The Leadership Guide to Surviving the Loneliness Epidemic

Summary

Podcast Summary: The Leadership Guide to Surviving the Loneliness Epidemic

Podcast: EntreLeadership
Host: Ramsey Network (featuring John Felkins and Dr. John DeLoney)
Date: May 18, 2026

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Episode Overview

This episode dives into the pervasive issue of loneliness among business leaders and entrepreneurs. Host John Felkins sits down with Dr. John DeLoney—mental health and wellness expert—to unpack how loneliness manifests, why it’s especially rampant among leaders, its consequences, and practical strategies to build meaningful relationships while leading at the top. With candid stories and actionable insights, this discussion highlights both the warning signs of isolation and the real-life payoffs of prioritizing connection in a business leader’s life.

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Key Discussion Points & Insights

The Hidden Crisis: Why Leadership Is Lonely

• Loneliness as an Epidemic: The episode opens with a recognition that modern leaders often carry immense professional burdens without adequate relational support. Business has become increasingly isolating due to technology, relentless focus, and the all-consuming nature of entrepreneurship.

  "We've just created the loneliest generation in human history. We outsource all of our relationships to our phones, to our calendars..."
  —Dr. John DeLoney (01:18)

• From Connection to Isolation: Loneliness typically develops incrementally as leaders sacrifice personal connections for business demands, eventually finding themselves with no one to celebrate victories or face challenges with:

  "...you wake up and you have a success or you have a failure, you got a challenge, and you got nobody to celebrate with."
  —Dr. John DeLoney (01:53)

The Darkest Depths: When Loneliness Turns Destructive

• A Stark Example: Felkins shares a poignant coaching story of a client who’d spent more time calculating his family’s insurance payout than planning for his future, underscoring how loneliness can spiral into self-destructive thinking.

  "I have spent the last year calculating how much insurance Money my family would get if I took my life."
  —John Felkins quoting a client (02:18)

• The 'Burden' Mindset: Dr. DeLoney explains how chronic loneliness can devolve into believing one’s absence would benefit loved ones—an urgent signal to seek help.

  "The next layer underneath loneliness is this idea that I'm a burden, that other people would be better if I'm not around."
  —Dr. John DeLoney (02:45)

Recognizing Loneliness—Even in a Crowd

• Physical and Emotional Clues:
  • Waking up at 3 AM frequently.
  • Heightened anxiety about existential or unsolvable problems.
  • Feeling lonely even among family or work teams.
• Types of Loneliness:
  1. Literal—having no one at all.
  2. Perceptive—feeling isolated despite being surrounded by people.

  "You can feel lonely surrounded by people... It's looking at, is my body trying to keep me alive and is it shining all these other alarms? Often it's relational in nature."
  —Dr. John DeLoney (06:10)

Pathways Out of Isolation: Practical Steps

• Break Secrecy, Seek Vulnerability:

  • Confide in a friend, pastor, coach, or therapist.
  • Don’t expect family or friends to automatically sense your struggles—communicate openly.

  "Shame eats secrets for breakfast. Loneliness eats secrecy to survive. And so the path forward is to find somebody... to say, here's the real."
  —Dr. John DeLoney (06:52)

• Allow Yourself to Be Known and Supported:

  • Leaders must intentionally bring down their guard at home or with their support network, after ‘wearing their armor’ at work.

  "You have to be able to put on. Get your shield and get your sword and go to battle during the day and have a place where you sit down and you allow yourself to be seen and known."
  —Dr. John DeLoney (09:18)

• Intentional Transitions:

  • Use physical or mental rituals to separate work and personal life (e.g., changing clothes, leaving the phone in the car, taking time to decompress before going home).

  "Jocko has the best description of how he made that transition. He always kept a T-shirt, a pair of board Shorts and flip flops in his jeep..."
  —Dr. John DeLoney (11:24)

The Necessity of Community for Leadership Success

• You Can't Do It Alone:
  • True leadership, healthy marriage, or parenting depends fundamentally on sharing the load and living in genuine community.

