If you’re stuck in a spiral of overthinking — replaying conversations, asking 15 friends what to do, imagining every worst-case scenario — this episode will feel like a deep exhale.

Overthinking isn’t you being “careful.”

It’s a self-trust deficit.

And that is a skill gap, not a character flaw.

In this episode, I break down:

• Why anxious rumination feels so real and so urgent
• How patriarchy, people-pleasing, and fear of rejection trained you not to trust yourself
• The difference between careful planning and dress rehearsing tragedy
• Why outsourcing decisions to friends keeps you stuck
• What self-trust actually is (and why it’s messy, imperfect, and learnable)
• Tiny, doable steps to rebuild your self-trust today
• How this plays out in dating, boundaries, and big life decisions
• A framework to stop overthinking and start acting from your gut

If you’ve been doubting yourself for years — in your dating life, your friendships, your career, your boundaries — this episode will teach you how to finally have your own back.

Self-trust is a skill. And you’re about to learn it.

Work with Lily

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A feminist guide to breaking dumb dating rules and finding love
Order here: https://datebrazen.com/book

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Show transcript:

Lily @ Date Brazen (00:00)

Hey, gorgeous friends. I’m so glad that you’re here because we’re going to talk today about how to stop overthinking everything, how to stop that anxious rumination that’s going on every time you have a big decision to make, especially in your love life, how to stop doubting yourself all the time. Because that’s what’s really happening with the overthinking — it feels like that for me at least. I struggle with anxiety; I have in the past, I do today. And whenever I’m overthinking something, I know now because of the work that I’ve done that the root of that is self-trust, right? The fear of trusting myself because something’s gonna go wrong and I haven’t prepared for something, that I haven’t done enough worst-case-scenario planning, that everything’s gonna go to shit if I take my hand off of the vice grip that I have of overthinking.

But I now know that overthinking is a waste of your time, okay? It’s draining you of your energy and your life force, and it is slowing you down from creating the life that you actually want to live. You think — I have thought in the past — overthinking, that anxious rumination, is me just trying to figure out every different scenario and trying to plan and be safe. And we can be compassionate toward that version of ourselves if you resonate, if you’re with me in this.

Both—and in this episode, I’m gonna teach you how to stop doubting yourself all the time, how to build the bedrock of self-trust, what self-trust even means. I’m gonna define this shit. And by the end of this episode, you’re gonna have a plan of action to take action for what you want without overthinking it so much so that you can have more peace, so you can have more clarity, and so you can just have an easier day.

Okay? And ease your day, and ease your week, and ease your month, and ease your life. Because overthinking is making your life unnecessarily hard. So let’s get into this.

So how do you know if you have an overthinking problem, if you have a self-trust deficit that can be filled with a skill set — because self-trust is a skill set. So maybe you’re stuck in anxious rumination, okay? Maybe it’s your brain’s chemicals and maybe you’re getting support — I hope you are — from a health practitioner who you trust. However, for me, how I notice when I have a self-trust deficit or when there’s an opportunity for more self-trust: I’m in a circular thought pattern. I am dress-rehearsing tragedy constantly. Sometimes I can’t catch a deep breath. I am really struggling to—like, people will tell me logical things that are like, “But Lily, why would you be afraid that that thing would go wrong because of X, Y, Z?” And logically that doesn’t really make sense. And I’m like, it’s cool that you think that it logically doesn’t make sense, but in my head I am worst-case-scenario planning like my life depends on it, because in my brain, it literally in that moment does.

It feels like my life depends on — my belonging depends on, my acceptance in the world, my success in the world depends on — me anxiously ruminating on this topic to death so that I can protect myself. We gotta get one thing straight: we’re not in control, and that really sucks. We’re in control of very few things — our brain and how we treat it when it’s struggling, how we allow growth into our lives, the people we choose in our lives, the boundaries that we set. However, anxious rumination, dress-rehearsing tragedy, planning for the worst-case scenario is not actually going to prevent anything from happening.

Brené Brown talks about in one of her books — I think it’s Daring Greatly — this man that she met who was saying, like, his wife had passed, and he was saying, “I held myself back from fully loving her because I was always afraid that she was gonna die. And now that I look back, now that she has passed, me worrying about it didn’t make it any less hard now.” And I wanna pass this along: the anxious rumination, that cycle of thought — I’m gonna help you get out of it. Sometimes it feels, at least for me when I’m in it, like I’m fucking helpless to this shit, but we’re gonna get there in a moment.

