E384 | 21 Questions I've Never Answered Before on Training, Dating, Leadership and Life

Think about the last time you dealt with someone you were trying really hard to be professional with. Despite multiple miscommunications on their part — and what was clearly laziness, apathy, and them mailing it in — you kept trying to be the adult. You kept overcompensating for their lack of effort. You kept telling yourself, “Hold yourself to a higher standard.”   But it’s still getting you nowhere.   You want to lose it. You want to let them have it. But you hesitate — because everything in leadership and communication says “keep your cool.”   So the question becomes: At what point does that restraint stop helping and start hurting? At what point are you completely justified in going old-school — 1950s dad style — and giving someone a full-on ass-chewing?   What You’ll Learn:   •How to recognize when it’s time to stop playing nice and start holding the line •A real-world filter to help you decide when to confront someone directly •Why giving someone the business doesn’t mean losing your professionalism •How to hit someone with hard truth — without losing your message or your control   Why It Matters:   If you lead, coach, manage, or parent — this will give you a concrete decision-making lens for high-friction moments. You’ll stop second-guessing yourself when someone needs to be checked, and you’ll know how to do it in a way that’s firm, clear, and productive.   Come see us in: 📍Oakland, CA – July 12-13 📍Melbourne, AUS – August 23-24 📍Murfreesboro, TN – October 25-26   Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

“Is there anything I can do to help?” It’s interesting and unique how we’ve all been asked this question by a spouse, friend, co-worker, or boss—but it never feels like that question leads to you getting actual help. It often feels like answering that question will cause you even more issues.  But, people are asking it with good intentions, so how can we actually seize this moment and get some relief from the overload? We’re always told as leaders that we need to delegate, delegate, delegate—so how can we respond to this request without adding to our overwhelm? In today’s episode, Brett is going to give us all the answers—and much more—to this age-old question we all somewhat cringe when we hear. Lean in as he covers: The psychology and first principles behind why we often decline help—even when we need it Cognitive overwhelm—how to reduce it, cut through the fog, and get the help you need Practical strategies to truly show up for someone and show you care Default requests you can use to get quick results based on their competence and ability How to respond with honesty that eases the emotional friction you might feel Iron Sharpens Iron You say you want to be the best—then stop avoiding the conversations that actually test you. This isn’t another feel-good workshop or conference where you can sit back, take notes, and disappear into the crowd. The Apprenticeship is fully interactive. We throw you into live, role-play scenarios and teach you how to navigate real conflict, difficult personalities, and power dynamics with clarity and control. No fluff. No theory overload. Just gritty, practical reps that expose your blind spots and sharpen your communication under pressure. Everyone could use some help—and if you're part of the audience we focused on in last week's episode, you'll even earn 1.6 CEUs!  Come see us in: 📍Oakland, CA – July 12-13 📍Melbourne, AUS – August 23-24 📍Murfreesboro, TN – October 25-26 (Im)Perfect Relationship Course One of our most popular offerings, for the married, divorced, dating, or anyone who wants to show up better in the relationships that matter most. We cover real stuff: communication strategies, attraction styles, love languages, parenting, money—and yes, even the topics usually left behind closed doors. Nothing’s off-limits. 🗓️ November 3 – December 2 This is a 30-day, 100% online challenge with live Zoom sessions each week. *Bonus: It’s also our most affordable course—so if you’ve been looking for a low-pressure, high-value way to go deeper with our material (whether you’re partnered up or preparing for “the one”), this is your chance. Join the waitlist now! Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

