The #1 Question You Can Ask Yourself Today

What do you want most out of life and how will you achieve it? Those are tough questions to answer, aren’t they? That’s because they’re the wrong questions to be asking.

A better approach is to ask yourself this: What does winning mean to me?

For me, winning means endurance racing. I once completed 50 Ultra events and 14 Ironman events in a single year. Heck, I did the Vermont 100, the Lake Placid Ironman, and the 135-mile Badwater Ultra in one week. And Badwater ... well, that race is bad. It starts 100 feet below sea level in Death Valley, with temperatures in the 120s, and it climbs 8,500 feet up Mt. Whitney.

For me, winning also means being successful with Spartan Race—creating and building a new global sport from the ground up.

But that’s me. What does winning mean to you? And no, it doesn’t have to be endurance or obstacle course racing or building a successful business or any of that stuff. Just don’t tell me it involves sitting near a pool with a drink in your hands. Living an easy life is not winning. It’s not even trying. It’s clocking in and clocking out and getting comfortable in your very deep rut. Wait and want. Want and wait. Boring.

In the book Flow: The Psychology of Optimal Experience, psychologist Mihaly Csikszentmihalyi writes, “The best moments in our lives are not the passive, receptive, relaxing times. ... The best moments usually occur when a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile.” So basically, according to Csikszentmihalyi, it’s human nature to embrace and love a challenge.

I agree. Finding an obstacle, voluntarily taking it on, and eventually overcoming it is the key to happiness. It’s also how I define winning. This doesn’t mean I don’t want to finish first in every race, because believe me I do. And sometimes I accomplish that. But what’s really important for me—what winning really means to me—is facing and overcoming the challenge no matter what it is. Winning is defined by the effort that I put into something as much as the results I get out of it.

To define what winning means to you, ask yourself: • What have I always wanted to do, but haven’t even attempted? • What do I want to achieve, but think I can’t achieve? • What am I willing to sacrifice to realize these dreams? • What am I not willing to sacrifice?

When you’ve got answers to these questions, you know what winning looks like for you. And don’t forget about that last question. It’s important. For me, it’s my family. I’m not willing to sacrifice my family. Not ever. Not for anything.

Beyond that, everything is on the table. And I prove that every day. I gave up a cushy life on Wall Street to create Spartan Race, putting my life savings and an absurd amount of time into the endeavor, refusing to take no for an answer and pursuing my dream. You can, too. You just need to know what your dream is. Once you know your dream, you can win your dream. So let’s get started!

Ready to give Spartan a try? Here’s everything you need to know to find your race.