Lead Like Shackleton: 5 Secrets to Unforgettable Hikes

Shackleton’s Survival Playbook for Group Hikers

How One Leader Saved 27 Lives—And What It Teaches Us About Adventure

Ever felt the pressure of keeping your hiking buddies safe, smiling, and still speaking to you by the end of the weekend? I get it. Every year, I with a few other hiking veterans, lead a crew of friends; some seasoned hikers, others who think "outdoorsy" means drinking on patios, on a weekend adventure. It's amazing, hilarious, and stressful all at once. That's why lately, I've been obsessed with Ernest Shackleton.

In 1914, Shackleton’s Antarctic expedition went spectacularly wrong. His ship, The Endurance, was crushed by ice, leaving 27 men stranded in one of the harshest environments on Earth. Yet, every single one survived. How? Shackleton mastered three key leadership skills—skills you can easily apply to your next hiking adventure:

• Clear, honest communication (no sugar-coating)

• Defined roles (everyone has a job)

• Regular check-ins (mental and physical)

Here's how to hike like Shackleton (minus the frostbite):

Communicate Clearly & Early

• Set expectations upfront: pace, distance, terrain, weather.

• Share your plan openly—no surprises.

Assign Roles (Yes, Even Silly Ones!)

• Navigator: Keeps the group on track.

• Medic: Handles blisters and bruises.

• Cook: Fuels the crew.

• "Vibes Coo-rdinator": Keeps morale high (and snacks flowing).

Regular Check-Ins

• Ask during breaks: “How’s your body feeling on a scale of 1–10?”

• This simple question invites honesty and helps prevent injuries or meltdowns.

Be the First to Hike, Last to Eat

Shackleton led from the front, never placing himself above his crew. On the trail, leadership means:

• Staying calm and positive when conditions get tough (cold, wet, tired).

• Modeling good habits: snack regularly, hydrate often, layer clothing properly. Others will follow your lead.

• Checking in regularly without micromanaging. Keep morale high by genuinely caring about your group's well-being.

Tip:
Your attitude sets the emotional temperature for the entire group - especially for newer hikers. Lead by example.

Plan to Pivot

Shackleton constantly adapted his strategy.

On group hikes, flexibility is critical:

Have backup plans: a Plan B, Plan C, and a shortcut route ready.

Watch for subtle signs of struggle:

Fatigue, mood shifts, or slowing pace. Don’t wait until someone asks for help.

Be okay skipping a summit or shortening the hike: Safety always beats ego.

Pro Move:
Brief your group on backup plans beforehand. Say clearly: "If X happens, we'll do Y." It builds trust, clarity, and confidence.

Build Trust with Small Moves

Leadership isn't about being the loudest, it's about caring the most. Shackleton showed empathy in small, meaningful ways. On your next hike, try these simple moves:

• Share your snacks: Nothing boosts morale like unexpected trail treats.

• Celebrate small wins: A tough incline conquered, a tricky creek crossed—acknowledge these moments.

• Stay present: Around the campfire, make space for everyone. Notice who's quiet and gently draw them in.

Adventure Weekend Tip:
You don’t need to be the loudest leader. You just need to care the most.

The Shackleton Takeaway 

Whether you're leading 27 men across Antarctic ice, or guiding your best mates up a mountain, great group experiences don’t happen by accident. They’re built on:

• Clear expectations

• Thoughtful preparation

• Humble leadership

• Adaptability

• Genuine care for your group

As I pack for this year’s Adventure Weekend, I'm channeling my inner Shackleton. Because leadership isn't just about surviving the wilderness, it's about bringing your people through it together, and making them eager to join again next year.

What's the most unforgettable group hike you've ever been on?
What made it challenging, and how did your group pull through?

THAT’S ALL FOR THIS WEEK

Thank you for reading Mowser’s Musings. I hope you found it helpful.

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Until next week.

Stay well,

Mowser

Helping hiking enthusiasts explore the great outdoors