But I just want to let you know in case you’re really attached to the idea that you’re actually planning for the worst-case scenario in an effort to make things better — it actually doesn’t make things better. It makes your life harder and it makes life more exhausting. So the truth that I wanna invite you into in this episode with me is that we don’t know what’s gonna happen in this life, and it’s possible that you haven’t experienced everything, and it’s possible that good things can happen that you don’t expect.

Life is 50/50. Brooke Castillo talks about life being 50/50 — 50% hard, 50% amazing. And so if we just acknowledge like, okay, life’s gonna be 50/50, period, then you can give yourself permission to notice the anxious rumination that you’re maybe stuck in and engage the plan that I’m gonna outline for you.

Those facts, those thoughts alone that I’m passing along to you — I’m not saying, well, that should fix your anxious rumination. No, we’re just level-setting with some truths to help you stop overthinking, help you stop doubting yourself so fucking hard.

You know that you have a self-trust deficit when you’re overthinking everything. Overthinking every decision, you’re asking friends — you’re asking 15 friends for their advice on something before making a decision because you think potentially that asking friends for their opinion will make you a smarter decision-maker.

Now, in some cases, it’s important to consult your people. Yeah? If you had a board of directors for your life, your closest, closest friends would be on that board of directors. I’m not saying that their opinions don’t matter, but you know you have an overthinking problem or a self-trust deficit when you’re turning to friends for all of the decisions and outsourcing the best decision-making to other people instead of making a decision based on what you know to be true.

And I think that goes back to: you’re afraid. What are you afraid of? You’re afraid that the decision that you make will be the wrong one, that you’ll hurt people, that people will reject you and leave you. At the bottom of all of this is just the pure human desire to not be rejected, to not be judged, to be loved, to be in belonging, to be in community. Pretty basic human stuff.

We fear rejection like we fear death, because when we lived in caves, when our ancestors would be rejected, literally they would die. They would be put out of the cave and they would die of exposure. So of course you have this baseline fear of being rejected. And of course, then you would sublimate that fear by going to all of your friends and asking them for all their opinions, especially in your dating life. If you identify as a late bloomer, you haven’t dated very much, or you just got out of a 15-year marriage, and you are afraid to be in a bad relationship again — whatever the case — there might be a self-trust deficit because you have the thought, “My friends know more than I do. Other people know more than I do. They have better decision-making than I do.”

And look, maybe that’s the case for some things, right? I have a friend who is in corporate America. I’ve never really been in corporate America. She knows so much more. If I ever had a question about corporate America, she would definitely know more than I did. I am not a mother yet. I don’t know when that’s gonna happen for me — no plans in the works right now — but that’s something that I want in the future. I don’t know anything about that. I think I do because of delusions of grandeur sometimes, but I don’t know anything. I would go — if I had a question about motherhood — I would go to a friend who’s a mother. I have a couple of them that are really close to me.

I’m not saying that other people don’t know things that you don’t know about things in the future that you haven’t experienced yet or things that you haven’t experienced period. I’m just saying that when it comes to decisions about what’s best for you, when it comes to decisions about who you stay with and who you bless and release, when it comes to decisions about what you want for your future — the vision you have, the career you want, the friendships that you want, the relationships you want, the boundaries that you know you probably need to set — that’s on you, my friend.

And that’s on you building self-trust enough to know what you want, give yourself permission to know what you want, and take massive action based on what you want. Ultimately, you are the best decision-maker for you, period.

Building self-trust is a necessary tool to living a good life. Building self-trust imperfectly is a necessary tool to living a good life — living a rich life, attracting the best partnership of your life, being in the best partnership of your life. And the problem with this idea that you’re behind because you’re single, or the problem that you don’t know this big thing that you want in your future — you don’t know how to be in the right relationship — guess what? There are a lot of people in relationships who don’t know how to trust themselves. And you know what? It causes a lot of overthinking and a lot of misery.

Now — self-trust doesn’t mean that you’re gonna know what to do in every scenario perfectly. Self-trust is never perfect. It’s a buildable, learnable, imperfect skill set. And so I think that the self-trust deficit that you might be struggling with right now — it’s impacting you by wasting your time with the wrong people, overthinking every decision that’s slowing you down. Your life becomes more essentially about everyone else when you’re outsourcing all your decision-making to your 15 friends in your group chat.

