The Art Of Coaching

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

Ever had a discussion that felt like quicksand? You’re trying to solve one thing, but somehow you end up defending three other things that weren’t even part of the original issue. The topic shifts, the tone changes, and before you know it, you’re stuck in a loop.   In this episode, Brett breaks down why some people constantly derail conversations—whether by changing the subject, twisting words, or moving the goalposts—and how to stop that cycle before it eats away at your time, energy, and credibility.   This isn’t about learning debate tricks or “winning” arguments. It’s about keeping conversations grounded in reality, staying emotionally regulated, and getting back to the real point instead of getting baited into someone else’s chaos.   ⸻   You’ll Learn: •Why arguments loop in the first place — and the psychological drivers behind conversational derailment. •How to identify the real issue beneath the noise so you stop reacting to symptoms and address the actual source. •Three simple tactics to regain control mid-conversation without escalating the conflict or looking defensive. •How to spot conversational manipulation early and shut it down before it snowballs. •When to walk away — and how to end a circular argument cleanly, without guilt or drama.   ⸻   Who This Is For: •Leaders who keep having the same meetings that go nowhere. •Couples or parents tired of every discussion turning into a blame game. •Coaches, managers, and business owners who deal with emotionally charged people and high-stakes conversations.   If you’ve ever left a talk thinking, “We just went in circles again,” this one’s for you.   ⸻   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.

At some point, every one of us becomes “the bad guy” — the person who says no, sets a line in the sand, or disappoints someone who wanted a little too much. And truthfully? That’s a good thing. In this episode, Brett breaks down why being willing to let people down is essential if you want to keep your sanity, your focus, and your self-respect. Because saying yes to everything doesn’t make you a better leader, coach, or friend — it just makes you a doormat. We’ve all seen how it happens: someone asks for a small favor here or there, and before you know it, your time, energy, and attention are getting siphoned off in a hundred directions that don’t serve your goals. This conversation is about drawing the line, protecting what actually matters, and remembering that you’re not supposed to serve everyone. Sometimes, being the “bad guy” is what keeps you effective, grounded, and able to keep doing the work that actually helps people long-term. If you found this helpful, check out:   •The Apprenticeship – our live workshop on communication and influence.   •Speaker School – for anyone who wants to present and persuade more effectively.   •Join our community at ArtofCoaching.com/community for bonus materials and episode breakdowns.   🎤 Art of Coaching Live Events Let’s be honest—most workshops leave you with a notebook full of tips and no real plan for change. Ours are built different. At Art of Coaching, you won’t just sit and take notes. You’ll engage in real scenarios—role-plays, peer feedback, video breakdowns, and live evaluations—designed to help you sharpen your communication, think on your feet, and handle tough conversations with more clarity and control. Whether you’re dealing with a passive-aggressive coworker, trying to be more assertive without burning bridges, stuck in tension at home, or just tired of second-guessing yourself socially or professionally—we can help. This is potent personal and professional development that actually sticks. No fluff. No filler. We offer multiple pricing tiers and discounts—reach out at [email protected] and we’ll help make it work for you. Upcoming Workshops:📍 Charlestown, MA – Nov 15‑16  (The Apprenticeship™) 🔗 artofcoaching.com/events Real Coaching for Real Life Let’s be honest—everyone says they want growth, but putting in the work? That’s where most people just stick to what’s comfortable.. That’s why we created a mentoring service built for the real world. Whether you’re stuck on a professional decision, starting a business, writing a book, dealing with pressure at home, or just trying to get out of your own way—we can help. This isn’t therapy. And it’s not a rah-rah, feel-good session either. It’s direct, tailored coaching from people who’ve been in the trenches—leaders, operators, educators, business owners. Our team of 15 comes from a wide range of backgrounds, so you’re matched with someone who understands your world and knows how to push you forward. Everyone needs a coach.We’re here when you’re ready. 🔗 artofcoaching.com/mentoring Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

