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)

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.

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.

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)

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)

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.”

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.

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)

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)

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)

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)

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)

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)

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

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

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.