If you’ve ever found yourself doing everything right and still feeling exhausted, this conversation is for you.

In this episode, Lily sits down with Maureen, a writer, educator, and book coach who transformed her life from chronic burnout and perfectionism to joyful, sustainable main character energy.

They dive into:

✨ How perfectionism becomes emotional armor (and how to take it off safely).

✨ Why joy—not hustle—is the most powerful growth strategy.

✨ The role of self-celebration and community in creating a life that feels like your own.

Maureen’s story is a reminder that you don’t have to blow up your life to change it. You just need new tools for how you treat yourself while you grow.

Connect with Maureen:

🔗 narrative-drive.com

📝 narrativedriven.substack.com/

Work with Lily:

🌸 Main Character Life Mastermind — A 6-month small-group experience starting in January to release people-pleasing, build rock-solid self-trust, and become the main character of your life in 6 months or less.

Get early access + bonuses: https://datebrazen.com/life

Free Live Training: Stop People Pleasing and Build a Stupidly Joyful Life — December 3rd: https://datebrazen.com/joyful-life/

Get Lily’s Book: Thank You, More Please HERE

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel

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Show transcript:

Lily Womble (00:00)

Hey gorgeous friends, welcome to another episode of The Late Bloomer Show. I’m so glad that you’re here. Today marks a very special kickoff of a series that we’re gonna be running for the next few weeks, all about building your main character life—your main character energy in your life beyond just your love life. Because I know that dating is a microcosm of every hope, joy, dream, fear, insecurity, and desire that we have as humans. Dating matters to your well-being.

I also believe that the lessons that we have been talking about for your love life are going to change your life as a whole, not just your love life. If you apply these lessons that we’re teaching on this podcast to areas of friendship, work life, relational life as a whole—relationships with your family maybe even—the relationship you are fostering with yourself, it’s going to change everything.

So what I see gets in the way of your main character energy in your life in general—not just in your dating life, but there too—are a couple of things. Specifically, people-pleasing: the act of prioritizing other people’s wants and needs over your own. The act of shrinking yourself to be palatable or to belong.

That people-pleasing instinct that you were taught being raised in this patriarchal culture that we were all steeped in—that people-pleasing habit—is getting in the way of you living your biggest life possible. When I think about your main character life, I think about this story that exemplifies why I do what I do.

I was at Gilmore Girls Fan Fest. Those of you who’ve listened to the podcast for a while will remember this story, perhaps. I was at Gilmore Girls Fan Fest. I loved doing karaoke. It was karaoke night at the fest.

There were dozens of people there late at night doing karaoke. I sang “I Will Always Love You,” the Dolly Parton version that Lorelei sings to Luke in a later season—but I digress. I do this karaoke thing, I have a blast doing it.

This woman comes up to me and kneels next to me and is like, “Hey, I don’t know you, but I have always been afraid of doing karaoke and have always wanted to do it.”

So this instinct to not be embarrassed or not have people perceive her as whatever the fear was of getting up on that stage—“other people are gonna think X about me, and I can’t do that because it wouldn’t be safe, so I’m not gonna try”—that was what was going on before. And then she said, “But I saw you do karaoke, you were so comfortable. Would you mind coming up on stage with me so that I can do karaoke for the first time?”

And I said, “It would be my honor. Nothing would make me happier.” So we go on stage, she chooses “Waving Through a Window” sung by Ben Platt from Dear Evan Hansen, and we start singing together. By verse two, she confidently steps forward without regard for the fear of what anybody else thinks of her. She steps forward, she’s having a great ass time. I am able to step back and do harmony on the chorus.

And I just watched this person go from feeling small and shrinking what she wanted—which was always to do karaoke on stage—to living a bigger, more joyful, connective life in which she is the main character. That is what happens when you ask for aligned support to be the main character—to bring main character energy to your life in general.

That is what happens when you learn how to release people-pleasing and the fear of rejection, the fear of judgment as your default. Your life gets bigger. You do the thing you’ve been desiring to do for years, months, decades perhaps, and you end up attracting experiences, opportunities, friendships that you have always desired but maybe never thought were possible.

Like this woman at the Gilmore Girls Fan Fest who did the thing she’d always desired to do because she asked for aligned support to do it. She acknowledged her desire, she gave herself permission, she trusted herself to ask for help, and then she took massive messy action to get what she wanted in a room that had her back.

That is exactly what we do in my mastermind, Main Character Life, which is opening for enrollment on December 3rd, 2025.

Today, you’re gonna hear a story from a current client in Main Character Life, Maureen, who talks about why she joined us—what felt like her sticking points, why main character energy had such a hard time taking root in her life before she decided to join us, and what tangibly in her life has changed since developing this skill of main character energy in this group.

You’ll hear tactically what it’s like to be coached by me for your life, not just your dating life, inside of this high-level small-group mastermind.

If you’re interested in the mastermind, you can register for my upcoming live training called How to Stop People Pleasing and Build a Stupidly Joyful Life. You can go to the description of this episode to get your seat saved or just go to datebrazen.com. The link to join us will be in the banner of that page.

You can also read all about Main Character Life: The Mastermind. It’s a six-month small-group mastermind to release people-pleasing, build rock-solid self-trust, and become the main character of your life in six months or less.

In the process, you’re going to heal from hyper-independence and finally start building those friendships and relationships you’ve been dreaming of. You’re going to claim a hundred dares and start boldly going after them in this container to build the life that you’ve been dreaming of but have been afraid isn’t possible for you.