Your decision-making becomes essentially about other people’s bits and pieces. And then if you make a decision based on what your friend said you should do instead of really listening to yourself and trusting your own gut — and again, that’s a learnable skill — when you outsource to somebody else and then it doesn’t go the way you want it, you’re like, “See? I can’t make any good decisions.” But really, you were making a decision based on what somebody else thought was the right decision and not based on what you thought was the right decision. So of course you weren’t in alignment; it didn’t work out.

So your decisions — your life — when you’re outsourcing your self-trust to other people (“Other people know more than I do”) it’s really making your life about them and not about you. It’s like when people come to me — you know, I have this program, Main Character Dating, and then I have Main Character Life, the mastermind that is opening in a few days — when people come to Main Character Dating and they say, “My friends made over my dating profile.” And then I look at their dating profile, I’m like, this is the most — generally, sometimes there are exceptions — but I generally see that it’s a dating profile that is so essentially little bits and pieces of other people, and it’s not essentially that client. It’s not essentially that person. It’s basically these bits and pieces of the client with a lot of external judgment from friends and thoughts from friends and best practices from friends who are not you, who don’t want the same relationship that you do, who don’t want the same things that you do. It’s making your dating profile essentially about them and not about you.

Same-same with outsourcing your decision-making.

Maybe the impact of the self-trust deficit is that you’re talking in circles in your therapy sessions. You’re really struggling with making decisions and having peace about the decisions that you want to make.

Maybe a symptom of a self-trust deficit is that you’re looking to a bunch of different gurus or teachers or coaches or fill-in-the-blank people to have the answer for you. Now, I am in the coaching industry. I think the coaching industry is an amazing place. I think just like anything, just like there are therapists who are amazing and therapists who are terrible, I think there are coaches who are amazing and coaches who are terrible. I think that, you know, in terms of who to look to to help you grow — whether that is a coach or a therapist or a book that you read that you really liked — when it comes to choosing who you want to inspire you in the direction that you want to grow, it’s important to look to people that you admire, whose work you admire, whose work feels aligned.

But it’s also important — and I had to learn this lesson the hard way — to never outsource your agency to another person, a coach, not even me. I really want you to learn the skill of self-trust, trusting yourself, just with this free fucking podcast episode. To learn the skill of self-trust, to know who you want to grow with.

be inspired by, but knowing that at the end of the day, you’re the best decision maker. At the end of the day, you’re on your journey, you’re in your timing, and it’s right for you. At the end of the day, no one has better answers than you do for you. And that’s why as a coach, my practice, whether it’s in my dating program or in my mastermind, my practice when people do wanna

partner with me to grow, to learn self-trust, to have their own back more fiercely, to learn how to care for their nervous system, to learn the skills to be in the best relationship of their life with themselves and a future partner.

My practice of coaching always goes back to the question of like, okay, what do you think? What’s beneath this thought process for you? What do you think would be best for you? People do not come to me to be the knower of all things dating. I know a lot. I’ve done a lot of research in my client base. I’ve had hundreds of clients on this work for seven, going on eight years. I know a lot, both and.

I don’t know more than you do about what you want, about who you are, about your story, about what’s to come. I just know that I get to hold up the lantern for you to walk through your path more courageously. What a gift this work is. I want you to be aware of how you might have in the past outsourced your agency to a guru or a teacher

with the thought, I don’t know what I’m doing, they do, let me just do everything that they tell me to do, period, without question. I learned this the hard way. Like I said, I had a huge self-trust deficit when I started my business, but really, I’ve been in business for a while, like seven, almost eight years. I started this business from just an idea. I had like five side hustles, I was babysitting on the side, I was still matchmaking when I started Date Brazen on the side.

And I didn’t go full-time in my business until like two years in. I wasn’t matchmaking two years in. I just had a year of matchmaking overlap. And then I did like babysitting and personal assisting and really like hustling in New York to make it work. Then 2020 happened, and I really was afraid that no one would want to talk about dating or think about dating. And I was afraid that I would ⁓ lose my business, and it was a very normal fear. And so

I decided to work with a couple of coaches, and some of them, I think back, I’m like, what a great decision, I love their work. Some of them, I look back and I’m like, hmm, wow. I was doing this whole prescriptive thing that they gave me instead of asking myself what was best for me and where I wanted to go and what kind of business I wanted. I just did their prescription instead of learning how to trust myself in my work. Interesting.

