On Reinventing My Life in My 40s, Becoming a Stepmom, and Building a Second Act — with Aaron Leatherbarrow

Today I'm talking about what it looks like to honor the parts of yourself that make you, YOU, even when life is changing rapidly. Relationships, kids, moves, career changes—they can all shift us so deeply that we can lose ourselves if we aren't careful. Join me from the living room in my historic Southern home for an intimate and honest conversation about how to honor the woman you've always been and make room for the woman you're becoming. Remember this: you're allowed to change your mind. You're allowed to want different things than the people you love. You're allowed to have something that's just yours. And you're allowed to keep becoming without leaving yourself behind. PS - If you're in New York on August 20th, I'm hosting an intimate champagne dinner for six women. Bring me your book idea. Your manuscript. Your Substack. Your author brand. Your publishing questions. The creative business you're trying to build. The thing you can't seem to figure out on your own. You'll get my eyes on it. We'll talk about what's working, what isn't, what I see for you, and what I think your next move should be. I know some of my biggest shifts have happened that way. Over a fabulous drink at a fabulous table with fabulous women. Sometimes you just need the right environment to help you think bigger. I'd love to create that for you. Grab your ticket here: https://caraalwill.thrivecart.com/champagne-with-cara-new-york-city/

What if the sentence that changes your life is the one you almost didn't publish? In this episode, I'm sharing the story of how a single sentence from an old blog post unexpectedly ended up on a billboard in Europe, and why it completely changed the way I think about creativity, publishing, and trusting your work. If you've been sitting on an essay, a book idea, a Substack post, or even a single paragraph because you're waiting for it to be better, this episode is your reminder that you don't get to decide which piece of your work will resonate with someone else. Your job isn't to predict the outcome. It's to keep showing up. By the end of this episode, I hope you'll give yourself permission to stop overthinking, start publishing, and remember that one honest sentence has the power to change everything. 💖 Your homework: Before you go to bed tonight, write one sentence that feels true for you. Let it be unedited, imperfect. And don't delete it! Sit with it and see where it leads you. You have no idea what it might become. Want to write with me? ✨ Substack Queen is my five-week mentorship for writers who are ready to publish consistently, find their voice, and build a writing practice they actually love. Join us here. Or, if you're looking for focused, one-on-one support, I have a limited number of Substack Power Hour sessions available. Grab your spot now.

Today on the show, I'm joined by my fiancé, Aaron Leatherbarrow, for one of the most honest conversations we've ever had. We talk about what it's been like to reinvent my life in my 40s—from leaving New York and becoming a stepmom to navigating a blended family, building a creative life together, and redefining what a healthy relationship looks like. We also get into homesickness, identity shifts, separate beds, afternoon sex, and why the best relationships leave room for both people to keep becoming who they are. 🖤 If this conversation resonated with you, you can find more of my writing on Substack  🖤 Want more from Aaron? Check out his new private audio drops  

  Today's episode is for anyone who's ever fallen in love, ignored a red flag, or romanticized someone who absolutely did not deserve it. I'm joined by writer and author E.M. Gallagher, whose memoir Ugh. Anyway… dives into love, heartbreak, ambition, and the beautifully questionable decisions that come with dating in New York City. We published this book through my imprint, Pink Ink Press, and it's already building a cult following. In this conversation, we get into: What it really takes to write about your exes (and actually publish it) The line between love and delusion Writing through heartbreak vs. writing after it Navigating real people on the page How New York shapes the way we love (for better or worse) What happens when you finally tell the truth about your life This one is honest, funny, a little chaotic...and very real. If you've ever thought, "I could write a book about my exes"… this might be your sign. Get the Book Ugh. Anyway… by E.M. Gallagher — available now on Amazon + Barnes & Noble Connect with E.M. Instagram: @emgwritingthings Substack: emgallagher.substack.com Connect with Me Instagram: @thechampagnediet  Website: https://www.carasaysitall.com/

