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.
Episodes
36 episodes
The Higher You Go, the Less You Actually Hear
Ryan Calkins and John Moore get into the leadership echo chamber; how it forms, why it's usually the leader's own doing, and what it costs when the people around you stop telling you the truth. If you've ever wondered whether your team is actua...
Being a Woman in a Male-Dominated Industry — One Leader's Story
Ammie Bird (Brandon) led operations for 15 years at a Fortune 250 waste management company, one of the most male-dominated and physically dangerous industries around. She joins Ryan Calkins and John Moore for an honest conversation about earnin...
When Leadership Gets Personal
Ryan Calkins and John Moore talk through what happens when you can't separate the manager from yourself; when your team's struggles start to feel like your own failures. This one's for anyone who's ever cared too much about people who didn't as...
When Being the Go-To Person Becomes the Problem
Every team has the person everyone depends on, and sometimes that person is the leader. Ryan Calkins and John Moore discuss what happens when that dependency stops being a strength and starts becoming a trap, for both the leader and the team th...
The Nice Boss Trap
Ryan Calkins and John Moore talk through what happens when the instinct to be understanding slowly slides into avoidance, and why the thing that feels like kindness ends up being harder on everyone. A real conversation for anyone who's been let...
Accountability Without Authority
Ryan Calkins and John Moore both came up through project management, and they've both felt what it's like to be responsible for something you don't fully control. This is an honest conversation about navigating accountability when the authority...
The Promotion That Exposed You
Getting promoted feels like validation... until you get there and realize what you actually don't know. Ryan Calkins and John Moore talk honestly about the transition from high performer to new manager: the imposter syndrome, the peer dynamic t...
From the Corner Office to the Zoom Room
The corner office used to be shorthand for authority. Now leadership happens through a camera icon, a chat message, and a lot of trust you didn't have to build the same way before. Ryan Calkins and John Moore have a real conversation about what...
The Call Nobody Wants to Make
Ryan Calkins and John Moore get into what it actually feels like to be forced into a decision when you don't have nearly enough information, but can't wait any longer. An honest conversation about perfectionism, pressure from above, who absorbs...
Fix Your Face
Most leaders know they're supposed to stay composed. Very few talk honestly about how hard that actually is, or what it costs when you don't.Ryan Calkins and Erny Epley get into the part nobody puts in a leadership manual: the moment you...
When Being the Bottleneck Is the Whole Problem
Most of us started our careers being told what to do. Some of us had bosses who yelled. Some had bosses who kept everything to themselves (every client, every process, every piece of institutional knowledge) because that's how they stayed neces...
When Your Best Employee Keeps Asking for a Promotion
When a high performer keeps pushing for a promotion, the easy instinct is to either reward the performance or buy time. But Ryan Calkins and John Moore get into why both of those can backfire, and what's actually underneath a promotion decision...
"Soft Skills" Aren't Soft — They're the Hardest Part of Leading
Most leadership development focuses on the technical side: how to run a meeting, how to build a plan, how to hit a number. Emotional intelligence doesn't fit neatly on a training checklist. And that gap, Ryan Calkins and John Moore argue, is co...
Why "We're Like a Family" Can Backfire
The "we're like a family here" pitch is everywhere... and for a lot of people, it sounds like exactly what they want. Belonging. Loyalty. People who have your back.But Ryan Calkins and John Moore have both lived the other side of that st...
The Generation Gap: Managing Boomers, Millennials, and Gen Z on the Same Team
Ryan Calkins and John Moore get into one of the most frustrating realities of modern management: you're not leading one kind of person, you're leading four generations at once, each shaped by different economics, different work cultures, and wi...
When Management Won't Do Anything About a Problem Employee (feat. John Moore)
Every team has had one; the person everyone's complained about, more than once, and nothing visibly changes. Before you write off your leadership, Ryan Calkins, John Moore, and ErnyEpley get into what you might not be seeing, and what it actual...
Respect vs Likability (feat. Rene Guerrero)
Do you need to be liked to be an effective leader?In this episode of Leading Ain’t Easy, Ryan and Erny sit down with Rene Guerrero, Assistant Public Works Director for the City of Ontario, to talk through one of the most ...
PIPs Aren't the End of the World
A Performance Improvement Plan (PIP) can feel like a career death sentence.For a lot of people, getting put on a PIP feels deeply personal. It can hit your confidence, make you question your future, and leave you wondering whether you ar...
Leading When You Don’t Like Someone
You’re a leader. You’re not supposed to say it out loud. But let’s be real: you’re not going to like everyone you lead.In this episode, Ryan and Erny talk about what to do when someone on your team gets under your skin, without letting i...
Executive Presence (feat. Frank Hopkins)
A lot of people think “executive presence” means being polished, charismatic, or loud.It doesn’t.In this episode, we’re joined by executive coach Frank Hopkins, who works with CEOs and executive teams (primarily community b...
Leadership Mistakes That Can Negatively Impact Culture
If we're being real, workplace culture doesn’t live in mission statements or speeches, it lives in what happens every day.In Episode 15, Ryan and Erny break down the leadership mistakes that can erode culture over time: preaching standar...
Leading When You're the Youngest on the Team
What do you do when you’re the newest leader… and everyone you’re leading is older than you?In this episode of Leading Ain’t Easy, we get real about what it feels like to lead without seniority, including the anxiety, the impost...
Being the FNG (F’ing New Guy): Earning Trust From the Start (feat. Matt Quinn)
Being the "new guy" is hard. Being the new leader is harder.In this episode, Ryan Calkins and Erny Epley sit down with special guest, Matt Quinn, to talk about what it really takes to earn trust when you walk into a new job with zero ...