People pleasing -  we’ve all seen it before (whether we recognized it or not) - constantly being agreeable, always saying yes, never setting any boundaries - all to the point of self-destruction.  If you haven’t experienced it yourself, it’s likely you’ve witnessed someone else demonstrate these behaviors. And although it may have short-term benefits, we know that these self-destructive tendencies are not sustainable, and can lead to mental, physical, and emotional exhaustion and burnout. If this is something you think you might struggle with, or if you know someone who does, today’s episode provides a wide variety of perspectives on what “people pleasing” can look like in the day to day world, a number of root causes, and a handful of different solutions you can use to help you manage these behaviors. More specifically, I dive into: Quotes that hit - some of the most impactful sound bites I’ve heard on the topic What drives you?  How our drives can lead us into unhealthy people pleasing behaviors The downside to many of the mainstream self-help resources that address the topic The necessary self-reflection that has to take place before we can make long-lasting behavioral changes Referenced Resources: E210: Assertiveness: How To Ask For What You Want & Get What You Need E207: How Perception Impacts Communication & Relationships E208: Robert Greene: Mastering Human Nature and Facing Your Flaws E200: What To Do When Trying To Help Makes Stuff Worse E176: When Positive Thinking Doesn’t Work E22: The Value of Self-Doubt E130: How Understanding Drives Helps Build Buy-In Quiz: What Drives You? Online Course: Valued - mentioned in today’s episode regarding opportunity cost, this life-time access course help you to identify your values and take control of your career Other AoC Resources: 1:1 Virtual or Group Mentoring/ Staff Development Group Mentoring (The Coalition) Online Courses Live Events Request Us As a Speaker   If you found this helpful, check out:   •The Apprenticeship – our live workshop on communication and influence.   •Speaker School – for anyone who wants to present and persuade more effectively.   •Join our community at ArtofCoaching.com/community for bonus materials and episode breakdowns.   🎤 Art of Coaching Live Events Let’s be honest—most workshops leave you with a notebook full of tips and no real plan for change. Ours are built different. At Art of Coaching, you won’t just sit and take notes. You’ll engage in real scenarios—role-plays, peer feedback, video breakdowns, and live evaluations—designed to help you sharpen your communication, think on your feet, and handle tough conversations with more clarity and control. Whether you’re dealing with a passive-aggressive coworker, trying to be more assertive without burning bridges, stuck in tension at home, or just tired of second-guessing yourself socially or professionally—we can help. This is potent personal and professional development that actually sticks. No fluff. No filler. We offer multiple pricing tiers and discounts—reach out at [email protected] and we’ll help make it work for you. Upcoming Workshops:📍 Charlestown, MA – Nov 15‑16  (The Apprenticeship™) 🔗 artofcoaching.com/events Real Coaching for Real Life Let’s be honest—everyone says they want growth, but putting in the work? That’s where most people just stick to what’s comfortable.. That’s why we created a mentoring service built for the real world. Whether you’re stuck on a professional decision, starting a business, writing a book, dealing with pressure at home, or just trying to get out of your own way—we can help. This isn’t therapy. And it’s not a rah-rah, feel-good session either. It’s direct, tailored coaching from people who’ve been in the trenches—leaders, operators, educators, business owners. Our team of 15 comes from a wide range of backgrounds, so you’re matched with someone who understands your world and knows how to push you forward. Everyone needs a coa

We all get busy. Work piles up, routines take over, and before you know it, years have gone by since you last checked in with people who actually mattered to you. This episode is a reminder — and a bit of a kick in the ass — that it doesn’t take much to change that. You don’t need a reason, a holiday, or the “right time.” Just reach out. Call someone you haven’t talked to in five or ten years. Shoot a text. Reconnect. The longer you wait, the harder it gets, and the truth is, life’s too unpredictable to assume you’ll always get another chance. This one’s short, direct, and human. No fluff. Just a practical reminder to stop overthinking it and make the damn call. The returns—personally and professionally—are worth it.   If you found this helpful, check out:   •The Apprenticeship – our live workshop on communication and influence.   •Speaker School – for anyone who wants to present and persuade more effectively.   •Join our community at ArtofCoaching.com/community for bonus materials and episode breakdowns.   🎤 Art of Coaching Live Events Let’s be honest—most workshops leave you with a notebook full of tips and no real plan for change. Ours are built different. At Art of Coaching, you won’t just sit and take notes. You’ll engage in real scenarios—role-plays, peer feedback, video breakdowns, and live evaluations—designed to help you sharpen your communication, think on your feet, and handle tough conversations with more clarity and control. Whether you’re dealing with a passive-aggressive coworker, trying to be more assertive without burning bridges, stuck in tension at home, or just tired of second-guessing yourself socially or professionally—we can help. This is potent personal and professional development that actually sticks. No fluff. No filler. We offer multiple pricing tiers and discounts—reach out at [email protected] and we’ll help make it work for you. Upcoming Workshops:📍 Charlestown, MA – Nov 15‑16  (The Apprenticeship™) 🔗 artofcoaching.com/events Real Coaching for Real Life Let’s be honest—everyone says they want growth, but putting in the work? That’s where most people just stick to what’s comfortable.. That’s why we created a mentoring service built for the real world. Whether you’re stuck on a professional decision, starting a business, writing a book, dealing with pressure at home, or just trying to get out of your own way—we can help. This isn’t therapy. And it’s not a rah-rah, feel-good session either. It’s direct, tailored coaching from people who’ve been in the trenches—leaders, operators, educators, business owners. Our team of 15 comes from a wide range of backgrounds, so you’re matched with someone who understands your world and knows how to push you forward. Everyone needs a coach.We’re here when you’re ready. 🔗 artofcoaching.com/mentoring Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb