Confidence Classic: Chase Failure, Build Courage, and Go After What Scares You with Ryan Leak

Summary

Creating Confidence with Heather Monahan

Episode: Confidence Classic: Chase Failure, Build Courage, and Go After What Scares You with Ryan Leak
Date: February 10, 2026
Guest: Ryan Leak (Executive Coach, Author, Speaker)

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Episode Overview

This episode explores what it truly means to chase failure as a strategy for personal growth and success. Heather Monahan welcomes Ryan Leak—executive coach, bestselling author of "Chasing Failure," and sought-after public speaker—to discuss the transformative power of pursuing what scares you, building courage, and reframing your relationship with fear and imperfection. The conversation journeys through Ryan's unlikely leap from church league basketball to an NBA tryout, the importance of seizing every opportunity, learning from rejection, and the mindset shifts required to take your confidence—and your life—to the next level.

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Key Discussion Points and Insights

1. The Myth of Pre-calculated Failure & Getting Started

• Ryan Leak opens with the idea that many people “pre-calculate” their failure, talk themselves out of taking action, and thus abort their dreams before even starting.
  • "Way too often we pre-calculate failure and just abort mission altogether. We literally talk ourselves out of our own dreams every single day." (00:00, Ryan Leak)
• On taking the leap: "You can't sell a book that you don't write. You can't get people to listen to a podcast you won't record." (00:16, Ryan Leak)
• Heather shares the importance of showing up, even if it means facing the possibility of failure or being alone.

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2. Ryan Leak's Journey Into Speaking

• Ryan attributes his start to growing up in the church and becoming comfortable in front of people, learning that speaking is about building others up, not self-promotion.
• He highlights the “give your best to the opportunity in front of you” philosophy:
  • "You will never crush it with 10,000 unless you crush it with what's in front of you." (03:55, Ryan Leak)
• His career-defining moment: seven-minute talk at a conference (which felt “disrespectful” short at first):
  • He “grand slams” the opportunity, which leads to speaking to 45,000 people six months later.
  • "You never know who's watching, you never know who's in the crowd." (05:06, Ryan Leak)

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3. The Importance of Conciseness & Staying Ready

• Heather references an Abraham Lincoln quote about the challenge of short speeches:
  • "It is so much more challenging to be incredibly concise and tight versus to get up and storytell.” (05:39, Heather)
• Ryan: "Stay ready so you don't got to get ready." (06:07, Ryan Leak)
• On preparing athletes before a game: focus on fun and perspective, not just pressure and expectations.
  • "Sometimes the check is so large … what it can do is actually suck the life out of what used to be how you got started, which was fun." (06:46, Ryan Leak)
  • "Enjoy what we do because we can't take it for granted … there's not many resources that teach you how to enjoy it once you get it." (08:10, Ryan Leak)

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4. The “Chasing Failure” Story (NBA Tryout & Lessons Learned)

• Ryan recounts his documentary journey:
  • After a viral wedding story, he’s invited to meet Kobe Bryant. Inspired, he decides to “chase failure” by pursuing an NBA tryout as a Division III college basketball alum.
  • He experiences imposter syndrome and almost talks himself out of the dream.
  • “That’s like giving yourself a failing grade on a test you refuse to take.” (10:10, Ryan Leak)
  • "Way too often we pre-calculate failure and just abort mission altogether." (10:18, Ryan Leak)
• Instead of only fantasizing, he cold-emails all 30 NBA teams, framing his quest as a motivational project.
• Phoenix Suns say yes, and he documents the tryout—even though he eventually fails.
  • “Chasing failure took me further than chasing success ever did because it got me way out of my comfort zone and landed me in an NBA practice court.” (14:48, Ryan Leak)
• Lessons:
  • Sometimes you’ll only know you’re the exception if you ask.
  • There are more ways to achieve your dreams than the obvious route.
  • The value in rejection and learning from every “no.”

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5. Living with Fear, Doing It Scared

• Heather asks if Ryan is immune to fear now.
  • “Oh, I deal with it all the time. If you can’t beat the fear, just do it scared.” (16:35, Ryan Leak, quoting Glennon Doyle)
  • He intentionally signs up for things that intimidate him.

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6. Perfectionism, Failure & Publishing

• On writing “Chasing Failure:”
  • First book was 60 self-published pages, with several typo-ridden drafts.
  • “People have this idea, ‘I’m not going to move forward until it’s perfect.’ Well, guess what? Then you will never move forward. It’s never going to happen.” (20:18, Ryan Leak)
  • Each version got better, but he kept moving forward despite flaws—eventually leading to mainstream success (USA Today Bestseller).
  • “I am consistently every single day moving toward something that intimidates me. But it’s good for me because that means I’m always learning and, and always moving forward.” (21:39, Ryan Leak)

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7. Culture of Failure, Resilience, and Encouraging Others

• Thousands have contacted Ryan sharing how “Chasing Failure” inspired them to take bold action, even if scared.
  • "I'm so impressed with what they've done, way more than what I did to play a part in that." (25:28, Ryan Leak)
• Heather relates Sarah Blakely’s (Spanx) upbringing, where family celebrated failure. Contrasts with the more common fear of judgment and shame.
• Ryan on predicting failure:
  • "They're predicting: 'According to my assessment, I will fail. Therefore, I won't even try.'” (26:47, Ryan Leak)
  • “Successful people were willing to go sit in the bookstore and be by themselves. They were willing to try the thing and fail.” (27:33, Ryan Leak)

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8. Scarcity Mentality & Comparison Trap

• Many overcomplicate their dreams, held back by the idea that only the best deserve to try.
• “People overcomplicate it... There is this mentality of championship or bust. … No, dude, just give your best.” (29:08, Ryan Leak)
• Unique voices matter—even if topics aren’t “original.”
  • “Say it in your way and help the people that are listening to you.” (30:09, Ryan Leak)
• There’s enough opportunity ("pie") for everyone; abundance is not a zero-sum game.
  • "There's enough pie at the table, I think, for all of us to eat." (31:28, Ryan Leak)

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9. Communication Across Diverse Audiences