This isn’t personal, but it’s been a long time coming. This episode is aimed directly at the legacy industries of Art of Coaching, Strength and Conditioning, and let’s throw overall fitness in there too. If you work in high performance, physical therapy included, you’re included.  We know everyone deals with some version of this, but we’re speaking to the world we know best. The message? Most of you say you want to be the best. Most of you say you’re “in it for the right reasons.” But you’re not. You’re full of shit. You’ve built a self-serving feedback loop—one that props up your ego and avoids any real discomfort. You’ll do anything but face your actual weaknesses. You whistle past the graveyard, pretending it’s all about the best exercises, protocols, or the next certification.  You could have the greatest program in the history of the world, but if you can’t work with the humans executing, it means nothing.  Today’s episode will hit each listener differently. Some will take it as a wake-up call. Others will feel like they’re getting roasted. And a few of you might even hear it as a love letter—meant for a group of talented people who are in desperate need of a gut check. Turn it up, as Brett pulls no punches covering: The massive divide between what people say they want—and what they actually do CEUs and continuing education: how they keep you feeding the machine Are you really a lifelong learner, or just another body fogging a mirror in the weight room? Why real progress looks more like a boxing gym and less like a resort Let us know what you thought of this episode. Whether you loved it or hated it, we welcome the discourse. Send your feedback to [email protected]—we genuinely want to help those in our legacy audience who are ready to get honest and do the work. The Apprenticeship You say you want to be the best—then stop avoiding the conversations that actually test you. This isn’t another feel-good workshop or conference that lets you hide in the crowd. At The Apprenticeship, we throw you into live, high-stress role-play scenarios and teach you how to navigate real conflict, difficult personalities, and power dynamics with clarity and control. No fluff. No theory overload. Just gritty, practical reps that expose your blind spots and sharpen your communication under pressure. Because if you can't lead a conversation, you’re not leading anything. 📍Oakland, CA – July 12-13 📍Murfreesboro, TN – October 25-26   Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Ever feel like you're coaching on repeat?  You've handed a client every tool they need, yet they keep circling back with the same issue.  Or maybe you're working with an athlete who hears everything you say, but nothing seems to land. It’s as if they’re outsourcing ownership of the entire process. It can start to feel like a rehearsed dance. You say your part, they nod along, and both of you move forward on autopilot. But this doesn’t have to be just frustrating—it can be an inflection point for us.  In today’s episode, Brett breaks down how to navigate this all-too-common dynamic and use it as a way to better understand what we bring to the table. Because when we hone in on and embrace our unique intangibles—those strong qualities that might even turn some people off—we create opportunities to lead more effectively, grow our business, and stand out in a noisy, boring world where everyone just wants to fit in. In this episode, we cover: No matter what they say, clients come back for more than just results Questions to ask a non-responsive client to encourage ownership—without assigning blame How to get feedback and gain insight into what sets you apart (hint: it’s not your experience or certifications) Determine if there’s a “psychological nutrient” you’re providing—or withholding Bonus: An excerpt from Brett’s Observed Absurdity file about department stores, including some hilarious, can’t-miss euphemisms and analogies The Apprenticeship If you're tired of struggling through hard conversations or avoiding them altogether, this is your chance to train for them. We’ll put you in realistic role-play scenarios and teach you the frameworks that help you navigate conflict, power dynamics, and tough personalities. No fluff. No gurus. Just pressure-tested strategies you can actually use—because the best coaching skills don’t perish. Everyone has a coach in their life, and the ability to communicate clearly under pressure pays off in every area—not just work. 📍Phoenix, AZ – June 7-8 📍Oakland, CA – July 12-13 📍Murfreesboro, TN – October 25-26 Retreat. Reset. Recalibrate. RELOAD! This September, we’re hosting a retreat in Phoenix, AZ—built for those who carry it all. Ten years in the making, this event is designed to give you tools to slow down, recalibrate, and breathe again. We're teaming up with professionals like Taylor Somerville and Lauren Vestal to introduce breathwork, recovery strategies, and techniques to help you downregulate and bring some peace back into your day-to-day life. You’ll also get space to move, connect, and troubleshoot how to have the tough conversations you've been avoiding—so you can show up for yourself as much as you do for everyone else. Stay tuned at artofcoaching.com/events and email us at [email protected] for more details. Executive Mentoring That Fits Your Life Struggling with anxiety before a big presentation? Leading difficult meetings? Trying to figure out how to handle a staff issue, or even a challenge at home? One of our 15 coaches has been