Leading Ain't Easy

Episode 3 - Loneliness at the Top

Ryan Calkins

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0:00 | 44:34

No one really tells you how lonely leadership can get, especially the higher you climb.

In this episode, Ryan and Erny talk candidly about the isolation that comes with being the one everyone turns to. The pressure, the silence, the responsibility you can’t unload on your team, and the shrinking safety net as you move up.

They discuss:
• Why support turns into “context,” not coverage
• The truth behind “that’s why you get paid the big bucks”
• Taking the blame when the public or leadership is angry
• Holding your team accountable without favoritism
• Being the buffer (even when you’re struggling yourself)
• When past toxic workplaces follow you into new roles

If you’ve ever felt like leadership puts you on an island (with or without the title), this conversation will feel real and grounding. You’re not the only one feeling the weight, even if it seems like you’re the only one carrying it.

Leading Ain’t Easy, but you don’t have to do it alone.

Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

  • Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
  • John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
  • Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

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