• Ryan’s approach: focus not on differences between audiences, but on their universal problems.
  • "The way I see communication is it is a communicator's job to solve the audience's problems." (33:41, Ryan Leak)
• Negative thought patterns are universal and can be tackled in corporate, church, or youth settings.
  • "No one is going anywhere with negative things. So I just try and think stuff like that." (37:45, Ryan Leak)

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10. Self-Awareness and Ryan’s New Book: "Leveling Up"

• Ryan’s forthcoming book arises from his executive coaching practice during the pandemic.
• Book centers on 12 “loaded questions” for self-leadership, such as:
  • “What’s it like to be on the other side of me?” (44:49, Ryan Leak)
    • Explores self-awareness in relationships, workplace, and beyond.
  • Powerful anecdote: Friends worry their stories may not “measure up”—Ryan intentionally works to stay curious and present with everyone, regardless of their background.
• Course launching alongside the book: six modules to help move from “a life you tolerate” to a life you “get to” enjoy.
  • "At the end of my life, I want to be able to look at hundreds of speakers that I’ve said, ‘Hey, I’ve helped you figure out ways to communicate your story and help people solve their problems.’" (52:07, Ryan Leak)

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Notable Quotes & Memorable Moments

• On overcoming fear of failure:
  “That’s like giving yourself a failing grade on a test you refuse to take. Like, how do you know you’re gonna fail unless you actually try?”
  — Ryan Leak (10:10)

• On moving forward despite imperfection:
  “People have this idea, 'I'm not going to move forward until it's perfect.' Well, guess what? Then you will never move forward.”
  — Ryan Leak (20:18)

• On finding the edge of possibility:
  “Chasing failure took me further than chasing success ever did because it got me way out of my comfort zone and landed me in an NBA practice court.”
  — Ryan Leak (14:48)

• On communication & empathy:
  "It's a communicator's job to solve the audience's problems ... Everyone wants to thrive in their life in some way, shape, or form. There's just no way that you're going to do that with that much stinking thinking."
  — Ryan Leak (34:00, 37:30)

• On abundance & collaboration:
  “There's enough pie at the table, I think, for all of us to eat.”
  — Ryan Leak (31:28)

• On radical self-awareness:
  "What's it like to be on the other side of me?"
  — Ryan Leak (44:55)

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Timestamps for Key Segments

• 00:00 – Opening wisdom on pre-calculating failure (Ryan Leak)
• 02:53 – Ryan’s journey into speaking and early lessons
• 05:39 – The challenge of being concise on stage
• 06:46 – Advice for professional athletes: bringing back fun and perspective
• 09:21 – The full “Chasing Failure” story begins
• 16:35 – Handling fear: do it scared
• 19:43 – On writing and rewriting “Chasing Failure”: perfectionism and typos
• 24:59 – Reader stories & the ripple effect of chasing failure
• 26:47 – Predicting failure and not even trying; book signings and mediocrity
• 29:08 – Overcomplicating dreams and the “championship or bust” trap
• 33:41 – Bridging business, church, and youth audiences with empathy
• 44:02 – Introduction to “Leveling Up” and key coaching questions
• 47:49 – Self-awareness anecdote: “Matt Damon effect” and empathy for others
• 50:52 – Course details and moving from tolerating to thriving in life
• 53:20 – Where to find Ryan Leak’s work and offerings

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Resources & Where to Find More

• Chasing Failure (Book & Documentary): Stories and resources at ryanleak.com
• Upcoming book - Leveling Up: Preorder and information at ryanleak.com
• Social Media & Speaking: Follow Ryan on all major platforms at @RyanLeak

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Closing Thoughts

• Embrace imperfect action over inaction.
• Stop self-selecting out of your dreams based on “predicted” failure.
• Self-leadership starts with asking great questions—the kind that make you a better, more empathetic, and impactful person for those around you.

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Transcript

[Ryan Leake]

Way too often we pre calculate failure and just abort mission altogether. We literally talk ourselves out of our own dreams every single day. They're predicting, according to my assessment, I will fail. Therefore, I won't even try. You can't sell a book that you don't write. You can't get people to listen to a podcast you won't record. Even this morning it was like, hey, are you going to do a book tour? I'm like, well, what if I go to a Barnes and Noble in New York and nobody shows up? No, like, you got to put yourself out there. I think the difference between people who are successful and people who don't get all that they want from their life is that successful people were willing to go sit in the bookstore and be by themselves.

[Confidence Creator (Host)]

Come on this journey with me each week when you join me, we are.

[Podcast Announcer/Ad Voice]

Going to chase down our goals, overcome adversity, and set you up for a better tomorrow.

[Confidence Creator (Host)]

I'm ready for my close up.

[Podcast Announcer/Ad Voice]

Tell me, have you been enjoying these new bonus Confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to. So these bonuses are a great way to help you find the ones you may have already missed. I hope you love this one as.

[Confidence Creator (Host)]

Much as I do. Hi and welcome back. I'm so excited for you to meet my guest today. Ryan Leake is an executive coach, bestselling author, and motivational speaker that gets to inspire over 50,000 people every month and train over 20,000 leaders every year. He's widely known for two documentaries, the Surprise Wedding and Chasing Failure. Ryan is also the CEO of the Ryan Lee Group, LLC that is a leadership development firm in Dallas, Texas. They have the privilege of working leaders and teams all over the world, from MBA teams to Fortune 500 companies. Ryan, thank you so much for being here today.

[Ryan Leake]

Yes, it is my privilege to be here with you.

[Confidence Creator (Host)]

Okay, so I get a lot of DMs, you're an incredible speaker. And guys, just a little behind the scenes, a very good friend of both of ours, Jordan Montgomery, who you know was on the show earlier. If you haven't heard that episode, go back and check it out. Introduced us on text and in typical fashion, I'm being sarcastic with people. I didn't even know Ryan. I didn't know who he was yet. And I'm saying, gosh, Ryan, you're not even active on this thread. You better be on the PST time zone because this is pretty lame of you. He hits live video on his camera and is literally about to take the stage in Atlanta for chicks filet in front of thousands of people. And I was eating my word. So all I want to say is this man takes the biggest stages in the world and speaks more than anyone. So, Ryan, so many people DM me all of the time asking, how do you get into speaking? How does a speaking career even materialize? And I know we were talking about it a little bit off air, but can you give us that backstory on how you ended up where you are today?

