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The Ryan Leak Podcast

The Story Behind Difficult People

30 Mar 2026

Transcription

Chapter 1: What is the main topic discussed in this episode?

1.263 - 30.578 Ryan Leak

Hello, my friends. Welcome back to the Ryan Leak Podcast, where we love to keep things short and sweet for you each and every week. This week's episode, I believe, at least my hope is, that it would give you empathy for a difficult person in your life. I don't know who your difficult person is. I don't know if you're married to this person. I don't know if it is the parent.

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31.047 - 57.882 Ryan Leak

of the person you married, could be an in-law, could be a colleague, could be a boss, could be a neighbor, could be somebody you go to church with. It could be somebody that cuts you off at the grocery store. You name the person. And my hope is that over the next 10 to 12 minutes that we have together,

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Chapter 2: How can understanding someone's backstory improve our empathy?

58.908 - 79.606 Ryan Leak

That somewhere in your mind, somewhere in your heart, you would actually grow in your empathy for a difficult person. Today's episode is entitled, The Story Behind Difficult People.

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Now, I have what I like to call a corporate superpower.

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88.928 - 111.949 Ryan Leak

And my corporate superpower is I can get just about anybody to tell me how they're really doing. For some odd reason, if you drop me into a boardroom, a conference, a green room, or a random airport lounge, somehow, someway,

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people start telling me how they are really doing.

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117.051 - 137.395 Ryan Leak

I'm not talking about my friends, okay? No, I'm not talking about my family. I'm talking about complete strangers go from zero to 100. And maybe in the TMI world, you know, where it's too much information, we don't call that keeping it 100.

Chapter 3: What is PostSecret and how does it relate to difficult people?

137.556 - 142.982 Ryan Leak

That's like 110. You're like, I don't even think I should know that. But for some odd reason,

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I tend to get the real person, not the LinkedIn version. Not the, I'm doing great. I'm doing good. Yeah, everything's good. Family's good.

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156.015 - 163.646 Ryan Leak

No, I don't get the polished people. I don't get the highlight reel version of human beings.

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Chapter 4: What are some revealing secrets shared by people about their struggles?

164.928 - 197.037 Ryan Leak

I get the honest version. And here's what I've learned. People are not doing nearly as well. as their LinkedIn profile might suggest. People are not doing nearly as well as their Christmas photo might tell you otherwise. People are not doing nearly as well as their vacation Instagram post might otherwise sell you on this belief that life is just a beach in their world. That's not the case.

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198.058 - 218.938 Ryan Leak

And what I have come to learn from hundreds and thousands of conversations is that behind every difficult person is a difficult story. In college, I was exposed to a rather interesting book at Barnes & Noble.

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Chapter 5: How can we recognize the signs of someone in distress?

219.659 - 253.733 Ryan Leak

And there's a website and there's been different versions of this book that comes out in a variety of different ways every couple of years, I think. It's called Post-Secret. PostSecret. It's created by Frank Warren. Interestingly enough, he started this over a decade ago where people would anonymously mail in postcards with secrets that they had never told anyone. No names.

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but also no filters, just raw truth. And so he posted his address or PO box, if you will, on a blog, I think it was, over a decade ago. And people would just send him the most insane secrets that... That would just blow your mind.

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Chapter 6: What does the concept of sonder teach us about others?

277.019 - 299.738 Ryan Leak

And what I would actually do is I would buy, it's kind of like a picture book. So the graphic design is remarkable. The artwork is incredible. And I would actually leave it on my coffee table in college in my apartment because I wanted it to be a reminder of why I do what I do. Like there are a lot of people in the world who are hurting.

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299.959 - 325.247 Ryan Leak

And I would always just kind of flip through it as a reminder of like, man, people are not doing as well as they would tell you. And so it just would challenge me to take conversations just a little bit deeper. If you picked up this book, you would... You'd cry, I think. I'm not a big crier, but you would have a deep moment.

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Chapter 7: How can curiosity about others' stories change our perspective?

325.287 - 354.663 Ryan Leak

How about that? Okay, we're not going to take you all the way to tears, but there are things in that book that you go, could I possibly be working with somebody who feels that way? I wrote down just a couple, just for you to be able to get what I'm trying to tell you here. One guy wrote, I smile at work every day, but I haven't felt happy in years.

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355.725 - 385.474 Ryan Leak

Another person wrote, my biggest fear is that I'll live an ordinary life and no one will ever really know me. I tell everyone I'm too busy to hang out, but the truth is I feel like I don't belong anywhere. I stayed in a relationship for years because I was afraid no one else would choose me. Another person wrote, I'm successful on paper, but I feel like a fraud in real life.

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Another person wrote, the people who think I'm the strongest have no idea how close I've been to quitting.

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Chapter 8: Why is compassion important when dealing with difficult people?

396.164 - 430.397 Ryan Leak

Now, think about this for a second. These aren't just, you know, random people. I mean, technically they are random people. But what I want you to understand is that these are people that could be sitting next to you right now. These are people that you could be in meetings with in an hour. These are people that you could be having dinner with tonight. Like you just, you just never know. Like,

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431.778 - 452.023 Ryan Leak

Whenever you're experiencing a difficult person, I want you to start imagining, man, I wonder if they've got a difficult season that they're going through right now. Because now what you're looking for is the why behind the what you're experiencing with this person.

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453.324 - 477.213 Ryan Leak

Like the minute you heard me say a difficult person, somebody popped up in your mind, you know, your coworker, employee, boss, family member, whoever it was. And it's easy to reduce them to a moment. You could just say, well, they're just negative or they're hard to work with or they've got a bad attitude or they're a pessimist.

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477.713 - 510.114 Ryan Leak

They're always like this or just like their mom, just like their dad. It's easy to sort of write people off. But what if you're just experiencing one scene in a very large story that you don't know? And I can just tell you what I've learned is that when people feel unseen, they act out. Because subconsciously, that's what they've learned is the only way to be seen.

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511.115 - 541.907 Ryan Leak

When people feel unheard, they get louder. When people feel insecure, they overcompensate. When people are hurting, it starts to leak into every area of their life. It always leaks. And sometimes when it leaks out, we call that difficult. And I'll just tell you, I've had some conversations that would change the way you see people for forever.

543.845 - 569.16 Ryan Leak

A boss or an executive who seems intense all the time, I promise you, is carrying pressure from a company that's barely holding it together. The employee who might seem disengaged, I'm telling you, they are dealing with something at home that they could never talk about at work. Maybe you got somebody in your life who comes across as arrogant, right?

570.423 - 599.468 Ryan Leak

I promise you, the most arrogant person you know is deeply insecure. And what they're trying to do is protect themselves. The one who always pushes back, you're like, why? Why? They don't feel safe. That's why they do what they do. But we would never know that unless we slow down long enough to see it and hear it.

602.148 - 636.506 Ryan Leak

In my learning time the other day, and every single day I set aside some time to just learn something new. Stories, reading, writing. It's just part of my growth process. I came across this word, sonder. S-O-N-D-E-R. Sonder. It's interesting. It's a very, very interesting word. Sonder is the realization that every person you pass is living a life as complex as your own. Yeah.

637.408 - 670.146 Ryan Leak

The sobering realization. That every person you interact with online and offline, in your office and in your home, is living a life as complex as your own. And if you believe that, it'll change how you go to work. It'll change how you lead. It'll change how you parent. It'll change how you respond. Because now, you're not reacting to behavior. You're not reacting to behavior.

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