  "You cannot be the leader that you think you want to become if you're doing it by yourself, period."
  —Dr. John DeLoney (14:04)

The Payoff of Community: Dr. DeLoney’s Personal Example

• Building a ‘Gang’:
  • Dr. DeLoney recounts how pursuing standup comedy unexpectedly gave him a close-knit community, enriching his professional and personal life in unexpected ways.

  "You come off stage when you crush it, and you have a gang celebrating with you... when you bomb, they're there to pick you up, laugh with you..."
  —Dr. John DeLoney (16:41)

• Actionable for Anyone:
  • The activity (comedy, cooking, woodworking, group hobbies) is less important than the intentional investment in shared, vulnerable experiences.

  "Nobody has time. This isn't another thing to do. This is you getting underneath all the stuff you have to do and giving yourself a real foundation to go do it."
  —Dr. John DeLoney (18:48)

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Notable Quotes & Memorable Moments

• On the Sneaky Progression of Loneliness:

  "It just happens by degrees..."
  —Dr. John DeLoney (01:27)

• On Crisis Warning Signs:

  "If you find yourself waking up at 3 AM every night... your body is waking you up because it senses you got nobody else covering anything."
  —Dr. John DeLoney (04:28)

• On Bringing Vulnerability Home:

  "The things that make you successful in your job will destroy your personal relationships..."
  —Dr. John DeLoney (08:41)

• On the Power of Rituals:

  "For me it is a—I have a process... so that when I walk in [at home], I'm not radio guy, I'm not helper guy, I'm dad."
  —Dr. John DeLoney (12:09)

• On the Universal Requirement of Community:

  "For all of human history, we've lived in tribes, and all of a sudden in the last few years, we decided, no, I can do this by myself. And we're all collapsing under that weight."
  —Dr. John DeLoney (14:04)

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Important Timestamps

• 00:05: Introduction—Leadership loneliness, episode context
• 01:18: Why leaders are uniquely prone to isolation
• 02:18: Coaching story of a client considering suicide
• 04:28: How to recognize loneliness in yourself
• 06:52: Steps to counter loneliness—seeking relationships
• 09:18: The dangers of bringing 'work armor' home
• 11:24: Rituals for separating work and home life
• 13:08: Achievement without anyone to share it with
• 14:04: The critical importance of community
• 15:00: The ‘payoff’—how building community has changed DeLoney’s life
• 16:41: Stand-up comedy and forming a new ‘gang’
• 18:16: Practical advice: making room for relationships
• 18:48: Framing community as foundational, not optional

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Final Takeaway

The episode powerfully challenges the myth of the solitary leader. Instead, it frames robust, intentional community as non-negotiable—not just for personal well-being, but for effectiveness in business and leadership. The actionable strategies and honest stories here remind listeners that everyone needs to "have a gang"—and that the first, hardest, and most important step is to intentionally let others in.

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For more resources or to join a leadership community, check the episode description for links.

Transcript

[A]

In all our years of working with business owners, we've learned that leadership can be a lonely place. You're making the hard calls, carrying the weight of the business, and showing up for everyone else. But who's showing up for you? I know what it feels like to carry that weight alone. And I also know the power of surrounding yourself with people who get it, leaders who walk beside you, tell you the truth, and make sure you don't lose yourself along the way. The truth is, you don't just need strategy. You need connection. And today, Entre Leadership's head coach, John Felkins, is sitting down with mental health and wellness expert Dr. John DeLoney to talk about how to deal with loneliness as a leader, how it can show up, how it affects you, and what to do about it. So let's get to it.

[B]

Well, John, thanks for being here.

[C]

Good to see you, man.

[B]

I know on your show you get all kinds of crazy calls.

[C]

Yeah.

[B]

But one of the themes, it seems like you get a lot of calls about loneliness. And we're seeing in entrepreneurship, in business ownership, like, it's like 50% of the people are reporting that loneliness is a problem. Why do you think that is? What are you seeing?

