The good, reliable, everyone-comes-to-me best friend. You’ve been praised for that role your whole life. What if it’s the reason you can’t get yourself to shoot your shot, ask for more, or take up space with your desires?

This episode names the pattern hiding under all of it: people pleasing. Not being nice. The habit of self-abandoning in real time to avoid being misunderstood, judged, or abandoned. Lily breaks down where it lives and how to start unhooking from it.

Inside episode 280:

→ The two categories of people pleasing: the interpersonal kind (the date you stay on too long, the resentment you never voice) and the internal kind (the imagined judgment that keeps you from hitting post, asking for what you want, or flirting IRL)

→ Why people pleasing is self-protection dressed as politeness, and why it’s actively emptying your cup

→ The main character energy formula that moves you through the fear: permission, self-trust, massive messy action

→ Why self-trust isn’t one-and-done. It’s small choices built on small choices

→ The people pleasing detox: take inventory, choose one pattern, run it through the framework

Your richest, biggest life is on the other side of this pattern.

💎 Join my free live training, How to Quit People Pleasing: https://datebrazen.com/best-friend

Work with Lily:

💎 Get the book, Thank You, More Please: https://datebrazen.com/book

💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating

💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook

💎 Follow me on Instagram: https://www.instagram.com/datebrazen/

💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen

💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

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Show transcript:

lily (00:00)
In coaching hundreds over the last eight years, I’ve seen that the number one reason that you are paralyzed with fear to shoot your shot, to ask for more, to take up space with your desires, to learn flirting IRL, and to do it successfully is because you were socialized to people, please. And this makes sense because you were steeped in the fiery hellscape of the patriarchy, where you were taught that it was normal and expected of you, and in fact made you safer to make other people happy or to try to make other people happy, which Q hypervigilance.

for other people’s needs, bending over backwards to try to make and appe make people happy and appease people who never were gonna be happy from your actions in the first place. It is a a pattern in your life, this people pleasing that has to stop. If you want to start living freer, if you want to start getting more of what you want, if you want to start dating with more joy, if you want to start attracting bigger and better opportunities at work and in friendship, you gotta quit people pleasing.

Okay, and I know easier said than done, but that’s why today I’m coming at you with an episode to help you with just that. So you can step more fully into your main character energy and finally ditch the people pleasing pattern as your default. Let’s get into it.

Gorgeous friend, you gotta know that this episode is brought to you by my upcoming live training. I’ve never led this training before. It is called Quit Being the Best Friend: How to Shoot Your Shot Unapologetically in Love, Friendship, and Work Without Overthinking and Anxiety.

Inside, you’re gonna learn how to step into your main character energy in every relationship. You’re gonna learn what playing the reliable everyone comes to me best friend is actually costing you, and how to take up space in your own life instead of living in the background of everyone else’s. You’re gonna learn why you’re still not taking action, even though you’ve done the therapy, read the books, and know all the right things. You’ll learn why insight was never the thing standing in your way and the unconventional formula that gets you off the couch and into action.

You’re gonna learn how to cast an audacious vision for your future and actually follow through this time. You’re gonna learn how to name what you want without apology, even if you’ve never been able to answer that in love, friendship, and work. And we’re going to build a plan to make it happen this year. And then finally, you’re gonna learn my main character energy formula: how to complete 30 dares in 30 days to increase your main character energy in love, friendship, and work.

So that you can shoot your shot unapologetically and start getting more of what you want in all of those domains. This training is on September 15th. You’re going to want to be there live to ask questions, to get your face coached off, and to learn more about my program, Main Character Era, which is opening on that call for the first and only time this year. Applications are opening on that live call.

Main character era is my six month small group coaching experience where people pleasing burnt-out feminists come in, learn how to give fewer fucks, stop playing small, and finally get what they want in love, friendship, and work. Inside of this group program, you are going to complete 100 audacious self-serving dares in just 100 days.

To become magnetic to the friendship, love, and work life that you desire and deserve. This program is a high-touch small group. And I can’t wait to see your application come in. We only open once a year, and this is the time we’re opening. And I cannot wait to see you at the live training called Quit Being the Best Friend.

