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The Art Of Coaching

E402 | The Benefits of Being the Bad Guy: Boundaries, Expectations, and Protecting Your Time

The Art Of Coaching

Brett Bartholomew

Health & Fitness, Education, Business

4.9 • 649 Ratings

🗓️ 10 November 2025

⏱️ 15 minutes

🧾️ Download transcript

Summary

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 info@artofcoaching.com 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

Transcript

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0:00.0

Here's a question I have for you. If you are not willing to invest in yourself in general, let alone during hard times. Why would you be surprised when others are not willing to invest in you? And I ask you this question because so many of you are really sharp talented people,

0:27.1

but you get in your own way.

0:28.8

You overthink things.

0:30.1

You make yourself busier than you need to.

0:32.6

You fall into this trap of thinking,

0:34.3

it's not the right time and it's not good enough

0:36.4

and you're not ready and that's a lot of this stuff

0:38.2

that'll give you back.

0:39.5

This is what our live events and our coaching

0:41.8

are made for to help you overcome this. Whether it's our apprenticeship program, which focuses on how to have better hard conversations, how to negotiate, how to manage through conflict, how to do things that every coach and every leader is gonna have to do, but do it better, or our speaker school, where you can become a more confident, clear speaker. These are things that give you immediate return on investment. They're things that help you earn more your career. They're things that help you deal with the inevitable power dynamics that you're going to deal with. And there tends to be this kind of mis- this misattribution of, oh, are these things only for people who struggle to communicate? Absolutely not. These are programs for people who know they don't want to leave any stone unturned in terms of self-development, professional development, development in all aspects. So if that's you and you

1:28.8

value investing in yourself and you want others to invest in you, whether

1:32.5

that's to pay you to come speak around the world or whether that's just to

1:36.1

value your work and see the true inside it provides, then get to artofcoaching.com

1:40.6

slash events right now. We have interest free payment plans. We have student discounts, first responder discounts, but the bottom line is we have a ton of resources that can help you. We're never going to be able to come to everybody's city. We are going to be able to provide you with research based outputs that are pragmatic, get you out of your comfort zone, and at the end of the day are also a lot of fun to take part in. They're interactive to get around a wide range of individuals and we would love to see you

2:08.2

there.

2:09.2

So go to artofcoaching.com slash events.

2:11.9

Artofcoaching.com slash events.

2:14.2

That's artofcoaching.com slash events right now. Check it out, check it out. 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. This podcast is for everybody who is fascinated with solving people problems. So if you're in the no-nonsense type who appreciates frank conversations, advice you can put to use immediately and learning how others others navigate the messy realities of leadership, you're in the right place. I'm glad that you're joining us. Let's dive in. Check, check. This thing on. Welcome back to another episode of the Art of Coaching podcast.

3:25.9

Listen, throughout the rest of the year, we're going to do some more bite-sized episodes for you guys. We've had some really great feedback to the last few. Now, it doesn't mean we're not going to go back to long form. We absolutely will, but you're going to get some quick hitters now. And today is all about when it benefits you to be the bad guy, right? the bad guy in the sense that listen,

3:44.5

a lot of times we're gonna have to tell people

3:46.0

things they don't wanna hear.

3:47.7

True respect and accountability, oftentimes is telling people what they don't wanna hear or what other people will not tell them, right? Otherwise, we can easily fall into being enablers. It is also about just understanding that some people are gonna be pissed because you can't serve them the way they wanna be served. And you're not going to be able to meet everybody's expectations. And actually, that's okay. So I'll ground this. And thank God the example I'm going to give here, I'll give an example of somebody in our community who I think did this tremendously well, Eve Weber, we love you. And then of course, I'll share some experiences where these things did not go so well. So context, I'm not sure how many of you know this, but over the past year and a half, I've been helping my uncle, who's in his 70s, and going through a tough time in life, right? Really, really successful guy, somebody who's very sharp, intelligent, amazing, kind of went through a tough season of life, right? Needed some help. We're happy to help him. He's helped me through many things as well. He's a great uncle to my son. But it's something that in addition to me,

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