Five with Fry

Everybody usually knows why the retreat is happening before the retreat ever starts. The problem is that teams often build the agenda around relief instead of clarity. So people leave with photos, a few good moments, and the same tension waiting for them the next week. This conversation gets underneath that pattern. Jen talks about why vague goals like “we need to communicate better” keep teams st...

This season kept coming back to the same place: leadership starts with self. Not with strategy. Not with authority. With your patterns. Conflict does not come out of nowhere. Your responses were shaped long before this role, this team, or this title. Family systems, early authority, and unspoken rules taught you what felt safe, what felt risky, and what felt necessary when tension showed up. If yo...

Repair is where leadership gets exposed. Not when things are smooth. Not when the meeting goes well. After you interrupt someone. After you dismiss a concern. After you get it wrong. Most leaders don’t struggle with saying “I’m sorry.” They struggle with what happens next. The explanation comes quickly. The intent gets clarified. The wording sounds mature. But the impact remains untouched. When yo...

Leaders love to say their door is always open. That sounds generous. It also keeps you comfortable. Power doesn’t disappear because you’re approachable. It shows up in who has to walk toward you. It shows up in who speaks first in meetings. It shows up in how long someone pauses before telling you your idea is off. The real measure isn’t access. It’s speed. How quickly can someone tell you you’re...

There’s a moment that happens in feedback conversations all the time. Someone asks a question or tries to explain their perspective, and the response is, “You’re being defensive.” The label lands, and the door closes. What could have been dialogue turns into shutdown. This conversation slows that moment down. I walk through the difference between actual defensiveness and healthy self-defense. Inte...

Do you do this, too?  Something feels off, and before you say a word, your brain writes a full script about what the other person meant, why they did it, and how it’s probably not great. I call this the “shower lawyer” habit, where you're arguing a case in your head that no one else even knows exists. This episode is about interrupting that pattern, because those private narratives feel prote...

Conflict doesn’t break relationships. What breaks them is unmanaged emotion. The moments where we shut down, get sharp, avoid the conversation, or expect other people to absorb what we haven’t dealt with ourselves. This episode is about that gap — between what we feel and how it lands — and why leadership always starts there. I talk about growing up without language for feelings, how avoidance bec...

Some words hit harder than they should. A comment like “calm down” can flip a switch in your body before your brain has a chance to weigh in. In this episode, I’m talking about what happens when you get triggered and what that reaction is actually telling you. We look at the patterns that show up under stress, like going quiet, getting sharp, or speeding up, and trace where those responses were le...

Most leadership problems show up in moments of tension. Not the dramatic blowups, but the everyday heat in meetings, feedback conversations, or decisions that carry weight. This episode is about what you do with yourself in those moments. The habits you built early around conflict still show up now, whether you learned to get loud, go quiet, or stay busy to avoid the feeling. You can’t lead past p...

Leadership gets clearer when you stop avoiding the hard parts and start asking where your habits came from. In this episode, we dig into conflict roots. Those early lessons taught you whether to speak up, shut down, smooth things over, or push harder. Those patterns do not disappear with age or job titles. They show up in feedback, decision-making, and how much trust your team feels under pressure...

Fresh starts are overrated. What actually changes us are the layers we’re willing to look at honestly. This season, Five with Fry is narrowing its focus to one thing: conflict. Not the dramatic kind—the everyday moments where things get tense, words get awkward, and most of us either push through or shut down. After experimenting with different formats, the answer was clear: depth matters more tha...

We’re not doing “new year, new me.” We’re doing new year, same person—just less exhausted and more honest . 2025 was a lot. And pretending it wasn’t doesn’t set you up for a breakthrough—it sets you up to quit by February. So in this episode, I’m talking about how to claim 2026 as a breakthrough year without tearing your life down to the studs. This is a remodel, not a demolition. We get specific...

Some holidays don’t feel festive. They feel quiet in a way that echoes. If this is your first holiday alone, your kids are somewhere else, you’ve moved, divorced, or lost someone, the pressure to “make it special” can feel like way too much. Especially when your energy is already thin. In this episode, I talk about that loneliness without dressing it up—and about what actually helps. Including a c...

If your meetings are polite and nothing is changing, that’s not a culture win. It’s a warning sign. In this episode of Five with Fry , we talk about how “being nice” often becomes a way to avoid telling the truth—especially when power is involved. Politeness gets praised. Discomfort gets labeled a tone problem. And real issues stay safely untouched. This isn’t about being rude or reckless. Respect...

The first “no” is brave. The fifth “no”? That’s the one that tells people you’re serious. In this episode, we dig into a very real holiday scenario: you set a simple boundary— if grandpa uses slurs, I’m leaving —and suddenly the family group chat is acting like you’re detonating the traditions of the free world. Your sibling says “just ignore it,” your aunt pulls the “he doesn’t have much time” ca...

What actually happens when you stop tiptoeing around someone’s feelings and start telling the truth with care? In this episode, we dig into the real work of hard conversations: be clear, be kind, and stop pretending emotions don’t exist. No sugarcoating. No “maybe kinda sorta.” Just honest language delivered with respect. We start by calling out the myth of emotion-free feedback. It doesn’t work,...

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...