And if it feels like the right fit after that training, submit your application to work with me in this small group coaching container.

lily (04:04)
You can RSVP in the link in the description of this episode, or just get on over to datebrazen.com to save your seat. When you sign up, you’ll be sent a confirmation email immediately with your link to add it to your calendar so you don’t miss the live session. And I cannot wait to coach your face off there soon. With that, let’s get into the episode.

lily (04:21)
Okay, so what is people pleasing? People pleasing isn’t being nice. That’s not what we’re talking about, right? It’s the habit of self-abandoning in real time to avoid being misunderstood, judged, or abandoned. It’s sidelining what you want because of fear. And it’s on purpose. Again, you were steeped in the fiery hellscape of the patriarchy, only made worse by you know, intermingling oppressive forces like white supremacy, like

ableism, fatphobia, racism, homophobia, transphobia. It makes sense if you have one or multiple marginalized identities. Why you were taught to people please in order to belong and be emotionally, sometimes even physically, safe. So I just want to add an air of like self-compassion to this. This pattern makes sense. If you notice yourself shrinking what you want, if you notice yourself overgiving on dates or in friendships and not receiving anything in return and being okay with that or not doing anything about it.

If you find yourself overgiving it work and and calling it, you know, being reliable, but you’re the one taking on all the projects and being the you know the one that holds everything together, right? A lot of times people pleasers can take on this role of caretaker. and they’re lauded for it in their life, right? It becomes an identity, it becomes a value system of like, you’re the reliable one, you’re the caretaker. You always help other people. And in in that process, there’s nothing wrong with being a caretaker. We need caretakers in this life, and hopefully we care for each other in this life.

But I think the problem is that you, if you identify with this, have learned to self-abandon in order to be safe. You’ve learned to self-abandon in order to belong. And in doing so, that depletes your energy, your life force. You cannot pour from an empty cup. And people pleasing is actively emptying your cup. It’s the reason, one of the main reasons why you’re burnt out. It’s one of the main reasons why you feel exhausted.

So one the main reasons why you can’t seem to get yourself to act on that big dream that you have, whether a creative project, a business, you want to start dating, or you want to build a new core group of friends, but you can’t seem to get yourself to do it, it’s probably because of people pleasing. People pleasing also looks like choosing comfort for others over honesty for you.

That can look like smiling and nodding through dinner while someone says something that deeply hurts you or offends you because you don’t want to ruin the vibe. It looks like shrinking to avoid judgment, editing your opinion in a group chat, keeping it light so no one thinks you’re too intense, too deep, or too much. It looks like disappearing to stay good, not following up on that dream project because your friends, your partner, your boss, your parents might not get it.

And you don’t want to look ridiculous, rock the boat, look selfish, or self-aggrandizing, or risk being seen as the difficult one. Saying yes when your body is screaming no, that means agreeing to help someone with one more thing: the party, the work favor, the phone call, even though you’re exhausted, so you won’t disappoint anyone. And finally, people pleasing can look like trying to manage everyone’s emotions with scanning and hypervigilance, just in case you need to jump in and save the day.

This looks like over-explaining your decisions, tiptoeing around every text, triple checking your tone, because God forbid someone thinks that you’re too selfish or uncaring. You wanna basically manipulate others’ perception of you so that you feel safe. Because, and I say manipulate because none of us are in charge of what other people think. None of us are able to reach into somebody else’s brain and make them have positive thoughts about us. But in this world, we’ve been.

socialized to believe that you having positive thoughts about me makes me safe.

people pleasing is self-protection dressed as politeness, and it’s got not getting you where you want to go, right? I want to talk about how this might show up, and there are two categories. I just mentioned a couple different categories of how this shows up.

But I think it shows up interpersonally, right? On the date that you stay on, even though it’s been an hour and you’ve had a drink or a coffee and you’re done with the date

you know, a friend has asked you to travel to see them multiple times and has never offered to see you and you are avoiding asking them and are quietly resentful of this.

Then I think of another type of people pleasing. I think there are two categories. The other type is IBS, internal bully syndrome. Okay. This IBS form of people pleasing, internal bully syndrome.