Whenever I followed somebody else’s prescription for what I needed to do, it never really led to ease. It led to stress. It led to out-of-alignment decisions. It led to kind of a miserable state of affairs for a while until I could kind of get back onto like, okay, what do I think, Lily? What do I think? Okay, so then I got some amazing clients, more amazing clients, they were coming in, I was like feeling so good. And then there was this one decision, ⁓ my goodness, where I had an influx of clients, I was so grateful for them. And I thought the answer must be…

I didn’t think the answer is to double down—look how much success you’ve had by trusting yourself, Lily. I thought the answer to growing in the next phase is to invest every dollar that I—you gotta spend money to make money, right?—to invest every dollar that I had made in a huge month into this thing, this like… I’m not gonna say what I invested in, but basically I was like, I need to invest in a bunch of team members. Like I made a very genuine—like a lot of people do this and sometimes it works out, sometimes it doesn’t. For me, I was choosing to invest in somebody else’s vision for what I should do because they told me, you should hire all these people right now and then you’re gonna have a double—like double enrollment. And what happened was because I outsourced my decision-making to somebody else and thought they know more than I do, I’ve never been in this place in business, I shouldn’t—even though I have this like inkling of like, okay, well, why don’t you just repeat what you just did? It worked. And I was like, no, I need to change everything and look to this person who knows better than me and who’s done this a billion times. And it did not work out. It really did not work out. And it led to this, I would say, a year of financially

having to recover. And that was just my one story of how a self-trust deficit cost me money, cost me time, and it created misery. Not because anybody else doing their thing was wrong—because people do their thing and it works for some and doesn’t work for others—but because I was not yet in touch. I was not yet giving myself permission to know what I wanted and needed.

I was instead outsourcing my agency, outsourcing my self-trust to someone that I thought knew more than I did. Now again, I wanted to learn from some of these people and I did and I grew, but the most growth happened with coaches that helped me learn how to trust myself, who asked me, what’s your mind, Lily? What do you want? What’s your vision? And then helped me from there instead of following somebody else’s prescription for what I should do.

So that’s how you know that you have a self-trust deficit. Now, why don’t you trust yourself now? Let’s get into like some of the reasons why. You might be screaming at me through the podcast or through this video, Lily, but you don’t get it. I’m untrustworthy. I cannot make decisions based on my self-trust. It’s not gonna happen.

Okay, maybe you think you’ve done something that proves that you’re untrustworthy. For example, when I ⁓ spent a lot of money—I’m talking tens of thousands of dollars, tens of thousands of dollars that I did not get back, that led to a year of financial struggle in my life—that I, for a long time, about a year after that, had the thought I’m untrustworthy because I made that decision and I knew in my gut that I should just like not…

Whatever. I thought, I shouldn’t have made the decision, I shouldn’t have made that mistake, I can’t be trusted, lashing myself. Right. Maybe you think in your relationship life, I was with the wrong person, so I can’t be trusted because I was with the wrong person. I mean, been there. I remember—and I wrote about this in my book—but I was with my ex. I don’t mention his name on the podcast. I was just thinking about what I call him in the book. I think I call him Dylan. I don’t remember. Whatever, you read the book, it’s really good.

You’re gonna learn about this whole story. But I was with this guy who was my relationship that I was in before I met my husband, Chris. And I fell in love immediately. He was my first love. He was the first person I ever had sex with. Like, I had hooked up with some people before him, but it was the most intimate, like, sexual experience of my life. I had never been in love as an adult.

I had never been told as an adult, I love you. I had this like 16-year-old romance where I literally thought I was gonna marry him and he broke up with me telling me I was too much. Again, full story in the book Thank You More, Please. I was with this guy as an adult. I was like 25, I believe, and we fell in love very quickly. About two months into the relationship, we decided to go to Paris together. It’s what I thought that a credit card was made for—did not have a dollar to my name. Still paying that off.

LOL to decisions made when I was 25 that still come around to talk about self-trust. At the time, I thought I trusted myself. I thought, this guy is in love with me. I want to go on this trip. Let’s go, let’s go. Like, spending money, money is energy, look, whatever. Go to Paris with him. We’re sitting on the Seine, okay? And I’m looking on the Seine and I’m like, oh my God…

I’m so grateful to be right here with this guy that I love. He loves me—he says he loves me. We’re in this relationship, we’ve committed to each other, we’ve decided to be monogamous. I’m like, what a gift, okay? And you look—his, the blood drains from his face. He looks at me and he says, Lily, I have realized and I’ve known for a long time actually that ⁓ I can’t be in a relationship unless it is open.