The answer is your main character energy—and I can’t wait to see you in this live training to show you how you can start bringing main character energy into your life to release people-pleasing, build rock-solid self-trust, and become the main character everywhere.

So let’s get into this episode with Maureen. It is going to be so juicy.

And again, if you’re interested in learning more about Main Character Life, my small-group mastermind that I open about twice a year, go to the link in the description of this episode or just go to datebrazen.com. Let’s get into this episode.

Lily Womble (07:01)

So glad that you’re here today. We have Maureen with us, who is a fabulous client of mine in my mastermind Main Character Life, which is opening for enrollment soon. I wanted to bring Maureen on because she’s a badass and her story is so beautiful. I think that we’re going to get into what’s been going on with her main character energy and what has happened in her life in the past few months of working together. But first, just want to connect and see how you’re doing, Maureen. Hello.

Maureen Wiley (07:37)

Hi, Lily. It’s so good to be here. Really excited to talk to you today.

Lily Womble (07:38)

Hi, I’m so glad you’re here. So what feels important to know about you before we dive in?

Maureen Wiley (07:45)

I am a huge fan of coaching. Coaching has changed my life—and your work specifically, Lily, has really helped me to kind of embody that main character energy. That’s really important to me because I’m a writer, and I coach people on writing their own books. So I like to think about things in terms of characters. I also like your kind of playful vibe, and so I’m excited about just being inspired every day to step into that more and more.

Lily Womble (08:11)

I love it. Okay, so where do we begin? Tell me—life before meeting me, what was going on? How did you feel day to day? Give me some info.

Maureen Wiley (08:25)

So I’m one of those people who would call myself a recovering perfectionist. That’s maybe not the most helpful label anymore, but it’s just a useful way to frame it. I used to be the classic academic overachiever—always setting new goals. I’m a Capricorn, and so I love a to-do list and a plan, and I can be quite intense sometimes about the things that I want to do in life.

But I did notice, especially a few years ago, that I was sort of skirting around the edges of the things that were big dreams of mine. I felt a lot safer pursuing traditional goalposts. And especially during the pandemic, I had a lot of time to reflect on my life.

Lily Womble (09:04)

Mmm.

Maureen Wiley (09:15)

I had reached a level of success that from the outside would look like I could just kind of coast and enjoy my career for the rest of my life and then chill out—and that’s just not my vibe at all. So I was actually at a retreat in the spring of 2022 and had this huge breakthrough around the vision I had for my life and how I was limiting myself because I was afraid to step into an identity that didn’t feel like me.

I had followed this traditional path and had a very stable, secure, government-type job. I was at this retreat watching someone get coached about their business goals for their small business, and it never occurred to me before that I might be able to take some of my skills and creativity and put them into my own thing that I created myself. It just started this whole journey.

Simultaneously, I found your work and was introduced to Date Brazen. I really appreciated how much you spoke openly about all the messaging you had gotten in your life about being too much and feeling like you had to shrink yourself—and how that’s total bullshit. I also really liked your joyful, playful approach to things, because in the world of self-development and personal growth, it can feel kind of heavy sometimes.

It’s a lot about limiting beliefs and digging deep into trauma, and I really appreciated seeing the lightness—how it can be fun even to pursue a big goal that feels scary or beyond our current capacity.

Lily Womble (10:55)

Yeah.

Maureen Wiley (11:15)

I’m an educator, and I’m well-versed in helping people move from their comfort zone into what’s called the zone of proximal development, which is just a fancy way of saying how we can stretch ourselves without reaching a level of frustration or shutdown. I started to see how, as much as I hadn’t seen myself as this potential creative entrepreneur and writer, I actually had a ton of skills that I could translate and write a new story about.

I think your work and especially your book really helped me with that. Seeing you go through that process and be really vulnerable and authentic—I was like, that’s the same thing I want to bring to this journey for myself.

As a result, I was like, well, I gotta sign up for Main Character Life. And it’s been really wonderful, because I get the practical advice—like, “Here’s where I’m at with building up my business or getting more comfortable being visible and sharing my work online”—and then I have this soft landing place to come to in your coaching space.

Lily Womble (12:11)

Yeah. Thank you for sharing all that, Maureen. And I want to touch down on that breakthrough at the retreat. Where were you?

Maureen Wiley (12:47)

I was at Clutch College, which is a coaching program with Kara Loewentheil, who I believe is a friend of yours. She was a huge inspiration to me when I found her podcast all about looking at our thoughts and noticing how they lead to emotions that drive our actions.

That whole framework really resonated with me. As soon as it was possible to go to a Clutch College live in person, I went. I had actually made some friends through her program during the pandemic who I had never met in real life, and we met in person at this retreat.

I was watching people get coached on all different topics, but all coming back to the same idea—that women especially really hold themselves back from having these bigger dreams because there’s so much messaging around staying small or not rocking the boat, or that people will be upset with us if we try to change something about our lives or even how we see ourselves.

I remember the last day of the retreat was about money mindset. I thought, “I don’t really need this day.” Like, this isn’t an area of coaching I need particular help with. That just felt like maybe it’s that Capricorn in me—I’ve been reading personal finance books since college. But that day kind of blew my mind because it wasn’t about how to budget or save or scrimp. It was about how we as women can break through limiting beliefs about making our own money and having our own agency.

It made me think, “Where am I applying that same scarcity in my own life?” Scarcity in my capacity—because I do have a very consuming full-time job—will I be able to also pursue these other things that are interesting to me? Will I be able to have the capacity to start to write a new story of my future and what my life is going to look like?

