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The Art Of Coaching

E401 | Most Listened To E299 | How to Quit Being a People Pleaser

The Art Of Coaching

Brett Bartholomew

Health & Fitness, Education, Business

4.9 • 649 Ratings

🗓️ 3 November 2025

⏱️ 51 minutes

🧾️ Download transcript

Summary

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 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 coa

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

2:08.0

you there.

2:09.0

So go to artofcoaching.com slash events.

2:11.9

Artofcoaching.com slash events.

2:14.3

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, advise you can put to use immediately and learning how 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. All right, let's get into it. This is all about how to overcome being a people pleaser. We're going to talk about a lot of different things here and it is going to be in a format that is pretty informal. That is because there's a lot of ground to cover. Now I'll say this right off the bat. There's only so much we can cover in a podcast and within a certain context. This is a topic that my next book is going to speak a lot about. So if you struggle at all with being a people pleaser, and it doesn't matter if you struggle all the time, just some of the time where you know somebody that struggles, make sure that you go to artofcoaching.com slash book. That's artofcoaching.com slash B-O-O-K. And sign up for updates. The book is going to come out as long as everything goes well next fall or depending on when you're listening to this fall 2024. So you might be listening to this during a time when it's already out. At that point it doesn't matter that we'll redirect you to the site. I'm not going to give away the title of the book right now but we are going to cover aspects this. And so many other things that tie into the messy realities of leadership and life. So I think that you'll really like that. I've been working very hard on it. So check that out. Some other complimentary episodes. And this is by no means an exhaustive list. And it is not an order necessarily. One, go to episode two 10. That is assertiveness. That's episode 210. You can find this on Apple Podcasts, Spotify, anywhere you listen to podcasts. Episode 207, Perception and Relationships. There's a lot of tie-ins here as well. Episode 208 with myself and Robert Green from the 48 Laws of Power and so many other books is all about facing your flaws and understanding human nature. And then another one that I thought was going to be good for you is episode 200. What to do when trying to help make things worse? I almost forgot one. 176 when positive thinking doesn't work. So these are nice pairings. 210 207 208 2176. Remember, no matter when you start listening to the podcast and we've evolved a lot over time, there is something for everybody. We really try to put some straightforward topics out there that impact people on all walks of life. All right, aside from that, I think all the disclaimers are out of the way, except for excuse my voice. If I sound like 1999 Slim Shady, I have been battling a cold or bronchitis or God knows what that my three-year-old has given me for some time, but I did not want that to keep me from doing the episode. So let's dive in. One of the reasons I decided to do this right now is I recently spoke at an event, and I had a really thoughtful question and I'm going to paraphrase for the sake of time. But essentially it was from a general manager of an organization that admitted struggling with being a people pleaser. Now their context was they had an employee that wanted some additional resources and they weren't able to give that to this particular employee. For any other reason, then that resource pool was limited. They had to allocate these funds or these resources, and I can remember which one it was, and or elsewhere. So that inevitably meant that they had to give that employee some bad news. I can relate to this as a business owner. I've been able to relate to this as a coach. I've been able to relate to this as a spouse. And I'm sure many of you have as well. So we're getting into the root cause and some things that we're going to lay out informally. And I'm not going to give you my full advice until we get after it. But essentially, you know, game some advice. And I said, this is normal. And you'll hear some repetitiveness in the episode as well. I said, any part of leadership is going to have some moral ambiguity to it. It is. Even when you think you're doing the right thing, it is going to have a trade-off. It is going to negatively impact other people. So we're going to work our way through this. Like I said, I'll give you some of those tips as we go through the episode. But that is a real good kind of clarifying depiction of what it looked like in that person's life.

7:29.8

Now I know many of you also listen, some of you like quotes, quotes really take home with you. All of you like strategies. I'm going to try to balance this. I am a recovering people pleaser. I realize that I can write books, I can write tweets, we do a newsletter multiple times a month,

7:47.0

we can do the podcast, of course,

7:48.2

we're not gonna be able to cover all of them, but I'm gonna make sure that I give you a wide range of things that help all of you. So I'm gonna read off some quotes here. Maybe one of them sticks with you, maybe it doesn't. Then we're gonna get into the root causes of being a people pleaser, what is that even look like as well?

8:05.8

And then some solutions, okay?

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