And like I say in the book, like I say on this podcast, non-monogamy is an option for a lot of people that they love, that serves them. I knew in my body that it was not the right decision or relationship style for me. It was actually something that was very activating for me as someone who felt they’d never been chosen. And I know that that’s a thought—that non-monogamy means you’re not being chosen. That’s a thought, not a fact. However, at the time I really needed this relationship structure of monogamy to…

build a new romantic relationship with somebody, as I had never built one as an adult before. That’s just what I needed. And I knew that. I knew that. That self-trust was talking to me, screaming, no, no, Lily, this is not right for you. I don’t like this. This is really hurtful that he would bring this up on our first night in Paris, when we’ve spent all this money. I think I paid for most of the trip. I think that—right?—it was this dreamy, like I had always wanted to go to Paris with

somebody that I was in a relationship with, and then he tells me this information. Blood drains from my face. My body is screaming no, no. And what did I do? I said to my body, saying no, I said, you must be wrong. You must be wrong because nobody else wants to be with you. You must be wrong because nobody else has wanted to be with you.

So why would… Why would you be right about this? Why would you… In my head, I was like, you need a relationship to prove that you’re worthy of one, Lily. So buckle in for something that you want, right? You want a relationship—even if it’s not the structure that you want, it’s a relationship. You are in love. So I had this self-trust voice—no, this fierce voice. And I said, wrong, you’re wrong.

You’re wrong, Lily, for wanting what you want. I shrunk myself and my needs for fear that what I want didn’t exist. And I wish—looking back years later, makes me kind of want to cry—I wish that in that moment… I mean, that was the beginning of months and months and months and months and months. I was with him for about a year total. That was—10 months later we would break up, but that was the beginning of the next 10 months of crying every day, of misery.

Of trips together that felt so out of alignment and felt so difficult and hard. I wish that I had in that moment in Paris looked at him and said, okay, I hear you. I hear what you want. You know what my self-trust is saying? It’s not aligned with what I wanted. Didn’t even have these words. ⁓ I wish that I had said, doesn’t sound aligned for me and I wish you the best. And I’m gonna go…

and you can stay in that apartment that we rented and I’m gonna go get a hotel. I wish that—and I’m gonna have a great fucking week in Paris. I wish that I had said that. What a badass, boss, main-character-energy thing to do if I could have said no and gone on and had like a fantasy week in Paris by myself. And I didn’t. And I stayed with him for 10 more months, and it was miserable.

And he couldn’t meet any of my needs. And turns out, non-monogamy to him meant lack of accountability, lack of structure, ⁓ lack of communication, which I had done. Y’all know I’m type A. I did so much research on non-monogamy and the different forms of it. And I had defined what was right for me in non-monogamy. I said, I want this kind of non-monogamy. I want to be your primary partner.

I want—I didn’t yet know about like hierarchical structures of relationship, whatever. Like, I just did my research at the time and was like, here’s what I think would work for me. And he agreed. And then none of the conditions were—none of the communication preferences were met. None of the follow-up was met. ⁓ And in fact, I felt like a burden on his life and I stayed for 10 months. There were many times where I thought,

This means you can’t trust yourself, Lily, because look, you were in that bad relationship. But now, years removed, I see that it wasn’t that I didn’t have self-trust. It was that I didn’t listen or act on it. So it might be true that I knew what I wanted then. I knew it wasn’t right for me then. I made a choice that I wouldn’t make again today. Welcome to being human.

I’m not gonna use that as a weapon against my self-trust any longer—that’s what I realized a few years ago. I’m not gonna let that define whether or not I get to trust myself in this life. Did I make a decision? Was I with somebody that I wouldn’t be with ever again? Yeah—human. That’s human. How human of me. In the words of Kara Loewentheil from her book Take Back Your Brain. So good. So maybe you’re not trusting yourself because you haven’t been in a relationship.

And you think, there must be something wrong with me that I haven’t attracted someone by now. Maybe that’s you. And if that’s you, then I would counter with these questions—these high-quality questions: What if you just haven’t met your person yet? What if other people in your life have landed in a relationship not because they’re better than you, but because they landed in a relationship for whatever reason—maybe they met their person, how great. What if they settled?