Lily Womble (15:01)

Yeah.

Maureen Wiley (15:39)

It’s not some clear-cut path where the clouds parted and everything was straightforward from there. It actually took me a couple more years before I really started to imagine I could do some of those things. I was in an idea germination phase and things hadn’t yet started to sprout.

But in retrospect, when I look back, even when I thought I was too fearful or still figuring things out, there was stuff happening underneath the surface. I was working through things that were holding me back.

One of the things that was happening was that I had signed up for this book coaching certification. I had written a novel that I finished in 2022, and as soon as I finished it, I was like, “Wow, there’s a lot more I need to know about how to write a novel that works.”

I heard about this book coaching certification program, and I had the thought that I could either pay someone to look at my manuscript and tell me what the issues are and how I could fix them—or I could sign up for this program and become a book coach and learn what a book coach would have told me about my own manuscript.

I signed up for that out of curiosity. I teach writing classes in my day job and have a degree in creative writing, so I was curious about it from that side of things. And when I finished the program in 2024, I realized I actually really love this.

It combines everything I love about my day job—helping students overcome their own limiting beliefs about writing and mindset stuff. What I was finding with my practice clients was that they had the skills. They knew how to write a novel that works, but they were unsure about how to query an agent or pitch their writing or build an audience.

When I finished the book coaching program, that was the moment where things started to come together. I thought, I think I actually want to do this.

Lily Womble (17:56)

Yeah.

Mm-hmm.

Maureen Wiley (18:22)

So once I received my certification, I actually cold-pitched someone whose Substack blog I had been reading for about a year. And this person had mentioned that they wanted to write a book. And so I wrote them an email basically saying, I’m a fan of your work. I’m a certified book coach. I want to work together. Like, here’s the link to book a call with me. I’d love to chat with you about your book proposal.

Lily Womble (18:22)

Hmm.

Maureen Wiley (18:51)

That was my very first client — signed up to work with me as their book coach. And we navigated the process of them writing their book proposal, rewriting their book proposal, because it was quite a journey of uncovering what it is she actually wanted to center her book idea around. And she submitted her book proposal to a publisher who was hosting a contest last month. So we’re going to—

Lily Womble (18:53)

Oh my God, Maureen.

Mm-hmm.

Maureen Wiley (19:18)

Cross our fingers, and I feel really great about it. And we’re gonna continue on this journey regardless of what happens. And that was, yeah, that was my first client. So now, I have been, for just over a year now, working with clients as a book coach — helping people write novels, helping them revise their novels, because there are a lot of people out there who have a sort of messy first draft and they want those eyes on them the same way I did when I finished mine. And I’m also working with—

Lily Womble (19:27)

Oh my God.

Yeah.

Maureen Wiley (19:45)

Authors, like a children’s book author, and I’m now working with somebody who wants to just write on Substack, and they want some guidance on how to build the capacity to be visible and share their writing with a wider audience.

Lily Womble (19:59)

I love it, Maureen. Congratulations on all of this growth. And it sounds like, you cold-pitching, you had so much main character energy in that moment — just like the permission, self-trust, massive messy action. And so, I just want to take a second to really celebrate where you’re at right now and that you’ve created something that didn’t exist before from your brain. And that’s so brilliant.

Maureen Wiley (20:25)

It’s been super fun. Thank you. It’s really nice to celebrate.

Lily Womble (20:31)

And if people want to work with you, they can go to narrative-drive.com.

Maureen Wiley (20:36)

That’s right. Or they can check out my Substack, because my Substack is where I post a lot of things — like when I do, I do a lot of free group coaching calls just because I love coaching and I can’t get enough of it. And then I also do challenges — like seasonal challenges.

Lily Womble (20:51)

I love that. So we’ll put all that info in the description of the episode. I am curious, in the vein of talking about main character life and the mastermind, what precipitated you deciding to join? Especially because, from what you’re sharing — I’m just putting myself in the listener’s perspective — what I’m hearing is like, check, check, check. You had so much courage and main character energy along this journey. What was the reason that you wanted to do this mastermind?

Maureen Wiley (21:26)

Yeah, so I would say that from the outside, it’s easy to think that like, yeah, she did the certification program and then cold-pitched a client and signed the first person that she met with, and, you know, all of that stuff. But there was so much internal emotional work that was required behind the scenes to get to that place. As I said, I’m such a fan of yours and I’m such a fan of your coaching style and your—

Lily Womble (21:37)

Yeah. Yeah.

Maureen Wiley (21:53)

Kind of joyful, playful, like super energizing style of holding space for people. And I knew that I would benefit from having someone in my corner. So whether it was that I just needed someone to celebrate with — because that has been probably my favorite part of Main Character Life — has been doing the brags and doing the celebrations.

Lily Womble (22:01)

Hmm. Mm-hmm. Mm-hmm.

Maureen Wiley (22:19)

And even the dares project, which we’re currently working on, I sort of see them as being: we do a dare and then we brag about the dare with the group and we get celebrated. I don’t think that there can ever be enough of that, because we have to counterbalance so much of the narrative that women receive around not bragging, not looking too—

Lily Womble (22:45)

Don’t be too big.

Maureen Wiley (22:47)

Too big, or too full of themselves, or too conceited, or to think even that these accomplishments are worth celebrating. Because I certainly have felt that way — that the things that I want to celebrate are not necessarily the same things that society wants to throw a big hoopla for. And so it’s been really nice also to have that space where it’s like, those things are equally—

Lily Womble (23:08)

Mm-hmm.

