Humility & The Art of Letting Go with Doug Holladay

Summary

Revenue Builders Podcast:

Episode: Humility & The Art of Letting Go with Doug Holladay
Hosts: John Kaplan & John McMahon
Guest: Doug Holladay (Author, Educator, Founder of Path North)
Date: June 7, 2026

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Episode Overview

In this memorable episode, the Revenue Builders podcast delves into the nuanced themes of forgiveness, humility, and personal growth with guest Doug Holladay. Holladay shares a deeply personal story of long-held resentment, the challenge of letting go, and the transformative possibilities that come with forgiveness. Through candid discussion, the hosts and Holladay extract practical lessons for leaders, sales professionals, and anyone grappling with old grudges or the desire to move forward.

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Key Discussion Points & Insights

The Burden of Unforgiveness

• Resentment Carried for Decades:
  Doug Holladay recounts a story of holding onto resentment against someone from his 1985 undefeated Bowling Green football team, describing it as a "boulder" he'd carried for 35 years.
• Physical & Emotional Toll:
  Holladay is candid about the burden, admitting:

  "I didn't believe that I would be able to control myself physically. If I saw that person. And I just didn't want to embarrass myself. I didn't want to embarrass my teammates." ([02:05])

• Headspace Consumed:
  John Kaplan observes:

  "Boy, that's taken up a lot of headspace and in your life." ([02:15])

The Unplanned Encounter

• No Escape:
  Despite thinking the person wouldn’t be present, Holladay finds himself face-to-face at the reunion.

  "I had a boulder removed from my heart because I had no place to go." ([03:42])

• Unexpected Reconciliation:
  The former adversary approaches Holladay with unexpected warmth and respect, commenting on Holladay’s career achievements.

  "I know you hate me, and I just wanted to tell you I been following your career for the last 15 or 20 years, and I... just wanted to tell you that." ([04:06])

The Nature of Forgiveness

• Letting Go Isn’t About the Other Person:
  Holladay emphasizes self-work:

  "Forgiveness, it doesn't have everything to do and very little to do with the other person. It's really the work that we need to do." ([00:34])

• No Special Words Required:
  John Kaplan notes that we often expect “magic words” for closure, but true forgiveness doesn’t depend on perfect apologies:

  "We got to stop looking to try to find magic words... That’s never going to happen. So I think... the first step is not have any expectations." ([04:29])

• Learning vs. Feeling:
  Holladay shares insight given to younger athletes:

  "If I had spent more time thinking about, okay, what am I learning right now and not what I'm feeling... what I'm learning will be so much more powerful." ([07:55])

Self-Reflection & Accountability

• Owning Your Part:
  Both Holladay and the hosts stress the necessity of personal inventory. Holladay admits:

  "At least 50% of that scenario was my issue. I brought my own stuff to that table." ([14:56])

• Power in Humility:
  The episode connects humility with freedom from resentment. Holladay references Abraham Lincoln’s quote:

  "I'm so much worse than they could ever know." ([12:19])

• Humility as Key Virtue:
  Referencing ancient teachings, Holladay concludes:

  “There’s four [virtues]: Humility, humility, humility, humility. That’s the whole ball game.” ([13:45])

Memorable Illustrations

• Family Example:
  Holladay relates an episode where he had to seek forgiveness from his children for imposing his own agenda, highlighting the everyday application of humility and self-correction. ([05:40])
• Linguistics of Meekness:
  A vivid exploration of what “meek” truly means in the original Greek, reframing “humility” as the channelling of internal strength for positive outcomes. ([13:10])

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Notable Quotes & Moments

• "I thought I was going to punch this guy in the throat. I've been waiting for this for 35 years, but it was gone in 15 seconds."
  – Doug Holladay ([03:10])

• "If I had focused on what I was feeling... I'm going to take [it] with me for the next 35 years. What I'm learning will be so much more powerful."
  – Doug Holladay ([07:55])

• "All I can do is try to be as sincere as I can. And I think that requires humility."
  – Doug Holladay ([13:30])

• "We are all wounded, but our wounds can be used in the service of others, to heal others by looking at our own wounds."
  – Doug Holladay ([13:35])

• "If you're humble... you are redirecting this force, this power you have. But for good, you're not using it in destructive ways."
  – Doug Holladay ([13:55])

• "Immediately. When that person helped remove the boulder by their act towards me, the only thing that was left was what I owned."
  – Doug Holladay ([14:56])

