Here are 3 signs you’re demoting yourself to the “best friend” role in love, friendship, and work…

You’re the designated listener in your friendships, always the one reaching out first, making the plans, overgiving and caretaking. In dating, you’re hesitating to ask for what you want for fear of scaring them off, settling for good enough or settling for inaction. At work, you’re logging in past 9p.m., trying to fulfill your coworkers’ needs because you fear that shutting down your computer will let people down and mean you’re not seen as the go-to person.

It’s exhausting to demote yourself to the “best friend” role. And it’s time for your main character era.

This week’s episode is about the skill set that will take you from “best friend” to main character. Main character energy isn’t something you’re born with. It’s learnable. In this episode, you’ll learn the exact three-part framework Lily uses in her own life and teaches her clients to finally stop shrinking and start taking up space in your dating life, your friendships, and your work.

Inside episode 278, you’ll learn:

■ The three signs you’ve been demoting yourself to the best friend role across dating, friendship, and work

■ The three-part skill set that makes up main character energy: permission, self-trust, and massive messy action

■ How to build self trust (even if you’ve never had it before)

■ What it actually means to shoot your shot unapologetically in every area of your life

Ready to step into your main character era? Join Lily’s free live training, Quit Being the Best Friend, on September 15th to learn how to break free from people-pleasing and finally get what you want in love, friendship, and work. Sign up: https://datebrazen.com/best-friend

Links + Resources:

📚 Buy Lily’s book Thank You More Please: datebrazen.com/book

💖 Work with Lily: datebrazen.com

🎥 YouTube Channel

📱 TikTok

📸 Instagram

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Show transcript:

Lily @ Date Brazen (00:37)
Hey, gorgeous friend, coming to you live from a walk around Brooklyn. And I’m just gonna walk and talk. Like I gave you a call. We’re chatting on the phone on this walk. It’s one of my favorite things to do is walk and talk with friends. And so I’m glad that you’re here. I’m glad you picked up. Today I want to talk about your main character energy. Because I see and have seen for the past few weeks, months, years, honestly,

most people that I work with, struggle with, and that I really struggled with, is demoting yourself to the best friend role. Here’s what I mean by that. In my own life, I was demoting myself to the best friend role by being the designated listener in my friendships. I was always the one to reach out first. I was always the one to make plans. I was overgiving and caretaking.

in every single relationship that I was in, because I thought that was what was necessary for me to belong. my demoting myself to the best friend role in my love life looked like really acquiescing in my past terrible relationship about ten years ago to whatever he wanted, his

I sort of like lowered my standards to fit his capacity. I didn’t talk as much on the phone with him because that’s what he wanted. I didn’t go on as many dates with him because that’s what he wanted. I didn’t get introduced to his friends because that’s what he wanted. Looking back, I have trouble recognizing that version of myself. But there she was demoting her desires to the best friend role instead of the main character.

And it makes sense because of the way that I and probably you were socialized to shrink ourselves in order to belong, in order to be in relationship, friendship, and otherwise. And then at work, I was demoting myself to this like best friend role by being er trying to be everything to everybody, trying to pick up the slack from other people, trying to

hustle to make a job work that I was fundamentally burnt out from and did not enjoy. ten years ago I was a professional matchmaker. And though from the outside it looked really shiny, I was the third most successful matchmaker out of 160 at the National Firm Hello. On the inside I felt miserable. I felt burnt out. I was burning the candle at both ends.

I I was not paid enough to live on. I wasn’t I was not thriving in my work life at all and I was trying to hustle in order to prove my worthiness at a job that fundamentally didn’t feel like the right fit for me long term. Aka demoting myself to the best friend role. And

I share this because again, from the outside, my life looked really shiny. I had a boyfriend for the first time in my adult life. I had felt like a late bloomer. I felt like finally I can talk about my love life with my friends and I can have something to contribute instead of just listening to their relationship updates. Instead of making my dating life the butt of the joke, I can have something to contribute. Looked shiny from the outside, I thought. My work life, again, shiny from the outside. My friendship life. I had a group of friends that I would like hang out with.

And I thought, this looks shiny, right? But inside it did not feel sub I did not feel supported or that I was in a group that reciprocated like I wanted them to. But here’s the deal, I had this awareness of like I want more, but then in the same breath, judgment of myself that I was wanting too much. That’s the trap of the best friend role, is that you’re not allowed to want more than the bare minimum, really.

