EPISODE · Feb 10, 2026 · 50 MIN
Confidence Classic: Chase Failure, Build Courage, and Go After What Scares You with Ryan Leak
from Creating Confidence with Heather Monahan · host Heather Monahan | YAP Media
What if the only thing standing between you and your dream is a story you made up about how it will end? In this episode, I sit down with executive coach, bestselling author, and speaker Ryan Leak to talk about the dangerous habit of pre-calculating failure and talking ourselves out of our own potential. Ryan shares the story behind his documentary Chasing Failure, including how he convinced an NBA team to let him try out (yes, really) and what he learned when he didn’t make it. We dive into why successful people are more willing to “sit in the bookstore alone,” how to stop overcomplicating your dreams, and why perfection is the fastest way to stay stuck. Get ready to stop talking yourself out of your dreams and start doing it scared. In This Episode You Will Learn Why you PRE-CALCULATE FAILURE and quit before you even start. How CHASING FAILURE can take you further than chasing success. The mindset shift that separates those who WIN from those who WON’T TRY. Why you must give your BEST to the opportunity in front of you. How to DO IT SCARED instead of waiting to feel ready. The most powerful SELF-AWARENESS question you can ask to elevate your leadership. How to move from a life you tolerate to a life you intentionally LEVEL UP. Check Out Our Sponsors: Shopify - Sign up for a one-dollar-per-month trial period at shopify.com/monahan Quince - Step into the holiday season with layers made to feel good and last from Quince. Go to quince.com/confidence Timeline - Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Northwest Registered Agent - protect your privacy, build your brand and get your complete business identity in just 10 clicks and 10 minutes! Visit https://www.northwestregisteredagent.com/confidencefree Resources + Links Learn more about Ryan Leak HERE Get your copy of Leveling Up by Ryan Leak HERE Listen to The Ryan Leak Podcast HERE Call my digital clone at 201-897-2553! Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/ Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Ryan on Instagram & LinkedIn
What this episode covers
What if the only thing standing between you and your dream is a story you made up about how it will end? In this episode, I sit down with executive coach, bestselling author, and speaker Ryan Leak to talk about the dangerous habit of pre-calculating failure and talking ourselves out of our own potential. Ryan shares the story behind his documentary Chasing Failure, including how he convinced an NBA team to let him try out (yes, really) and what he learned when he didn’t make it. We dive into why successful people are more willing to “sit in the bookstore alone,” how to stop overcomplicating your dreams, and why perfection is the fastest way to stay stuck. Get ready to stop talking yourself out of your dreams and start doing it scared. In This Episode You Will Learn Why you PRE-CALCULATE FAILURE and quit before you even start. How CHASING FAILURE can take you further than chasing success. The mindset shift that separates those who WIN from those who WON’T TRY. Why you must give your BEST to the opportunity in front of you. How to DO IT SCARED instead of waiting to feel ready. The most powerful SELF-AWARENESS question you can ask to elevate your leadership. How to move from a life you tolerate to a life you intentionally LEVEL UP. Check Out Our Sponsors: Shopify - Sign up for a one-dollar-per-month trial period at shopify.com/monahan Quince - Step into the holiday season with layers made to feel good and last from Quince. Go to quince.com/confidence Timeline - Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Northwest Registered Agent - protect your privacy, build your brand and get your complete business identity in just 10 clicks and 10 minutes! Visit https://www.northwestregisteredagent.com/confidencefree Resources + Links Learn more about Ryan Leak HERE Get your copy of Leveling Up by Ryan Leak HERE Listen to The Ryan Leak Podcast HERE Call my digital clone at 201-897-2553! Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/ Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Ryan on Instagram & LinkedIn
NOW PLAYING
Confidence Classic: Chase Failure, Build Courage, and Go After What Scares You with Ryan Leak
No transcript for this episode yet
Similar Episodes
Mar 26, 2026 ·1m
Jan 2, 2026 ·47m
Dec 21, 2025 ·46m