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Timestamps for Key Segments

• [00:34] – Doug introduces the story of forgiveness
• [02:05] – Admitting the intensity of lingering resentment
• [03:10] – The encounter and instant transformation
• [03:51] – Discussion on reconciliation vs. forgiveness
• [04:29] – The futility of waiting for “magic words”
• [05:40] – Example of seeking forgiveness from children
• [07:55] – Lesson to young people: learning over feeling
• [12:19] – Abraham Lincoln's humility and self-awareness
• [13:10] – True meaning of “meek” and humility
• [14:56] – Reflection: owning one's part in past conflict

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Episode Takeaways

• Forgiveness is largely an internal process. Relief often comes when we let go of expectations about how others should apologize or behave.
• Humility and self-inventory are essential. True healing begins when you focus on your own role, rather than policing others’ actions or words.
• Learning transcends feeling. In moments of emotional charge, ask “What can I learn?” rather than “How do I feel?”
• Humility is power redirected. It’s not weakness, but the constructive handling of your own strengths and pain.

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This compelling episode offers listeners tools for personal development, practical management insight, and a profound lesson in humanity — all with candor and warmth from both guest and hosts.

Transcript

[John Kaplan]

Foreign.

[Podcast Host]

Welcome to the Revenue Builders podcast, hosted by John Kaplan and John McMahon. This podcast is brought to you by Force Management Today, a segment from our episode on Forgiveness and Gratitude with Doug Holliday. Doug is an author, an educator, and founder of Path North. In this clip, Doug shares a powerful story of forgiving someone he resented for 35 years. Let's dive in.

[Doug Holliday]

Forgiveness, it doesn't have everything to do and very little to do with the other person. It's. It's really the work that we need to do. So let's talk a little bit about kind of the how. Because I had. I've had. Actually this year, I had two major. Two major opportunities for forgiveness, which were. Which were deep, deep, deep, deep, deep, deep. And old and painful. And, you know, believing that I was going to pick that rock up and carry that rock for as long as I had to carry it. And I went to a reunion. 1985. They honored the undefeated team for Bowling Green, which was rated 20th in the nation at the time. It's the.

[John Kaplan]

Oh, that is pretty good. I forgive you for that.

[Doug Holliday]

Yeah, it's probably the best. It's probably the best team that. That they've had in, you know, certainly since, you know, since the 50s or what have you. But so there's an. There was a person there that I even, you know, I'm just going to be a little bit authentic here. I wasn't going to go. If this person was there, I wasn't gonna go.

[John McMahon]

You still had carried resentment, Mr. Cassidy.

[Doug Holliday]

Deep. And I didn't believe. I'm 62 years old, and I didn't believe that I would be able to control myself physically.

[John Kaplan]

Oh, wow.

[Doug Holliday]

If I saw that person. And I just didn't want to embarrass myself. I didn't want to embarrass my teammates. I didn't want to. And so I carried this around.

[John Kaplan]

Boy, that's taken up a lot of headspace and in your life.

[Doug Holliday]

Oh, God. Didn't give me a choice on this. I called the day before and said, this guy's not going to be there. Right? And they said, yes. Well, I get to the dinner and he's there.

[John Kaplan]

Oh.

[Doug Holliday]

And so I didn't really have a choice. And the amazing thing to me was how just happened. And I probably. It wasn't me that was forgiving. It was like. I think I was kind of in a captive audience. And the experience that I had. I'm sorry, I'm rambling a little bit, but it was so amazing. I carried it for 35 years, at least. And I thought I was going to punch this guy in the throat. And when there was no way to escape in this small room with 150 guys, this guy made a beeline right to me. My whole body tensed up, and I think, this is it. I'm punching him right in the throat. I've been waiting for this for 35 years, but it was gone in 15 seconds.

[John Kaplan]

Wow.

[Doug Holliday]

35 years. Now. I didn't have the choice. I was in a room. The two guys standing next to me were 65280. I couldn't even move. And what I will tell you if we could move into the how part, because I'd like you to help people with that. I got lucky.

[John Kaplan]

Yeah.

[Doug Holliday]

I had a boulder removed from my heart because I had no place to go.

[John McMahon]

Well, hold on. Did you reconcile with him and then you forgave or what?

[Doug Holliday]

How.

