Leading Ain't Easy
Leadership looks shiny on social media. But the reality is it’s messy, isolating, and full of self-doubt. Leading Ain’t Easy pulls back the curtain on the side of leadership nobody puts on their résumé.
Hosted by Ryan Calkins (Marine Corps veteran, career/leadership coach, and founder of Reframe & Rise) and Erny Epley (public-sector leader and founder of Bus Pro Network), this show dives into the raw, unfiltered truths of leading others; whether it’s in the military, the public sector, or the private world of business.
We’re not here with corporate buzzwords or textbook definitions. Instead, you’ll hear:
- Honest stories about the challenges and failures that shaped us.
- Real conversations about the doubts and decisions leaders wrestle with every day.
- Lessons, frameworks, and laughs that remind you you’re not alone in the struggle.
Episodes run 45-60 minutes (long enough to go deep, short enough for a commute) and drop weekly. Some weeks it’s just us, other weeks we’ll bring in guests (current and aspiring leaders) to share their own unfiltered journeys.
If you’ve ever wondered whether you’re cut out for this role, questioned yourself after making a hard call, or felt like a fraud even with the title… this podcast is for you.
Because leading ain’t easy, but you don’t have to do it alone.
Leading Ain't Easy
Episode 11 - Managing Up: How to Lead Without Authority
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Managing up is one of the most important leadership skills and one of the least taught.
In this episode of Leading Ain’t Easy, Ryan Calkins and Erny Epley talk about what it really looks like to lead when you don’t have authority over the people who influence your success: your boss, senior leaders, and cross-functional departments that control the data, budget, timelines, and decisions you’re expected to execute.
If you’ve ever been told “figure it out” without support… if you’ve been burned by a surprise that climbed the chain… or if you’ve struggled to communicate your vision clearly under pressure... then this episode is for you.
In this episode, we cover:
- Why leadership hates surprises (and how to avoid blindsiding your boss)
- How to tailor your communication to how your boss receives information
- How to challenge leadership without being seen as “difficult”
- Why documentation matters (and how to protect yourself with clarity)
- The mindset shift: clarity beats competence
Question for listeners:
Where do you struggle most with managing up; clarity, timing, politics, or trust?
Key takeaways
- Don’t let your boss get blindsided; give heads up early.
- Communicate to be understood, not just heard.
- Lead with the solution, then support with context.
- Use data to paint a clear picture fast.
- Document agreements and decisions (protects everyone).
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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