I think of it as you’re imagining the judgment or jeering of others. And so you don’t take action. For some of my clients who want to build a business, for example, they are thinking about what their friends might say about them when they see a post on social media telling that saying that their business is open for business and that they’re looking for new clients, right? They’re they’re imagining this like internal bully looking at their business.

business post and saying, how pathetic and how how they’re never going to amount to anything A lot of people have this thought with dating too. This like IBS internal bully syndrome, like, people are gonna see me dating and I’m in my late 30s or 40s and I’ve never done it before and they’re gonna think

how pathetic that that she’s starting to date, or they’re starting to date at this age, they’re so behind, right? This imagining this rejection, judgment, abandonment, that this this this jeering, mean, like bully in middle school vibe that is keeping you from trying new shit, that is keeping you from hitting post, that is keeping you from asking for what you want, that is keeping you from trying to flirt.

Internal bully syndrome goes for like why you’re avoiding going up to somebody and saying, hello, who’s cute? Because you’re imagining that they’re going to be rude or mean or gonna superjudge you, and you’re filling in the gaps with all of these really self-protective but maladaptive voices that are trying to keep you safe but are just mean to you. And by the way, let’s say that does happen that you approach somebody and they do look you up and down and

Say out loud, who do you think you are that you would talk to me? If we that would be embarrassed. I would feel if that were me, I would feel embarrassed. And I also would walk away. Maybe I’d need to leave the bar or the restaurant really quickly. And maybe I’d feel shame. But what I think that I’d come to afterward is this sense of what a fucking asshole. And by the way, if they did offer that.

Bully response. And it felt so stressful because you were afraid that they were right and they were proving all of these fears, right? It’s like when my high school boyfriend broke up with me saying, You’re too much for me. You’re too much. It was like, my worst fears are confirmed. And I guess I am too much. But I had the opportunity then to grow into my main character energy, into my agency, obviously years later, but but we’re here to speed up your process right now.

Overcoming people pleasing and growing out of relying on the internal bully to keep you safe. Growing out of that means having such a richer, fuller, more joyful, more magnetic life. Your dream life is on the other side of unlearning people pleasing and instead learning the skill set of main character energy. I just know it.

To be a fact, because I’ve seen it every single day with the hundreds of clients that I’ve gotten to coach over the last eight years in my own life. Like when I learn how to overcome this default of people pleasing, which I still work through with these tools, I’m gonna unpack the tools in a minute. But like your richest, biggest life is on the other side of this pattern. And I what I want you to get to with this main character energy is more unbothered.

More unbothered by assholes who would look you up and down and say, Who are you to talk to me? What a fucking jerk. Who who the hell do they think they are that they are talking to me this way? That’s where I want you to get to, right? I want you to get to the place where, like one of my clients who had this internal bully syndrome happening, keeping her from hitting post on her first post about her business or hitting post on a newsletter that she

was creating for her business, That was keeping her the internal bullies under the sphere of judgment. What we did together was root her back into her main character energy, which was it’s permission, self-trust, massive, messy action. So permission sounded like permission to do something new, permission to do it while feeling cringy and like f afraid, permission to do it scared, permission to believe in

Her desire for the business that she wanted to start enough to try something vulnerable instead of believing the internal bullies more than she believed her own desires, right? You just need a little more tip of the skills toward believing your own desires than believing the internal bullies to finally build momentum and start building this pattern of main character energy. Self-trust is interesting. It sounds like small choices built over a series of days, weeks, months.

That then creates a pattern of self-trust, as opposed to what I think a lot of y’all think of self-trust as is like this like one and done. This like, I either am a self-trusting person or I’m not. Either I would have not made those mistakes and I could have trusted myself, or I made those mistakes and I can never trust myself. Self-trust is iterative, it is buildable, it is small, small choices built on small choices. It is not a one and done. I can make, I can have.

made mistakes in my past that I don’t want to repeat how human of me and still trust the fuck out of myself today and not know exactly what’s going to happen next and know that I figured things out in the past, I’ll figure things out in the future. It’s this sort of like predictive element. It can become this predictive element of safety. When you trust yourself, you can become safer and safer to take bigger and bigger swings and risks, building a bigger, richer life.

