🎢Disneyland's Sunk Cost Fallacy


No #162 | March 30, 2025

by Matthew Boyd

Good morning, welcome to the weekly Lead It Cool newsletter.

The Boyd family has now returned from their adventures in Las Vegas and California with some great stories to tell and the sunburns to prove it😜.

In this week's Lead It Cool newsletter:

  • 🎢Disneyland's Sunk Cost Fallacy
  • 🏈Just Win, Baby
  • 🤣Vacation Distractions
  • 😎Cool Links

🎢Disneyland's Sunk Cost Fallacy

Picture this.

You’re standing in line for Tiana’s Bayou Adventure (formerly known as Splash Mountain) at Disneyland. You've already been waiting for an hour. It’s 30°C. No shade. The sun is doing its best impression of a heat lamp. Your family is starting to melt. There’s still another 30 minutes to go, at best, and the ride keeps glitching, pausing every few minutes like it’s deciding whether it actually wants to keep operating today.

So what do you do? What do you do?

This moment, standing there in the sweltering sun, surrounded by frustrated kids and ominous mechanical creaks, is a textbook example of the sunk cost fallacy.

What’s the sunk cost fallacy?

It’s the idea that we continue investing time, money, or energy into something not because it’s the best choice going forward, but because we’ve already invested so much. "We’ve come this far…" becomes the reason we keep going, even if it’s no longer worth it.

That was us. Standing there. Boiling. Wondering if the ride would shut down before we even got on. We debated leaving the line—cutting our losses, grabbing a churro, and finding something else to do. But the sunk cost fallacy kicked in hard. We'd already waited 60 minutes. We couldn’t “waste” all that time.

So we stuck it out.

Eventually, we made it on the ride. Victory, right?

Well, sort of.

I got seated in the front row.

Which meant I took the full force of the final drop like a human sponge. I was soaked. I might as well have jumped into a swimming pool fully clothed. My family (and a bunch of complete strangers) laughed at my misfortune.

Thankfully, it was hot enough that I dried off quickly, but in hindsight…

Yeah, we probably should’ve just walked away... 😂


🏈Just Win, Baby

One of my favorite ways to prep for a trip is to learn about the local sports franchises.

You can learn a lot about a city through its relationship with sports: its values, its history, and the identity it chooses to rally around.

Las Vegas, now home to the Raiders, offers a fascinating case study. But to understand the team’s presence in the desert, you have to go back a few decades, and dive into one of the most complicated relationships in sports history.

The ESPN documentary Al Davis vs. The NFL does a brilliant job summarizing the turbulent history of the Raiders. It focuses on the longtime feud between Al Davis, the team’s iconic owner, and NFL Commissioner Pete Rozelle. Davis was brash, rebellious, and relentlessly competitive, a man who didn’t just play in the league, but challenged it at every turn. He moved the team from Oakland to Los Angeles, back to Oakland, and eventually set the stage for a final move to Las Vegas in 2020. The journey wasn’t just about stadium deals and market size, it was about control, defiance, and vision.

But here’s what stood out most in the documentary: no matter where the Raiders played, they carried with them the same identity. The same swagger. The same edge. The same culture.

And that culture was rooted in a simple, unforgettable phrase coined by Al Davis: “Just win, baby.”

It wasn’t just a slogan. It was a vision statement. Clear, concise, and impossible to misinterpret. Everyone in the organization, from players to coaches to front office staff, knew what the goal was.

No frills, no fluff. Just win.

In leadership, we talk a lot about the importance of vision. But too often, vision statements get watered down by jargon or become lost in complexity. The best ones (like Davis’) cut through the noise. They provide a compass, a standard, and a shared purpose. Whether you’re leading a football team, a business, or a government agency, clarity of vision is everything.

The Raiders may have changed cities, stadiums, and zip codes. But their identity has remained consistent, proof that a powerful vision travels well.

Because when your purpose is clear, location is just logistics.

Just win, baby.


🤣Vacation Distractions

It actually works... 😂 (source)


😎Cool Links

😊High Agency in 30 Minutes. This is a fantastic article by Georg Mack on the idea of high agency and how to achieve it. Well worth the full read.

🤔A Surprising Route to the Best Possible Life. You want to reach out to these kids and lighten the load, reduce stress, make everything easier. And yet I have found that paradoxically life goes more smoothly when you take on difficulties rather than try to avoid them. People are more tranquil when they are heading somewhere, when they have brought their lives to a point, going in one direction toward an important goal. Humans were made to go on quests, and amid quests more stress often leads to more satisfaction, at least until you get to the highest levels. The psychologist Carol Dweck once wrote: “Effort is one of the things that gives meaning to life. Effort means that you care about something.”

📞The Game of Numbers. Apparently in the financial planning biz, a huge part of the game is COLD CALLING. You gotta pick up the phone and pitch yourself to potential clients. Can you guess where this is going? Resistance.

💌Share it on LinkedIn

Thank you!

Let’s connect! 💬 You can find me on LinkedIn and Twitter

Lead It Cool - by Matthew Boyd

🌟by Matthew Boyd | mid-career MBA survivor, strategist, pragmatic leader 📚✍️ 🔥 Passionate about storytelling through the lens of popular culture and humor 📨 Creator of the 'Lead It Cool' newsletter - your weekly leadership / pop culture digest 🎬🎧

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