Maureen Wiley (23:13)

Celebrated and seen. I think being seen is such an important part of your program — even just the ability to say, “I would like some witnessing for something that I’m going through.” Not necessarily needing coaching, although that’s obviously available if we want that. So I was pretty sure that the program would help me—

Lily Womble (23:13)

Yes.

Maureen Wiley (23:35)

In that way of having this space to celebrate the wins and to also kind of help me keep the momentum going. Because it’s really a lot easier for me to focus on my creative projects — like writing my own novel. I’m working on my second historical fiction novel this year and have learned a lot from my book coaching program. So I’m learning more this time around and also building up my book coaching business. It’s a lot easier for me to do that when I was on summer break, for example, and that coincided with this program. I knew that once the semester started and life got busy again with teaching and grading and committee work and things like that, it would be really helpful to have a space to come to — to stay accountable towards my dares project, as well as a space where I could come to process the feelings. Because, you know, one of the things that—

Lily Womble (24:06)

Mm-hmm. Yeah.

Maureen Wiley (24:29)

Happened is, when I got really busy and life got really complicated for a month, I felt a lot of big feelings of disappointment that I couldn’t put the same amount of energy into my creative work that I was able to do, let’s say, in July. And being in your coaching program meant that I could share that and I wouldn’t be dismissed or invalidated in my feelings. And that just, unfortunately, is kind of a rare experience — to have a space to go to where the feelings don’t need to be fixed, but they get witnessed. And if I wanted coaching on them, if I wanted suggestions for how I can process some of the feelings, you’re always there with that kind of loving witness energy. And then also that, like, “I’m in your corner” coach energy. So I had a feeling—

Lily Womble (25:01)

Hmm. Yeah.

Maureen Wiley (25:23)

That I would have that as a result of joining the program. And also, one of the things that I wanted was the perspective from somebody who didn’t follow the sort of what I think of as the “business bro hustle culture” program for having an online business. And so I also just knew it would be very practical to be able to be like, “How did you navigate this?” or “This thing happened,” and to know that you would have a similar experience or understanding of what can happen when we start putting our work out there. And then we have those shame waves that hit us of like, “I was too vulnerable,” or “This is really hard,” which has, you know, been super enjoyable — and like, the total extremes of emotions on both sides.

Lily Womble (26:07)

Mm-hmm. Huh. Yeah.

Maureen Wiley (26:19)

There’s been some great times and some hard times.

Lily Womble (26:22)

Yeah, and it’s been my honor to support you and those in this container. It truly is the most magical thing to show up every week, show up in Slack each week, show up in the monthly reviews that we do that are more one-on-one focused, and really see your progress toward creating a life where you are easier on yourself — where you celebrate yourself more, where you process your feelings knowing that you’re normal and okay and safe to do so.

The tactical implications of that, that I see on the other end — whether it’s in month one, month six, or after someone graduates — are that you get more epic shit done. You do attract more clients as a bonus result. You do attract deeper friendships as a bonus result. More satisfaction, more pleasure in your day-to-day life.

And I think that, especially for recovering perfectionists — especially for women and people socialized as women — that is not taught to us at all. It’s very much like, hustle culture, burn yourself out to be trying. And in doing so, I think it is automatically shrinking folks. I know I felt that way before I started practicing these skills for myself. And so it’s such a joy to be in this container with you and to be your coach.

Maureen Wiley (28:02)

Thank you so much. Yeah, it’s been really, really awesome. I’m glad you mentioned the burnout piece because I think that’s the part that keeps coming up for me — that, you know, to me, burnout is a result of the unprocessed emotions that we’re resisting. And so something I didn’t mention before that was part of my journey is that I had really bad chronic pain. I had daily chronic

Lily Womble (28:21)

Mm-hmm.

Mmm.

Maureen Wiley (28:31)

…back and leg pain for about six years. And I think it was — I know it was — a manifestation of repressed emotions and stress and the toll on my body of years of holding myself to these perfectionistic standards. And so part of that same journey of starting to create a new vision for what my life could look like came from healing from chronic pain by learning about how to actually meet and process my emotions without fear and instead with curiosity.

And so it’s so interesting to me how those skills translate into other goals in the same way that so many people who are in main character life have goals in these different arenas. Like, it oftentimes comes down to…

Lily Womble (29:08)

Mm-hmm.

Maureen Wiley (29:30)

…building safety, building this sense of safety in our bodies and safety with our emotions. And so I see a connection between the healing that I did to feel safe in my body — which helped me cure myself from chronic pain, which was a huge hindrance to my enjoyment of life — like, it’s very hard to even enjoy anything positive in your life when you’re in pain every day. And I now see how…

Lily Womble (29:56)

Mm-hmm.

Maureen Wiley (29:59)

…I wasn’t going to be able to do anything creative — I wouldn’t have been able to finish that first novel if I was racked with chronic pain. And so I had to go through this journey of learning how to hold space for my emotions and process my emotions and build that self-compassion, which is such a foundational part of your coaching approach.

So the self-compassion, the self-trust, the lack of judgment that we know of our own emotional reactions to things — which are very normal, which are very natural — but we’ve sort of created a society where those things have become demonized, stigmatized, pathologized too. So this program to me is also…

Lily Womble (30:32)

Mm-hmm.

Yeah.

Maureen Wiley (30:56)

…really helpful to not fall back into seeing my emotions as a problem that I have to resist or fight off or defend myself against. Instead, I’m sort of invited, with a lens of self-compassion, to get coached on it in the coaching calls or in the Slack or do some of the self-care…

Lily Womble (31:04)

Yeah.