[C]

I think there's a meta trend, which is we've just created the loneliest generation in human history. Right. We outsource all of our relationships to our phones, to our calendars, and then I think particularly in the entrepreneur space, that takes a ton of time and a ton of focus, and you're doing 15 different jobs at once, especially when you get going. And so slowly, over time, you can't hang out with your buddies anymore. You don't respond to the text threads anymore, and you text your wife, I love you, instead of being home for dinner every night. And it just happens by degrees. And suddenly you wake up and you have a success or you have a failure, you got a challenge and. And you got nobody to celebrate with.

[B]

That reminds me, one time when I was working with one of our clients, was coaching him, but I could just tell, like, it was not landing at all. We were doing that wheel of life thing, you know, trying to set goals for his life. And it was like I was just talking to a fence post, and I, you know, I stopped and I looked at him and I was like, what's this like for you? Like, what's going on right now? And he looked at me and he said, I'm really struggling to think about my goals for the next year because I have spent the last year calculating how much insurance Money my family would get if I took my life.

[C]

That's it.

[B]

And I was just like, oh, man. And it was so sad in that moment. And I know you kind of mapped out, like, this is how people become lonely, but that feels next level to me.

[C]

The next layer underneath loneliness is this idea that I'm a burden, that other people would be better if I'm not around. And then if you've got good life insurance, there's a number attached to that. Right. I've talked to a lot of men, especially men in that situation that make the calculation, oh, I'm not a part of the daily rhythm of my family's life. I come home and I bring stress and chaos to my own house. Man, they could get a million dollars if I was just out. And that's when, you know, man, I need to call somebody asap. Like, that's. I've got. I've crossed over to where this is extra unhealthy now. Yeah. Yep.

[B]

And that's. Honestly, I was super stumped.

[C]

Yeah.

[B]

And I just looked at him, and I basically said to him, like, forget all that. Forget all of this stuff we're talking about. Pick up the phone and, like, you know, go talk to your pastor. Go talk to your high school friend. Go talk to your family.

[C]

If you're calculating insurance, you can call a professional. Yeah, yeah, yeah. I mean, if you're there where. If you actually believe, you look in the mirror and think, the people who I love the most would be better served with me not being in their life. You gotta call somebody. Yeah.

[B]

So that's, you know, thankfully, at least in my experience, and us working with clients in coaching, that's. That extreme is pretty rare. It's not the only time it's happened. We've had to do. We've had some other situations also, but when it's not quite that extreme, what would you say people should be on the lookout for? Like, you know, everybody that's watching this, right. They're thinking, gosh, that I'm like, that ain't me. Yeah, but what would you say to them? What would you kind of tee them up for?

[C]

So I want to back out. Right. And often people look for. When they. When they hear somebody like me running my mouth about all of y' all are lonely, do you instantly go to your Rolodex? No, I'm not. Right. I've got my wife, I got my kids, I got a couple of buddies. I still have this long text thread from my old friends. Whatever. Here's. That's not the place to go first. The place to go first is to back out and know this statement is true. Your body would be failing you if it let you sleep all night knowing you're the only one you've got. So if you find yourself waking up at 3am every night, yes, you wake up and you're scanning. That's a clue. Your body is waking you up because it senses you got nobody else covering anything.

[B]

You're not safe.

[C]

Right. If you can't have a deep, connected, romantic evening with your spouse because your body knows we don't have time for this. We are trying to not die. Right. So if you are anxious about things that normally bothered you or annoyed you and now they keep you up all night, the world economy's gonna. The new AI is gonna. Right. When you start getting existential, that's often a sign that your body is trying to solve all the problems in the world itself because it knows it's got nobody else to help you. Okay. And those are big flashing lights. My body has identified. I got nobody else. And that might be real or it might be imaginary, but that's a good place to look. And there's two kinds of loneliness. There's lonely like I literally have nobody, or there's probably what that client of yours was experiencing, which is I. I feel lonely in a crowded room. My wife is right here, and I know she loves me, and she has no idea how scared I am about our finances. My two ride or die co workers are with me right here, and I haven't fully told them how fragile our business is. Right. And so you can be completely. You can feel lonely surrounded by people. Right. And so it's. It's. But it's looking at. Is my body trying to keep me alive and is it shining all these other alarms? Often it's relational in nature.