there and dealt with that. This is real-world guidance, tailored to your needs, on your schedule. Nothing cookie-cutter about it. Every leader needs a coach. The best ones know when to ask for help. Learn more at artofcoaching.com/mentoring. We’d love to help! Referenced Resources: FREE Download: How To Build Trust With Anyone Article: What Shamu Taught Me About A Happy Marriage Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Coaching youth sports can be one of the most rewarding things you can do, whether you're a parent, a former athlete, or someone who just wants to make a difference. It’s an incredible opportunity to connect with people in a way that can genuinely shape who they become. Youth sports span the full range—from high-priced, high-stakes travel leagues to your local rec department. From paid coaches with professional experience, to the dad who just answered the 7,000th email asking for help. You won’t find a show that cares more about coaches than this one, so this isn’t one of those episodes that’s here to bash the people who’ve stepped up when no one else would. What this episode will be is a look from multiple angles, through the lens of someone who’s coached at a high level and is now a parent on the sidelines.  What does real coaching actually look like? What should a good practice feel like? And how do we make sure we’re giving kids our best—not just for them, but for the people who care the most and invest the most in their development: their parents. In this episode, we dig into those questions and more, including: A no-nonsense breakdown of what good coaching actually looks like—and what it absolutely isn’t Quick-hit checklist to help overworked coaches stay focused and run practices with fewer vague corrections, clearer demonstrations, and a whole lot more fun Common habits that hijack practice—like overtalking and underengaging—and what to do instead A simple, realistic framework for structuring practice time so the most important lessons actually stick Creative ways to split the room or field into stations that maximize engagement for every kid, no matter their skill level 🎯 Want to create a coaching environment that truly resonates with every athlete? Check out our free video presentation, Creating the Optimal Coaching Environment, for actionable strategies to enhance your coaching impact.  Visit artofcoaching.com/optimal/ to see Brett’s presentation from the iconic Mamba Academy. The Apprenticeship If you're tired of struggling through hard conversations or avoiding them altogether, this is your chance to train for them. We’ll put you in realistic role-play scenarios and teach you the frameworks that help you navigate conflict, power dynamics, and tough personalities. No fluff. No gurus. Just pressure-tested strategies you can actually use—because the best coaching skills don’t perish. Everyone has a coach in their life, and the ability to communicate clearly under pressure pays off in every area—not just work. 📍Phoenix, AZ – June 7-8 📍Oakland, CA – July 12-13 📍Murfreesboro, TN – October 25-26 Retreat. Reset. Recalibrate. RELOAD! This September, we’re hosting a retreat in Phoenix, AZ—built for those who carry it all. Ten years in the making, this event is designed to give you tools to slow down, recalibrate, and breathe again. We're teaming up with professionals like Taylor Somerville and Lauren Vestal to introduce breathwork, recovery strategies, and techniques to help you downregulate and bring some peace back into your day-to-day life. You’ll also get space to move, connect, and troubleshoot how to have the tough conversations you've been avoiding—so you can show up for yourself as much as you do for everyone else. Stay tuned at artofcoaching.com/events and email us at [email protected] for more details. Executive Mentoring That Fits Your Life Struggling with anxiety before a big presentation? Leading difficult meetings? Trying to figure out how to handle a staff issue, or even a challenge at home? One of our 15 coaches has been there and dealt with that. This is real-world guidance, tailored to your needs, on your schedule. Nothing cookie-cutter about it. Every leader needs a coach. The best ones know when to ask for help. Learn more at artofcoaching.com/mentoring. We’d love to help! Referenced Resources: FREE Presentation: Creating the Optimal Coaching Environment  Related Episode: E136 | Dealing With Pushy Sports Parents E275 | A Parent's Guide to Effective Dialogue With Difficult or Negative Sport Coaches Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