Bummer. Right? I hope for everyone in a relationship that they’re in the best relationship of their life. But I know that a lot of people, because of societal pressure, because of internalized pressure, because of biological-clock pressure—for whatever reason—have landed in relationships that they wouldn’t want for their future. Maybe you just haven’t settled. Period. What if you’ve been building a life that you love and you haven’t experienced everything that you’ll ever experience in your life yet? Maybe there’s more to come.

I want to also mention that you probably don’t have the skill of self-trust yet because you were raised, like all of us, in a patriarchal, racist, capitalist, homophobic, transphobic, ableist world. Of course you didn’t learn self-trust. Of course you were taught to outsource your agency and your decision-making to someone else or something else that knew more than you, quote unquote. I think that from the work that I’ve done over the past

(let’s just say) 10 years with the matchmaking included, seven–eight years with Date Brazen—about every single person, I’d say 99.9% of people—know what self-trust feels like and sounds like in their body. And the practice is then about acknowledging it and acting on it, and doing so imperfectly. That’s the skill set. It’s not that somebody else has self-trust and you don’t. It’s that you’re not yet

practiced at acting on what your body is telling you. You’re not yet practiced at listening, acknowledging, giving yourself permission, and then imperfectly acting on it.

That’s the skill-set gap. That’s all that it is. And it’s learnable. And I wrote about it in my book Thank You More, Please. I’m gonna go to page 140 and read to you about this because I think that it really will resonate. So if you have been listening to the podcast episodes in the past few weeks, we’ve been focusing on the skill of main-character energy, which I have defined as three skill sets beneath the umbrella skill of main-character energy:

Number one: self-permission—giving yourself permission to want what you want.

Number two: self-trust—which is where we’re focusing today.

And number three: massive messy action.

So here’s page 140 about building main-character energy. Specifically, this chapter is about in-person dating, but it can be applied to literally anything. Let’s be real. You have a great gut instinct. Whether it’s loud or soft, it’s there. What most people are lacking, especially in their love lives after years of disappointment and false starts,

is the skill of acting on that gut. Maybe you’re at a jazz show and the drummer keeps making eye contact with you, sexy, and aside. You know that there’s a flirty vibe happening and a part of your gut says, go, say hi, give them your number. But instead, after the show is over, you avoid more eye contact, ask for the check, and run out of there faster than you’ve ever had before. There are a zillion reasons why you might not acknowledge or act on your gut. Maybe you were taught that you were untrustworthy.

Maybe you’re healing from trauma and you’re just getting back in touch with that little voice inside of yourself. In this patriarchal, racist, homophobic, transphobic and ableist world that we were raised in, you probably were actively told to outsource your trust to someone or something else that held greater power, wisdom or unearned privilege. That’s why building self-trust is so fucking hard.

Whenever I talk about self-trust in your dating life, I always get some form of, but Lily, I trusted myself and I got into a terrible relationship, or I’ve never trusted myself in a relationship, or I’ve never been in a relationship before. How could I trust myself in my dating life? Self-trust feels high stakes for most people I talk to, and that makes sense. You are the only person that you’re born with and that you die with. You wanna trust yourself that you can drive in the right direction.

In most of these panicked questions underneath the surface, I hear the assumption that self-trust is all or nothing. Either you have it or you don’t. Either you were taught it or you weren’t. Either you are or you aren’t trustworthy. By now, you know how I feel about either or statements. They suck. In Daring Greatly, Brené Brown describes the act of building trust like this:

Trust is a product of vulnerability that grows over time and requires work, attention, and full engagement. Trust isn’t a grand gesture. It’s a growing marble collection.

I believe the same goes for how you can build self-trust in your love life and your decision-making. It’s built in small moments, piece by piece, choice by choice. Having an instinct, listening to your body, and taking messy, imperfect action is the skill

of self-trust. It takes practice to master. But creating a thriving life—I say love life in the book, but I’m talking about your whole fucking life—but to create a thriving love life and life, especially in person, you must learn this skill. One of my favorite thoughts is I’m doing the right thing when I trust myself. What would your love life be like? What would your life be like if that felt like the truth?

So here’s how to build it. Here’s how to build self-trust from the deficit that you’re noticing. Not a problem, just human. How to build that skill of self-trust and acting on it.

Number one, you gotta decide to learn something new, period. You don’t know everything yet, okay? That may come as a shock to my high achievers out there. You don’t know everything yet. And that’s okay, because you’re human. Practice the thought, I’m learning how to trust myself. Instead of that all or nothing.

Practice the thought, I’m learning how to trust myself. And then from there, you need to start a lot smaller than you probably are thinking you need to start, right? Because what can happen with building a new skill set, especially for high achieving feminist humans who probably are burnt out, is that you’re thinking, my efforts won’t be enough, I’ll fuck up, I’ll just end up in the same cycle over and over again. You’re trying to go too big. And instead you gotta start really small, okay? Start really small.

Are you going to the bathroom when you need to go to the bathroom? Are you feeding yourself when hungry? Are you reaching out to a friend when you need to? Are you closing your computer when your eyes start burning? Because you need a rest from the lights. Are you noticing what you need in the moment and taking small actions to get your needs met? That is building

self-trust. Even those tiny, tiny things. And I’m imperfect at this. There are times when I will sit at my computer and think, I can eat in 30 minutes, I can eat in 30 more minutes after that. I’m ⁓ I’m so addicted to my work sometimes. And then I think, God, Lily, why did you do this again? You’re hungry and you’re hangry now because you didn’t listen to self-trust and you didn’t act on it. Blah, blah, blah, lashing, lashing, lashing. And then it’s about, I forgive myself. How human of me,

evolving. This is all in progress. So to get like aware of your needs and start building the self-trust on that like baseline level, it requires a skill that I’m calling needs granularity. Needs and wants granularity. I may come up with a different

to describe it at another time. But that’s what I’m calling it today. Needs and wants granularity. I’m inspired for this by the work of Dr. Lisa Feldman Barrett, who coined the term emotional granularity, which means that the more emotion words you have to describe your experience, the more easily you’ll move through that difficult emotional experience, right? So if you were having a moment of like, my God, I’m overwhelmed or whatever, you’d look at a feelings wheel, name the feeling. And this is, you could do without a feelings wheel, but this is how I’ve done it.

Look at a feelings wheel, name the feeling that you’re feeling, say, God, I’m feeling shame. God, I’m feeling overwhelmed. God, I’m feeling anxious, whatever it is. Just even naming it helps to let it pass. Feelings are bodily functions designed to flow.

So getting granular with your needs and wants actually is a practice. Noticing them in the moment and naming them is a practice. So when you notice that you’re hungry or you need to close your computer or you need to go on a walk or whatever, notice it.

take action for what you want, and then say thank you more please. No win is too small in the process of building self-trust to release overthinking.

So let’s give an example for if you’re overthinking, if you’re in a spiral thought pattern. Let’s say you blessed and released somebody and you are unsure of that decision now

and you’re backtracking in your head, what did I do? Did I do something wrong? Did I exhaust all options? Did I ask all these questions? Maybe I could have made it work. ⁓ maybe I released the wrong person, right? Acknowledge that you’re overthinking. Woo, I’m overthinking.

What’s your need or want? Probably to know that you made the right decision for yourself. To know that you, because underneath it is the fear that you’re going to die alone, that you made the wrong decision, that you’re never going to find anybody, that setting a boundary means that you aren’t going to find somebody. Okay, so if you can run through, am I hungry? Do I need to drink a water? Do I need to go to the bathroom? Run through your physical needs. Then emotionally,

Maybe you need to talk about it with a friend. Maybe you need to journal about it. Maybe you need to practice self-compassion, right? Notice your overthinking and notice the need beneath it, the need for warmth, for comfort, for clarity, and then act on that need. You can do it.

And then after addressing that need, whether it be physical or emotional, you can then have more agency and more availability to make a next decision that

will be in your best interest. Because if you’re overthinking a bless and release, you’re ultimately thinking I made the wrong decision. Maybe you just need to like notice a need that you have, notice a want that you have for clarity, do a self-compassion. Of course I feel this way. Of course I’m struggling with this. Of course I think there’s a right and wrong decision. I just want to find a partner and I haven’t found one yet and that can be really tough.

both and it might be possible, here’s a thought to pass along for that overthinking scenario. It might be possible that I was picking up on important information. It might be possible that I make good decisions. It might be possible that I haven’t met my person yet. And that’s hard sometimes, and that’s okay, because I’ve now opened up more space for the right person to come in.

then you like acknowledge it, say thank you more please. I’m meeting my own needs. ⁓ I’m listening to my gut. I’m listening to my body. I’m acting on it, right? I’m releasing so much overthinking in place of, I’m replacing that with some more self-trust skills. I’m learning this skill, doing it messy. My friend Gina Knox says, raindrops make oceans. These small tiny steps, noticing overthinking, slowing down, taking a deep breath, practicing self-compassion or

noticing a physical need, acting on it, thank you more please, these small steps—raindrops make oceans. Do it messy, messy, messy.

Then the next step, after you take these small baby steps and say thank you more please, the next step is the high-quality questions. Where is self-trust calling you to step into your power, to believe yourself, that you exist on this earth and that you get to create a life that is more epic?

that is more aligned, that is more powerful. Where are you currently caregiving? Because you’re afraid no one will show up for you. That gets back into self-trust too. Building that next skill of self-trust is noticing, where am I caregiving? Because I don’t currently trust myself and my worthiness. Where am I people pleasing? Because I don’t yet trust myself and my worthiness.

Where can you start believing? How can you start believing a baby-step version of the thought that an awesome person will want to be around me? Awesome people want to be around me? Maybe the baby-step thought: it might be possible that people want to be around me, that people find me awesome too. It might be possible that I can trust that I’m enough.

It might be possible that I’m learning how to trust that I’m enough. It might be possible that I’m learning the skill of self-trust and that it’s gonna pay off big time, right? Don’t try to toxic-positivity your way into self-trust, it’s not gonna work. Choose baby steps, okay?

And you can apply this framework to noticing your self-trust gaps and starting to fill them with baby-step actions and baby-step thoughts. You can apply this to your love life, your work life, your friendship life, your home life. I’m here asking you: where is self-trust asking you to take

to a bigger stage, to take up more space with what you want and who you are, asking you to believe that you deserve to exist on this planet. And maybe you’re worthy of getting more of what you want. Maybe you’re worthy of deeper relationships. Maybe you’re worthy of more boundaries. Maybe you’re worthy of showing up for yourself more.

Self-trust, imperfectly done and consistently practiced,

feels like more calm, feels like more it’s all working out, more expectation of imperfection instead of expectation of perfection. Sounds like more of I get what I want, I might get what I want.

By the end of main character life mastermind, the last round, clients were consistently every single week practicing the thought and really seeing the impact of this thought: I get everything that I want, period.

Because they were building such strong self-trust with messy action, noticing what was happening in their body and acting on it, getting their needs met, triaging support for themselves, that they really started believing and started living: I get everything that I want. It was so powerful.

What if you weren’t fundamentally broken or flawed? What if you were just a human on this earth who was about to or was transforming?

Last Cultureista’s podcast is one of my favorite podcasts. It was like last year or the year before they were talking about their Charizard era. I don’t know much about Pokémon, but I remember the Charizard Pokémon, and it’s this fiery thing. I’m not gonna pretend like I know what I’m talking about, but Pokémon go from little tiny babies to then the medium versions to then the big boss versions who are more powerful.

This is just your Charizard era of growing into

a more essentially you, more essentially powerful, more essentially self-trusting version of yourself—to not only attract the right partnership romantically, but to have a more easeful, epic life, to have more connected and intimate and reciprocal friendships, to start dreaming of what else could be in your career life if you’re feeling stifled or stuck, to imagine what it would be like to have more boundaries with people in your life who are currently crossing them,

to imagine what it might be like to live a life by your own fucking design as much as possible. This self-trust step is just one of three steps of main character energy: permission, self-trust, massive messy action. I talked about all three in this episode, really.

This is powerful life-changing stuff. I hope that you today will identify just one little baby step, baby area where you notice a self-trust deficit and you choose to start

building the skill of self-trust by noticing what you need, giving yourself permission to need that thing, taking small actions to get that need met, and then celebrating it. And that cycle will allow you to release overthinking as you practice. It will allow you to notice your anxious rumination and to start relieving it, releasing it step by step.

You’re still gonna have moments of overthinking. You’re still gonna have some anxious rumination. You still might have things in your life where you’re like, shit, I wish I would have made different decisions. But you’re not gonna use those things as a weapon against your future self-trust anymore, I hope.

So that’s the imperfect episode on self-trust.

Your main character energy is calling and let’s fucking go. You’ve got this and I’ve got your back. I’ll talk to you all next week.