If you’re casting yourself in that role like I was. I think about Lane and Gilmore Girls. I’ve talked about this before on the podcast, but Lane from Gilmore Girls is this brilliant character and she’s Rory’s best friend. And we rarely get a thorough picture of Lane’s life. We rarely get more than like with best friend characters and movies and TV shows, we get their role to support the development of the main character.

And that’s where I saw myself, and that’s where I see so many of you struggling in dating, in friendship, and work. And the deal with being the best friend or demoting yourself to the best friend character role in your own life is that it is fixable. You can learn.

How to enter your main character era. It is as simple as a skill set. Y’all know that I’m type A, I love a skill set, I love a one, two, three. And I have been very successful in my own life of using this skill set to step into my main character era in love, friendship, and work. This skill set is what helped me finally break the cycle of settling in my love life, break the cycle of settling in my friendship life.

And break the cycle of settling in my work life. The this skill set is what really helped me become an entrepreneur, begin date brazen, do things that felt scary as shit because of the skill set of main character energy. I felt emotionally safe to do the scariest shit I ever had. Put myself out there, build a social media following, build my business because I had the main character energy skill set. And for my clients in

Nine to five roles. The skill set of main character energy is what helped them finally promote themselves to main character and ask for the promotion effectively. Navigate hard political waters at their job with boundaries effectively. What helped them get offline at 6 p.m. unapologetically and not overgive to their coworkers effectively.

Main character energy in friendships for my clients when they build this skill set looks like finally asking for more from the people in their life, effectively setting boundaries without mind drama, and building core groups of friends that reciprocate.

And in love, y’all already know I talk about it all the time. What does this look like in your love life? It looks like unapologetically asking for what you want, shooting your shot, and getting more of what you want in every single date and being unbothered by the people who are wrong for you. That’s what the skill set of main character energy will do in your love life as well. It’s what helped me like acknowledge

That Chris was my person, main character energy, it helped me to receive that level of love that I had not previously received, which is can be overwhelming to one’s nervous system. And main character energy, this skill set helps me to thrive in this new state of being where I was in the main character, my main character era. And it’s what helps my clients do the same. Main character energy. Okay, let’s talk about the skill set. Because I hear you asking like, okay, Lily, what is it? What is it?

It’s three things. Simple, simple, simple. Number one, permission. Number two, self-trust. Number three, massive, messy action. So permission, if we think about what does that look like? Let’s just take friendship as an example. Permission in your friendship life to enter your main character era looks like giving yourself permission to try something new. Permission to acknowledge what’s not working.

Right? Acknowledge where you are overgiving and caretaking in order to belong. Notice where you are, you know, like going to therapy sessions and talking all about how your friend keeps walking over your

boundaries and you keep restating them but you aren’t doing anything about it. you’re having trouble following through on the boundary. You’re having trouble following through on the work you’re doing in therapy, right? Permission to to acknowledge what’s not working and permission to figure it out. Permission to finally follow through on the thing that you’ve been wanting to, right? Permission to do it imperfectly. That’s the skill set of permission. It’s like noticing.

Then we have the skill set of self-trust. This is tough, right? Because you were probably socialized to not trust yourself. Plus, you have like years of experience of either making mistakes or being with the wrong people for you or being told you are too much, you want too much. So self-trust can be hard if any of those things have happened and you know self-trust has felt eroded. You might say to me,

I have a bad pick or I can’t trust myself. Or you might say to me, Well, Lily, like I have so much overthinking and anxiety, I could never trust myself. Self-trust is creating emotional safety enough, moment by moment, tiny decision by tiny decision, to advocate for yourself and to listen to yourself over the shoulds. Okay, that’s all it’s self-trust at a basic level is listening to yourself over the shoulds.

And making small decisions that stack on top of each other to build up a well of self-trust. It starts with something as small as I need to put down my laptop and go to the bathroom right now. If you need to go to the bathroom, instead of waiting and like holding it for five more emails. It looks like instead of you know, your friend texts you, Hey, can you meet me in my neighborhood at 8 p.m. and I can do a forty-five minute hang before I have to go.

for the night instead of saying yes even though you you really want to s stay in or you want to meet closer to you or whatever, instead of just saying yes, you give yourself permission to notice that that doesn’t feel right. And you trust yourself that you can say a small like, hey, can we meet in the middle? And it’s gonna feel uncomfortable to start advocating for what you want. And you can trust yourself in that moment that like it’s okay for me to advocate for what I want in this relationship. It’s okay for me to

Have a desire here. I don’t always have to do what she wants me to do. I don’t always have to do what he wants me to do. I get to take up a little more space. So self-trust is like small decisions stacked on top of each other that are self-serving. Then finally, massive, messy action that’s sending the text. That’s shooting your shots, using 10 seconds of courage to ask for the thing, do the thing, say the thing. Right? And this is the skill set rinse, repeat.

That will have you entering your main character era in friendship, love, and work so that you can start setting boundaries with ease, receiving more at work than you ever thought possible, getting that promotion, building a core group of friends that finally reciprocates like you do, building a love life that is unapologetic and joyful and full of like main character energy and shooting your shot. I’m gonna teach you how to implement and build this skill set.

On my upcoming live-free training called Quit Being the Best Friend. How to unapologetically shoot your shot in friendship, love, and work without overthinking or anxiety. dance on over to my website or to the link in the description of this episode and sign up for this live-free training. This is your this is your call out.

You’ve been demoting yourself to the best friend for too long. It’s time for your main character era. Okay? Only you know what that means, and I’m gonna help you to claim it and to step into it in this live free training. And on this training, my mastermind opens, which is called main character era, and you’re gonna learn more about it at this live training. But I just want you to get your butt to this training because it’s time for you to stop demoting yourself to the best friend role. It’s time for you to start taking up space with your desires, it’s time for you to learn self-trust.

Time for you to finally start building the expansive life that you’ve been dreaming of, that you’ve been judging as too much or impossible. I’m gonna teach you how to make what you want possible in friendship, love, and work at this live free training. This is for you if you’re one of these four types. You are the caretaker. So you have been caretaking in all of your relationships, like deferring to everyone else’s needs, really picking up the slack for everyone around you because you

Think of that as your love language, but really it’s burning you into the ground. It is making you feel like a shell of yourself, and it’s meaning that you are burnt out in your friendships, in your work life, and your love life because you are caretaking in order to belong. And we want to interrupt that pattern with the skill set of main character energy. You know this is for you if you are a blocked builder, if you have a project, a business, something creative, something generative on your

Heart and mind to build. You’ve been thinking about it and talking about it with friends or putting it in your notes app for years, but never taking action. It’s like dreams and the drawer vibes. Then we need to interrupt that pattern with the skill set of main character energy. Number three.

If you are a therapy grad, meaning you have been to therapy for years, you’ve read the books, you’ve listened to the podcast, you know yourself really, really well, but you cannot seem to get yourself to take action. You are insight-rich, but action poor, and can’t figure out why you can’t get yourself off the couch. You can’t figure out why it still feels paralyzingly frightful to and terrifying to shoot your shot. And so if you’re a therapy grad who has felt stuck

After a ton of personal development, but you don’t know where to go from here and you don’t know how to take action, we need to interrupt that pattern of inaction with this skill set of main character energy. And then finally, if you’re the overthinker, if you research everything to death for weeks, months, years, you haven’t taken action.

You haven’t gone to the event, you haven’t reached out for support, you haven’t asked for the help, you haven’t, you haven’t done the thing that you’ve been researching forever. We need to interrupt that pattern of inaction with the skill set of main character energy. All of this means that you are going to shoot your shot unapologetically in friendship, love, and work. And in doing so, get more of what you want and start building the expansive, self-trusting life.

That you have only imagined was possible, that you really hope exists but didn’t know how to create. I’m teaching you how on September 15th at this live training. I can’t wait to coach your face off soon. It’s one of my favorite days of the year when the Mastermind opens. This is our first and only time that we’re opening the Mastermind this year. It’s a six-month small group coaching experience where burnt-out feminists learn how to stop people pleasing, give way fewer fucks, and complete 100 audacious self-serving dares.

In friendship, love, and work. And we do it in a coven cheerleaders. This cohort begins at the end of September 2026. And I cannot wait to see you at this live training to tell you all about the program and to teach you the skill set of main character energy. Alright, friends, talk to you next week. Bye.