Five with Fry

The holiday glow can flip into a pressure cooker the second you step through a familiar door. In this episode, we dig into why even steady healing can wobble at home, how old family dynamics reactivate like muscle memory, and why one simple comment can launch you straight back to age sixteen. We talk about the “home script” that pulls you into past roles—and how to rewrite it. You’ll get practical...

Thinking about entering the transfer portal but not sure if it’s a launchpad… or a trapdoor? In this episode, we take a clear, no-nonsense look at what really happens when athletes chase a new home after the season ends—separating hype from hard numbers and feelings from facts. We talk through the stuff no one tells you: once you hit the portal, your current coach isn’t obligated to hold your scho...

If you’ve been around Five with Fry for a while, you know we talk a lot about the difference between what’s hard and what’s complicated—and if you haven’t, go back and catch up, because those episodes are gold. In this one, Dr. Jen Fry gets personal. She shares what she learned after her mom, Carol Fry, passed away in June 2020, using that experience to break down how grief and logistics collide....

What if the difference between obscurity and breakout success is just one more shot on goal? We pull back the curtain on how companies actually find product-market fit, using NVIDIA’s lesser-known journey—from early misfires to a gutsy Sega contract pivot—as a clear-eyed case study in persistence, access, and timing. We start by demystifying product-market fit with plain language and practical sig...

Ever been told you’re “being defensive” the moment you try to explain yourself? In this episode, we break down the fine line between defending your choices with context and showing up as defensive through tone, body language, or shut-down phrases. Jen walks through real-world examples of how calm, grounded explanations can actually strengthen trust and clarity—at work, at home, and anywhere dialog...

The group chat got leaked, and the spin started fast. Racist, antisemitic, and homophobic “jokes” from 24 to 35-year-old political operatives were quickly brushed off as “just edgy humor.” Commentators framed them as “kids who made a mistake,” even though these are adults with real influence in shaping public culture. In this episode, we look at what was said, who said it, and how the focus moved...

Have you ever skipped revisiting a course or concept because you thought, “I’ve already done that”? In this episode of Five with Fry , I unpack why that mindset might be holding you back. During a drive back from Martha’s Vineyard, I listened to a course about repeatable intellectual property that totally flipped my thinking on what it means to “learn.” There’s a huge difference between something...

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...

When you’re in the chair—whether as an Athletic Director, head coach, or top leader—everything starts and stops with you. Most books don’t prepare you for that reality. Leading means holding steady when the boat feels like it’s tipping and people are looking for direction. In this episode of Five with Fry , I talk with Allison Kern, Associate VP and Director of Athletics at Cal State East Bay, abo...

Have you ever noticed how often people say, “I’m sorry if I offended you” when they’re called out for something they said? In this episode of Five with Fry , I talk about why that phrase sounds like an apology but actually avoids accountability. Adding the word if shifts the problem away from our words and onto someone else’s reaction. It suggests the issue isn’t what was said, but the fact that s...

Ever had that satisfying moment when you finally figure something out after hours of wanting to throw your computer across the room? That’s what this episode of Five with Fry is all about—the messy, frustrating, and ultimately rewarding process of persistence in a world that wants everything instantly. I share a personal story about building a new website using what I call “vibe coding”(i.e., natu...

Kindness and niceness might sound similar, but they’re very different in how they shape our communication and leadership. Too often, leaders avoid hard conversations because they want to be “nice.” The problem is that what feels compassionate in the moment—sidestepping conflict, staying vague, or quietly reducing someone’s responsibilities—creates confusion and toxicity. People can tell when somet...

The world of athlete representation is complicated, and the stakes are higher than ever. Whether you’re a high school athlete thinking about your future, a college player navigating NIL deals, or a pro looking at new opportunities, you need to know how to protect yourself before you ever sign with an agent. That’s why I brought in Luke Fedlam, a non-agent sports attorney who calls himself a “prote...

