Chasing Failure: Kobe Made Me Do It

The steps of a man are established by the Lord, when he delights in his way; though he fall, he shall not be cast headlong, for the Lord upholds his hand. — Psalm 37:23-24 ESV

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Everything negative — pressure, challenges — is all an opportunity for me to rise. ~ Kobe Bryant

How do you impress Kobe Bryant? This was the question I asked myself over and over before I met with my lifelong hero in 2013 following a Lakers game.

Long story short: I proposed to my wife and surprised her with a wedding on the same day. We filmed the whole thing, and it went viral. (More on what became known as “The Surprise Wedding” in chapter 7.) One of the highlights of our fifteen minutes of fame was going on The Queen Latifah Show, where my wife surprised me with a video of Kobe Bryant inviting me to the Staples Center to meet him and the Lakers. I lost my mind but then gathered myself to get ready to meet a man I had admired for over a decade.

When preparing to meet one of the greatest basketball players of all time, I didn’t want to be like every other fan he’d met. I didn’t want an autograph (well, I did, but I had to play it cool, you know). I didn’t want a photo to show to my friends. If I’m honest, I really wanted to make an impression on him because he had made one on me. I knew that he had met people from all over the world, so I wanted to have a conversation he would remember.

I figured the only way to get the attention of Mr. Bryant was to engage him in a conversation about a topic that was irresistible for him: competition. Whether Kobe was competing for the NBA Finals or a game of checkers, you’d get the same beast. I thought for us to have an engaging conversation, my attempting to work out with an NBA team would do the trick. (I imagined checkers wouldn’t get his attention as effectively.)

I didn’t just prepare to have a little meet-and- greet with Kobe. I prepared to play against Kobe if the opportunity presented itself. Before you laugh too hard, you should know I was an All-American at a small Division III-ish college. (Our university’s Division III status was pending when I played, and we were a part of the NCCAA, which stands for National Christian College Athletic Association. So among the Christian athletes in America… I was pretty good.) Nevertheless, I never pursued the pros. After training for a month or so, I played one-on-one against a friend who had just been cut from an NBA team. We played four or five games, and he won all of them by a fair margin. I remember thinking, If he got cut from the league, then what on earth makes me think an NBA team would be interested in putting me on their roster? I left the gym that day with the realization that if I tried out for an NBA team, I would most likely fail.

So I decided to give up on my dream. But then I realized I had never failed at becoming an NBA player before, so how could I know the outcome without even trying? And what’s so scary about failing anyway? What’s the worst that could happen if I tried and didn’t make the cut? This was the day I decided to start chasing failure. I began to envision a world where people weren’t afraid to fail, and it was such an amazing picture that I had to find out for myself if failure, at the highest level, was really as bad as we all think. Most people entering into the NBA played Division I college or had international professional experience. I had none of the above, but neither did Kobe—he entered the NBA straight out of high school.

I had to find out for myself if failure, at the highest level, was really as bad as we all think.

When my wife and I arrived at Staples Center the night we were going to meet Kobe, the atmosphere was electric. A security guard came to our seats toward the end of the fourth quarter and led us to a private room in the back of the arena. I thought there would be cameras, public-relations employees, and private security in there with us, but it was just Amanda and me. I looked at her and said, “Where is everybody? You don’t think it’ll just be… ,” and before I could finish my sentence, the five-time champion walked into the room. I knew I was about to receive an education on greatness that I couldn’t learn from anyone else.

Kobe knew absolutely nothing about me except that I had planned a surprise wedding. Yet when he walked into the room, he sized me up like he was ready to play one-on-one in street clothes. We started off with small talk about his wife and kids. In the back of my head, I was getting a little nervous because I had rehearsed how I would tell him that I was training to be in the NBA soon. As I was trying to take it all in, I kept thinking: Abort mission. This is the worst idea you’ve ever had in your life. Are you really about to tell one of the greatest basketball players of all time that you’re just going to randomly join the National Basketball Association? It’s not a church league, Ryan. Do you really want to experience the most embarrassing moment of your life with Kobe? Be cool.

I mustered up all the courage I could and finally just laid it out there…

“Hey, Kobe. So I’m working on this new documentary thing. It’s called Chasing Failure. The idea behind it is that people are so afraid to fail that they do nothing at all…”

Kobe was staring at me with the most intense focus any man has ever given me, and I just couldn’t get a solid read on what he was thinking.

“I’m out to show the world that failure ain’t so bad after all. Instead of running from failure, what if people embraced it? I want to encourage every person I know to take their dreams off the shelf and stop being scared to lose.”

At this point, I paused before continuing on, curious to see what Kobe’s initial thoughts were… Nothing but crickets for ten seconds.