So for her, this client who I’m talking about who wanted to start a business, self-trust sounded like, okay, I’m nervous. I want to ship my pants. I have permission to do it scared, but and self-trust sounds like I might just be okay no matter what. I’m going to make the choice to hit post. And predictively, I’m gonna freak out because of that internalized bully and that fear. and I have the skills to move through that. I have self-compassion. I have so we had a whole system and an ecosystem for her to move through that fear.

into self-trust, into safety in her body. A lot of it was like nervous system regulation, which we do all the time in main character era. and I teach you skills to do it swiftly and effectively to care for big feelings as they come up to move through them effectively instead of getting stuck in them. So self-trust was this like choice of like I’m choosing to do this new thing. I know I’ll freak out afterward and I’m gonna choose to lean on my tools. I can trust myself. Massive messy action looked like doing it. This is why

On our group coaching calls, I’m go in main character era, I give very directive coaching. I’m like, okay, you you want to do this thing, you want to hit post on a video or a newsletter, or or you want to ask someone out, or you want to shoot your shot, or you want to build a new friendship with somebody that you met last week and you’re afraid to to reach out because you’re afraid you’re too much. Let’s do permission, self-trust, massive, messy action, go right now. And being in a coven of cheerleaders who is hyping you up to live bigger, to make bigger choices, to take bigger swings.

To live in your main character energy is gonna change everything. It’s gonna change your baseline of existence. and that’s what this client who who ended up using this permission, self-trust, massive, messy action framework of main character energy, that’s what she found changed her life, allowed her to start building this business after years of it being in a drawer. and and that’s what helped my other client build a new core group of friends who reciprocated.

That’s what helped another client you know acknowledge that she was burnt out at work, start resting like she never had before, start advocating for her own needs like never before. She ended up healing her burnout with the skill set of main character energy, quitting her soul-sucking job, building a consultancy that she had always dreamed of, and moving across the world like she’d always dreamed of, because of this simple yet effective skill set of main character energy that moved all of these clients from people-pleasing patterns, both interpersonally.

Right? and the internally, the internal bully syndrome, like when you build a different relationship with that voice in your brain, when you start to unhook from the need to have other people’s approval for you to be safe, you start getting free.

Period. I think, you know, I I was journaling the other day about the the feeling of freedom that I’ve started to even more embody in my life because I I live and work these tools every single day. I really have struggled with people placing. I’ve really struggled with the internal bully in my head. I still notice her in my head.

And I lean on these tools to create more and more freedom for myself and more and more results in my friendship, love, and work life because of the skill set of main character energy. And the image that I was journaling about the other day, and it might sound trite, whatever.

But I really I love horses. I’m a horse girl. I did not get to grow up with horses, but as an adult, I recently went on a vacation where I got to to ride a horse through a valley and it was unbelievable, incredible. I connected so deeply with this horse.

I think that, you know, in reflecting on my own journey, I was raised in the deep south. I was raised in a culture where women, like the church that I went to, like women weren’t allowed to be pastors for adults. They could be pastors for children, but not for adults. And you know, I I saw women really shrinking themselves in marriages that weren’t happy, but like they they were, you know, I I can think of several women that

know were dying on the vine in their lives because they you know this societal standard was to be married and partnered in order to belong and you know I just remember very deeply learning people pleasing was a survival tactic. I remember, you know, at Thanksgiving my big I have a big family and we had like a yearly family reunion at Thanksgiving and

You know, the women are doing all of the fucking work and the men are sitting and watching football. I mean, I just remember hearing this. I remember hearing one of my I remember hearing somebody say, like, yeah, the reason Bill cheated on Hillary is because she prioritized her own career. I mean, just like fucking bullshit stuff that I’m sure that if you go back in the logs of your memory, you can point to moments where you were taught that a woman’s

Place was to please and a man’s place was to lead. Now, maybe maybe you didn’t experience that, but that’s definitely that was definitely my story.

And I was just thinking about how related it was to the former version of me who was taught to people please in order to belong, was literally like a horse in a pin taught to prance around and jump in a very certain way and walk in a very certain way. And you know, I think about English writing, no shade to English writing, but it it’s very, you know, that or like, you know, prancing or

The dressage or whatever. Horses are taught to behave in a very certain way in that pin and perform for an audience. That’s people pleasing. And I just then imagined like a wild horse or a horse that got to run. And how I just think that overcoming the pattern of people pleasing means you get to run and feel freer. And using main character energy is the is the unbridling factor.

That allows you to run freer.