[Ryan Leake]

Yeah, for sure. You know, I. I grew up in a church, and, uh, my dad was a pastor. I just thought my dad did a great job of just adding value to people's lives. And he got to. He was so involved in the community, and I just was so mesmerized that people would come together every single Sunday and hear him talk. And I thought, man, what. What an awesome way to impact somebody's life. And you don't use stages to beat people up. I think you use stages to encourage people and build people up. And so I just kind of enjoyed it. And I just kind of had a knack for. And I was pretty comfortable in front of people, and I just tried to work on my craft and just serve people and trying to add value as best I could. I started speaking at a bunch of churches around the country. One day, an executive from a. What was the name of that company? They were a credit union. Okay. They said, hey, will you come and just do, like, our staff development day? And I was like, sure. And so I did. And I just. I. I'm a. I'm a proponent of give your best to the opportunity that is in front of you. Not the opportunity you want in the future. No, the opportunity that's in front of you. You're given an opportunity to speak to 10 people. Go crush it with those 10 people. You will never crush it with 10,000 unless you crush it with what's in front of you. So I just tried doing that every single week. Whatever opportunity I was given, I just tried to give my very best to it. I remember getting invited to. To speak at a conference in Atlanta, and the event planner said, hey, you got seven minutes. And I felt disrespected by that. I felt like, seven minutes. I'm flying all the way here just for seven minutes. Like, really? But then it was just like, no, dude, give your best to seven minutes. Crush the seven. Like, this dude had never heard of you before, and you have. You have to kind of own that. Like, some people, it's like you're a household name in their household, but then their neighbor has no idea who you are. And so you gotta have, I think, a self awareness in that. And so I went and I just tried to grand slam that seven minutes. And when I did, he called another friend who had me speak to 45,000 people. Six months later he said, hey, I just had this guy speak. He did something in seven minutes I've never seen before in my life. And so I always encourage people, give your best to the opportunity that's in front of you. You never know who's watching, you never know who's in the crowd. You never know whose kid is in the crowd. You never know whose mom is in the crowd. I just consistently try to give my best in whatever room I'm in. It could be a boardroom, it could be an arena, it could be a church, it doesn't matter. I just try to give my best and it's helped me build a pretty great career.

[Confidence Creator (Host)]

There's a great Abraham Lincoln quote that I'm sure I'm going to botch, but it's something like this. Ask me to speak right now for one hour. I'll take the stage. Ask me to speak for 30 minutes. I need two days. Ask me to speak for anything under 10. I need months. It is so much more challenging to be incredibly concise and tight versus to get up and storytell. So that's really impressive that you were able to pull that off on the spot.

[Ryan Leake]

I get asked to do all sorts of stuff, you know, I just again, stay ready so you don't got to get ready. And I work with a lot of athletes right before games, and so you have a very short window of time to impact them and give them a thought that doesn't throw them off, but inspires them to play, but also gives them something to chew on about their life. And it, it's, it's difficult, but I think it's a muscle that I've just tried to, to work on over the years. And I think the more you do it, the better you get at it.

[Confidence Creator (Host)]

What are some of the things that you say to professional athletes before they're about to take the court at an NBA game? How, how do you encourage them or what words do you share?

[Ryan Leake]

One of the things that I think is vitally important for a professional athlete, it could be a coach or a player, is gotta have fun. Gotta have fun. Sometimes the check is so large, the media pressure, all of these talks around the sport, what it can do is actually Suck the life out of. What used to be how you got started was you went to a park where kids go and you have fun. Now you're a businessman. Now you're a businesswoman. Now it's, it's your job, it's a career. And sometimes the person that's paid the most has lost their passion for the sport. So what I try to do is bring them perspective to say, hey, just so you know, did you know you get paid to play a game tonight? It's amazing. Like, we can't lose sight of that. And there's just times where I'm getting ready to speak where I. I'll say that to myself, like, did you get paid to talk today?

[Confidence Creator (Host)]

Like, that's insane.

[Ryan Leake]

It's remark. Like, do you know, like, there are people who work all year long to get paid what I could get paid to speak one time. It is absolutely absurd. But I just, I always have to just step back and just go, man, we got, we got to enjoy what we do because we can't take it for granted. We work so hard to get where we are. But you can go to so many conventions, so many conferences, and read so many books and listen to all these different podcasts on how to get success. There's not many resources that teach you how to enjoy it once you get it. And so I just, I love to tell an athlete right before a game, hey, enjoy the fact that you get paid to play a game that kids play in parks. Don't forget to have fun in the midst of all that is going on. And ESPN is not real life. Hey, like your life is here right now. Enjoy it. And I just try and give them a little bit of perspective in that because I just remember even being an athlete myself, there's so many games I had. It was like the pressure of the world was on my shoulders. And I look back and I go, I didn't enjoy it enough.

[Confidence Creator (Host)]

I love that you just shared that you were an athlete, because that takes me into the best story that is really the foundation of Chasing Failure, which I would love. Your first book, Chasing Failure. How falling short sets you up for success. If you could get into that. Amazing. It's literally mind blowing. I still can't even believe you did it. It's so incredible.