Maureen Wiley (31:23)

…practices and having my own back. And I have my own different things, but I also appreciate the suggestions — I think recently you suggested that I stomp my feet and go for a walk and stomp my feet on the pavement to let out some pent-up anger that I had been feeling, and that was super helpful. So just even having someone who…

Lily Womble (31:35)

Yeah.

Maureen Wiley (31:50)

…can help be a guide through that has been really life-changing.

Lily Womble (31:53)

Yeah.

Yeah, well, I think that chronic pain sucks, and it sounds like you’ve done so much work to identify its source and move through it. And I also want to say that, like, the unprocessed — who would have taught us how to process these feelings? I think as children, you know, these patterns start of being treated as a problem for big emotions or being treated as, you know, like, too much.

And I think that’s where a lot of people’s “too much” story sort of originates from — mine included. And so, like, creating a space where feminist humans who all have this sense of “there’s more for me, and I currently feel behind, too much, not enough,” fill in the blank — there’s more for me, but I still feel this sense of shrinking and fear — like, in this mastermind, we’re really building a bridge to that version of yourself who knows and is claiming and is creating the more for themselves.

And for my client, for those listening who currently have chronic pain or who are moving through that, I just want to say: it’s possible to be kind to yourself and get epic shit done if you are able to listen to your capacity and honor it.

And I think blowing past capacity — not knowing how to honor or recognize our own capacity day-to-day — is also a contributor to burnout. So I think creating a space, wherever your body’s at, however you are doing, to be safe, to be human and imperfect and squishy, is so life-changing.

One of my clients said this beautiful thing a couple of sessions ago with the mastermind. She was like, “This is a portal to my freedom.” And that’s what my intention is. That’s — I hope that’s felt, you know — that this is about creating your own emotional freedom in your life to create a world that you like, that you’re making better by contributing in the way that feels most aligned for you, and creating a better life for yourself by just taking up more space in this goddamn planet and fucking around and getting messy and doing fun things.

Maureen Wiley (34:21)

Yeah, definitely. Love, yeah — and not needing to, not needing to quit your job and move into the forest and all this, you know, like, what I like is how much it’s kind of grounded in, “Okay, let’s look at these different things. Maybe there are some areas that we want to make some big changes in,” but…

Lily Womble (34:32)

Yeah.

Maureen Wiley (34:45)

…everything feels very doable, very approachable, because it’s not just about, “Okay, well, what action steps could we take?” but also like, “How am I going to care for myself as I take these action steps?” And…

Lily Womble (34:54)

Yeah.

Yeah, so important. I think that’s so missed — right? This like, “Here’s the plan, you’re gonna do all these big things, and it doesn’t matter how you feel about it, and you’re gonna push through because that’s the only way to get the result.” And I think that causes so much unnecessary burnout and mind drama and emotional turmoil.

Maureen Wiley (35:11)

Yes.

…or even fear that stops people from even starting, right? If you think, “The only way I’m gonna have to do this is grit my teeth and push through, and, you know, I’ve got to follow these action steps and I have to do them perfectly.” You know, those people who create the perfect ideal morning routine or they create a content creation calendar, and then they — you know, saying that, I have been victim to all of that kind of thinking too, which is why it’s really helpful to have someone remind me that that’s…

…maybe not going to be the most effective way to actually enjoy the experience. But thinking that we have to follow this routine of success might actually stop a lot of people from getting started. I would say that was probably the case for me for several years, because it was kind of in the back of my mind that, you know, I really love — I just feel like I love to teach and to coach.

So even in my classes, I teach college writing classes, and I have always had a sort of mindset, almost like a coaching-based approach with a lot of my students. And I work in the writing center at the college where I teach. So often what the students need is not someone to tell them, “Okay, you need to do this, this, this, this, this,” or “make these changes.” They need someone to help them see the approach that they have — maybe their mindset is a fixed mindset versus a growth mindset — and that they don’t need to…

…that good writers are not born that way, that it’s a set of skills they can develop over time. And then when I saw how that applied to other areas of life, I was so excited to start sharing that with more people beyond the classroom because…

Lily Womble (36:56)

Yeah. Yeah.

Maureen Wiley (37:08)

…that is not what most people out there are saying. Most people are saying, “You’ve got to create your schedule and you’ve got to stick with it, and you’ve got to do the wake up before dawn and do the ice bath cold plunge.” And that’s just not going to work for a lot of people. And then they might either blame themselves if they try and don’t stick with it — which just leads to more and more self-criticism. And it’s a spiral that can cause people to…

Lily Womble (37:17)

Yeah.

Maureen Wiley (37:38)

Just completely give up, or they don’t even start in the first place because that doesn’t, you know, it’s kind of like not a very appealing offer. If you think, okay, I’m going to have to feel really bad. I’m going to have to push through, and it’s going to feel really draining, and I’m going to feel really fearful and uncomfortable and anxiety-inducing. Who wouldn’t not ever try, you know, who wouldn’t just feel completely shut down by that? So.

Lily Womble (37:41)

Yeah.

Yeah.

Yeah. Well, I would love to drill down into some tactical things in the Mastermind that you have enjoyed the most. Like, what do you feel like—obviously, we’ve talked about showing up to the calls and being a safe place for witnessing—but in terms of, you mentioned that making change is a set of skills. It’s not necessarily a rigid checklist of action items. And in Main Character Life, the Mastermind, we have three skills that make up main character energy: permission, self-trust, massive messy action, rinse, repeat. So is there anything in the Mastermind that stands out to you as being really meaningful or helping you move forward in a way that you didn’t expect?