College sports have entered a whole new era. With NIL (Name, Image, and Likeness) deals and the recent House settlement allowing schools to pay athletes up to $22.5 million, freshman athletes are walking onto campus with multimillion-dollar expectations on their shoulders. But what does it mean to be 18, adjusting to college life for the first time, while also carrying the weight of donors, corpor...

Ever think about the human cost of leadership development? Those first teams you lead are really the guinea pigs for your trial-and-error experiments in figuring out what kind of leader you’ll become. I know this firsthand. At 27, I jumped into my first head coaching role with big ideas—new offense, new defense, new culture, new handbook—without really knowing what I was doing. My players became p...

Can truth hurt without harming? In this episode of Five with Fry , we dig into the difference between being direct and being rude and why so many people confuse the two. I break down an eye-opening video from Conflictish, a social media voice on healthy communication, and connect it to a powerful story from one of my workshops. In that workshop, a deaf participant shed light on the stark differenc...

We’ve been taught that “good” relationships are the ones without conflict, but I’m calling BS on that. In this episode of Five with Fry , I’m digging into the idea that conflict isn’t a sign of failure. It’s actually proof of depth. Think about it: when you care enough to wrestle with discomfort, speak hard truths, and work through disagreement instead of walking away, that says something. Real re...

Why Didn’t Anyone Teach Us This? Most of us were never taught how to handle conflict. We picked up habits by watching family or just winged it. And now we're out here navigating disagreements, tough conversations, and daily tension without real tools. In this episode of Five with Fry , I’m sharing why building conflict skills is essential—not just for your relationships, but for your mental h...

Ever wish you could handle tough conversations without feeling like you’re losing your cool or your integrity? In this episode of Five with Fry, Dr. Jen Fry dives into the real reason conflict feels so messy, and why most of us have never been taught how to do it well. Jen shares insights and stories from her new book, I Said No: How to Have a Backbone and Boundaries Without Being a Jerk , reveali...

Think elite athletes are just born different? Not so fast. In this episode of Five with Fry , Dr. Jen Fry sits down with sports psychology consultant Dan Mickle to unpack the real difference between good and great athletes—and it’s not just about talent or hustle. It’s about mindset. Dan shares five powerful shifts that can change the game for athletes, coaches, and parents alike. From reframing n...

What happens when a mental performance coach and a conflict and culture expert, who is also a former athlete and coach, team up? You get a real, raw conversation about youth sports that every sports parent needs to hear, whether they want to or not. In this episode of Five with Fry , Dr. Jen Fry sits down with mental performance coach Dan Mickle to unpack five uncomfortable truths about youth spor...

What if your next favorite place wasn’t even on your radar yet? In this episode of Five with Fry , I’m taking you on a quick tour of five destinations that changed the way I see the world, and just might do the same for you. From the bold flavors and street energy of Havana, Cuba, to the warm, luxurious but still affordable vibes of Bali, these places are more than just beautiful. They’re transfor...

“Just listen.” Sound familiar? It’s one of the most repeated pieces of conflict advice and one of the most misunderstood. In this episode of Five with Fry , I’m coming for the myth of active listening. Because expecting people to magically “just listen” during a heated argument—when they’ve never actually been taught how—is setting them up to fail. We talk a big game about communication, but most...

Why does conflict make your stomach twist, your hands sweat, and your words disappear? If you’ve ever frozen in the middle of a hard conversation or walked away replaying everything you should have said, this episode is for you. For years, I struggled with conflict. I bottled up my feelings until they came out sideways—loud, messy, and usually unproductive . Growing up, I didn’t learn how to navig...

The Real Test of Team Culture Isn’t Positivity—It’s Conflict It’s easy to talk about team culture when things are going well. But what about when they’re not? In this episode, Dr. Jen Fry gets real about what truly defines a strong team culture—and it’s not just about staying positive. While a lot of teams focus on creating upbeat environments, many fall apart the moment tension hits. That’s becau...