[Ryan Leake]

Yeah, so I played college basketball at D3ish school. The ish is that it wasn't fully D3. Our D3 status was pending the years that I played there. And what we were in the nccaa, which stands for National Christian Collegiate Athletics Association. So I like to tell people amongst Christians, I'm really good at basketball. Church league MVP is how I like to see myself. But I had never pursued the pros. Me and my wife, we went on the Queen Latifah show because of a surprise wedding, which is a whole nother thing. But my wife told her friends she thought it would be cool to get engaged and married on the same day. Had no idea what that meant, so I guessed, planned a wedding behind her back over the course of two years. That's a viral wedding story documentary on YouTube. Because of that, we got to go on the Queen Latifah show. On the Queen Latifah show, my wife and the queen surprised me by getting me connected with the late, great Kobe Bryant. And Kobe comes on a video, says, hey, Ryan, heard about this fabulous wedding that you had for your bride and just wanted to return the favor and invite you out to Staples center to come hang out with me and the Lakers. I passed out on Queen Latifah's couch, and I had three months to prepare to meet Kobe. And I was thinking, like, man, I've never actually, like, tried to really go for this professional basketball thing, but I've always, like, I would go to games and I would be like, man, he should went left. Man, he should have went right. Like, I always had this idea, like, I could do their job better than they could, but I'd never actually done anything about it. And so in getting ready to meet Kobe, I said, I'm going to get back in all American D3 is shape, and I'm going to go for it. Started playing a friend of mine who had just got cut from the Chicago Bulls, and he beat me every single time pretty easily. I'm six three, 205 pounds, he's six five, about 245. So there was a pretty big gap between us. And I was like, man, just forget this, dude. Like, you're. You're not going to make it in the league. Just go meet Kobe, take a picture like a normal person, and just go home. And I thought, man, that was pretty fast. Like you had a 1 percenter idea, like being an MBA and you gave up on it in like 24 hours. That's like giving yourself a failing grade on a test you refuse to take. Like, how do you know you're gonna fail unless you actually tried way too often? We pre calculate failure and just abort mission altogether. We literally talk ourselves out of our own dreams every single day. And so this was a day where I say, I'm actually gonna talk myself into it. And so I started asking people, you know, what would you do if you knew you couldn't fail? And so when I asked that question, it was like, well, hey, I'd be in the NBA. So I meet Kobe and I say, hey, I'm doing a documentary called Chasing Failure. I'm actually going to ask a lot of people, what would you do if you knew you couldn't fail? And I'm going to go for something that I think I'll probably fail. But there's only one way to find out, and that's for me to try. So I say, I'm going to be in NBA. And he's like, yeah, do it. And I was just like, no, that's the wrong answer. You were supposed to tell me how hard it is. You were supposed to tell me about 4am workouts. You were supposed to tell me about the nutritionist. You're supposed to tell me about the politics of it. Like, but now he. He just stuck with the Nike slogan, just do it. And so I did not know how to get into the NBA. For people that don't understand how the NBA works, it's the National Basketball Association. It's not a church league. There's a protocol. You need to go to Duke, North Carolina, play overseas. You need to have an agent. You need to go to the combine that there's a protocol. They're not really looking for motivational speakers to join their team to boost the morale of the squad. Like, that's not a thing. So I did the thing we all do when we don't know what to do. I googled it and I found the public relations emails for every NBA team. And I just started emailing them one by one saying, hey, you got a bunch of fans across the city that are afraid to fail. I don't think they should be. I think they should embrace failure. I think you should embrace this idea enough to let a complete stranger work out for your basketball team. I'll probably fail, but what if I don't? My name's ryan leak. I'm 6, 3, 205 pounds, looking for failure. And I had sinned. It felt illegal. I was like, ryan, what are you doing? This is crazy. And then the Celtics rolled me back. And they're like, hey, this is a great story. It's just not for us. I was like, that sucks, man. Ryan, this idea is so bad, they won't even let you fail at it. Like, this is terrible. Like, what are you thinking? But Then I thought, did the Celtics just email you back? Like, this is amazing. Like, I'm gonna make a documentary about being told no by all 30 NBA teams. This is going to be amazing. Like, what can we learn from no? And so I always encourage people, you want to take notes on every single rejection because there's a lesson in there. So they weren't actually even giving me a rejection. They were actually giving me MBA language that I didn't have before. So I started changing my pitch. Every single email, fifth email goes out to the Phoenix Suns. They're like, hey, we love this idea. Come on Monday. I was like, Monday? What? Are you serious? They said, yeah, bring your camera crew. I was like, camera crew got no camera. Yeah, yeah, yeah. You know, like, we'll, we'll be there first thing Monday morning. So I called my homie Chuck. I said, hey, man, let me holler for a second. We ain't talking a little bit. We need to go to Phoenix. He's like, what are we going to Phoenix for? I said, don't ask questions, just trust me. It's going to be awesome. So I got a two day workout with the Phoenix Suns and I made a whole documentary about it, and it's called Chasing Failure. Spoiler alert. I failed. And so now I get to teach people all about all of the lessons that I learned from failing in Phoenix. And at one point, the drills are basically like, hey, you're going to take 20 shots. Our guards make 18 out of 20. That's the NBA standard. I was making like 15 or 16 out of 20. So again, I'm good. But they're great. I fit in. But that's the problem. NBA players don't fit in. They stand out. They're outstanding. They are absolutely remarkable. So I, at one point, I'm looking down at the court, I got my head down, I'm feeling shame, I'm feeling embarrassed, like, man, like you're not good enough. And I look down and I see this logo and it's the Phoenix Suns logo. And I asked myself, ryan, how'd you get here? Because there's a lot of places you could be. And I realized chasing failure took me further than chasing success ever did because it got me way out of my comfort zone and landed me in an NBA practice court. I'd done a lot of things in my life up until that point, none of which landed me on an NBA practice court. And so now, in hindsight, it's very interesting to think, number one, NBA teams don't give workouts to motivational speakers from convincing email. That's not how it works. But what I learned in Phoenix is sometimes they make an exception. And you'll never know if you're an exception unless you're willing to send an email. The second thing that I've learned in hindsight from that whole experience now that I get to work with about five different NBA teams, is there's more than one way to be in the NBA. And I never, I would have never seen that or known that had I not been willing to, to go out there and say, hey, let me, let me give it, let me give it a shot. So, so, yeah, so that, that, that's the chasing failure story. That, that's what I try to help people get past some of their own barriers and try and help people get out of their own way.

[Confidence Creator (Host)]

And so for you, you no longer are stopped by fear, is that correct?

[Ryan Leake]

Oh, I mean, I deal with it all the time. I just have to. Just as weird as it sounds, Glennon Doyle says it this way, if you can't beat the fear, just do it. Scared. So for me, I'm just consistently doing a lot scared. I just sign myself up for stuff that I can't do and I just like, just go for it and if it flops, it flops. But I just kind of have that model of just like, hey, let's just, let's just see what happens. And you won't know unless you decide to put yourself out there and try some stuff that you've never tried before.

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[Confidence Creator (Host)]

Confidence Cleaver, I.

[Podcast Announcer/Ad Voice]

Ask you to try to find your passion.

[Confidence Creator (Host)]

Were you fearful writing the first book, Chasing Failure?

[Ryan Leake]

Oh my gosh. So in Chasing Failure, I tell a story about the first version of Chasing Failure. The Chasing Failure that's out with Thomas Nelson now nicely buttoned up and whatnot is the fifth version of Chasing Failure. So the first version I self published it was like 60 pages. It was essentially the same story. Somebody watched the documentary, was like, hey, I don't really like documentaries. Can you write it in a book? And I was like, oh sure. So I self published it, hit print on like a thousand, and just like handed it out to my friends and people in my church. And somebody walks up to me, they go, hey, I hate to break it to you, but there's three typos in it. I'm like, oh crap. So I fixed those three typos and reprint it. And then I'm speaking at one of the largest churches in America and a woman walks up to me, she says, hey, there's about four typos in your book. Can I help you? I'm like, jesus, what is wrong with you Ryan? You can't get. And you have no idea how many people proofread it, including me. So then we do a third version and we're like, hey, why don't we, why don't we update it and like give it a new look and feel it's been like two years now with all these typos. And then somebody was like, hey, can you add like some verses to it? Like, I, I like it to be a little bit more spiritual. So I made a little bit thicker one and never even put that one on Amazon. So there's like four versions out there. My mom has every single version of Chasing Failure. And so I talk about typos in Chasing Failure because people have this idea I'm not going to move forward until it's perfect. And I'm just like, well, guess what? Then you will never move forward. It's never going to happen. So I just decided I'm going to move forward with imperfection. So I'm reading the audiobook, doing my own audiobook for Chasing Failure, and I find two typos. And I was livid. I was livid in the studio, but then I just thought, yeah, but in the book I write, hey, you might find two typos. Ironically, people haven't actually found them yet. I know where they are, but I actually haven't. It's been out for 18 months and no one has, has actually caught it yet. And that's just me just maybe being super anal about it, whatever. But I am consistently every single day moving towards something that intimidates me. But it's good for me because that means I'm always learning and, and always moving forward.

[Confidence Creator (Host)]

Well, I'll tell you, that book, as you know, became a USA Today bestseller. And I mean, to have that level of success is incredible. It's funny, my first book, Confidence Creator, I self publish, much like you. I just said, okay, I'm just going to write this book having no idea what I was doing. There's three mistakes in the book. I never thought to redo it, by the way, so kudos to you. I just left them and thought, you know what? Let my imperfections rock. I'd always rather be the person that wrote the imperfect book than the person on her deathbed. That said, I never wrote that book that I had inside me and never got it perfect. Writes on to me. I love that you had the mistakes and I also love that you continue to evolve it and that once it got to this level, that's when it completely took off. But that would have never happened had you never sat down and written that small first version.

[Ryan Leake]

Oh, for sure. And you know, it's, it's interesting. When we were first working on this latest version of Chasing Failure, talking with the publisher, talking with the team, and you know, one day I just Said, hey, it'd be great if I hit New York Times. Like, let's just go for it. And then here's what's interesting. Everybody started working harder. I'm like, where was this at before? Like, where. Where y' all been? Where are you? You not now. I get to a game now. Now that I. Now that I've set. Set our goals a little bit higher and I started working harder. So that, that was for everybody. Well, we sold within the first two weeks, I think we sold like 13 or 14,000, which is incredible. Which is enough to hit New York Times. In fact, like, you can, first off, this is all public information. You can see how many units every book on the New York Times. Like, you can see it. So I should have been number three week one, and number six, week two. But you can, you can literally see the numbers. So when, when a book comes out, it comes out, and then you have to wait a whole week before all of the numbers come in. And so that whole week was just so nerve wracking because you're like, yo, we are. We're going for New York Times. We have enough to hit New York Times. But it's like, are you a big enough name? Are you. You know, there's a whole bunch of unknown boxes that you, you have to check. And so when I get the email, it says, hey, you did not hit New York Times, but you hit USA Today. And, oh, we're talking with the Wall Street Journal. We don't know why you weren't on their list because you obviously sold enough. I mean, we put like a six figure marketing plan together that worked. Like, we did everything in our power to get the dub and we lost. And it's just like, oh, poor you, you landed on USA Today.

[Confidence Creator (Host)]

I was gonna say, and Ryan, how many people have come to you after reading your book to tell you their story of how they broke through fear and failure because of chasing failure?

[Ryan Leake]

Oh, thousands. Thousands of people. I mean, people. I got people out there trying all types of stuff. Even stuff that even. I'm like, hey, man, I think you might have took the book a little too little. I don't know. I. I don't. I don't know about that one, buddy. Yeah, did that one. That one. I didn't say get a second mortgage. Okay. I said explore it. Okay. I said send them an email. I like you, you took it a little too far. But people are so resilient. People are so brave. I'm impressed with the emails that I get from people every single day. There, there are people that have just pitched movies, business proposals, book proposals, that have started podcasts and YouTube channels, all because they, they just did it scared. And I, I just, I'm. I'm so impressed with what they've done, way more than what I did to play a part in that. But, like, there, there's a lot of brave people out there, and there's. There's nothing more rewarding than that.

[Confidence Creator (Host)]

I'll never forget interviewing Sarah Blakely from Spanx. And she explained her father every day when they would sit down for dinner, would say, share your failures. Tell me your failures for the day. And her family celebrated failure so much. So it was ingrained in her that this idea of trying something new that she knew nothing about, she. It was very normal for her. Oh, of course I'm going to do this. Unlike 99% of us who had been, you know, basically the messaging of, you've got to be able to win. Don't do it. You'll look, you'll look bad. You're going to be judged, you're going to feel, you know, ashamed. And cut to, you know, this woman becomes a billionaire by stepping into failure on the regular. Which is entirely your message. It's. It's incredible for me to see how many of us, the majority, are held back by failure.

[Ryan Leake]

And I think a lot of people aren't just held back by failure. That the fear of it, the predict. Like they're predicting. All right, according to my assessment, I will fail. Therefore, I won't even try. That's where I try to help people go, hey, you can't sell a book that you don't write. You can't get people to listen to a podcast you won't record. Even this morning, it was like, hey, are you going to a book tour? I'm like, well, what if I go to a Barnes and Noble in New York and nobody shows up for this book? Sign of, like, then I'm just sitting in Barnes by myself. It's just like, no, like, you. You got it. You got to put yourself out there. I mean, you gotta have a plan, too. But, yeah, I think the difference between people who are successful and people who don't get all that they want from their life is that successful people were willing to go sit in the bookstore and be by themselves. They were willing to try the thing and fail, whereas most people would rather just acquiesce to the status quo and settle for mediocrity.

[Confidence Creator (Host)]

I'll tell you, I settled for my version of mediocrity. Being in corporate America for 14 years and saying, I have golden handcuffs. I've got to stay. You know, because this was my excuse, right? It was because I was afraid of what else? What else could be out there beyond what I saw in front of me and what I knew to be what I thought a truth. And it was funny. I was on a call yesterday with this very successful gentleman and in his business, quote, unquote, corporate world, right? Which again, golden handcuffs. And I get the whole thing. I understand. At the end of the call, I said, one more thing I wanted to bring up to you. I've been dreaming about launching a podcast for five years. I've actually recorded episodes. I have a whole list of the people that I'm going to interview when I actually launch it. I have. And he starts. He tells me this whole business plan. It was incredible. And his face was lit up the whole. Nothing like the last 20 minutes when we had been on the call. He was a different person. And at the end of the call, I said, I really don't care about anything you've said on this entire call other than the podcast. I'm holding you accountable to launch this thing. I will get you the right people. I will plug and play. You have got to launch this. You got to pull the trigger, because otherwise you're going to let that dream die. I mean, isn't that the real reason?

[Ryan Leake]

Oh, absolutely. I think people. I think people overcomplicate it. I really do. I think people really overcomplicate their dreams. And there is this mentality of championship or bust. It's gotta be the number one podcast in the world or it's failure. It's an Academy Award or bust. It's Grammys or bust. Like, it's so I think people feel like they have to be the best in whatever industry they're in. I'm like, no, dude, just give your best. Like, there's millions of podcasts out there. Just be good at the one you got and do your best with. With what you've been given. But I think that there is this intimidation factor of, like, you know, I was talking to a friend two days ago, he said, man, I just feel like the things that I have to say have already been said. I'm like, yeah, but the other person that said it doesn't have the people following them that are following you. So say it in your way and help the people that are listening to you. Like, there can be this. Well, so and so is already doing it. And I already follow this person who's already. This is like, yeah, but the world doesn't follow them just because they have a million followers. It was like, oh, man, that's the whole world. No, that's actually a very small portion of the world. Like, there's. What I've learned in business is the pie is incredibly large. It is the biggest pie. That. And we just feel like, man, if, if. If they already own the pie. So there's. There's not enough. It's like, nah, you can eat. And. And I can eat, which is why I'm like, like, I love plugging you with different clients in my. I love plugging our friend Jordan Montgomery. I love plugging different friends of mine that I think are good speakers. And they're just like, well, you're plugging somebody else. I'm like, guys, you know how many events there are in the world every single day? You know, well, one. I'm. I'm one person. I can maybe do 120 maybe. And that's pushing it. It's like, what are we afraid of? Like, I think we feel like, well, I can't say this, and I don't want, like, I heard this other person. It's just like, no, like, leverage your perspective. Leverage what you've got to say. Bring it to the table. And there's. There's enough pie at the table, I think, for all of us to eat.

[Confidence Creator (Host)]

I love that. And I heard this analogy the other day that resonated with me. You know, when we open up the door for abundance and we, you know, offer abundance to others, like, like, you do so generously and connections and whatnot, that is the normal way of being, and it allows abundance to flow back to you, much like, the same way you would with your health. You wouldn't say, oh, I'm working out a lot, taking care of myself. I should probably stop for a while. Maybe somebody else needs this health out in the world, and hopefully it will find them. I'll be sick for a year or two, right? Maybe say, I'm going to show up as the best version of me every day. I'm going to give it my all. Hopefully I inspire other people to do the same. There is no, you know, finite group of people that can be healthy or campy or can be abundant or can't be. We have just bought into this scarcity mindset from media, from the messaging that we're receiving out there that really has so many people stuck. And that's where your books and work resonate so incredibly well. One of the things I Wanted to ask you because I've never done this. I've never preached in a church. I've never done some of the spirit.

[Ryan Leake]

You haven't?

[Podcast Announcer/Ad Voice]

I have not.

[Confidence Creator (Host)]

No. No. Well, I never. I never.

[Ryan Leake]

Okay, we're going to have to change that. I got you. I got you.

[Confidence Creator (Host)]

I will be so honored. Oh, my God. Yeah, but so I've never done that. It's interesting to me. I've always spoken at events, corporations, and business because that's my past. Right. That's what I've feel comfortable doing. Right. So it's interesting to me. In my mind, I try to reason, how can you communicate the same message? Like, like you said that first time someone said to you in business, they saw you in a church, and then they said, hey, can you take out the verses and still be as effective? And you're like, yeah, I'll figure that out. To me, it's so interesting to think, how can you communicate effectively and profoundly in a church as well as in a business, as well as with youth. Right. Versus not just adults? You're. You're crossing so many sections of people and locations and diversity. How are you able to do that effectively?

[Ryan Leake]

Great question. The way I see communication is it is a speaker's job, it is a communicator's job to solve the audience's problems. So if you can understand a business's problems, if you can understand a churchgoer's problem, if you can understand a student's problem, I think you can be an effective communicator. And so what I started realizing the more I started doing business coaching versus pastoral counseling is people in the church as well as people that work at a Fortune 500 company often have the same problem. They often have the same hurdles. People in church and people in business have mental health issues. People in church, people in business, they get divorced all the time. I mean, the divorce rate in the church is the same as the divorce rate. In fact, there are people that are in business that go to church. And so I just started seeing the world sort of blending a little bit of just going, hey, wherever you are, there are people that are hurting. Help them, encourage them. Make a smile today. Help them have a good day. Give them something to think about. Help them overcome their biggest hurdle. What I also learned from the church that I bring to business is business is so numbers driven more than people driven. So when I walk in a room and I say, hey, how are you? I was like, good. I'm like, no, but for real, like, how. How are you? Like, how are you doing? People are like, wait, wait, wait, wait, wait, wait, wait, wait, wait. Wait a minute, wait a minute, wait a minute. Is there somebody here that cares? I'm like, yeah. And like that. Giving people that space in a business setting to tell somebody else, like, how they're actually doing is, like, revolutionary for some people. They're just like, no one has actually asked me how I'm actually doing, and I'm drowning. But to quit, I'm about to, hey, don't quit, man. Hold on. Wait a second. And it's the first time they've been able to actually talk about it because it's go, go, go, go, go, go, go, go. Deliver results, Deliver results, deliver results. And family's falling apart, marriage falling apart. Many things in their life that are just plaguing them. And so I just started talking about those things in the workplace, and I started asking questions. I started saying things like, hey, here, here's. We all get 6,000 thoughts per day on average. 6,000 thoughts. Some people get 60,000. Those are overthinkers. They. Whoever they is, I don't know if it's scientists, whoever. I just read about it says 80% of our thoughts are negative. 80%. It's 4, 800 to 48,000 negative thoughts every single day. 95% are repetitive, which means you and I have the same negative Spotify playlist going on in our brain every single day. So the question that I would ask in a church is going, how are you supposed to grow in your relationship with God with that much thinking? Thinking. The question I would ask in business is, how are you supposed to grow a business with that much stinking thinking? How are you supposed to be a good leader with that much negative thinking? How are you supposed to be a good parent? How are you supposed to be married? How are you supposed to have a thriving romantic relationship? How are you supposed to be a good parent? How are you supposed to lead a team? How are you supposed to come up with creative ideas with that much stinking thinking? So I think that's how I sort of bridge the gap between the two of just saying, hey, whether I'm at a church in elementary school, a nonprofit, entrepreneurs, athletes, hey, everyone wants to thrive in their life in some way, shape, or form. There's just no way that you're going to do that with that much stinking thinking. So, hey, let's be intentional about our thoughts. And then that's where I kind of. I kind of help people. So that's kind of how I. I kind of see different audiences and how I kind of stay comfortable with it because I could share that illustration literally in any room in the world because everyone would go, man, if I'm gonna be that negative, there's no way I'm gonna accomplish my goals. You're right. So hey, let me give you some positive affirmation. Let me give you some positive thoughts that you can take with you to help you achieve your goals. Let me give you some positive thoughts that can help you grow in your relationship with God. Let me give you some positive thoughts that can help you grow in your marriage. So I could be speaking at a marriage conference. I could be speaking at a leadership conference. I could be speaking to a marketing team. But no one is going anywhere with negative things. So I just try and think stuff like that.

[Podcast Announcer/Ad Voice]

Meet a different guest each week.

[Confidence Creator (Host)]

Confidence.

[Podcast Announcer/Ad Voice]

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[Confidence Creator (Host)]

Confidence.

[Podcast Announcer/Ad Voice]

I asked you to try to find your passion.

[Confidence Creator (Host)]

You know, what you did differently than I. I was looking at it as what is so different about each of these buckets. You were looking at it as what is similar across all of them. And, and I think that's, you know, that's a great perception shift for anybody. Instead of focusing so much on what's different and why it can't work, let's start focusing on what is similar and what can work. So I love that you did that. Now you've got a new book coming out, leveling up 12 questions to elevate your professional and personal growth. Give us some insight into what we're going to get there.

[Ryan Leake]

So during the pandemic, I started in executive coaching practice because I was home a lot and had a whole lot more time than I had thought. And so a lot of clients that I speak for would say, hey, you know, would you coach me? Would you? You know, so I, I kind of fell into executive coaching. Like, it was just, it just, it just kind of happened. And naturally, as I started having these different sessions, I was learning just as much as they were, like, learning from, from me. And I was, I was learning more about some of their nuances and some of the things that they were navigating. And everyone obviously got sent home. And so work life balance became, like, obvious because, like, right now, like, you're in my home. There is something about that. It's just like, okay, you can, you can see, you know, my family on, on the wall. Like, you're like, you're in my home office. And so if one of my children bust through the door right now, it'd be like, oh, like. And obviously that's happened for a lot of us. I was on Zoom the other day and some lady had two cats in the background full on boxing. I was like, ma', am, do you see what's happening in the background? Like, that would never happen five years ago, but it's like, now I know something about her that I didn't know before, and that's actually kind of Interesting. And so it's like, I would have never thought, oh, what this woman had to deal with this morning was her cats are fighting. Except for some people, it's their kids are fighting. For some people, it's, we're actually not even on speaking terms anymore. And those things became very, very real. And so from those sessions, I started to realize people were really struggling with burnout. People were really struggling with like just kind of been a lull, really stuck coasting. People were kind of having a life that they tolerate, but they didn't really feel like they had permission to like really thrive in their life. And so I started the way I do executive coaching is I don't like to tell you what to do, I like to ask you questions, I like to get you thinking. And so as different questions began to formulate, I came up with 12 questions that I think are essential for a person to really lead themselves. If I equip you with the right question, you don't need me in the room because you're asking the right questions without anybody in the room. And sometimes when people are in the room, it's good to ask them that question too. And so, for example, one of the questions in the book is, what's it like to be on the other side of me? What's it like to be on the other side of me? I think every single person should be answering that question. Hey, what's it like to be on a date with me? Hey, what's it like to be married to me? What's it like to be parented by me? What's it like to be on the other side of an interview for me? What's it like to travel with me? Me. What's it like to be at a Thanksgiving table with me? What's it like to be stuck in a group chat with me? What is it like to get an email from me? What's it like to get a reply all from me? What's it like? Like, I don't think people really think about what it's like to be on the other side of them. And so we can all think of somebody in our life or our business that isn't self aware like that definitely aren't asking that question. But at some point I think we all have to be considerate that because sometimes I say, hey, you know, have you thought about what it's like to be on the other side of you? They're like, yeah, it's awesome. Yeah, it's amazing to be on the other side of me. To be Married to me or you?

