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The Art Of Coaching

E404 | The Hardest Conversation I've Ever Had with My Son - On Loneliness, Conviction and Doing Hard Things

The Art Of Coaching

Brett Bartholomew

Health & Fitness, Education, Business

4.9649 Ratings

🗓️ 24 November 2025

⏱️ 14 minutes

🧾️ Download transcript

Summary

This episode dives into one of the most personal and difficult conversations Brett’s ever had — not with a client, colleague, or friend, but with his son.   It started when Bronson said he felt lonely — that the kids around him didn’t like to do hard things, didn’t stick with commitments, and quit when things got tough. What followed was a raw conversation about what it really means to live with conviction, pursue mastery, and stay committed even when it feels isolating.   Brett unpacks how this moment with his son connects to leadership, resilience, and the reality that walking your own path often means walking it alone — at least for a while. This isn’t about parenting advice or some polished motivational talk. It’s about what happens when you realize that the same lessons we try to teach others are the ones we have to keep learning ourselves.   ⸻   What You’ll Learn: •Why loneliness isn’t always a bad sign — it’s often proof you’re growing •How to reframe discomfort and isolation as signals of progress •The link between conviction, curiosity, and finding your real tribe •How to talk about hard truths with kids — or anyone — without sugarcoating •What it means to model lifelong learning instead of preaching it   ⸻ Related Resources: •Want help improving your communication, leadership, and decision-making under pressure? Apply for our 1-to-1 or small-group mentoring programs at www.artofcoaching.com/mentoring. •Join us for our next live Apprenticeship Workshop in Phoenix, AZ – May 2026, where we’ll dig into influence, power dynamics, and the practical side of human behavior. Details and registration: www.artofcoaching.com/events.   Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Transcript

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0:00.0

If you've ever been in a position where it seems like no matter what you say, people are just not listening to you or feels like somebody needs to hear it from a different voice, because even with your credentials and your experience, something is just not getting through. I mean, we've all heard that phrase, the expert is out of town. Consider our inservices. We have helped organizations around the world ranging from Turner Construction, Apple, major league sporting organizations, engineers, first responders with inservices geared around conflict resolution, having hard conversations, communicating across silos, how you can help members of your upper level management, better gel with or get along with other aspects of management. I mean, one of the most recent ones we did, there are some folks in the workforce of this particular organization that felt like they were being bullied. And upper level management felt like, listen,

1:05.9

we're just giving them directives.

1:07.2

This is something that we've always done in this company. We know that we need to be socially agile, but sometimes the job is the job. On the other end, the folks in the other side of the company just felt like, hey, we get that the job is the job, but there also has to be some middle ground in terms of how you communicate with us,

1:23.3

and it can't just be directives

1:25.0

and pressure tactics all the time.

1:27.1

We help you deal with the messy realities of leadership. We're never going to come in and just be a parrot or an echo chamber. We are going to come in and help you guys work through honest, straightforward issues that cost organizations in some instances hundreds of millions of dollars or a lot of time wasted. You don't have to do much research to find this.

1:46.4

Miscommunication is really costly for organizations.

1:50.0

So if you want to get more work done waste less time and have a more well-rounded or at least

1:56.0

more communicative staff, reach out to us at info at artofcoaching.com.

2:01.3

That's info, I-N-F-O as an information at ArtofCoaching.com. We would love to work with you. Welcome to the Art of Coaching Podcast. I'm Brett Bartholomew and at a young age, poor communication nearly caused me my life. Now, I help others navigate the great area of social interaction, power dynamics, and communication so they can become more adaptable leaders regardless of their profession, age, or situation.

2:45.5

This podcast is for everybody who is fascinated with solving people problems.

2:50.8

So if you're in the no-nonsense type who appreciates frank conversations, advice you can put

2:55.3

to use immediately and learning how others navigate the messy realities of leadership,

3:00.1

you're in the right place.

3:01.3

I'm glad that you're joining us.

3:02.8

Let's dive in. [♪ OUTRO MUSIC PLAYING [♪ Alright, heads up. We're doing an episode on this topic because it was just something that we put out on our newsletter that a lot of you just said it hit home. And this could be sad for those of you that are parents. I think many of us can relate to this on some level, but I also really love and appreciate those of you that are friends of mine. There's one in particular who's gonna remain nameless that said that even him and his wife really, really felt this and him and his wife really, this resonated with them. And I wanna ground it. So I was having a conversation with my son the other day.

3:45.0

And it was one of the most difficult conversations I had ever had with him. He's about to turn six in December and he really did tell me something that stopped me cold. We had just got done reading, we had set our prayers, we had brushed his teeth. I always lay with him for a while as he falls asleep and he just said, Dad, you know, sometimes I feel lonely. And so naturally I was taking a back.

4:06.9

Like we, I made it about me and I'm like, Dad, you know, sometimes I feel lonely. And so naturally I was taking a back.

4:06.9

Like we, I made it about me and I'm like, oh my God, am I not being a good dad? Because we spent a lot of time together. I mean, those of you that follow me on Instagram if the algorithm actually shows you, I document a lot of the fun we have together. We just have a blast, we play, we laugh, We build forts, we have John Wick style Nerf Wars.

4:24.9

We do movie nights, all the things that a dad and son,

4:27.8

or you know, mother and son, we have John Wick style nerf wars, we do movie nights,

4:25.9

all the things that a dad and son or, you know, mother and son, whatever, but I'm his dad should do. So, you know, I had asked what he meant. And I said, well, what do you mean by that, buddy? You know, do you not feel like daddy plays with you? And he had just said, well, not like that. When I go to Ninja Kids or it's an obstacle course based play place he goes to sometimes

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