[John McMahon]

What Specific. You don't have to get into specifics, but because we're talking about forgiveness and

[Doug Holliday]

also reconciliation, this dude came up to me and said, I know you hate me, and I just wanted to tell you I been following your career for the last 15 or 20 years, and I. It's just unbelievable what you've done with your life. And I just wanted to tell you

[John Kaplan]

that

[John McMahon]

without his hands allowed you to reconcile with him.

[Doug Holliday]

Because of that, I think it's the Holy Spirit without. That's a whole nother conversation. We can have a whole nother podcast.

[John Kaplan]

I think also there's something here that we. We are expecting a certain language to come, like you would have preferred. If he would have said, I'm so much easier.

[Doug Holliday]

If he put his fist together. And I think so much easier.

[John Kaplan]

Or if he said, and, Cap, I want you to know I really wronged you, and I'm so sorry, but he didn't do that. But remember, language is funny. He said that, but not with words. By his presence, by him approaching you. So I think we got to stop looking to try to find magic words where somebody, our partner, our kid, or somebody's going to say these things. You know, all of us, when we've been wrong, if somebody came up to us, said, doug, I just want you to know I was talking behind your back and trashing you. And I. That was so wrong. I don't why I did it. I'm so sorry. Course I'd forgive. That's never going to happen. So I think. I think what we have to do is get over these expectations. So I think that's the first step is not have any expectations. To do everything. The second thing is to do everything in your power to do an inventory and say, okay, what is it? From my side of the equation, I've done wrong. And, you know, I find that true with my kids. Like, I had a. I had something recently. My boys are. They do music scores for films, and they're doing one with Adam Sandler right now, which is a big opportunity for them. And he's a big Knicks fan. So I'm talking to my boys. They're unlike their father, who has a million ideas. They just do the work. Well, all of a sudden, Knicks fan, I said, oh, I know Bill Bradley, the. He's one of the most famous Knicks and two time champion Rhodes scholar senator, won two national championships, hall of Fame. I can get Bill to autograph Jersey. So I call him. And I could tell the hesitation. It's like. And I'm rolling them. I'm like, gotta do this. I'm shaming them. This would be unbelievable. Come on, guys, get with the pro. And then I slept on it. And I went back to. I said, I just gotta ask your forgiveness. That I'm just trying to impose my M.O. on you. And that was wrong. Would you forgive me?

[Doug Holliday]

Very relatable.

[John Kaplan]

And. And they, they basically, dad, we know you. We love how you show up. We're just different. I said, great. I thank you and thank you for giving me.

[Doug Holliday]

Before I saw this guy, the team had invited me to speak. The current team, not the older guys. So I go to speak to the current team and I can talk a dog off a meat wagon. Anybody heard me on this podcast. I can talk a dog off a meat wagon. I'm ready to go and have a conversation with these dudes. And 30 minutes before I find out that this other guy is 30 minutes away. And at a dinner that they drove me to, then I had to go to a dinner and I got up there for the first time, I would say, in my adult life, I went blank.

[John Kaplan]

Wow.

[Doug Holliday]

For the first time in my adult life, I went blank in a professional setting.

[John Kaplan]

Yeah, yeah.

[Doug Holliday]

And Doug, listen to what happened. What I said was, if I could, if I. If I could do it over in my life sitting in the chair that you're sitting in now, you're getting ready to go, you know, compete at a very, very high level. I would have focused more on what am I learning in this moment versus what I'm feeling in this moment. And this is the message that I left to them. And these words were just coming out of my backside because I don't know where they came from. But I said, if I had spent more time thinking about, okay, what am I learning right now? And not what I'm feeling. Because what I'm feeling, I'm going to take with me for the next 35 years. What I'm learning will be so much more powerful. And then. So what happened to me is the rest of the story is when that dude started walking towards me, the first thing I thought of is, what are you learning right now? Because if I had focused on what I was feeling and I said, what am I learning? I was saying, why the hell is this happening? How did I just have a conversation 40 minutes ago to the current team and now, okay, what am I learning? And I tell you, Doug, the only thing I thought was, open. Be open. He's walking to me. I'm not walking to him. He's walking to me. So listen. Open.

[John Kaplan]

Yeah.

[Doug Holliday]

And it was clear he had intent to address me. If he had intent to raise his fist to me, that would have been easy. But he didn't. He had intent to address me.

