Leading Ain't Easy

Leading Ain't Easy

By Ryan Calkins and Erny EpleyBusinessCareersManagement
Download on the App Store

Leading Ain't Easy episodes

  • The Generation Gap: Managing Boomers, Millennials, and Gen Z on the Same Team

    Got a story like this one? Text us!

    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 wildly different ideas about what work is even supposed to feel like.

    What they explored in this conversation:

    • The loyalty question: why older workers stayed seven or eight years and newer workers leave in three, and whether that's really about character or just doing the math differently
    • What it actually felt like to manage experienced drivers twice your age with no authority to fall back on, and what Ryan did instead of pretending to be the expert
    • Why John spent years giving more to companies than they gave back, and what finally made him stop
    • The cross-training habit John built after watching teams get held hostage by the one person who knew how everything worked
    • How economics (housing, healthcare, dual-income households,etc.) shape the expectations of the people you're managing right now
    • The best piece of leadership advice John ever received, and why two words have held up for 30 years

    "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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    54 min
  • When Management Won't Do Anything About a Problem Employee (feat. John Moore)

    Got a story like this one? Text us!

    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 actually feels like to be on the other side of that silence.

    They cover the full picture: what's actually happening behind the scenes when HR is involved and managers can't say so, why the top producer who's also a problem creates a genuine strategic dilemma for leaders, and what happens to a team's culture and accountability when that dilemma goes unresolved for too long.

    Key topics from this episode:

    • What's actually happening on the other side of the silence — building a case takes time, and leaders often can't tell you any of it.
    • The producer-problem tradeoff — When the person driving results is also the person creating conflict, leaders face a genuinely hard call. This episode doesn't pretend otherwise.
    • Managerial ethics and the friendship problem — What happens when that employee is also someone you went on vacation with last month.
    • The domino effect of doing nothing — Standards don't just erode quietly. They collapse fast, and they take your best people with them.
    • Inheriting a broken culture — What it looks like to walk into a team where problems have been ignored for years, and how to start rebuilding without losing everyone in the process.
    • What to actually say — When you can't share details, there's still something honest and useful you can tell your team.

    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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    41 min
  • Respect vs Likability (feat. Rene Guerrero)

    Got a story like this one? Text us!

    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 common tensions leaders face: the balance between being respected and being liked.

    Rene brings nearly 30 years of experience in engineering and public works leadership and shares what he has learned about credibility, trust, transparency, and tough decisions. Together, they explore how leaders can build real respect without becoming cold, rigid, or disconnected from their teams.

    The conversation covers:

    • the difference between wanting to be liked and needing to be liked
    • why respect is built through consistency and integrity
    • how transparency helps people understand hard decisions
    • why authenticity matters when stepping into leadership
    • and how to avoid drifting into fear-based or approval-based leadership

    They also share personal stories about being the face of difficult decisions, navigating leadership transitions, and learning that it is okay if not everyone likes you.

    If you have ever struggled with trying to be a “good” leader without becoming a people pleaser, this episode will hit home.

    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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    49 min
  • PIPs Aren't the End of the World

    Got a story like this one? Text us!

    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 are already halfway out the door.

    In this episode, Ryan and Erny talk about PIPs from both sides.

    Ryan shares what it was like to be put on a PIP himself, including how hard it hit when it felt personal instead of productive. Erny talks about how leaders should approach performance issues before they ever get to that point, and why no employee should be blindsided by critical feedback at evaluation time.

    They also get into:

    • when a PIP is being used the right way
    • when it starts to feel weaponized
    • why accountability matters
    • how leaders can communicate clearly and empathetically
    • and why a PIP does not automatically mean your career is over

    This episode is for leaders who want to handle performance issues better, and for employees who need the reminder that one hard moment does not define the rest of their career.

    A PIP may be a setback, but it does not have to be the end.

    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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    45 min
  • Leading When You Don’t Like Someone

    Got a story like this one? Text us!

    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 it turn into bias, favoritism, avoidance, or over-correction. 

    We get into staying objective, using data and clear expectations, managing your ego, and keeping the main thing the main thing: results, culture, and consistency.

    You don’t have to be their friend.
    But you do have to lead them well.

    "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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    51 min
  • Executive Presence (feat. Frank Hopkins)

    Got a story like this one? Text us!

    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 banks across the Southeast). Together, we break down what executive presence actually is: carrying authority before you speak; and reinforcing it through judgment, composure, clarity, and behavior under pressure.

    We get into the difference between authority and credibility, why “confidence theater” fails, and why the leaders people trust most are the ones who stay regulated when the stakes go up. Frank also explains a hard truth middle managers live every day: you’re accountable up and you’re responsible down — and if you complain down, you’ll lose trust fast.