This episode is for a very specific type of person.  Those of you who are hard on yourself, and if you're being honest, it's to an unhealthy degree. The perfectionist who struggles to recognize their own accomplishments, who tears themselves apart over minor slip-ups, and maybe even finds it hard to fully celebrate the wins of others. Not because of jealousy, but because the voice in your head has been trained to fixate on what’s missing instead of what’s been earned. Maybe you’re not wired this way all the time, but after a big achievement, you felt... nothing. Maybe even a little depressed that it didn’t feel like more. We know many of you in our audience fall into one of these camps—and this episode is for you. Here’s a little premeditated tough love: at some point, it has to be good enough.  So how do we move past this all-or-nothing mentality we’ll never win? How can we celebrate our accomplishments without dulling our edge? In this episode, Brett breaks down: The 70% Rule—it’s immeasurable value and how it can be applied in both creative work and business How to celebrate milestones while preserving the lessons from when you fell flat on your face Who drains your joy, how to cut them out, and the hard truth: you might be doing it to others too Ways to be your own hype man without softening your edge Practical tools for when you hate your own work—and how to get to the root of why that happens During the episode, Brett opened up about the various challenges he’s faced while writing his new book. If you want early access to updates, release info, and behind-the-scenes content, follow along at artofcoaching.com/book. Retreat. Reset. Recalibrate. RELOAD! This September, we’re hosting a retreat in Phoenix, AZ—built for those who carry it all. Ten years in the making, this event is designed to give you tools to slow down, recalibrate, and breathe again. We're teaming up with professionals like Taylor Somerville and Lauren Vestal to introduce breathwork, recovery strategies, and techniques to help you downregulate and bring some peace back into your day-to-day life. You’ll also get space to move, connect, and troubleshoot how to have the tough conversations you've been avoiding—so you can show up for yourself as much as you do for everyone else. Stay tuned at artofcoaching.com/events and email us at [email protected] for more details. Executive Mentoring That Fits Your Life Struggling with anxiety before a big presentation? Leading difficult meetings? Trying to figure out how to handle a staff issue, or even a challenge at home? One of our 15 coaches has been there and dealt with that. This is real-world guidance, tailored to your needs, on your schedule. Nothing cookie-cutter about it. Every leader needs a coach. The best ones know when to ask for help. Learn more at artofcoaching.com/mentoring. We’d love to help. Upcoming Live Events: There’s never been a better time to invest in skills that don’t have a shelf life. Our live events are built to help you think, speak, and lead more effectively under pressure, in any environment. These aren’t lectures. They’re hands-on, challenging experiences with an immeasurable return on investment. We offer three different payment plans and want to meet you where you’re at. If you have questions or want help finding the best fit, reach out to us anytime at [email protected]. Brand Builder This one’s for the person trying to grow something real. Whether you’re turning your book into a business, scaling your podcast, or running a brick-and-mortar that needs a stronger foundation—we cover it all. Pricing, positioning, branding, managing your team, building out systems. You’ll walk away with clarity and a real plan. 📍Folsom, CA – August 9-10 Referenced Resources: Article: The Imperfectionist  E208 | Robert Greene: Mastering Human Nature & Facing Your Flaws Related Episode: E259 | Understanding and Overcoming Perfectionism Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Why can't someone else step up and do this? How come I'm always the one who has to do everything? What more do I have to do before someone finally takes some initiative? If you’ve ever asked yourself these questions—or just quietly felt them—you’re not alone. That heavy sense of responsibility, the emotional and cultural weight of having to carry your team day after day, will wear you down. And if you don’t have a plan to offload that burden and bring others into ownership, it’s only a matter of time before burnout sets in. But what do you do when some team members aren’t exactly charismatic—or worse, seem like they’re only halfway committed? This episode hits close to home, pulled straight from a challenge one of our mentoring clients has been facing for years. It’s also something Brett knows firsthand. In this episode, we’ll cover: The main shortcoming of servant-based leadership, and how to overcome it How to diagnose energy leaks in your ecosystem before they push you into burnout The 3 types of energy brokers on your team—and how to actually get contributions from each How to create a system of shared ownership and delegate tasks based on real strengths Leading strategically by removing barriers and making sure you’re not the one holding the team back You Do Everything for