[John Kaplan]

Well, he's obviously been troubled by it, and it's probably as good as you can get, but it's a moment you can put that behind. The other piece that we're all hovering around, which I really want to focus on is other people's actions. Yeah. They affect us. We've been harmed at all. I'm learning more and more that the focus needs to be, where do I need the change? Where have I screwed up? So if you have an interaction with somebody where, you know, some objective person said, well, that was. 90% of that was John's fault, and 10% was you. I don't really care. I've got to go do the work and try to go, and then eventually go back and say, john, I can't believe it. I. I was late again and interrupted you and did all that. I'm. I'm really sorry. And that was wrong. You don't forget what they've done. So I think that's. That makes life easier when the only thing I need to do is do my own inventory about my thing. And I. I learned that lesson in an interesting way by hearing this amazing story about Abraham Lincoln, who was in. Back in those days, the White House was really accessible, and people would just show up and hang out and do all this crazy stuff. Well, the equivalent of a press conference one day. You got to remember, Lincoln was not at a central casting. He was gangly, awkward, not articulate. The. The orators of the Day would speak for two hours, his Gettysburg address with what, 20? I don't know. It was, it was like 40 words or something. So it was just so different. He was not. Didn't go to the elite schools in the East. All the presidents to that point were from Virginia or Massachusetts. He was from Illinois, Schoolyard, was a wrestler. I mean, there's nothing about this guy that should have been present. So. So they were up there. And the press, what's funny, we think the press is. Press is kind of crazy today. You read those old press, they were, they called it yellow journalism. It was brutal. So in the equivalent of a press conference, one of the, one of the reporters said, Mr. President, you have been vilified and called ugly and stupid and, and inarticulate and you don't know what you're doing, you're incompetent. What is your response to that? He just paused and said, I'm so much worse than they could ever know. And I thought, wow, when I start feeling self righteous and I'm so much worse than anybody could ever know. And so I think that's got to be the starting point of doing our own inventory and just trying to get our own house in order. And that makes life so much easier. And it's also very humbling. And that gets to your other point, John, about humility. I think it takes real humility. It's easier to blame, it's easier to be vengeful, it's easier to point fingers. But to be humble enough to say, golly, I am, I am. A guy I know wrote this book called Wounded Healers. He said, we're all wounded, but our wounds can be used in the service of others, to heal others by looking at our own wounds. So I think it's simpler on one hand because if I felt like I had to police others and try to gauge did they forgive me adequately, did they say the right word? That's a fool's errand. All I can do is try to be as sincere as I can. And I think that requires humility. There was a 4th century saint and they asked him once what. What are the cardinal virtues of being a good soul, a good man? He said, there's four Humility, humility, humility, humility. That's the whole ball game. If you're humble and, and see, humility's gotten a bad rap. There is. The New Testament was written in something called coin, a Greek. So Koine Greek was not classical Greek, it was street Greek. So a lot of time you've heard this thing about when you were in Sunday school or whatever, Jesus, meek and mild and all that kind of thing. Well, in the Sermon on the Mount, it talks about blessed are the meek, which are the humble. But you look at. What is that in the original Koine Greek, what does meek mean? It's the same word that's used for breaking a wild stallion. It's taking all that energy and channeling it for a positive good. That's what it means to be meek. That's what it means to be humble. When you are humble, you are redirecting this force, this power you have. But for good, you're not using it in destructive ways. You are using it for goodness. But that is really powerful. That is really powerful.

[Doug Holliday]

I like it. You know, the humility part for me, I'll just put a bow on this one for me personally. Immediately. When that person helped remove the boulder by their act towards me, the only thing that was left was what I owned. Yeah, he took what he owned. And the only thing that was left is what I owned. And I tell you, I went back to my hotel room and I sat up a long time that evening. And where I came to was at least 50% of that scenario was my issue. Yeah, I brought my own stuff to that table. And I'd never been willing to really look at it that way because it was easier for me to.

[John Kaplan]

But he gave you the answer. You know, I'd say the only additional thing you might want to do is jot him a handwritten note and just say, that meant so much to me that you approached me. Forget who's wrong, right. What percentage. That's true. It meant a lot. It was a game changer. But you don't have to go into all the reasons. Just thank you for showing up like that.

[Podcast Outro]

Thanks for listening to today's episode. If you enjoy the content, please subscribe, rate and review the show to help us reach more people. This show is brought to you by Force Management, where we help companies improve sales performance, executing the growth strategy at the point of sale. Check out forestmanagement.com for more information.