In this episode, I'm joined by my good friend Amanda Frances for a real, unfiltered conversation about what it actually looks like to become an author today—and why self-publishing is no longer the "alternative"… it's the power move. Between the two of us, we've sold hundreds of thousands of books, built global audiences, and turned our writing into real businesses. And at one point, we both had the same realization: We don't need permission. In this episode, we're pulling back the curtain on the publishing industry, breaking down the myths, and showing you what's actually possible when you decide to do it your way. If you've been thinking about writing a book, sitting on an idea, or waiting to be chosen...this is your sign. In this episode, we talk about: The biggest myths about traditional publishing What book deals really look like behind the scenes Why self-publishing gives you more control, ownership, and income How to turn your book into a long-term asset (not just a one-time project) The identity shift required to become a visible, paid author What to do if you want to start writing your book now This episode is for you if: You have a book idea you haven't acted on You've been waiting for a publisher, agent, or "right time" You want to build a brand, business, or platform through your writing You're ready to stop playing small and actually put your work into the world Ready to become a self-published author? If this episode spoke to you, Self-Published was created for exactly this moment. Inside, you'll learn how to write, publish, and sell your book—on your terms. https://amandafrances.com/self-published/

The internet doesn't need more content. It needs more voice. It needs more SOUL. It needs people who know how to tell their story in a way that moves peoploe. Because when people are moved, they create movements. In today's episode, I'm digging into why your voice is your biggest business asset as an entrepreneur and how you can make yours stand out in a sea of AI-soaked posts and trends. If you've been thinking about starting a Substack, writing a book, or using your voice to grow your infulence, this conversation is for you. Join Hot Girl Writing House Here: https://www.carasaysitall.com/writing-house

It's time to stop glamorizing the things that are secretly destroying you. In this episode, I'm talking about the seemingly harmless habits, personality traits, and lifestyle choices we defend...even when they're keeping us stuck. Wine culture, exhaustion as identity, staying where it's comfortable, calling chaos passion. Many of us are telling ourselves pretty little lies about the way we're living and wonder why we're not reaching out potential. If you're ready to explore the "aesthetic" or glamorous ways you may be subconsioculy sabotaging yourself, this one's for you.

Six months ago, I burned down my old life. I left everything I ever knew in New York City and headed to Jacksonville, Florida. For love. For a fresh start. And for the chance to meet a new version of myself. But here's what nobody tells you: the move is the easy part. The indentity shift is brutal. In today's episode, I'm talking about the messy middle, the terrifying limbo that holds you hostage as you step into your new era. It's definitely not all sunshine and champagne, but if you navigiate it the right way, it's always, always worth it. If you're in-between two versions of yourself right now, this one's for you. P.S. - Join Hot Girl Writing House here. P.P.S. - Read my Substack here.

Sometimes the hardest person to be honest with is yourself. In this episode, I'm sharing the story of how I went from a $5,600-a-month luxury Manhattan apartment and endless freedom…to packing up my life and moving to Florida to step into the love, family, and future I didn't even know I wanted. It's about recognizing when the version of you you've been clinging to, no matter how glamorous, independent, or accomplished, has expired. It's about ghosting the old life that no longer fits, and having the courage to step into the one that's calling you. We'll talk about starting over, rewriting your story, and why telling yourself the truth will get you to your next era faster than anything else. If you've been feeling the pull toward something different, something bigger, this episode is your permission slip to stop fighting it and finally own what you really want. ✨ PS: Enrollment is open for Literary Queens, my signature storytelling workshop for women ready to own their voice and write their most magnetic stories. Join us here. 📖 For more stories like this, find me on Substack at Cara Says It All → https://caraalwill.substack.com

It's the episode you've all been waiting for… In this raw and unfiltered conversation, Aaron and I sit down to share the full story of how we broke up (more than once), how we found our way back to each other, and how we ended up engaged. We open up about: • Why our relationship ended and what finally brought us back together • The healing work we both had to do • Aaron's reaction to reading about himself in my book • What dating long distance (and in our 40s) taught us about real love • The moment I knew we were ready • Our proposal story (!!) • Why men commit, "if he wanted to, he would," and all the nuance in between PLUS: the urgent care trip for Viagra visit (yes, really lol), our blow-up fights, our mind-blowing makeup sex, the tears, the laughs, and the one moment that changed everything. It's messy, romantic, honest and hilarious. This is our plot twist. And we're so glad you're here for it. 💌 Want more of the story? Read The Plot Twist Diaries on Substack and grab my latest book, Don't Do Anything I Would Do.