[B]

Okay. So you give those two scenarios. I'm guessing. And it's a guess, but also based on working with a lot of people in our program. The second thing you said is probably the more frequent thing where they're alone in a crowd. You know, like we're sitting in here with the entre leadership team, you know, a lot of people, but it can still feel very alone.

[C]

Yeah.

[B]

You're saying don't look to your Rolodex.

[C]

Yes. Right.

[B]

You're picking up these signals. What do you do?

[C]

Shame eats secrets for breakfast. Loneliness eats secrecy to survive. And so the path forward is to find somebody, whether that's a friend, whether that's a pastor, whether that is a Coach. Whether that is a therapist to say, here's the real. And they will help you as you dump all of your feelings on the table. They will help you parse. That's not real. This one is. This is a challenge. We need to solve this. But you have to get other eyes on a problem. And the way I like when I talk to military folks, no military guy in the world would head off into a battle without there being eyes in the sky. That's what relationships are, without somebody right next to you going with you. So we wouldn't expect that of our warriors. I can't expect that of any other person. Right.

[B]

So you gotta have somebody to go into battle with you. But then also, you were saying, like, my spouse might be right next to

[C]

me, and she doesn't see me and she doesn't know me.

[B]

Yeah. So it's the vulnerability that is the. Is the wall between the two of you that is preventing you from experiencing your spouse as going into battle with you. Am I understanding you right?

[C]

They may not go into battle with you, but they know the extent of the battle you're in, and they. Y' all have talked about intentionally ways that y' all can support each other. Not every military guy goes on the front lines. Right. But the guys run on the front lines. Know, I got somebody watching up here. I got this crew taking care of the ammunitions. I got this crew taking care of the tanks. We're all. We're all playing a part here, right? Yeah. In marriage, we talk a lot about. You got to see and know and celebrate your spouse. For entrepreneurs especially, you have to allow yourself to be seen and actually known, and you have to actually accept celebration. And that's hard to do. Why?

[B]

That was my. Why is that so hard? Why do people.

[C]

Because the marketplace. If you show that in marketplace, they'll kill you. And so the things that make you successful in your job will destroy your personal relationships. You have to. If you're starting a new business and you're a salesman, you have to project. You should hire me. I have no. I am invulnerable. Right. I will show up, do the job below, budget on time. I'll crush this thing for you. I will help you, and that will destroy your marriage. You have to be able. That will destroy your friendships. That will keep you isolated and alone. You have to be able to put on. Get your shield and get your sword and go to battle during the day and have a place where you sit down and you allow yourself to be seen and known.

[B]

We'll get right back to that. But do you remember when you only worked 40 hours a week? Now that you're in leadership, you do that by Wednesday afternoon. Look, you want to be a part of something meaningful. You want to make an impact and still have a life. But as your company grows, your calendar fills up, meetings start stack on top of each other and you're doing more work that doesn't require your expertise. You don't have time to lead anymore. And that's where Belay comes in. Belay matches you with qualified US based executive assistants, marketing assistants, and accounting professionals. Real people who can help you protect your time. So you can delegate what doesn't require your leadership and focus on the work only you can do. Because growth doesn't come from doing more. It's. It comes from doing what matters most. If you're ready to build a business that runs without running you into the ground, download Belay's free resource, the 40 hour CEO work week planning guide by texting ENTRE to 55123. That's ENTRE 255123. That seems like two different modes of living. Is there a risk of, like, getting detached from who you really are if you're, if you're like, trying to show up as something that you're not? Is that what you're saying?

