Chasing Failure With Ryan Leak

Posted by John Livesay in podcast0 comments

 

While most people try to steer away from obstacles to avoid failure, there are those who go straight at them. And most of the time, these are the successful people. They have figured out that the path to success is to chase what others are afraid of: to fail. In this episode, Ryan Leak, the author of Chasing Failure, shares some lessons he has learned from failure and how it has helped him succeed. Looking at it from a psychological standpoint, he discusses how the fear lies in shame and embarrassment. Take a pause for a moment today and try to look at your biggest obstacles as the greatest opportunity to succeed. Tune in to this inspiring conversation as Ryan gives us a new perspective on what it takes to succeed.

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Listen to the podcast here

 

Chasing Failure With Ryan Leak

Our guest on the show is Ryan Leak, the author of Chasing Failure. In this episode, he talks about how there is no version of your life that is not risky, so you might as well take some risks that follow your dreams and that you can’t get better if you don’t get started. Enjoy the episode.

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Our guest is Ryan Leak, who is an executive coach, author, filmmaker, and motivational speaker that trains over 15,000 leaders and speaks to over 200,000 people each year. He teaches leaders how to solve problems that keep them from winning in life and business. He’s known as an ultimate risk-taker from his two documentaries, The Surprise Wedding and Chasing Failure. His most recent project is Chasing Failure, where he went on a journey to conquer his fear of failure by trying out for the Phoenix Suns. Through his books, films, and keynotes, Ryan gives organizations the tools they need to see their biggest obstacles as their greatest opportunities. Ryan, welcome to the show.

John, it is an absolute pleasure to be on your show. We got to connect a few months back, and I am super excited to chat with you.

One of the things that grabbed me when I first met you was your energy. I watched your speaking videos and thought, “Here’s an example of someone being completely authentic on and off the stage.” That is not always the case, whether you’re a speaker or an entertainer. I know a lot of people were sometimes surprised by certain talk show hosts not being the same person they were on the show as they were off stage. I want to talk about authenticity. Before we get into that, let’s talk about your story since this is all about the successful pitch and how to tell your story in a way that makes you memorable. You can go back to childhood or school. Where did you get the idea that this is the career you wanted?

My dad was a pastor, and he had a stroke when I was in fifth grade. I was super young, so I had to grow up pretty independent. I looked at my mom and said, “Keep dad alive. I’ll figure everything else out,” type of deal. I felt like I became an entrepreneur in sixth grade. I felt like I had to do that not to succeed but to survive. Throughout all of that, I noticed that whenever I was asked to speak or if I was asked for advice, it went well. It was one of those things where the way I view communication, speaking, and conversations are I’m always looking to serve the other person, and how can I add value to somebody else’s life.

What I learned is that whether it’s through consulting, coaching, or speaking, I learned that the way that I felt like I could add the most value to the world around me was through communication. That was a craft that even to this day, I would go, “I’m a good speaker.” Now, I would go, “I’m a dedicated and motivated speaker.” That so happens to be a book. For me, I don’t wake up going, “I got this.” I wake up every morning going, “How can I get better? How can I fine-tune some things in order to add value to people that are listening or watching?”

That’s a key thing for everyone, no matter where you are in your career. There’s this phrase that I used to have when I was in college, which was, “As soon as this happens, I’ll be happy. As soon as I graduate, as soon as I get out of the cold weather, as soon as I have this job, this car, house, or whatever.” It’s a very elusive way of not being in the present moment, but this thing you said, Ryan, is particularly interesting.

A lot of people think, “As soon as I get to this level, then I can take the foot off the accelerator and coast through the rest of my life and not have to learn anything new or make anything better. Good enough is good enough, and I’ll be fine.” The irony is it’s not a very satisfying way to live. Great athletes and actors are constantly working on their craft. For a lot of people who aren’t aware of speaking as a craft, you’re certainly someone who could speak to that. Do you look at footage of yourself like an athlete does?