Everyone. It’s Time to Reset. This September, we’re hosting a retreat in Phoenix, AZ—built for those who carry it all. Ten years in the making, this event is designed to give you tools to slow down, recalibrate, and breathe again. We're teaming up with professionals like Taylor Somerville and Lauren Vestal to introduce breathwork, recovery strategies, and techniques to help you downregulate and bring some peace back into your day-to-day life. You’ll also get space to move, connect, and troubleshoot how to have the tough conversations you've been avoiding—so you can show up for yourself as much as you do for everyone else. Stay tuned at artofcoaching.com/events and email us at [email protected] for more details. Upcoming Live Events: There’s never been a better time to invest in skills that don’t have a shelf life. Our live events are built to help you think, speak, and lead more effectively under pressure, in any environment. These aren’t lectures. They’re hands-on, challenging experiences with an immeasurable return on investment. We offer three different payment plans and want to meet you where you’re at. If you have questions or want help finding the best fit, reach out to us anytime at [email protected]. The Apprenticeship If you're tired of struggling through hard conversations or avoiding them altogether, this is your chance to train for them. We’ll put you in realistic role-play scenarios and teach you the frameworks that help you navigate conflict, power dynamics, and tough personalities. No fluff. No gurus. Just pressure-tested strategies you can actually use. 📍Phoenix, AZ – June 7-8 📍Oakland, CA – July 12-13 📍Murfreesboro, TN – October 25-26 Brand Builder This one’s for the person trying to grow something real. Whether you’re turning your book into a business, scaling your podcast, or running a brick-and-mortar that needs a stronger foundation—we cover it all. Pricing, positioning, branding, managing your team, building out systems. You’ll walk away with clarity and a real plan. 📍Folsom, CA – August 9-10 Speaker School You don’t have to be a keynote speaker to benefit from this. If you want to become more confident, clear, and persuasive when you talk—on stage, in meetings, or on camera—this course gives you the reps, feedback, and structure to sharpen your delivery and own your message. 📍Phoenix, AZ – October 11-12 Recommended Resource: Online Course: VALUED Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Everything is okay at work, but… yeah, work is fine—I just don’t know what I’m going to do. We’ve all felt like that at some point in our careers. Maybe you’re in that place right now. Call it a rut, stagnation, or just a funk. You’re motivated. You’re grateful. But you also want more. More fulfillment, more autonomy, maybe even a title change and a bigger office. You want to feel like your strengths are being seen and put to use. When that doesn't happen, dissatisfaction can start to seep into everything else—negatively impacting your mental health and personal life. So what do you do with that?  In this short episode, Brett breaks down how to get (and stay) unstuck, move forward with intention, and take ownership without letting that ugly feeling of bitterness creep in. What You’ll Learn: Why the premortem matters and how it keeps you from crashing Getting out of the entitlement trap around promotions How to discuss feelings of stagnation with leadership while still holding yourself accountable Establishing your non-negotiables to keep your head clear and your sanity intact Your need to decompress and the key elements required to truly unplug Come See Us at a Live Event! There’s never been a better time to come see us live. We’ve put on these events for years, working with people from all walks of life—coaches, business owners, military personnel, educators, and everything in between. These aren’t dry lectures. They’re interactive, challenging, and built to help you think, speak, and lead better under pressure. The Apprenticeship If you're tired of struggling through hard conversations or avoiding them altogether, this is your chance to train for them. We’ll put you in realistic role-play scenarios and teach you the frameworks that help you navigate conflict, power dynamics, and tough personalities. No fluff. No gurus. Just pressure-tested strategies you can actually use. 📍Phoenix, AZ – June 7-8 📍Oakland, CA – July 12-13 📍Murfreesboro, TN – October 25-26 Brand Builder This one’s for the person trying to grow something real. Whether you’re turning your book into a business, scaling your podcast, or running a brick-and-mortar that needs a stronger foundation—we cover it all. Pricing, positioning, branding, managing your team, building out systems. You’ll walk away with clarity and a real plan. 