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Five with Fry
Think of this podcast as your go-to for tackling the hard stuff with clarity and confidence. On Five with Fry, Dr. Jen Fry breaks down the rules, challenges the norms, and dives deep into the tough conversations that shape our lives—conflict, culture, family, sports, tech, and everything in between. This is where you learn to rely on yourself, embrace the messy, and come out stronger on the other side.
Five with Fry
39: Why Failure Delivers Your Greatest Breakthroughs
Ever notice how your best ideas show up right after something goes completely wrong? Same.
As someone who’s wildly competitive, losing has never sat well with me. Take this recent tech pitch competition. I was sure I’d win. When I didn’t, I was pissed. But somewhere between the stage and the drive home, the ideas started flowing. New directions. Better strategy. The kind of insight that only shows up after you’ve been knocked down a peg.
Here’s what I’ve learned: rejection creates the exact mental space where innovation happens. When we win, we rarely stop to question our process. When we lose, we’re forced to reimagine everything. That discomfort? It’s the birthplace of creativity.
The first version of your idea is rarely the best one. True excellence comes from iteration—refining, pivoting, and shaping until it shines. Like a diamond, brilliance takes pressure.
So, what setback are you facing right now that might actually be the beginning of your next breakthrough?
Follow me on Instagram, TikTok, and X at @JenFryTalks, or connect on LinkedIn at Dr. Jen Fry.
Friends, welcome to Five with Fry, where five is the magic number, whether it's five minutes, five questions or anything that fits in five. I dive into the big topics that matter, sometimes alone and other times with a friend. From navigating sports conflict to family dynamics, travel, tech, hard-hitting issues and even politics. Nothing and I mean nothing's off the table. This is where curiosity meets conversation, and we always sit at an intersection. I'm your host. Dr Jen Fry of Jen Fry Talks. Let's get into it. Oh, welcome to the newest episode of Five Minutes of Fry.
Dr. Jen Fry:Today I'm going to tell you something that's going to be hard for you. Beloved, beloved, beloved, beloved. You are going to learn the most when things don't go your way. I know you kind of stumbled a little bit. Let me help you and just take a seat, but I want you to know that you are going to do the best learning, that you are going to do the best learning. You are going to be hit with all the ideas when things don't go your way or you don't win.
Dr. Jen Fry:You know, I am a competitive person. I am so competitive and when I don't win I am so angry and upset. I feel like I should be winning everything. But I have realized, especially for Cordal, the best learning I have done is when I have not won, and I hate it y'all. I hate it so much. I think about an example that happened a while back that I did not win a pitch competition and if you know anything about tech, essentially you're going for money, you pitch with other people and you have to kind of hit on certain things and you're evaluated and then they have winners and I didn't win and I was upset, I was highly annoyed because I again think I should be winning everything, because I again think I should be winning everything. And when I was driving home talking to my mentor, ty, the ideas that I needed to be thinking about were flowing like rainwater, just fluttering down. And I will be honest in telling you, I probably wouldn't have had these ideas had I won, and the ideas that I had were phenomenal ones that can help different parts of my tech company.
Dr. Jen Fry:But again, they're not things I would have thought about, and I tend to see so many people that when they don't win, it's over, they're done, they don't want to do the thing anymore, they're pissed off, they're frustrated, they are just over and done because in their mind they were supposed to win, which, of course, rightly so. I'm always supposed to win, duh. But because they did not win, they thought that well, I just gave my best and I did not win. So therefore, what's the point of moving forward, what's the point of trying again, what's the point of going to the drawing board? And I want to tell you that that first thing you put out there, even maybe that second or third thing, is probably still not going to be the best one.
Dr. Jen Fry:Oh, I know, I hate that for you, my friends, I hate that, but that's the truth of it is that if you want to go to great, you have to keep iterating, keep iterating, keep changing ideas, keep pivoting, keep talking through things, keep diving into the nuance, look at your idea from different angles. You have to keep thinking of different stuff in order for the diamond to be essentially shaved down and shiny and shiny. You can't give up. The first time it doesn't go your way, because that first product should never be the final. Very rarely is what people end up with and their great idea the first thing. So you have to get that out of your head and know that if you want that thing to be great, it's going to take iterating no's and painful no's.
Dr. Jen Fry:Well, friends, that's it for this episode of Five with Fry your dose of five insights, ideas and inspiration. If you love what you heard, don't forget to head over to where podcasts are played subscribe, share and leave a review. Got a topic you want us to tackle? Drop us a message. We love to hear from you. You can come follow me on IG, twitter, the TikTok at Jen Fry Talks, or join me on LinkedIn. Look for me at Dr Jen Fry. Until next time, stay curious, stay bold and keep the conversation going. See you on the next Five with Fry.