    And then we land on the line that should be taped to every leader’s wall:

    “If you’re in charge, you’re responsible for everything.”

    What we cover:

    • What executive presence is (and what it is not)
    • “Authority without force” and getting people to follow you even when they don’t have to
    • Composure under pressure: calm isn’t passive, it’s containment
    • Clear decisions without hedging and over-explaining
    • Why consistency is the hardest part (especially when you’re tired)
    • Middle management reality: translating top-down changes without losing trust
    • Taking responsibility and shielding your team (and why it builds loyalty fast)

    If you’re trying to lead at a higher level (or you’re already there and feel the weight of it) this one’s for you.

    "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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    45 min
  • Leadership Mistakes That Can Negatively Impact Culture

    Got a story like this one? Text us!

    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 standards but tolerating contradictions, avoiding tough conversations, playing favorites, and overvaluing performance while ignoring behavior. They also talk through two real-world culture scenarios: the “impossible situation” where morale is already in the toilet, and the “good culture on paper” situation where a lack of accountability eventually creates serious problems.

    A big theme throughout this one: culture is what you allow... and if you want it to improve, you can’t ignore it.

    In this episode:

    • Why culture starts at the top (and how inconsistency kills trust)
    • The danger of chasing numbers while ignoring behavior
    • Why accountability protects your high performers (and your team’s morale)
    • How to hold standards without becoming a micromanager
    • Why recognition matters more than people think (kudos/shoutouts)
    • The burnout trap: trying to change what you can’t control

    If you’ve ever stepped into a messy team, inherited a culture problem, or felt yourself burning out trying to fight upstream, this one’s for you.

    "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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    46 min
  • Leading When You're the Youngest on the Team

    Got a story like this one? Text us!

    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 imposter thoughts, the pressure to prove yourself, and the temptation to overplay authority just to feel “legit.”

    Ryan shares what it was like being the youngest in the Marine Corps and then again in the workplace, including an early-career mistake that created an instant credibility problem. Erny breaks down what it means to be “new to power,” why “because I said so” backfires, and how humility and ownership are often the fastest path to real respect.

    If you’re the youngest manager in the room right now, this one’s for you.

    Key takeaways:

    • How to earn respect without demanding it
    • Why proving yourself through posturing kills credibility
    • The role of listening, consistency, and authenticity
    • How to introduce change without triggering resistance
    • Why “I was wrong” is one of the hardest (and most powerful) sentences in leadership

    "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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    49 min
  • Being the FNG (F’ing New Guy): Earning Trust From the Start (feat. Matt Quinn)

    Got a story like this one? Text us!

    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 social capital; especially when the people around you have been doing the work longer than you’ve been alive.

    They cover what to do (and more importantly, what NOT to do) in your first stretch, how to listen without getting played, why “past practice” can be a trap, and the surprisingly powerful leadership habit Matt tells every new manager: clean the bathroom.

    In this episode:

    • Why leaders should listen first before changing anything
    • How to avoid walking into a job and “moving pieces” you don’t understand
    • The difference between proving yourself and performing for approval
    • Why the best trust-builder is often: “I don’t know, can you teach me?”
    • “Past practice” vs best practice (and why that distinction matters)
    • The leadership lesson that sticks: clean the bathroom (AKA: do the job nobody wants)

    "Leading ain’t easy, but you don’t have to do it alone."

    This episode does contain some explicit language

    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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    47 min
  • Setting Boundaries w/ Your Boss

    Got a story like this one? Text us!

    Setting boundaries with your boss is about doing what matters without burning yourself out. Ryan and Erny break down how to set boundaries respectfully, stay consistent, and protect your time without damaging trust or credibility.

    In this episode of Leading Ain’t Easy, we talk about one of the most common leadership traps: being so responsive and available that you accidentally teach people your time doesn’t matter.

    We unpack:

    • How to set boundaries without sounding lazy or “bare minimum”
    • Why consistency matters (and why moving your boundary teaches people it isn’t real)
    • The difference between your boundary being the problem vs your environment being the problem
    • Tools that help: scheduled send, clear framing (“something else has to give”), and simple expectation-setting
    • The hidden issue for high performers: getting punished with more work
    • What happens when boundaries collide with real deadlines (and why you need backup systems)

    Listener question: What’s one boundary you know you need, but haven’t set yet?

    “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.

    Subscribe on Apple, Spotify, or wherever you listen. 

    Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates. 

    If this episode resonated, please leave a review as it helps more leaders find us.

    46 min

About Leading Ain't Easy

From the publisher's feed

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…