[Confidence Creator (Host)]

Kid.

[Ryan Leake]

They're lucky they struck gold, you know? And I'm just like, are you sure it's as awesome as you think it is? Because it may not be. And so I think each of us should enter into every room going, man, it might be harder than I think it is to work for me. Like, I think, like, like right now, I think somebody works for Ryan League. It's awesome. Like, of course it's awesome. It's like, ryan, are you sure? It's awesome. Like, it's like you're driving a school bus going 120 miles an hour. People are in the back scared.

[Confidence Creator (Host)]

You're like, oh, isn't this fun?

[Ryan Leake]

It's like, not for everybody else in the back that doesn't get to wear seat belts, you know? And so I consistently have to think about that, even for my family and the people that I work with and live with. And just think, man, what. What's it like to be on the other side of me? What's it like to be led by me? What's it like to have me on the team? What's it, you know, and it. One of my friends, he told me, because I asked, because I think it's important that you ask yourself this because I think it's a. It's a nice self awareness question. It helps. When did you verify it with someone else? To go, hey, what is it like to be on the other side of me? And he said to me something the other day that I just thought was so. So on point. And he told the story. He said, you know, sometimes I think about, if I ever meet Matt Damon, my biggest fear is that my life would not be interesting enough for him to pay attention. That's what he said. He goes, and I wonder if you have that effect on people. He said, because you, you do cool stuff, you meet cool people, you always have a story, you always have a travel story. You've always met someone. He goes, so sometimes people will come up to you and share a story. And I wonder if they have somewhat of a meter of going, how interested is he in my story? Given that it's not on the level of his. He's like, so if I were you, I would just be mindful of what it's like to be on the other side of you. So when someone comes up to me after an event, like, I just shared some stories about Kobe Bryant and the Lakers and NBA team, sometimes people will walk up to me and they'll want to tell me their story about how they scored a touchdown in seventh grade. And for me, because he told me that I have to put myself on the field with him in seventh grade and be on the edge of my seat like, so, did you score? Okay, wait, did you now? Did you jump over the guy or did you, like. Because now it's like, it's no longer about me. And I don't want them to feel like this, like, well, I guess I gotta be an NBA superstar to keep Ryan's attention. It's like, no, no, no. Like, whoever you are, like, I'm right here. I'm locked in. So again, I think that's the power of asking a very simple question. What's it like to be on the other side of me? So I call them 12 loaded questions in this book. And it helps a person really lead themselves. I think you should be asking yourselves the right question. Obviously, I could talk about every question all day long, but that's chapter two, right away.

[Confidence Creator (Host)]

It's so powerful because no matter how self aware somebody is, we all have moments where we lose it. I was at a wedding last weekend with a bunch of friends, and everyone was just, you know, taking the selfies. And we noticed that the groom had a setup where he wanted you taking Polaroids and leaving them with notes. We noticed this an hour after we got there. Ryan. I mean, it was one of those moments where you're like, okay, guys, we need self awareness right now. Let's dial it down. So I so appreciate your questions. And this time you didn't stop with just creating a book. You're also launching a course alongside of it. What does that look like?

[Ryan Leake]

So it's a self leadership course. It's taking people through six areas I think that they can master to level up in their life. Like I said, I think a lot of people settle for a life that they tolerate most of their life is. I have to. This course is designed to help you move into a place where you get to. And so one of the things we outline in the course is that there are six levels to living. The lowest level is aimless. Level six is mastery. Mastery is where you are in a position where you are doing so well that things aren't perfect, but you're doing well enough that you're actually investing in other people and teaching them how to do it as well. That's the goal of the course, is to get you in a position where you're, at minimum, thriving of going, like, man, you know what? I am not just on autopilot. My life is not on Cruise control. We are going somewhere. It doesn't mean we're going there fast, but it does mean that we are very, very intentional about our relationships and about. About our goals. And for those that, like, really are like, no, I feel like I want to live exponentially. Well, then the last module in this course is all about how to master that and how to essentially make an impact on other people. Yesterday, one of my friends and I were talking. He goes, so, what's your goal with all this speaking stuff? I said, well, my goal is actually to build other speakers. That's what I want to do. Like, at the end of my life, I want to be able to look at hundreds of speakers that I've said, hey, I've helped you figure out ways to communicate your story and help people solve their problems. And now they've built up whole speaking businesses and whole empires and books and podcasts and courses and being able to pull content out of people and help them package it in a way that actually helps other people. It's like, for me, that's exponential living. That's ripple effect living. It's not just about, how many courses can I create in my lifetime, how many books can I write in my lifetime, how many companies can I speak for around the world? No, those things are going to happen naturally based off of the trajectory of my life. But for me, I'm measuring that exponential growth of going, man, how can I invest into some other people and help them grow their businesses and see things take off for them?

[Confidence Creator (Host)]

Oh, purpose, passion, legacy, joy. You just nailed all of it. I couldn't agree more. Ryan, tell us, where can we get the book leveling up and where can we get the course?

[Ryan Leake]

Ryanleague.com you get everything, anything. Ryan Lee [e-mail] I'm on all social platforms. Ryanleague.com is where you can see some motivational keynotes and previews. You can see book stuff, course stuff. Everything's going to [e-mail] all right, I.

[Confidence Creator (Host)]

Will link that in the show notes below and check out the Elevation Youth keynote. It is incredible. Gave me chills. Ryan, thank you so much for the amazing work you're doing.

[Ryan Leake]

I appreciate it.

[Confidence Creator (Host)]

All right, guys, until next week, keep creating your confidence. I decided to change that dynamic around. I couldn't be more excited for what you're going to hear. Start learning and growing.

[Podcast Announcer/Ad Voice]

Inevitably, something will happen.

[Confidence Creator (Host)]

No one succeeds alone.

[Ryan Leake]

You don't stop and look around once in a while. You could miss it.

[Confidence Creator (Host)]

Come on this journey with me.