Maureen Wiley (38:49)

Yeah, I would say, I think it’s your sense of humor that probably, for me, makes the most difference. You know, it’s not that you don’t take things seriously—you take things very seriously. However, we can be serious, and we can have a playfulness, a levity at the same time.

So I’ll give an example of my very first coaching in the Mastermind. I was doing something that was like a big, exciting step way outside of my comfort zone. And I had gone to this polyglot gathering language convention that was taking place in Eastern Europe over the summer. And I was really excited—it was a lifelong dream of mine. Well, not lifelong, but it was a long-time dream of mine ever since I had heard about the gathering.

But I was very nervous about some of the interactions that I would have because I’d be speaking Spanish or French or German. And I was worried about getting caught in conversations. I was worried that I would get stuck and not know how to extract myself. And your coaching was so funny to me because basically you were like, “Who cares? Like, get up and leave. Say you have to go use the bathroom.” Like, you’re stuck in a conversation with somebody and you’re not enjoying it, or you’re feeling overwhelmed and you need a break and you need to step away. Just say, “Sorry, gotta go. I’ll catch you next time.” And that was the permission slip of just being like, I don’t have to sit there when I’m in a conversation with somebody who’s maybe like—

Lily Womble (40:10)

Yeah.

Maureen Wiley (40:32)

—talking at me. I’ve had this experience in language circles before where maybe I’m more of a beginner, and I’m talking to somebody, and they’re more advanced, and I’m struggling to keep up with them—which actually did happen at the gathering—or my big fear was that I would make a mistake and someone would correct me, and that inner perfectionist was just feeling like that would be intolerable. And I just loved the fact that you gave me permission to just, like, get up and say, “Gotta go.”

Lily Womble (40:55)

Hmm.

Maureen Wiley (41:01)

“See you at the next event,” or something like that. And I did exactly that. And so I was at this gathering of over a thousand people. I didn’t know anyone. I went completely on my own. And I just gave myself permission to celebrate whatever I did and not to be hard on myself for whatever I wasn’t available for. So, you know, on those days where I felt too tired to go to the evening socializing event because I had been trying to think in another language or even multiple languages throughout the day, I just went back to my hotel room, and I just chilled out and watched TV or read my book—and it was so nice. I would say just that was so helpful to me—just someone kind of saying like, this is for fun. And I almost feel like that applies to life—not to get too philosophical, but—

Lily Womble (41:30)

Mm-hmm.

Yeah.

Maureen Wiley (41:57)

One of the things that I need help with is to see how those little moments can be broadly applied. So it’s just like, I was going to this event because it sounded interesting, because it sounded fun. And when I was worried that I would feel emotions and not know how to process them or not know how to deal with them in the moment—that I was going to shut down—it was so helpful to just kind of have this reminder of, just like, this is your life, and you’re doing these things—

Lily Womble (42:03)

Right.

Maureen Wiley (42:25)

—for you, for fun, and you get to decide what that looks like and to really feel that embodied. And I think that that, plus the accountability of things like the Brag channel in Slack, where we get to report the big things that we’ve done—that has been really helpful for me to just sort of go for it. Because it’s almost like I want to bring something to brag about. I want to—

Lily Womble (42:27)

Yes.

Maureen Wiley (42:54)

—and we don’t always have to have an accomplishment. The brag can be like, I extracted myself from a conversation I was no longer enjoying, or I said no to going to the evening event because I was feeling tired, or I just didn’t feel like it, or my introvert batteries needed recharging. So I would say that the—and I really love to also approach my own clients, my own book coaching clients this way. I had this one—

Lily Womble (43:02)

Mm-hmm.

Yeah.

Yeah.

Maureen Wiley (43:24)

—with a client where they were kind of stuck because they had read some famous fantasy writer had said that you have to write three novels and throw them in the trash before you can write one that works. Or it was like six novels—something like that. And this person was like, “Well, you know, that’s what I have to do, you know, otherwise…” And they were like, “I don’t think I can do that.” And they were in this place, and I was like—

Lily Womble (43:39)

Yeah. Uh-huh. Mind drama. Yeah.

Maureen Wiley (43:52)

“Why have we decided that this—yeah, I was like, who cares? You know? Yeah, for that person, it worked. And maybe there are people who hear that, and they think like, okay, I have permission to write six terrible novels that I throw in the trash.” I never tell—I always tell people don’t throw anything away, because you never know. You might take a character from a novel that doesn’t work and bring it into a new one. So I think just that permission slip and also just the constant sort of poking at—

Lily Womble (43:53)

Cares?

For that person, it worked.

Bad things, yeah.

Maureen Wiley (44:22)

—our brain’s propensity to hear something from some person that we’ve determined is the position of authority, and then to create this new rule that we have to live by forever—and to kind of just poke at that a little bit.

Lily Womble (44:34)

Yeah.