So, how do you shift people pleasing? you get in a room of people who are normalizing and encouraging you to take up space. I I mean it when I say this this training alone is gonna change what’s possible in your year and your decade. so I really encourage you to get yourself there live and go to the link in the description of the episode to sign up. It’s called Quit Being the Best Friend. Being the best friend is essentially like people pleasing in order to belong, it’s demoting yourself to this.

This you know, role where you don’t get to take up as much space. and in I want you to be the main character. So first and foremost, get your ass in that door to be in a room of people.

Who are normalizing, taking up more space, and who are noticing and releasing people pleasing patterns in real time. I also, you know, we do the people-pleasing detox in month one of Main Character Era, my mastermind. And we’ve been doing it for a few years now, and the results are just incredible. And I wanna offer a few action steps to you that you can use, whether or not you join Main Character Era.

I want to take inventory of all of the interpersonal and internal IBS, internal bully syndrome, all the external and internal ways that you are people pleasing. Whether that is in your work, like just think about the three buckets. Where are you doing it at work? Where are you doing it in friendships? Where are you doing it in your love life? internal bully syndrome, the internal people pleasing for your dating might sound like not flirting, IRL, for fear that somebody’s gonna judge you. In doing so, you are protecting yourself from other people’s.

judgment by in theory pleasing them by not approaching them. You’re like making up a whole scenario where your presence is not a value add and where you’re not going to be received well. That is a form of people pleasing.

Take inventory. This is the beginning of the people pleasing detox. I ask my clients in main character era to put it in their notes app, right? Then I want you to choose one thing. Choose one thing, whether in friendship, love, or work, that you want to start shifting. And let’s run it through main character energy. Let’s run it through permission. What permission slip might you need to give yourself to break this pattern of people pleasing? Self-trust. What might self-trust a tiny bit of self-trust?

What might a tiny bit of self-trust sound like? Like, it might be possible that I can do this even if I’m scared, and that no matter what happens, I’ll have my back. It might be possible that this is just new and new things are scary and I have my back. That’s what like what does self-trust sound like? For me, it sounds like when I trust myself, I’m doing the right thing and I listen to my internal compass, something that I’m gonna teach you in the training on September 15th.

But I listen to my internal compass and align my actions with my internal compass. what is a self-trusting sentence that you can get behind that feels useful and true right now? Like, no matter what happens after this, I’m gonna be okay. And it’s safe to prioritize my own needs.

So then finally, massive messy action, you send the text, you do the thing, you commit to doing the thing, you go up to somebody this week and say hello. You go up to somebody this week using the flouring 101 lesson that I’ve taught in this podcast. and and say, so I think you’re cute. Like random question. Are you single? Even if you want to throw up, you shoot your shot at work, you you send the email, you send the ask. this is by the way, not only healing people pleasing, but healing patterns of hypervigilance and

hyperindependence that have kept you feeling really stuck and lonely potentially. so this is a holistic framework to feel freer in your life in general. So I want you to take inventory of the people pleasing. I want you to choose one way that you’re people pleasing. I want you to run it through permission, self-trust, massive, messy action compassionately. And then I want to share a few examples of what this can sound like in practice. And this is from the main character era workbook.

I’m learning that it might be okay to disappoint people I’m allowed to pause before saying yes. I’m practicing saying what I want, even if it feels awkward. Whew, my brain is having a lot of thoughts about keeping the peace. That’s hard, and I’m here for me. It’s okay if part of me wants to please them. I also get to check in with me. I don’t have to get this perfectly right. I just get to try. This feels uncomfortable because it’s new, not because it’s wrong.

Finally, I’m experimenting with what it feels like to take up space. Choose one of those useful and true thoughts and practice it every day this week. This is actively detoxing from people pleasing as your default to be freer in your life to take up more space. And by in doing so, get more of what you want because you will be asking for and receiving more when you are free from this pattern of people pleasing.

If you liked this episode, then you’re gonna fucking love my live training on September 15th. So go to the link in the description of the episode, sign up, get your seats saved. I can’t wait to coach your face off soon. And just know that applications open for the first and only time this year to my mastermind main character era on September 15th. So if you’ve been curious about joining this high touch small group program, then I want you to come to this live training to learn more and be the first to submit your application.

Spots are very limited for this cohort and we will fill up. So I cannot wait to see you in those doors. I can’t wait to see your application roll in. And I can’t wait to talk to you next week. Bye.