I work with a few different NBA teams, and I very much relate to them more than any other industry in terms of the amount of travel, sleeping in different places in different cities and different time zones, what you put your body through, and all of those things. I’m not running on a court, but the travel does take a toll on you physically. Also, having to be on at a very high level.

I very much approach it how someone might approach it in an athletic competition. I’m watching the footage in real-time, taking notes on what didn’t work or what was working. I’m always trying a new story, illustration, or joke. Sometimes I’ll say something on accident that people think is hilarious, and I went, “That’s interesting.” There are some times when I tell a joke that I think is hilarious, that nobody thinks is funny.

It doesn’t land. This is an interesting topic. I had the same experience when I was talking with somebody, “I read this research that taking a cold shower burns fat, fights depression, and reduces inflammation.” I go, “You had me at burns fat,” and he started laughing. I thought, “I wasn’t trying to be funny. I was just being me.” I wonder if an audience would think that’s funny.

I tested it, and they laughed. I’m like, “All right,” but sometimes the audience doesn’t laugh, and you’re like, “How bizarre is that?” Is it because of the time of day? Is it the delivery? What are your thoughts on that? If something’s funny 90% of the time, but not 10% of the time. Stand-up comics and Jerry Seinfeld is constantly refining what he does. What do you think is the reason? Should you throw it out then, or do you go, “No, this usually works?”

What I try to do is what I call my first base jokes. They’re jokes that I don’t you to be falling out of your seat laughing. I only need to know, “Do you smile?” Where are we at? Are we a target group? Are we a Walmart group? If you’re doing an event in Boston versus Atlanta, it’s two completely different mindsets about the world. There’s Southern hospitality in Georgia. There’s a natural emotional response to speakers that you’ll get in the South.

I went to Boston 4 or 5 times in 2022. Every time I landed there, the Uber driver was pissed off from the jump. If there’s a Southern hospitality, I call it sometimes a Northern pissivity. There’s a little bit of an edge already that you have to earn their respect a little bit more. I usually will kick off with things that don’t need to be funny, but let’s just see where their humor is and where everybody’s at. I’m always trying new things, trying to add, and trying to get better.

Your book Chasing Failure is a topic I want to talk about because so many of us feel like we focus on what doesn’t work the one time. If things work 9 times out of 10, but it didn’t work one time, then here’s where I see, myself included. I had to stop this behavior, which is all the way back to school. If I didn’t get an A and I got a C or something, I must be a failure. I’m a loser. Am I a great speaker if the audience didn’t laugh as much as they normally do?

I’m curious to see if you have this experience. Maybe you’re thinking, “I don’t know. This is going okay. It’s not going great. I’ve had to have the audience be a lot warmer.” You then get off stage, and people come up to go, “I loved what you said.” You’re like, “Somebody liked it out of the 500 people or whatever it was.” We can’t judge ourselves on what we’re experiencing at the moment. Is that what you’re saying?

Absolutely. Think of it like this. Somebody sends you a link to something funny. It’s a video. It’s an Instagram clip. It’s a meme. You might respond with a crying laughing emoji but you’re not. You’re like, “That’s funny,” in real life, but on text, you’re the furthest thing from crying or laughing. That’s what audiences are doing sometimes. We have to give ourselves some grace. Sometimes they’re going, “That was pretty funny,” but there’s no noise.

I did an event for a company where I spoke to 500 of their employees, and then they did two breakouts where they split the group in half and said, “Ryan, you’re going to speak to the whole group at 9:00, and then you’re going to speak to half of the group at 11:00. We’re going to break from lunch, and then you’ll speak to the second half at 1:00.” It’s pretty simple. I get my baseline by speaking to everybody in the morning. I go to that first half and a different talk, but that room was rocking. I’m like, “I know these people. I’ve spent the day with them.” I did the same talk at 11:00 that I did at 1:00. It flopped at 1:00, and it crushed at 11:00.

This is so valuable for everyone to read.

It’s the exact same slides, one room falling over laughing at some of the stories. There is some research out there that says after people have had lunch, they’re in that mode. A client will say, “What time do you want to speak?” I’m like, “I’ll speak whenever.” All time slots are not created equal. There are times when you’re the first thing in the morning at 7:30. I’m speaking. I’m doing a diversity, equity, and inclusion breakfast at 7:30 AM.

You have to prepare a little bit differently than your normal 10:00 AM keynote. One of the things that I have to tell myself before I speak is to make sure that I have fun, even if nobody else does. Enjoy the fact that you are one of the very few people on the planet that get an opportunity to talk for an hour and get paid for it. That’s amazing. I never let that leave me. I’ve never arrived. I’ve never like, “You all owe me this.” This is a privilege that I have, and I tell a lot of my professional athletes that too. I go, “Just in case you forget, you’re paid to play a game.”

[bctt tweet=”Make sure you have fun, even if nobody else does.” username=”John_Livesay”]

This is a dream very few people get to achieve.

Imagine somebody walking up to you and going, “Do you want to play Monopoly? We’re going to pay you to play Monopoly.” That’s your life. I feel the same way when it comes to speaking. I pinch myself every day to go, “I can’t believe I get to do this and get to add value to people’s lives.” Whether there’s a standing ovation or not, I say, “I want to make sure that at least I have a good time. I enjoy the fact that I get to be here and try to help people.” I am not trying to impress you. I am trying to help you go to the next level.

When I keep that at the forefront, then I’m not looking for affirmation from the audience anymore. I’m trying to help them. It positions you differently. Your countenance is different. One of the largest insurance companies in the world was having me speak. One of the questions I asked in pre-event calls is I say, “Who have you spoken to before that you love and why? Who have you had in the past? You don’t have to say their name, but I want you to tell me what they did that made you say we’re never going to have them again.”

I always like to make sure I don’t step on a landmine. This insurance company says, “The best figure we’ve ever had was Doc Rivers.” I was like, “Doc Rivers is a well-known NBA coach. That’s great.” It’s not a crazy surprise, but then I said, “Why was he the best figure you’ve ever had?” They said, “He was agendaless.” I thought, “Agendaless isn’t even a word.” However, it changed my approach to even how I work with clients going, “This next hour is not the Ryan show. It’s not about me. In fact, my only agenda is to help you.”

Here’s the interesting thing. Doc Rivers never used the word, “I’m agendaless.” It can be felt. There is something about a stage presence where people can feel when a speaker is trying to impress them versus going, “I’m here to talk about failure, and here’s what I realize about you. Sometimes it holds you back. Now, I’m going to help you reframe how you’ve seen this thing that has terrorized your career before.”

Right away, there is a difference, authority, and command of the room, “I don’t need you to like me. I want to help you overcome something in your life that’s holding you back. I’m going to tell you about some things that have happened in my life on how failure gave me a whole career. I keep trying to fail something every single day, and it has revolutionized my business.”

From there, you are more in command because you’re not trying to win them over. It’s like, “I’m trying to help you solve a problem.” When that’s the forefront of your brain, it’s amazing how relaxed and funnier you are because what you’re doing is you’re taking everyone’s guard down a little bit of going, “This guy’s a real guy. He’s an authentic guy. He’s not trying to sell me something right now.” I literally will watch people in the audience go from a folded arms position to a relaxed position.

The best I can ever get is when someone would come up to me after the talking, “I usually don’t pay attention to somebody talking that long. I’m on my phone or my mind wanders but those stories kept me engaged.” I’m like, “Great.” This concept of being agendaless is another version that is not being attached to whether someone likes us or what the outcome is. As you said, I’m not going to let my self-esteem go up and down based on whether I get a standing ovation or not.

No matter what your career is, do I need my boss to give me a rave review on my annual review, or do I know I did a great job or all those constant outside things that can make you feel less than others? This concept around chasing failure is interesting because most people, as you said, are terrorized by it, which is a great word. Why would I ever chase something that terrorizes me?

Can you tell us some of the lessons that are in the book that would get someone to go from, “If I ever meet a saber-toothed tiger, I’m running the other way, and I don’t care what you say?” This is not that kind of fear. This is fear of failure. Is it because we’re so in our heads, worried about what people think of us?

 

There’s a lot that goes on with that. When you look at the fear of failure from a psychological standpoint, it’s the fear of shame and embarrassment. What I’ve found is that there’s typically a particular person or group of people that we want to impress, somebody that we don’t want them to see us fail. It means that they were right. It means that our ex-girlfriend or ex-boyfriend will go, “Yes. I made a good decision.”

There is something underneath the hood of going, “If I fail, there’s somebody that’s watching, or at least, I think that they’re watching.” If they knew how this story ended, that’s what I’m afraid of. How I guide people through getting past this fear of putting themselves out there is a couple of things. One, every single person we look up to, admire, and read about has all failed.

We don’t realize that. We think, “This person’s always had success after success after success. Everything they touch turns to gold,” which is not true.

We have to dismantle the story we tell ourselves about other people that we watch their lives online. It’s not true. I’ll prove that it’s not true. I have a family photo. I’m on Zoom quite a bit. People are like, “What a beautiful family you have there. That’s great.” This is not indicative of how the day went at all. It was one of the worst days of our life. One of the kids was throwing up tons of stuff.

This was the only one picture of the thousands that we were taking that day because he was just trying to find one good photo and trying to get them in matching outfits and whatever, yet people will get my Christmas card and think, “What a beautiful family. This is how it always is.” It’s like, “No. That’s never how it is.” We can’t get them to sit on the couch for two seconds. If we’re honest, we don’t ever post our true story anyways. We post our very best and hide the rest. Everyone’s doing that. For you to be a failure, you have to deem somebody else successful. Why do you deem them successful?

It’s because of what they posted or because of what they showed you, but they won’t show you their pain. They won’t show you their scars, and oftentimes, they won’t show you their failures. What I started doing is I started showing people my behind-the-scenes. I started sharing about the different failures that I experience on a daily basis where I completely whipped it with a pre-event call or a sales call or completely lost a client. It’s like, “We won’t share that on LinkedIn, but it’s true. It happened all the time.” We’ve got to dismantle this belief that there’s somebody successful, that’s how I view success, and there’s me over here. It’s because usually, for us to be a failure, we have to be a failure compared to somebody else.

It’s a frame of reference.

We first have to navigate that. The second thing that is vitally important is whenever you’re thinking about trying something new or putting yourself out there, there’s no version of your life that is safe. There’s no version of your life that isn’t risky. Some people think, “I’m going to take my ball and play it safe in the corner. I’m going to do my 9:00 to 5:00.” Salesforce just laid off 8,000 people.

Companies are laying off thousands of people at the same time, and you’re going, “I thought you said it was safe.” Tell me, what is safe? I know so many people that have degrees from Stanford, Harvard, and Princeton that aren’t looking for jobs. Someone, please show me the safe route. I’ve yet to see it. The average CEO tenure is five years.

With CMOs, it’s eighteen months.

[bctt tweet=”If you learn from a failure, then you are not failing.” username=”John_Livesay”]

If you’re telling me, “My goal is to get here, and then I will feel secure,” that’s not a secure job. If you’re talking about doing it at a publicly-held company, good luck, buddy.

Look what happened at Disney. Bob Iger leaves, and then they promote somebody up. In less than two years, Bob’s back, and you’re out. Imagine that guy’s mindset.

I tell people, “There’s no version of your life that isn’t risky.” If there’s no version of your life or career that isn’t risky, you might as well do something that moves you toward your dreams. The other thing that is vitally important to understand about failure is you got to learn from it. If you are learning from your failures, you’re not failing. As long as you are taking notes on your failures, you are winning.

If you continue to fail the same way twice, you are just not taking notes. You’re not paying attention. You shouldn’t fail the same way twice. You should be tweaking something, a different angle, or something. The other thing that I write about in the book is as motivational speakers, we’re supposed to tell people to never give up. That’s terrible advice, especially if you’re talking to 1,000 people.

There are people that definitely should give up. We’ve seen them on American Idol. We’ve seen them on The Voice, and we went, “Somebody told you to never give up, but they should have told you instead to say, ‘Let’s see what some of these failures can teach us not to do.’” Again, you’re still learning. There are some things that I went, “Maybe I could. In my company, we tried doing Instagram 60-second documentaries.”

I thought it was going to be a hit. It flopped. It was terrible. It sounded like a great idea until it was fully flushed out. It was like, “No, it’s just an expensive 60-second video that people are just going to scroll by.” I learned that lesson. The platform isn’t designed for that. While I was trying to be innovative, sometimes you have to know when to give up.

One of the chapters in the book is to never gives up-ish. I’m like, “Go for it, but be smart.” Take some notes to go, “We’re going to try some things.” In the book, I laid out the top 100 companies in the world. I added up their research and development budgets. It’s billions. They’re failing on purpose every day in spending money to say, “We have to figure out a way to get this right.”

It’s because if we don’t, the competition will. If you look at Blockbuster, they used to be on every corner. The thought that that wouldn’t exist forever was like, “What else could ever place this? How did we live without this?” You also give a keynote talk on sales leadership. I love what you’ve said about putting your own spin on things. If you have heard of the concept leaders are readers, I like to say leaders or storytellers as well. You may not be somebody who likes to sit down and read a book. You found a way that works for you. Would you share what that is?

There are a couple of ways that I go about consuming content. One, I’m an Audible guy. I love listening to books. I can do that in a terminal. I can do that while I’m walking. I can do that while I’m exercising. Your brain can hear two times faster than it can talk. That’s why that scale is there on a lot of our audio devices to be able to do that.

Also, there’s another app called Blinkist, which gives you summaries of some of the top books in the world. There are some books that, for me, I love the person, but if I already know what you’re going to say, I am very familiar with a lot of your content, and I follow you, I only need the cliff notes. I need the one-liners. I need the overarching idea because that’s all I’m going to walk away with, anyway. I subscribed to Blinkist, and it’s amazing. You can get through a Blinkist in eleven minutes.

 

It’s another great tool. Your book is on Audible, Chasing Failure. Did you narrate it?

Yes.

I figured you did, as a speaker. That’s a whole process too. The concept that people think that you sit down and read your whole book in one take is not the case. Nobody usually has a session go more than two hours because you can’t keep the energy up. They listen to all the mistakes you made. You got to rerecord it and do pickups. If you’ve never thought about it or you go, “That Ryan is flawless in his reading.”

That is not the truth.

I mentioned Hoda in my book, and they’re like, “You’ve totally mispronounced her last name. We got to redo that.” I’m like, “Okay.” It is everything. Everything is a constant refinement of writing and recording your book. At the end of the day, people buy you. They buy your energy, vulnerability, transparency, and authenticity. That’s why you speak so frequently. I get it. You walk your talk. You don’t judge yourself, and therefore, people don’t feel judged when they’re in your presence. At least, that was my experience of being here.

One of the questions I often ask people is, “What does it cost to be you?” It’s a very important question because what people see is not always the true story of what it costs to be that person. They don’t see our flight schedule.

They only see the glamour.

They see the great photo, the arena, and the video highlights. They don’t see flight delays. They don’t see you jumping on one plane to catch another one. Whenever I see somebody that I admire most, I am like, “What does it cost to be you?” When people ask me for book advice, I say, “Don’t do it.” I don’t know that you have it. It’s not that I don’t think that you’re smart. It’s not that I don’t even that you can write a book, but writing a book is the easiest part about doing a book. Selling a book, marketing a book, and getting it into people’s hands are different. Do you have the schedule to sit in a studio and the patience and the cadence? You were like, “I want to tell my story.” It isn’t that easy. It’s not that simple. I’m like, “Unless you want this to be a thing, it’s going to cost you more than you think.” Know the cost. It’s not that I don’t believe in you. I’m only letting you know. It is harder than it looks.

