
I want to talk about chasing failure. I actually think that failure has something to teach us that success never could. I know we’ve been taught to fear failure but think about all of the other fears that you conquered in your life. What’s your biggest fear? Is it heights? Is it public speaking? Is it your spouse getting mad at you for forgetting to take out the trash?
The No. 1 fear that will hold you back in your career, that will stall your business, is the fear of failure. It is this fear of putting yourself out there and being rejected. I’m going to encourage you to get outside of your comfort zone. I’m going to encourage you to take a risk and go after a client who you think is ungettable or unapproachable.
I’m a risk-taker. That’s just who I am. One of the biggest risks I ever took was when I asked my girlfriend to marry me. When my wife and I were dating, I overheard her tell a friend that she thought it would be cool to get engaged and married on the same day. So, I began planning our wedding behind her back over the course of two years. On June 7, 2013, I got down on one knee. I said, “Amanda, will you marry me?” She said, “Yes.” I said, “Will you marry me today?” We opened a lounge room door, and about 85 of our family and friends were standing in there. We rolled in a dress, hair stylist, makeup artist — everything you would need to get engaged and married on the same day. Every single time somebody watches the surprise wedding on YouTube, they ask me the same question: “What if she had said no?”
But isn’t that the question that plagues all of us? You could spend time thinking about what if they say no, but you also could spend time thinking about what if they say yes. This is all about our mindset. I want to teach you to have a chasing failure mindset.
There are two things I want to encourage you with to embrace a chasing failure mindset. The first thing is take notes on every rejection. I have done extensive research on failure, and I’ve discovered that the No. 1 reason people fail isn’t because they had a bad idea. It’s because they had a bad execution.
The greatest marketing strategy that any of us has is doing a really good job, because if you do a really good job, people tell their friends. So, if you’re going to fail, make sure you err on the side of “Hey, I did my very best.”
The second thing I think is vitally important with a chasing failure mindset is just do it scared. Glennon Doyle says, “If you can’t beat the fear, just do it scared.” Do you know the number of things that you’ve gotten over? The number of things that you’ve done scared? Tired? Frustrated? You are more capable of pulling off the insane things in your life than you think you are.
As a part of the surprise wedding, my wife and I got to go on a couple of different TV shows. One was “The Queen Latifah Show,” where my wife had a surprise for me. On the screen came the late great Kobe Bryant. He said, “Hey, Ryan, I heard about this fabulous wedding that you pulled off for your bride. And we just wanted to invite you out to the Staples Center in Los Angeles to come hang out with me.” This was amazing. I chose a game that was about three months away. I had three months to prepare to meet Kobe Bryant. I came to the conclusion that the only way Kobe Bryant and I would have an engaging conversation was if I were in the NBA. I am 6 feet 3 inches and pretty good at basketball.
A friend of mine who played for the Chicago Bulls at the time got waived from the team. He came back to Dallas, and we started playing one-on-one. We played about five times. He destroyed me every single time. I thought, If they waived and cut him from the team, they are not going to give a guy like me a chance.
And so I gave up. And I thought to myself, Man, that was fast. You had a dream, you had a goal, and you gave up on it in 24 hours. How do you know that you are going to fail unless you actually try? And that was the day I started a new documentary called “Chasing Failure,” where I asked a lot of people this question: “What would you do if you knew you could not fail?” And when I answered that question, I said, “I’d be in the NBA.”
So, when I met Kobe Bryant, I said, “Mr. Bryant, my name’s Ryan Leak. I’m working on a new documentary. It’s called ‘Chasing Failure.’ I’m going to ask a lot of people: ‘What would you do if you knew you couldn’t fail?’ I think people are afraid to fail, and I don’t think they should be.” He looked at me and said, “Ryan, everybody in America needs to hear that message.”
I found the public relations emails for every NBA team, and I started emailing them one by one. I started with the Boston Celtics. I said, “Dear Celtics, You’ve got fans all across the city of Boston who are afraid to fail, and I don’t think they should be. Imagine if we could pull their dreams off the shelf together? I’ll probably fail, but what if I don’t? Why don’t you give a stranger a chance to try out for your basketball team? I’m 6 feet 3 inches, 205 pounds, and I’m looking for failure. Sincerely, Ryan Leak.” I hit send and closed my laptop. The Celtics wrote back and said, “Hey, Ryan, it’s a great idea. It’s just not for us. The best of luck in your future endeavors.”
I thought, Did the Boston Celtics just email me back? This is a great day. I’m being told no by all 30 NBA teams, and it’s going to be amazing. The fifth email went out to the Phoenix Suns. They wrote back, “Hey, Ryan, we love this idea. Come on Monday.” I said, “This Monday?” They said, “Yeah, bring your camera crew.”
Camera crew? Of course, anybody doing a documentary obviously has a camera crew. I didn’t. I had a homie from church named Chuck. I said, “Hey, Chuck, we’ve got to go to Phoenix right now. I’m trying out for the Phoenix Suns.” So, you can go to YouTube or to ryanleak.com and watch a documentary called “Chasing Failure.” You get to see a two-day workout with the Phoenix Suns. Spoiler alert: I failed, which is why I’m here today.
I realized chasing failure took me further than chasing success ever did. And here’s what I’ve learned. First, NBA teams don’t give workouts to complete strangers from convincing emails, but sometimes they make an exception. The second thing I’ve learned is now that I work with three NBA teams, there’s more than one way to be in the NBA. They get all sorts of positions.
You’ll be surprised what will happen when you stop being afraid to fail and you just take a step forward. What would you do if you knew you couldn’t fail? Would you approach someone in the Top 1 percent who you think is unapproachable? Would you reach out? What would you do if you knew you couldn’t fail? I would tell you what Kobe Bryant told me: “Just do it, MDRT.”