[C]

No, I think there's seasons. And so in my, in my experience, I ran huge organizations that had huge budgets attached to them. Sitting in front of spreadsheets all day making budgets takes my soul from me. Every time I sign, I signed up for a new responsibility in a large organization to lead. I knew that the first year or two, I'm the guy behind those spreadsheets. And then my job as a leader over time was to find people that, that gave life to, right? But in the beginning, I gotta take full ownership of this thing. And that meant me and my wife have to sit down and count the cost of. I'm headed into this new job. I'm gonna take every coffee, I'm gonna take every meeting, I'm gonna have to do every budget myself. I wanna put my eyes on it. And so when I get home, here's what I need vacation to look like. Here's what I want our romantic life to look like. Here's what I want my relationship with my kids to look like. And then she's like, got you. I'm gonna protect this here, right? And so Jocko has the best description of how he made that transition. He always kept a T shirt, a pair of board Shorts and flip flops in his jeep in his car. And he said, my kids are not military operatives. I will not wear my uniform into that house because in there I'm dad. And for him, changing, literally changing clothes was. I'm changing my hat, I'm walking in different. And for me it is a. I have a process when I leave here and I'm dealing with hard conversations all day long. My 10 year old daughter doesn't wear that. She doesn't know anything about.

[B]

She doesn't care about all that.

[C]

No. And so I have to know I am shifting from dad mode. And sometimes I stop at a coffee shop and I just need 30 minutes to read a book. Sometimes I talk to an old college buddy just to catch up. Like I have a process so that when I walk in, I'm not radio guy, I'm not helper guy, I'm dad. Right? And that's hard, right? It's hard. And there's. Sometimes I call home and say, I can't shake off this last one. Just know I'm coming in hot. And my wife's like, got you. Right? But we've established that beforehand.

[B]

I guess I'm just a little simple. I leave my phone in my Jeep.

[C]

Genius.

[B]

If I bring that thing in, it's like a demon follows me in.

[C]

Genius.

[B]

Yes.

[C]

Yeah.

[B]

Yes.

[C]

But knowing you, knowing yourself is that first key, right? I will never, as long as I live, forget. And some of the entree folks watching this have probably heard me say this. Writing a book, having on the way to my first book signing ever, getting a phone call, having the head of publishing, Preston, hand me the cell phone like this in the car, have Dave on the phone screaming, you're number one.

[B]

You did it.

[C]

And I was like, yeah, we did it. I called my wife, I call my mom, we go do this book signing. The line is wrapped around the door. Not because of me, because Dave said, you should go. And everyone did what Dave said. And I got back to the hotel and I had nobody to call. And I've got great friends. But in the course of writing this book and trying to do my business and trying to kick this show off the ground, I'd stop showing up to the Monday night gatherings, I'd stop calling back. I'd responded to the text, read with a funny emoji, and that was it. And I spent six, seven, eight months isolating myself. And then when the moment came, I had nobody to call, right? And I remember thinking, oh, I went with me, right? And so my job was on the Next book, I gotta have a gang with me. And that was important. Yeah.

[B]

How would you label this entire body of work of not letting yourself get isolated, essential, critical?

[C]

You cannot be the leader that you think you want to become if you're doing it by yourself, period. You can't be the husband, wife, parent, all by yourself in isolation. And for all of human history, we've lived in tribes, and all of a sudden in the last few years, we decided, no, I can do this by myself. And we're all collapsing under that weight. We can't. You can't. And so I would tell you, you have to sleep. You got to take care of yourself. You have to do all those things, and your body would be failing you if it knew you got nobody to cover. Cover things while you're asleep. And so I'm gonna keep myself well and whole. And that starts with having a gang.

[B]

That's. I think all of that is gold. I'm gonna push just a little bit further because it feels like as I listen to our conversation, it's a lot of warning in it. What's the other side? What's the payoff?

[C]

Okay. Can I tell you? Yeah. So I'm in my mid-40s. I'm in my late-40s now.

[B]

Young guy.

[C]

I'm an old man.

[B]

Young guy.

[C]

I'm an old man.

[B]

Young guys.

