257. Self-Trust for Anxious Overthinkers: How to stop dress rehearsing tragedy

Laura sat on her dream for years. She had already moved abroad, left her marriage, rewritten her book, built a whole new life in a new country… and yet the next thing she actually wanted to build — a business supporting women after divorce — stayed in a drawer. In this conversation, you'll hear exactly how she went from: • paralyzed by fear of judgment • hiding the work she'd been doing for years • waiting to feel "ready" • thinking she "should've figured it out by now" to owning her CEO energy, talking publicly about her work, pitching her idea in real life, and getting her first clients. We break down the exact moment things clicked, the messy middle, and the main character energy skills that helped her finally do the thing. If you've been circling a dream for months, years, or a decade… this episode is going to open something up for you.   Work with Lily ✨  Main Character Life Mastermind — Applications open now.A 6-month container where you'll choose your main character project, release people-pleasing, build rock-solid self-trust, and take massive, messy action with a community that has your back. The 10-minute application will increase your main character energy on its own. Apply HERE 📚 Read my book: Thank You, More PleaseA feminist guide to breaking dumb dating rules and finding love. Order HERE Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website

In this episode, Abby shares her late bloomer story with so much honesty and clarity. We talk about what it was like to be in her mid-30s, never having been in a serious relationship, carrying a loud "I'm behind" and "I'm weird" narrative, and feeling totally unsure how to talk about her dating history without spiraling. Abby opens up about moving to a new city, trying to date while feeling embarrassed about her experience, and struggling with the not good enough voice that made her avoid connection. She also shares what shifted for her as she started to process shame, build community, and trust herself enough to take up more space at work, in dating, and in her daily life. Inside this episode, you'll hear: how Abby learned to identify and quiet the "I'm weird" and "I'm behind" voice how belonging helped her stop self-isolating and start connecting what helped her ask for what she wanted (down to "I need 25% more texts") how she advocated for herself at work while doing two jobs how she built friendships, community, and eventually a healthy relationship what she wishes she could tell her past self, who felt so far behind This is a powerful example of what can happen when you stop avoiding your desires and start trusting yourself enough to move toward them. Work with Lily ✨ Join the live training: Stop People-Pleasing and Build a Stupidly Joyful Life live training-- December 3rd:  Sign up HERE ✨ Apply to Main Character Life, my 6-month mastermind where Abby did this work — the space to release people-pleasing, build self-trust, advocate for what you want, and go after the life you've been circling for years. Apply HERE ✨ Get my Book — Thank You, More Please, Buy the book + grab your bonus HERE Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website

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 ✨ Main Character Life Mastermind — Applications Opening soon!Sign up for my free training-- Stop People Pleasing and Build a Stupidly Joyful Life-- on Dec 3rd to be the first to apply. RSVP HERE 📚 Read my book — Thank You, More PleaseA feminist guide to breaking dumb dating rules and finding love Order here: https://datebrazen.com/book Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website

Feeling like the supporting character in your own story? This episode is your plot twist. We unpack Main Character Energy (MCE) as a buildable skill set—not a personality type—and show how tending to your needs heals burnout and expands your capacity to show up for the people and causes you care about. In this episode, you'll learn: The 3-part MCE framework: Permission → Self-Trust → Massive, Messy Action Why MCE isn't selfish—it's the power source that fuels your impact (both/and) The tiny tool that changes everything: 10 Seconds of Courage Five rapid-fire ideas to practice 10 seconds of courage today (self-care, belonging, shoot-your-shot) How to stop "best-friend energy" (people-pleasing, perfectionism, over-functioning) and step center stage Work with Lily Free Live Training (Dec 3): Stop People-Pleasing & Build a Stupidly Joyful Life —RSVP HERE Main Character Life Mastermind — Get details + apply (when open) or join the waitlist HERE Main Character Dating — My signature program to build a joyful, self-trust-filled dating life and attract an aligned partnership. Learn more: https://datebrazen.com/dating Get my Book — Thank You, More Please Buy the book + grab your bonus: https://datebrazen.com/book Follow Lily everywhere: 📸 Instagram 📲 Tiktok 📺 YouTube Channel Subscribe so you never miss an episode. You've got this—and I've got your back.