📍Folsom, CA – August 9-10 (Im)Perfect Relationship Course Our newest, and admittedly one of our favorites. It’s for the married, the divorced, or the single—anyone who wants to show up better in the relationships that matter most. We’ll cover communication strategies, attraction styles, love languages, parenting, money, and even topics normally confined to the bedroom. Nothing off-limits. 📍Location TBD – November 3 (Join the waitlist!) Speaker School You don’t have to be a keynote speaker to benefit from this. If you want to become more confident, clear, and persuasive when you talk—on stage, in meetings, or on camera—this course gives you the reps, feedback, and structure to sharpen your delivery and own your message. 📍Phoenix, AZ – October 11-12 Executive Mentoring That Actually Fits Your Life Struggling with anxiety before a big presentation? Leading difficult meetings? Trying to figure out how to handle a staff issue, or even a challenge at home? One of our 15 coaches has been there and dealt with that. This is real-world guidance, tailored to your needs, on your schedule. Nothing cookie-cutter about it. Every leader needs a coach. The best ones know when to ask for help. Learn more at artofcoaching.com/mentoring. We’d love to help. Related Episodes: E242 | Annie Duke: Quit! - The Power of Knowing When to Walk Away E353 | What to Do If You Feel Like You’re Stagnating Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

We’ve all felt it. That awkward disconnect when the vibe is off and you're wondering how you ended up across the table from someone who just isn’t where you are. Maybe you’re in different stages of life, chasing different things, or just not clear on what the other actually wants. Whatever the reason, the moment hits: this isn’t it. It’s not easy to find someone emotionally mature enough to show up. Someone who isn’t hiding behind the damage of past relationships or stuck reliving the pain of a breakup they never really moved on from. And even harder? Finding someone willing to do the work, to build something real, instead of ghosting or bailing the minute things get remotely tough or inconvenient. But this isn't just an episode for people looking for love. It's about communication, emotional availability, and knowing what you bring to the table—because relationships, romantic or not, reveal a lot about who we are and how we lead. In this episode, Brett gets personal and delivers the truth about: Confronting our cultural epidemic of “busy” and what it’s really masking When a relationship is worth fixing—and when to let it go How to assess emotional and logistical availability (for them and for you) Protecting your self-worth from people who chip away at it bit by bit. Why dating apps thrive in the same way every addictive algorithm does *BONUS* Brett’s best dating advice: simple but far from easy Coming Later This Year – The (Im)perfect Relationship Course If this episode hit home, there’s more where that came from. Hop on the waitlist here to be the first to know when doors open. And check out artofcoaching.com/events to stay up to date on our upcoming workshops, where we dive deep into communication, leadership, and the skills that actually build better relationships in work, life, and love. Folsom Brand Builder Are you a coach, entrepreneur, or speaker who wants to turn your expertise into something that actually pays the bills? Whether you’ve never made a dollar or just brought in your first million, Brand Builder is for you! Spend two interactive days in Folsom, CA, getting crystal clear on your messaging, attracting the right clients, and building a business that scales. You’ll leave with clarity, confidence, and a framework that lets you do what you love—on your terms. 📍Folsom, CA –  August 8-9 To register or get more details, visit:  artofcoaching.com/brand-builder-25 Private Growth Retreat Stuck? Burnt out? Just need space to think? Come spend a day or two at AOC HQ with Brett for a private retreat built entirely around you. Strategy sessions, time outside, good food, and honest conversation—plus maybe a lift in the garage gym. This is where you quiet the noise, organize the chaos, map your next move, and leave with clarity and confidence. Email [email protected] and let us know you're interested in a private retreat and we’ll work out a date. Writer’s Workshop – Put Pen to Paper Want to write a book but don’t know where to start? Brett self-published Conscious Coaching—and now he’s working with one of the world’s biggest publishers for his next one. Either one-on-one or in a small-group, he’ll share what worked, a whole lot of what didn’t, and how you can overcome the grind that writing can be, outline your ideas into a well-crafted message, and get it into the hands of those who need it most. Email [email protected] mention the Writer’s Workshop you heard about on the podcast and let’s start filling the page! Related Episodes: E339 | Scott & Jaime Livingston: Overcoming Challenges in Relationships Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb