbing the ladder at Goldman Sachs, and founding a venture-backed startup, Jesse decided to step off the corporate fast track, to follow the crooked path — the kind built through failure, creative discovery, and honest reinvention. Not the one laid out for him on Wall Street, but one that meant something. And while he’s exploring new creative frontiers — through writing, video, and documentary — he’s still learning to lead with not knowing. 

He’s asking the big questions  — what drives us, what blocks us, and how we find our way back to passion. 

. 

Key Topics Discussed:

· [00:02:40] Episode/Guest Host Intro

· [00:09:03] Identifying as a Public Service   

· [00:12:43] What Would Grandma Think?

· [00:18:17] Skippy Shows His Cards: Political Family History 

· [00:23:43] Partnership as Lead Domino, Partnerships is a Verb 

· [00:28:45] Selfishness in a Good Way 

· [00:29:50] Discipline and Practice 

· [00:32:55] What Worked for Weirdo (Skippy) 

· [00:34:20] Hitting the Decision Point  

· [00:36:20] Change of Environment 

· [00:37:43] From the Illusion of Confidence to Genuine Confidence 

· [00:40:07] It's More of a Spectrum of Growth than a “Before and After” 

· [00:49:30] Unrelenting Hope 

· [00:55:22] Ho to be an Unbogged Public Servant 

· [01:00:48] Skippy’s Happiness Parachute in Office (An Unsolved Bog) 

· [01:03:54] Time In Office and Campaigning for Conversation 

· [01:12:25] Leaders are the Wheel, not the Gas

· [01:16:20] SPONSOR: Skyrun Vacation Rentals: Use Code HOP15

· [01:17:15] SPONSOR: ELC (https://www.electedleaderscollective.com)

· [01:19:35] Comparison in a Bubble of Privilege 

· [01:24:46] The Dichotomy of Shame and Desire of Wealth 

· [01:26:12] Available Resources for Public Servants and its Consequences 

· [01:31:37] Financial Responsibility as a Constraint for High Function 

· [01:31:37] A Digression into Spinny Flippy Zone 

· [01:35:25] Safety and Risk 

· [01:39:25] Fear is a Yellow Light 

· [01:43:34] Skippy’s Theory of Travel (and tips!) 

· [01:54:12] How to Stay Charged While at Work 

· [01:57:16] Rapid Fire Q&A’s: From Favorite Color to Biggest Fear 

· [02:04:34] Skippy’s Zone of Genius: The Wellbeing of Leaders 

· [02:13:45] HealingOurPolitics.com 

· [02:13:50] “The Leader’s Handbook” (https://www.healingourpolitics.com/#newsletter) Newsletter

· [02:14:04] ELC (https://www.electedleaderscollective.com)

· [02:14:04] Support ELC 

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