Leadership Lessons From Miley Cyrus’s “The Climb”—My Go-To Power Anthem

As I build the playlist for Leadercast Kingston 2025, I’m realising it’s more than just curating background music—it’s a mini-therapy session. The road to this conference has truly been “an uphill battle” of sorting sponsors, selling tickets, and teaming up with the best (and a few stress-inducing surprise auditions—move over, Simon Cowell!). So when Miley Cyrus’s “The Climb” hit me right in the feels, I knew it was no accident: this is the unofficial leader’s anthem.

The Power of Perseverance Over Perfection

Let’s face it—leadership isn’t about the instantaneous, trophy-hoisting finish. “The Climb” reminds us it’s less about reaching the summit and more about who we become while we’re huffing and puffing up the mountain. Grit, not gloss, is what takes us higher—and sometimes that means we sweat through the fancy CEO shirt.

Embracing the “Uphill Battle”

Those inevitable obstacles? They’re the makings of a good leadership story (and great punchlines at the staff party). Leadership sometimes means accepting that not every plan will unfold like an Instagram highlight reel. So the next time you’re trekking through the mess rather than standing on the peak, remember—it’s all part of the playlist.

Redefining Success

Let’s belt it out: “Ain’t about how fast I get there…” In other words, it’s fine to take the scenic route. The leader’s legacy is built not on speed but on strength, resilience, and occasionally, spectacular detours. Challenge yourself to focus not on how many mountains you summit, but on the resilience and character you build while lugging the snacks up the trail.

Overcoming Internal Doubt

We’ve all heard that voice: “You’ll never reach it.” Turns out, that doubting internal monologue has never produced a chart-topping hit—or paid for the conference venue deposit! Leadership is partly about muting that critic (figuratively, of course… unless you have actual control of the playlist). Keep moving, even when you feel lost or directionless. Bonus: admit it aloud, and watch your team feel safe to do the same.

The Enduring Value of the Journey

“The struggles I’m facing / The chances I’m taking…” These lyrics remind us that the best stories aren’t the ones where everything was easy—they’re the ones filled with comebacks and coffee-fueled late nights. Every struggle, stumble, and stand-up-again moment is a trophy in disguise.

There’s Always Another Mountain

The punchline of leadership? There’s always another mountain—and another verse to sing. The summit isn’t the finish line; it’s just another spot for a selfie before the next big climb.

Podcast Reflection 🎙️

It’s Never Too Late to Launch a Business with Teri Dreher. Are you wondering if you’ve missed your peak? Teri Dreher proves it’s never too late to summit new mountains. From ICU nurse to pioneering patient advocate, Teri’s journey is a masterclass in reinvention, resilience, and entrepreneurial chutzpah. Grab your headphones and your favourite climbing stick; this episode is pure inspiration with a dash of “you got this!”

Listen and climb along: It’s Never Too Late to Launch a Business with Teri Dreher

Scripture Spotlight ✝️

“Let us run with perseverance the race marked out for us.” — Hebrews 12:1 (NIV)

The best playlist includes a track for endurance in every season.

Science and Humour: Why the Struggle Is Good for You

Research shows that those who persevere through setbacks, laugh at mistakes, and dance through adversity (even if off-beat) are happier, more successful, and more likely to inspire their teams. The next time your project misses a beat, try humming your favourite song—and keep moving.

Fun Fact of the Week 🤔

Did you know?

Most leaders listen to “The Climb” in secret before tough meetings. Others just call their moms. Either way, both work.

Interactive Poll 📊

Which lyric from “The Climb” best describes your current leadership adventure?

“It’s always gonna be an uphill battle…”

“Ain’t about how fast I get there…”

“Just keep moving, keep climbing…”

“Sometimes might knock me down, but no, I’m not breaking!”

“What’s a playlist, and where can I find the next snack?”

👉 Reply with your favourite lyric—or an embarrassing karaoke memory!

Resource of the Week 📚

Find Your Why by Simon Sinek. Are you stuck halfway up the mountain, wondering why you started the climb? This book will help you rediscover your leadership anthem. Grab it here.

Bulletin Board

Tune in to Flow 1 for a brand new episode of The Entrepreneurial You TV Show—Sunday at 8 PM, repeat Fridays at 10 AM JA time.

A new episode of The Entrepreneurial You podcast drops every Tuesday at 7 AM JA time at henekawatkisporter.com or wherever you find your favourite podcasts.

Save your spot for Leadercast Kingston! October 7, The Summit, Kingston. Early bird tickets at spurropen.com/leadercast. Cruisers get a US$20 credit for attending!

LeadHerShip Cruise 2025: Set sail November 3-7, 2025. Reserve your cabin for an unforgettable leadership voyage!

Interested in bringing the Boundaries & Brilliance Masterclass to your organisation? Email me: heneka@henekawatkisporter.com

Final Thoughts

Whether your climb is a playlist of wins, woes, or wild detours—remember, every mountain makes you stronger (and every wrong lyric is just bonus fun for the journey). Leadership is no solo ballad. Let’s summit, stumble, laugh, learn, and keep moving together.

With music, courage, and extra snacks,

Heneka Watkis-Porter

Mentor | Leadership Visionary Architect | Coach | Host, The Entrepreneurial You Podcast & TV Show

P.S. If you need a tune for your journey, start with “The Climb.” If you need a team for your summit, you know where to find me:  https://bit.ly/TEYNewsletter