For sure. And that’s why we start with the people-pleasing detox in month one, because there are so many places that you don’t realize you’re sort of complying to someone else’s rules—of how to be, to exist, how to work. And so really acknowledging and starting to like, choice by choice, shed that compliance to the rules that no longer fit you or never did, I think is just such a fun way to recognize and see how life can be different if you are more creative in your approach to life. I also—you help so many people, you shepherd and support so many people. And I think that something that I love about working with other coaches or even therapists, many of whom join Main Character Life or Main Character Dating, is that like—

People need support. Like, therapists need therapists. Coaches need coaches. Therapists might need coaches. Coaches need therapists. Right? Like, I think that this is an ecosystem of support for people, especially like you, who have poured out so much for others—that this is a space for you to like be held, seen, acknowledged, supported as you support others in an aligned way. So I love that. I also want to mention—

’Cause you mentioned this trip, and I have this image that came to mind of like, of a before—not for you necessarily—but I don’t know if you’ve ever been on a trip with a friend. I don’t know that I’ve ever experienced—maybe in like college or high school—and that friend, you think you’re really close, like things are good, but on this little weekend trip, that friend consistently makes small choices that deny you what you’re asking for maybe. Like you say, “I want to go eat Thai food tonight.” They’re like, “No, that’s not what I want to eat. I want to go eat this.” And then you comply, like, “Okay, well, let’s go to what you want.” And then, you know, “I want to actually lay down and take a nap and maybe take a bath and maybe we can meet up in like four hours.” “No, we need to make the most out of this trip and we need to make the most out of this experience. Let’s go out. No, you’re wasting the time.” Right? Do you—does that sound familiar?

Maureen Wiley (46:55)

Yeah, definitely.

Lily Womble (46:56)

By the end of that weekend, you may be totally burnt out, exhausted, maybe even disassociated from yourself, because maybe you’re angry because you can’t put your finger on why, but this weekend hasn’t been fun, and you thought you knew this person and you loved this person, and you thought this trip was gonna be great, but it wasn’t. That is an example of what life looks like before you learn the skill of permission and self-trust.

This constant denial. I’m thinking of like, maybe how you would have gone to that polyglot conference. Am I saying that correctly?

Maureen Wiley (47:37)

Yeah, it’s called the Polyglot Gathering, but it’s a conference for language nerds.

Lily Womble (47:41)

Amazing. So maybe before it would have been that energy of like, no, you need to go out there. You need to stay in this conversation because what if they think that you’re fill in the blank? If you leave, who do you think you are that you’re gonna leave? It’s like that chatter with a friend who’s denying you what you want. And the intention of this, based on this mastermind, which is why I’m so gratified that you feel this, is that you become a better fucking friend to yourself. And in doing so, let yourself off the hook. And then in doing so, you create more of what you want in your life.

Maureen Wiley (48:19)

Yeah, I think that voice that you’re talking about, that friend who says, no, you can’t do that, or like, no, you’re doing this. That was like my inner voice. That was the self-critic that was constantly telling me that I wasn’t allowed to do certain things or I shouldn’t or I should. A lot of times it was like you should, even sometimes about how I felt. I would say that my inner critic…

Lily Womble (48:31)

Yeah.

Maureen Wiley (48:48)

…was much more critical about — I think there’s a term for it, it’s called emotional perfectionism — where you judge your actual emotions as being correct or incorrect, oftentimes incorrect, obviously, because that’s probably what the brain is gonna fixate on.

Lily Womble (48:56)

Yes.

Maureen Wiley (49:09)

My inner voice is much more about how I should feel or how I should think about something. So a big part of this kind of work that’s super helpful to me is it’s very hard to recognize that that voice is not me if I don’t have a coach to help me get a little bit of distance.

Lily Womble (49:28)

Hmm. Mmm.

Maureen Wiley (49:35)

…or to provide another perspective or to kind of just start to know my patterns. I mean, the program is enough time that you can get to know each of us and our sort of thinking patterns, and you learn a lot about our lives and you learn a lot about our hopes and dreams and fears and insecurities, which means that it’s really easy to start to recognize when we are maybe unable to create that distance from the internal critic. And so I would say that’s been one of the most helpful things is, my inner critic often would tell me that I should feel differently, or for example, I should act differently — like I should have more capacity for spending, you know, all day at this conference — when internally, if I were to check in, I’d feel like, actually, I’m quite tired. And then the inner critic says, but you’ve wanted to do this for 10 years and you’re finally here and you gotta go to every single session. It’s like literally impossible because a bunch of the sessions happen concurrently. So you have to make choices. And so I think being able to make those choices by listening to my inner voice has been a big part of what I’ve been working on in this program. So it’s so great to have that be supported and be…

Lily Womble (50:44)

Mm-hmm. Mm-hmm.

Maureen Wiley (51:02)

…honestly be cheered on. I get really nice messages from other members of Main Character Life who say, that’s so awesome, I wanna do that. Or they even want to talk about things outside. So like forming friendships outside of the program to provide that same permission-giving and that same kind of loving witness energy, which I think we all could use.

Lily Womble (51:03)

Mm.

Maureen Wiley (51:29)

…a little bit of that. Like I think the world would be a better place if more people, regardless of their background, felt like their emotions were valued and valid and they were able to say them without someone kind of shutting it down out of their own discomfort, right? So.

Lily Womble (51:54)

Yeah, yeah.

Maureen Wiley (51:55)

That to me is like a revolutionary shift that I’m seeing happen. And I’m seeing it happen with therapists and coaches and books that are being written about people kind of saying that, you know, our emotions are at the heart of so many of our choices. And I also even see it now, like with my friends who have kids — you know, there’s more of a culture of maybe, you know, people can disagree with this approach — but like a culture of really trying to hear the child’s emotions and to understand where they’re coming from and make them feel like their voices matter and their feelings matter. And just how starving so many of us are for that feeling of being seen and heard and being told that, you know, our hopes and dreams, like they matter and that…

Lily Womble (52:36)

Mm-hmm. Yeah.