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

Ever catch yourself thinking: "Am I doing enough to find love?" That question sounds productive—but it's usually fear in disguise. Fear that time's running out. Fear that what you want might never happen. In this week's episode of The Late Bloomer Show, I walk you through the 10-step "Am I Doing Enough?" checklist—the one I give my clients when they start to spiral. You'll learn how to: 💗 Practice self-compassion (so you stop hustling for worthiness) 🎯 Create your Essence-Based Preferences 💎 Bring in community and support 🎉 Celebrate yourself like it's part of the plan—because it is You don't need to "just try harder" in your dating life. You need an effective plan that prioritizes your self-trust along the way. Work with Lily: → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book → Learn more about Main Character Dating: datebrazen.com/dating → Learn how to work with Lily: datebrazen.com Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel

Should you wait for the slow burn? Or chase the spark? This question keeps so many late bloomers stuck in overthinking, second-guessing, and dating people who aren't right for them. In this episode of The Late Bloomer Show, Lily breaks down the real truth about attraction and connection, including: The pros + cons of both the spark and the slow burn Why both approaches can lead to wasted time What to focus on instead (hint: curiosity > rules) How to ground yourself with Lily's Date Feedback Compass If you've ever stressed about whether you "knew" soon enough or felt enough chemistry, this episode will give you clarity and freedom. 🎧 Listen now and find out why curiosity—not binaries—is the most powerful dating tool. Work with Lily: → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book → Learn more about Main Character Dating: datebrazen.com/dating → Learn how to work with Lily: datebrazen.com Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel

Dating while struggling with body image fears can feel like an impossible task. In this episode, Lily is joined by Bri Campos, LPC, and body image coach, to explore the idea of body grief—the distress and loss we feel when our bodies change—and how it impacts dating. Together they cover: → The 4 aspects of body image you need to know → Why rushing to "body love" skips over the real healing work → How fatphobia and privilege show up in dating dynamics → Practical tools to move through body grief with compassion so you can put yourself out there and find love in exactly the body you're in If you're a late bloomer who's avoided dating because of how you feel in your body, this conversation will give you the validation, tools, and hope to take your next steps. Learn about Bri's work here→ https://www.bodyimagewithbri.com/ 💥 Want more support? Start here: → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book → Learn how to work with Lily: datebrazen.com Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel

In this powerful live coaching session, Lily sits down with Veronica for a live coaching session—a listener and Main Character Dating client—to explore what it really looks like to start dating again after a painful breakup…while also navigating chronic pain, a disability, and a world that often is deeply ableist. They explore: ✨ How to know if you're really ready to date again after a breakup ✨ Navigating dating apps with a disability ✨ Setting boundaries that honor your body and your bandwidth ✨ Why self-compassion is a dating strategy This episode is full permission to do dating your way. 💥 Want more support? Start here: → Main Character Dating-- closing 10/17/25: datebrazen.com/dating → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel

What do late bloomers most want to know about sex? In this episode, Lily sits down with Dr. Juliana Hauser—sex therapist, TEDx speaker, and author of A New Position on Sex—to answer the top 10 questions late bloomers have about sexuality, intimacy, and pleasure. They cover everything from starting with little or no experience, to disclosing your sexual history (or lack thereof), to navigating body image, chemistry, pain, and more. Whether you're 20, 30, 40, 50+ and wondering where to start, this conversation is a must-listen. 🎧 Listen in now and discover the tools, confidence, and compassion you deserve in your sexual journey. 📖 Grab Dr. Juliana's new book A New Position on Sex: A Guide to Greater Sexual Confidence, Pleasure and Authenticity available now right HERE 💥 Work with Lily: → Main Character Dating: datebrazen.com/dating → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel