Studying Failure with Jon Egan

6 Minutes Read

Episode 52

Nobody likes failing—it’s dejecting, exasperating, and difficult to go through. But like other things in life, it’s something inevitable. We all experience failure at different points in our life, and it’s the story we tell ourselves that dictates our journey. You may not see it with the haze of the present situation, but your mistakes and setbacks carry crucial learning points. And at the right moment, those failures will open the door for your purpose.

In today’s episode, the founder and host of the Studying Failure Podcast, Jon Egan, joins us for an insightful conversation about failure. He imparts the life lessons he learned after being let go from his previous jobs thrice. Jon also talks about how he shifted his perspective on failure in his sales career and on finding purpose. Finally, he shares some of his favorite books and resources, as well as his best advice for people struggling with failure.

If you want to unlock your next success after a failure, then this episode is for you!

Here are three reasons why you should listen to the full episode:

    1. Learn how you can shift your perspective when you find yourself struggling with failure.
    2. Discover pivotal thoughts on the role of failure in personal development and finding your purpose.
    3. Find out how you can embrace failure daily with a sales career.


Episode Highlights

The Experience That Led Jon to Study Failure

    • Ever since high school, his goal was to be a basketball coach, personal strength trainer, and conditioning coach.
    • The experiences he had acquired in and after college were leading him to his dream coaching career. 
    • However, after getting married, he had unfortunate experiences with keeping his job. He was let go of his previous jobs thrice, one after another within 18 months. 
    • The first was his job as a Lead Skills Basketball Instructor/Trainer after his wife got pregnant. The second was his job in sales after his daughter was born.
    • He had already started thinking then that he was a failure. On top of that, he was let go shortly after at his third job as a basketball coach.

Jon’s Enlightening Moment

    • Because of his previous experiences, he started identifying himself as a failure.
    • Even after starting personal training, they were still struggling financially on top of their emotional, spiritual, and physical instabilities.
    • After struggling for years, he realized he needed to get out of that mindset. He found High Performance Habits and searched for personal development podcasts.
    • He noticed that very successful people had failed a lot and in major ways. These failures, which are a crucial part of success, are not something we often talk about.
    • That’s where Jon started studying failure, leading him to start a podcast. He wanted to know how others responded and what their mindset was.

The Loop of Failure After the Three Let-Go’s

    • Listen to the full episode to know the reason why Jon was let go from his first and second job!
    • His mindset was if he got let go from the job, he failed at that job; therefore, he is a failure.
    • The outcome is just an outcome. It’s up to you how you attach yourself to that.
    • He didn’t see failure as a learning point then. In his mind, it was only a black-and-white of failure and success.

Personal Development and Personal Accountability

    • After many ups and downs, he landed a sales job where he’s still currently at.
    • At that time, he was able to look back and see how he could have handled things better at his previous jobs.
    • He had fostered a mindset where he wants to be better prepared the next time he gets into situations like those.
    • He now sees failure as winning because he’s constantly learning something from it.
    • Tune in to the full podcast to get valuable takeaways from the books Jon references!

How Personal Development Shaped Jon’s Thinking

    • As an NBA fan, he learned the three words every Sixers fan grew to know: “Trust the process.”
    • Trust the process where failures and setbacks are part of success; success and failure are two sides of the same coin.
    • Jon recommends the book The Purpose Factor by Brian Bosché and Gabrielle Bosché for people struggling with their purpose.
    • Failure is redeemable for a purpose. You can either apply what you’ve learned in your life or help somebody else learn something and grow.
    • He realized he wasn’t alone. Other people had gone through what he had gone through, and it’s an opportunity to connect and create a community.

Embracing Daily Failures with a Sales Career

    • He started his job in sales through personal training where he needed to start conversations with people at random. Some people would just walk away.
    • When he started in his business development role. He hadn’t done anything over the phone as his job required.
    • He started trying to see every phone call as the next call that could set him off for success. He also learned from experience to build rapport first when calling people.
    • He eventually moved into actual sales, doing demos of their platform. 
    • In his first year, he made over six figures because he tried to connect with the people he’s presenting to. He thought about how they would feel throughout and until the end.

How Jon Does Demos

    • He gets in 5 to 10 minutes before the start of the demo.
    • To calm down his nerves, he always listens to the Hot Pockets skit by Jim Gaffigan.
    • He asks himself how he wants the person to feel and what he wants them to get at the end of the demo.
    • The demo is about the client. You have to build trust.
    • Find something to build trust in the first 30 seconds to two minutes.

Jon’s Biggest Advice for Someone on a Failure Loop

    • You are not alone in this.
    • No matter where you’re at, your failure right now is not final for you.
    • Failing at something doesn’t mean you are a failure.
    • Your failure is the key to your success. Keep moving forward.

The Legacy He Wants to Leave

    • He wants people to know him for how loving, giving, and kind he was.

5 Powerful Quotes from this Episode

0:01 - “Trust the process, that those failures, those hard times, those setbacks, they are part of success. Yes, there are two sides: success and failure are two sides of the same coin. If I’m able to take something away from a failure or a setback, a mishap, whatever – if I’m able to take something away from it and apply it to, to my life, to my business to my entrepreneurial journey, then I’m winning.”

08:26 -  “We are missing a crucial part of their success. We’re not talking about a very, very important part, (that) led to Steve Jobs being Steve Jobs, or Oprah being Oprah. And it was the moment that they failed. What did they do? How did they view their failure? How did they respond? What did they learn from it? That’s where I started to study failure – I started to study these successful people, and started to see where they failed and how they failed and how they responded and what their mindset was.”

16:31 - “Whether you attach yourself to that outcome, that’s up to you. That’s how you interpret that outcome. Right? And so, once that outcome happens, then you’re like, ‘Okay, either I failed at that I’m a failure,’ or, ‘Yes, I did fail at that. But how can that failure help me achieve the success that I desire?’”

37:10 - “Every time I go into a demo, I try to find something to connect with them on. I try to humanize it to where it, so then it’s not that scary. And beforehand, I think about it. Okay. Before I go into this demo, how do I want this person to feel at the end of it? How do I want myself to feel at the end of it?”

42:10 - “No matter where you’re at, where you’re, if you’re 20, if you’re 55. No matter your age, no matter your gender, no matter what it is, your failure right now, it’s not final for you. It’s not, it’s really not. I promise you, it’s not.”


About Jon

Jon Egan is the host and founder of the Studying Failure Podcast, a show that focuses on normalizing the conversation about failure. He is presently an Inside Sales Representative at Grace Hill. Jon’s goal is to help people change their mindsets about failures, setbacks, and adversities. He aims to let people see failure as a key to unlocking their next life success.

If you wish to connect with Jon, you may visit his website. You may also reach out to him on Instagram and Twitter.


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Thanks for listening,


Picture of Darrell Evans

Darrell Evans

Darrell Evans is a serial entrepreneur, investor, and Co-founder/CEO of Yokel Local Digital Marketing Agency. He and his teams have helped businesses generate over $300M+ in revenue online. Every month, he leads virtual workshops teaching actionable strategies and tips from his experience helping companies market, grow, and scale.