Leadership Lessons from the Happiest (and Craziest) Place on Earth
Last week, I survived—*ahem*, I mean thrived—through a family Disney World trip with four generations in tow. Yes, four. From toddlers to my 76-year-old mom on a scooter. We braved lines, churros, and the occasional meltdown. And while Disney promises magic, let me tell you—it also offers a crash course in leadership.
If you can guide your family through that chaos, you’re more than ready to handle a high-stakes meeting or a tough project at work.
Here are four leadership lessons I learned (the hard way), with a sprinkle of magic and a whole lot of real talk.
Lesson 1: Even the Best Plans Go Haywire—Stay Flexible
We had a plan. A great plan. I mapped out rides, meal breaks, even bathroom stops. And then reality hit.
The toddler needed a nap. And it came on really suddenly in the stroller. My mom wasn’t sure about navigating the scooter in crowded areas as people cut her off and my sister and I gave her conflicting direction.
Here’s the thing - flexibility is your leadership superpower. Plans are great, but they’re just a starting point. Leadership is about rolling with the punches and keeping the big picture in mind.
Practical Tip: When things go sideways, take a breath, reassess, and adjust. Focus on what really matters—because clinging to your original plan will only make you (and your team) miserable.
Lesson 2: Play to Your Strengths—and Adapt When Needed
In my family, I’m the General—the one setting the agenda and rallying the troops. My sister? She’s the Coordinator who handles the logistics and executes. My nephew? He’s the one that loses his car keys and credit card. (Oh wait - that’s also me…) Anyway…
But some days, I wasn’t the General. I was the Sherpa, carrying snacks and strollers. Other days, I was the Chief Cat Herder, making sure my mom’s scooter didn’t get stuck in Tomorrowland traffic.
Leadership isn’t about sticking to one role. It’s about knowing your strengths and adapting when needed.
Practical Tip: Lean into your strengths, but don’t be afraid to switch gears. Whether you’re the General, the Sherpa, or the Cat Herder, stepping into the role your team needs in the moment is what makes you a great leader.
Lesson 3: Communicate Like Your Sanity Depends On It
Disney World with a big group is basically organized chaos. If you’re not communicating constantly, someone’s bound to end up in the wrong place, at the wrong time, with hurt feelings, or have to use the bathroom…on the other side of the park at exactly the same time as your lightening lane reservation.
But here’s the kicker—communication isn’t just about logistics. It’s about managing emotions, too.
I had a couple internal meltdowns. It was over the lack of humanity. Over free hot chocolate and cookies. Yep – “Free”. Hot chocolate and cookies! Because people kept cutting my mom off!
But here’s the leadership lesson: “Acknowledge when you lose it, course-correct, and keep moving forward.” My niece taught me an amazing lesson. She asked for multiple time outs. She’d say “I’m overwhelmed, I just need an attitude adjustment. I need 5 minutes” and would disappear” and I’d think “wow-zers – we all should be like her. Be self-aware. Know what you need. Ask for what you need. Prioritize yourself when you need to.”
Practical Tip: Over-communicate. Check in often. And when emotions run high (yours or someone else’s), take a moment to reset. Your team doesn’t need you to be perfect—they need you to stay present.
Lesson 4. Celebrate the Wins—No Matter How Small
At some point, my mom said to me, “No one’s smiling at the happiest place on earth.” I looked around and realized “she’s right!” – and challenge accepted!
From that moment on, every time I saw someone smile, I tapped her on the shoulder. Then her smile made me smile. My smile made my sister smile. And my my grown nephew got in on it. Before long, we were grinning like fools, singing little songs, making people smile, and spreading the joy.
The lesson? Find your wins, make your wins, and claim your success.
Practical Tip: Celebrate the little things. Acknowledge progress, no matter how small. Because those moments of joy are what keep people going—whether you’re at Disney or in the workplace.
So there you have it—four leadership lessons straight from Disney. Stay flexible, play to your strengths, communicate effectively, and celebrate every win. Because leadership isn’t about perfection—it’s about progress.
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(P.S. Thank you Disney for a memorable familly trip - meltdowns and all!)