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

Creating Confidence with Heather Monahan

Heather Monahan

Self-improvement, Education, Business, Entrepreneurship

4.8 • 1.1K Ratings

🗓️ 10 February 2026

⏱️ 54 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	way too often we pre-calculate failing and this abort mission altogether. We literally talk
0:05.2	ourselves out of our own dreams every single day. They're predicting, according to my assessment,
0:10.4	I will fail, therefore I won't even try. You can't sell a book that you don't write. You can't get
0:16.8	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 & Noble in New York and 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
0:38.3	themselves?
0:38.8	Come on this journey with me. Each week, when you join me, we are going to chase down our goals.
0:44.4	We'll overcome adversity and set you up for a better tomorrow.
0:48.9	I'm ready for my close-up.
0:50.9	Tell me, have you been enjoying these new bonus confidence classics episodes we've been dropping on you every week?
0:57.1	We've literally hundreds of episodes for you to listen to.
1:00.1	So these bonuses are a great way to help you find the ones you may have already missed.
1:05.0	I hope you love this one as much as I do.
1:07.5	Hi, and welcome back.
1:09.0	I'm so excited for you to meet my guest today. Ryan Leak is an
1:13.8	executive coach, bestselling author, and motivational speaker that gets to inspire over 50,000 people
1:21.2	every month and train over 20,000 leaders every year. He's widely known for two documentaries,
1:29.3	the surprise wedding and chasing failure. Ryan is also the CEO of the Ryan League Group LLC that is a leadership development firm in
1:35.5	Dallas, Texas. They have the privilege of working leaders and teams all over the world from
1:41.0	NBA teams to Fortune 500 companies. Ryan, thank you so much for being here today.
1:45.9	Yes, it is my privilege to be here with you.
1:49.1	Okay, so I get a lot of DMs.
1:52.5	You're an incredible speaker.
	...

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