[C]

And I recognized I've got great community with people I work with, and I've got a great church community. I've got my old school friends that I've known for 30, 40 years back in Texas. But I don't have deep connected friendships here in Nashville with guys that I don't have these other cross tentacles with. So I made a crazy choice. I had a lifelong dream of one day I wanted to do a stand up comedy set. I went up. It was way scarier than I thought. Way. There's a hundred people going like this. Make me laugh, boy. Right? It was terrifying, but it was like a drug. But what has happened over the last. So then I started living at the club. In fact, my wife calls the local comedy club here in Nashville. My dealer, right? She's like, why don't you just go to your dealer? You're being grumpy. But here's what's happened. I took learning the craft of doing stand up very seriously. And so I surrounded myself with craftsmen. And I just so happen. I get this is ridiculous. That the place where I go that's right down the street from my house is where Bargazzi, where John Crist, where Dusty Slay, Where Theo Vaughan, where those guys go to practice before they go on the road. And so I've gotten the blessing of sitting behind closed doors in green rooms with these guys who are master craftsmen, learning a new thing that I didn't know how to do. And in the process, you come off stage when you crush it, and you have a gang celebrating with you because y' all are all doing a thing together. Everybody's different, but you're all doing a thing together. And when you bomb and you'll bomb, they're like, oh, man. Right? And they're there to pick you up, laugh at you, laugh with you. And so here's what I have now, friends. I got a gang. And I didn't expect that. But I had to go first. I had to go be weird. I had to just go do a thing intentionally that I don't know how to do. And by doing that, I have ended up with this other weird community that I never in a million years would have thought I had. And I've got things in common with guys I didn't think I would have anything in common with. But now I got somebody to call on the weekend. Hey, let's go grab dinner. Hey, there's a funny guy coming to town. You want to come with me? Because my wife, she doesn't like this world at all, right? And now I've got people that I can go. I called one of the comics today with a business with a Ramsey question, right? Cause I want to get your outside perspective on this. I've asked guys on ticket sales stuff. I've asked stuff on things that make me better at my day job. Different perspective, different mindsets, different visions of the world. And it's made me a richer person.

[B]

So I want to make sure I'm clear on that. Because I know you're not saying, hey, everybody, you need to go be a stand up comedian. That's not.

[C]

Nobody needs to do that.

[B]

That's not what you're saying. But there's some core tenets to what you did that anybody can do in any pursuit.

[C]

Go take a cooking class, go take a woodworking class. And here's the thing. I'm a full time writer. I'm a full time. I co host two shows, right? I'm on the road all the time speaking. And I have two young kids and I've got a wife who is my whole world. And I got responsibilities in my church. I don't have time for this, right? If I look at my calendar, this is an intrusion into an already two full calendar. And as my wife told me, you don't have time not to. And so this became a priority so that I can go do all these other things way better. Right? And this has given me so much life. But it's signing up for the dance class, signing up for the shooting class, signing up for the woodworking class, going

[B]

on the hog hunt, going on a hog hunt.

[C]

Saying yes. Hey, several entree guys, maybe folks who are listening and watching this have come up to me after events and been like, I want to go hunt with you. I'm always like, okay, cool. Last year I said yes. I said yes to all of them. And I made great new friends, had wild adventures, had a blast. But it was me saying, I'm going to intentionally get out of this calendar, this comfort zone, and I'm going to go make memories, I'm going to go have experiences. And it's been enriching in every other part of my life. Right? So nobody has time. This isn't another thing to do. This is you getting underneath all the stuff you have to do and giving yourself a real foundation to go do it.

[B]

I love it. Thanks, Deloney. Appreciate you coming on here.

[C]

Thanks, man.

[B]

Take care.

[A]

Every leader should have community. I don't care what stage of business you're in. You need people around you who get it, people who are in the fight with you. That's what our advisory groups, Inside Entree Leadership Elite, are all about. These are groups of eight to 10 business owners who meet twice a month with a coach to help each other carry the weight of leadership. Folks who are walking through the same trenches, making the hard calls and refusing to let each other go at it alone. If that sounds like the kind of support and accountability you need, we'll leave a link in the description where you can apply for a group. And if today's episode encouraged you, be sure to, like, share and subscribe for more great leadership content. I'm your host, Dave Ramsey, and this is Entree Leadership.