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As CEO of the $96 billion Sam’s Club, Latriece Watkins is testing her mettle at the warehouse retailer that produced CEOs for Walmart, Target, and Walgreens

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Surging Treasury yields expose a brutal truth: America has no margin for error on its $39 trillion debt

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Current price of oil as of May 29, 2026
CommentaryLeadership

CEO of Tough Mudder: How to make the most of your mistakes

By
Will Dean
Will Dean
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By
Will Dean
Will Dean
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March 3, 2015, 12:00 PM ET
Courtesy of Will Dean

The Leadership Insider network is an online community where the most thoughtful and influential people in business contribute answers to timely questions about careers and leadership. Today’s answer to the question “What’s the best mistake you ever made?” is written by Will Dean, CEO of Tough Mudder.

I’ve failed many times before and I will do it again – so will you. It’s unavoidable. However, what separates the strong from the weak is what you do after you make a mistake. For instance, our first Tough Mudder event was filled with mistakes. When I was planning for the event, I was confident in my idea and the customer demand reinforced its promise – we expected only 500 registrations, but we got nearly 4,500. I was thrilled, but I had underestimated the complexity of putting on an event of that scale.

Obstacles were not built large enough to handle the volume of participants, long lines formed, we ran out of water, and parking was a nightmare. It was obvious to anyone at the event that some mistakes had been made. What was less clear – and what would ultimately decide the future of Tough Mudder – was how we would respond to them. The lessons I learned from this critical experience have been essential to the growth of Tough Mudder. Here are few tips to help you make the most of the challenges you face:

Ask “why”
Mistakes are the best learning opportunities we get – there’s no better chance to improve yourself and your company. I’m a firm believer in asking “why” over and over until you get to the bottom of a problem. Don’t just identify the problem on the surface — dig deeper. Keep asking “why” until you find the root cause.

Seek help when needed
As an entrepreneur, it can be tempting to try to learn and control everything about your company. I realized pretty quickly that while I’d like to know everything that’s going on, I don’t need to. In fact, it’s better that I don’t. After the first event, I knew that our team was lacking in engineering knowledge and event logistics and delivery. This led us to make a few key hires – experts in engineering and event management, who introduced new processes and improved our systems until we were delivering best-in-class experiences. Knowing when to ask for help or when to hire is important. It doesn’t mean you are weak; rather, it means you are smart enough to realize someone else can help you do it better.

Don’t hold back
After you make a mistake, it’s natural to approach the next situation with an abundance of caution. Fight that urge – if you stop taking risks, you’re guaranteed to fail. A few months after our debut event, we held our second in northern California. The jitters were still there from the first event, but the hard work paid off. The event delivery wasn’t flawless – it took us a long time to perfect our logistics – but it was vastly improved. We haven’t stopped making mistakes at Tough Mudder, but each lesson learned has helped moved our company forward.

About the Author
By Will Dean
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