Maureen Wiley (52:55)

…that we don’t have to fight ourselves to experience them, that it doesn’t have to be — I think that’s kind of the main thing that I really was drawn to — is that it doesn’t have to be this fight, that the experience, whatever it is we wanna do, whether it’s like people in Main Character Dating who want to find a romantic partner or they just wanna like feel more confident in their dating…

Lily Womble (53:00)

Yeah. Yes.

Maureen Wiley (53:25)

…if it’s someone in the mastermind who wants to move to a new community and make new friends, or they want to start a new job, or they want to build a business, or whatever it is they want to do — because I also moved during this time, so I was building up a community of new friendships and new connections here too — that it can be a joyful experience, that it can feel positive rather than that sort of traditional narrative of everything is like…

Lily Womble (53:33)

Mm-hmm.

Maureen Wiley (53:54)

…takes hard work and you have to feel — you have to be gritty and you have to push yourself. And I don’t know, that’s just like way too bro, like hyper-masculine culture for me.

Lily Womble (53:56)

Yeah. Yeah, totally. Well, and I wonder, final question here — what would you say to somebody who’s curious about this program who might feel the tug to apply?

Maureen Wiley (54:17)

I would say that you really can’t go wrong joining this program because whatever it is you want to do, whether it’s like more internal work of building up your sense of self-trust and being a better friend to yourself or building up your self-confidence, or even just starting to recognize and push back on that inner critic voice, like you can do that in this mastermind. Or if you have more external work that you want to do, like you want to make a new group of friends in your new city, or you want to start a business — these are just my own personal examples — you can also work on those things and they’re not actually that different. They require, in order to take these messy imperfect actions that lead to the life of our dreams, we also work on the — we also do the internal work. And I think…

Lily Womble (55:00)

Mm-hmm.

Maureen Wiley (55:13)

Lily has such a—you have such a great approach to combining those two. So, you know, some people might be thinking about doing a program like this and they’re like, but I don’t have a goal that I’m working towards. Like I don’t have this, you know, line item thing of like, by this time next year, I want to achieve X goal. But they just have a feeling that they would like to feel a greater sense of ease, less—

Lily Womble (55:26)

Mm-hmm.

Maureen Wiley (55:40)

—perfectionism. Maybe they’re feeling really burnt out. I know that that is obviously a big issue. Maybe they’re feeling really anxious about the future. Like those things are equally accessible in this space. Those things are equally accessible in this space. So I would just say that someone shouldn’t count themselves out because they don’t know before they start the program what it is they want to do or what they want to achieve. Because number one, there’s a ton of resources to help them uncover that. And that is a big thing that I’ve learned, is like, you might think—and I think I said this in the beginning—you might think that you need to know exactly what you want your end goal to look like before you get started. And that is just not really how it works. You have to kind of—

Lily Womble (56:30)

Mm-hmm.

Maureen Wiley (56:30)

—try something and make these little experiments. And then you learn, that’s interesting. Like, I didn’t really enjoy that, so I’m going to go over here and try this. Or I really enjoyed that, and so I’m going to go all in. Like, I did not expect that I would do the book coaching certification in order to actually work as a book coach. I wanted it for my own personal—like, I wanted to become my own book coach and help myself as a writer. And now I get to do both. And so it’s—and then—

Lily Womble (56:52)

Mm-hmm.

Maureen Wiley (56:59)

—I would also just say that the regular coaching calls, the Slack channel, the challenges, the workbook—it’s just a really nice way to stay connected to that inner voice that’s our inner champion that’s in our corner. And sometimes we need it to be sort of made manifest in the form of our coach, Lily, and that’s really helpful for me. I really like when I just need to be witnessed as I go through this thing. So I would say—that was kind of a long way of saying—you kind of can’t go wrong. Whatever it is you want to work on, there is room for that. And you’ll probably be pleasantly surprised by the clarity. I would say that’s been a big thing for me, is that I went in with an idea—

Lily Womble (57:32)

Yeah. Yeah.

Mm-hmm.

Maureen Wiley (57:55)

—but not a ton of clarity. And especially over the summer, during the first few months where we really started working on our main character life projects, is when I just started to feel so much more clarity. And so I highly recommend joining the Mastermind.

Lily Womble (58:09)

Mm-hmm.

Yeah, thanks, Maureen. I love hearing all of that. It’s such an honor. I think that like, you know, I like to say that my work is equal parts mindset and tactical strategy. And so I love that you’re reflecting that you created this emotional safety and that, like, there was this bedrock of celebration and main character energy, of permission, self-trust, massive, massive action. And then we took those skills and started applying them in month three to the 100 Dares Project, which I’ll share more about with y’all soon. You can also go to datebrazen.com to learn more about the 100 Dares Project at Mastermind—to make tactical that which you desire and to get massive clarity every single day toward building the life that you want. So I’m so glad to work with you, and I can’t wait to see what’s next for you. I know that so much good stuff is unfolding, and thank you for coming on the podcast to share.

Maureen Wiley (59:10)

Thanks for having me.

Lily Womble (59:11)

And again, if you’re interested in Maureen’s work for yourself or you know somebody who could use a coach like her, you can go to narrative-drive.com. And also, if you’re interested in the Mastermind, I have a new training coming up called How to Stop People Pleasing and Build a Stupidly Joyful Life on December 3rd. So you can sign up for that to learn more about the Mastermind and learn about the concept and tactical framework of main character energy in the description of this episode. Thank you so much for coming on, Maureen.

Maureen Wiley (59:44)

Thanks, Lily.