When I had a corporate job and I would have to travel and there would be a delay, I’d be like, “As if this job isn’t hard enough. Now, I got to deal with that.” Now, when I have a travel delay and I’m speaking, I’m like, “I will put up with anything because I love what I do so much,” versus I like my job, but not enough to want to get up at 3:00 in the morning to catch a plane to be in New York in time for a cocktail party or whatever was required.

When you figure out what it is, then your home mindset of being instead of the angry Uber driver, you’re doing something you love, and you go, “That’s the cost.” The joke is we speak for free, and they pay us to travel. People go, “What do you mean?” You’re like, “The odds of a crying baby, a mechanical, and the weather is up there and/or a cab ride that has a flat tire.” It’s 101 things. I look at everything as, “This will make a great story.” That’s how I look at it, or, “I wouldn’t have met this person had I not missed that plane because the connection was delayed or whatever.”

[bctt tweet=”You can’t get better if you don’t get started.” username=”John_Livesay”]

Otherwise, you can’t show up and be fully present and alive. Also, whether you’re watching an athlete an actor, or a speaker, they shouldn’t have to know what you went through. They want to, “I’m here now. Wow me. Entertain me,” or whatever. Nobody cares about your drama unless they want to go into it. You have to be able to let all that go and not walk on the stage with a chip on your shoulder for God’s sake. As you said, it’s a privilege.

It is a privilege. Being in DFW, I’ve had mostly great travel experiences. Kudos to all of the different airlines that service our business, but DFW is a pretty good place to travel out of.

I often have to go there, “There’s no nonstop, so you’re going through Dallas.” “Okay.” It’s out of Austin. Any last thought or quote that you want to leave us? This question is great, “What does it cost to be you? There’s no version of your life that’s not risky.” You’ve given us so many incredible things to think about and reframe how we see failure and how we see ourselves, especially other people, and not compare ourselves so much and come up short.

The last line I would leave everyone with is you can’t get better if you don’t get started. You can’t make a book better if you don’t start writing. You can’t make a talk better unless you write one. Stop waiting for an audience. The greatest tool that a speaker or anybody that’s wanting to do something public-facing is social media. It’s the great equalizer. You might speak for Coca-Cola now, and I might speak for Facebook tomorrow, but guess what? Both of us have the opportunity to record something for Instagram right now.

It will show you if that resonated or not, “You got so many views on that,” versus this other thing I posted, “I got a lot of views. What’s the difference?” It’s instant data feedback. You’re like, “That works.”

There are things that I’m constantly trying on the internet every day. The biggest difference between myself and somebody that may be struggling to get some things off the ground is I’m willing to fail every day. I’m willing to fail more than most people. I’m willing to write a chapter that’s just okay, “I wrote a chapter, and you didn’t.” I’m willing to post a video that doesn’t get that much engagement.

In fact, the videos that will get the least engagement get the most. The videos that I think will get the most engagement get the least. It is one of those things where, as I said at the beginning, I don’t think you ever arrive. You consistently put yourself in the position of a student of, “Here’s what I’m learning. Here’s what I’m seeing. Here’s how I’m going to utilize that information to help the people around me.” You can’t improve something you never got started in the first place. If you don’t start the podcast, write the book, or start the business, you can never improve something that doesn’t exist. That’s what I want to leave people with.

Thank you. The book again is called Chasing Failure. If you want to find out more about Ryan or book him as a speaker, go to RyanLeak.com. Ryan, thanks again.

I appreciate it, John.

 

Important Links

• Chasing Failure
• Ryan Leak
• Blinkist
• RyanLeak.com
• Better Selling Through Storytelling Method Online Course

 

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Tags: authenticity, Chasing Failure, Failure, Fear of Embarrassment, Fear Of Failure, Fear of Shame