Kobe’s silence felt like ten hours. But that’s when I quickly discovered that Kobe had been listening intently to every word. After he had let what I said soak in, he responded with, “Absolutely. Every kid in America needs to hear that message. I wanna see that documentary.”

Before I could respond, I had to take one last moment to consult with myself… I told him that I was chasing failure, but I didn’t tell him what I was actually going to do. He probably thinks I’m just gonna go run a 5K.

After making his statement, he immediately went back into an intense listening mode. So I decided to let the cat out of the bag and said, “So the thing I’m going to be looking to fail at is… being in the NBA.”

At this moment, I expected laughter or something along the lines of a sarcastic “Good luck, kid.” Perhaps he would have even felt disrespected that I, a mere fan with lower-level collegiate basketball experience, would even think I belonged in the same league with him. Instead, what I got was four words that would push me even further down the journey of chasing failure. These four words would help me get over the fear. Kobe Bryant looked me in the face, without flinching or hesitating, and emphatically stated, “Yeah, man. Do it.”

When your mom encourages you to chase your dream, it’s nice, but it’s what she’s supposed to do. When your best friends urge you to shoot for the moon, it feels good to have their support, but it’s not like you have to do it. But when a Hall of Famer tells you to go for it, you have now passed the point of no return.

“Chasing failure” went from a lofty notion to an irresistible destiny in just four words. As we wrapped up the last few moments of our hangout, he requested to see the film once it was completed. Kobe Bryant was waiting on me to start Chasing Failure. I bravely told him my plan, and then the only thing left was for me to figure out a way to actually accomplish it.

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Did you know that Kobe, as of 2020, holds the record for the most missed shots in NBA history? In his book, The Mamba Mentality, Kobe said, “I wasn’t scared of missing, looking bad, or being embarrassed. That’s because I always kept the end result, the long game, in my mind. I always focused on the fact that I had to try something to get it, and once I got it, I’d have another tool in my arsenal. If the price was a lot of work and a few missed shots, I was OK with that.”1

If isolated, that missed-shots statistic might make Kobe look like a failure, but in reality, that statistic, those failures, made him one of the best basketball players ever.

That’s why I think you have to be willing to fall short, miss a shot, or take a risk because chasing failure is more about who you’re becoming than what you’re achieving. Chasing success is circumstantial, whereas chasing failure is dependent not on circumstances but on your attitude, character, and mindset when the inevitable pitfalls, obstacles, and losses in life happen.

I’ll never forget where I was on January 26, 2020, when I learned about Kobe Bryant’s death. I was at lunch with two friends in Chicago when I saw a text message come through on my watch that said, “Is this fake news?”

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I still can’t believe he’s gone. I was looking forward to seeing his next chapter… I’m thankful for the impact he had on my life. He taught me the importance of criticism and how it can make you better, not bitter. He taught me that I don’t have to choose between my career and my family by the way he constantly made time in his schedule for both. He taught me that sometimes you have to play hurt. He taught me that missing the mark is how you get better at hitting your target. And he taught me that you can’t expect extraordinary results with ordinary habits.

You have to be willing to fall short, miss a shot, or take a risk because chasing failure is more about who you’re becoming than what you’re achieving.

Watch the book trailer

Watch Ryan’s documentary Chasing Failure

1. Kobe Bryant, The Mamba Mentality: How I Play (New York:Farrar, Straus and Giroux, 2018), 22.

Excerpted with permission from Chasing Failure: How Falling Short Sets You Up for Success by Ryan Leak, copyright Ryan Leak.

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Your Turn

For God gave us a spirit not of fear but of power and love and self-control. — 2 Timothy 1:7

Where in your life have you been afraid of failure? What would it mean for you to reframe your circumstances and actually chase failure? We’d love to hear your thoughts in the comments!

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“I’ve encouraged leaders for decades now to fail early, fail often, and to make sure you always fail forward. And what I love about Ryan’s book and story is he has found a way to make failure enticing enough to make people take steps they’d never dream of taking.”

— John C. Maxwell, Author, speaker, and leadership expert

“Chasing Failure lends its readers a perspective that allows them to see the obstacles in their story as opportunities to grow. Ryan Leak continues to figure out ways to help people win when they feel like they’re losing.”

— Sam Collier, Lead Pastor of Hillsong Atlanta

“One of the most powerful things we can give the next generation is believing in them even after they’ve failed because belief is what helps them get back on their feet again. It’s imperative for every parent, educator, coach, youth worker, and youth pastor to read Chasing Failure because students need Ryan’s positive perspective, especially when they’re experiencing setbacks.”

— Tim Somers, Youth Pastor at Elevation Church