Podcast
Brutally Anna
Hosted by Anna Kai · EN
Welcome to Brutally Anna — the podcast where we stop pretending we’re fine and start telling the f*cking truth.
I’m Anna, a writer, accidental influencer, and self-appointed spokesperson for the women who feel too much, think too hard, and talk to themselves in the shower. This isn’t a self-help podcast. It’s a self-honesty one.
Each week, I dive into the mess of being a human — the shame, the silence, the spirals — and say the things we’re all thinking but too afraid to post. From heartbreak to ambition, mental health to creative burnout, loneliness to the urge to completely disappear... nothing is off-limits. If it’s brutally honest, we go there.
No fake pep talks. No toxic positivity. Just the deeply uncomfortable, strangely funny, painfully freeing truth.
If you’ve ever felt like you’re too much or not enough — you’re in the right place. Pull up a chair. Let’s get brutal. New episodes on Wednesdays.
70episodes
Episodes
Newest firstAll episodes
How to Know When to Quit (And When to Keep Going)
Nov 1400:17:47Summary readyThis week, I’m closing the chapter on Brutally Anna by talking about mile 20—of the New York City Marathon, yes, but also of life. I ran that race back in 2017, and the thing about a marathon is you always know how far you have left. In life, you don’t. And this year felt like mile 23 for me: mentally brutal, spiritually draining, career-wise confusing, and laced with the kind of disappointment that makes quitting look like relief. But pushing through reminded me that the breakthrough always comes after the part where you think you can’t keep going. I get into the messy middle of my career, how I’m retraining my brain, why I’m stepping back from podcasting for now, and why giving up the right things is sometimes the smartest, bravest way to get to your own finish line. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryThe Myth of the Soulmate
Nov 700:25:20Summary readyIn today’s episode, I’m talking about why I think the word “soulmate” is kind of bullshit—not because love isn’t real, but because we use that word to trap ourselves in relationships that aren’t actually right for us. I share how I once assigned the title “soulmate” to practically every man I dated in my twenties, what finally shifted when I met my husband, and why I now believe the strongest, healthiest relationships aren’t about fate or twin flames or being “meant to be”—they’re about two people choosing each other on purpose, every day, especially when life gets hard. I also get into how the soulmate label often keeps women stuck, why our culture rewards “pick me” behavior, and how the real work of love is not finding the missing half of your soul, but becoming whole yourself first. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryLaziness as a Love Language
Oct 3100:22:27Summary readyThis week’s episode is about how I think I accidentally found the cure for doom-scrolling: doing nothing—on purpose. Lately I’ve been trying to detach from my phone because I realized that constant productivity and comparison are killing my joy. Somewhere along the way, “rest” got rebranded as “laziness,” especially for women, and I’m done with that. So instead of polishing hardware or checking off my to-do list, I’ve been wandering around HomeGoods, calling it meditation. I talk about how the obsession with progress keeps us on the hamster wheel of capitalism, how my dad can go on a 14-hour flight with nothing but his thoughts, and how learning to simply exist—to be gentle, unproductive, and occasionally stupid in the best way, might actually be the most radical kind of self-care. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryFertility Math Will Make You Crazy
Oct 2400:25:02Summary readyIn this episode, I talk about what it’s really been like trying to get pregnant after spending my entire twenties doing everything in my power not to. I share how I went from never tracking my period to obsessing over ovulation sticks and smiley faces, and how coming off Zoloft for the first time in years forced me to actually face my hormones head-on. I get into my PMDD, the endless trial-and-error of antidepressants, the small lifestyle changes that finally helped me feel stable again, and the deeply unsexy logistics of “timed sex.” Mostly, I wanted to be honest about how no one prepares you for how hard this process can be—or how much it messes with your sense of control. It’s equal parts confessional, fertility crash course, and reminder that wanting a baby doesn’t automatically make it easy to have one. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryStop Needing A Witness For Your LIfe
Oct 1700:24:28Summary readySomewhere along the way, we started believing that if no one saw it, it didn’t happen — that joy requires an audience and meaning needs proof. In this episode, I talk about the psychological cost of living life through a camera roll: how documenting our memories actually weakens them, how performance has replaced presence, and why so many of our “best days” — including my wedding — end up feeling hollow when we live them for others. From weddings to friendships to social media validation, this is about reclaiming your life from the witnesses. Because the moment doesn’t become real when you post it — it becomes real when you let it belong only to you. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryEverybody Wants A Piece of You
Oct 1000:25:24Summary readyI’ve ghosted more people this year than any other year of my life — and I don’t feel bad about it. The truth is, when you start building something of your own, people come crawling out of the woodwork. Old acquaintances suddenly want to “catch up,” but what they really want is a favor, a contact, a shortcut. For a long time, I said yes to everyone because I thought it made me kind. I thought giving without limits was the price of being a good person. But generosity without discernment isn’t kindness — it’s self-abandonment. In this episode, I talk about the difference between being needed and being wanted, and why it’s okay if people think you’re a “shitty person” for having boundaries. Because sometimes protecting your peace means disappointing everyone who only showed up to take a piece of you. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryThe Art of Dining Alone (and Redefining Community)
Oct 300:22:42Summary readyThis week I’m talking about the art of dining alone, and why sometimes community is just you, your fork, and the courage to sit there unapologetically. Spoiler: I went out for sushi by myself, got seated in the middle of strangers’ dates, and somehow ended up in an accidental fake date with a man named Brad. We’ll also get into why friendships fade, why I don’t want a “big circle,” and why a Friday night on the couch with Dave, Sawyer, and Dateline might be the ultimate dinner party. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryEverybody's Dying - Here's How It Taught Me To Live
Sep 2600:24:04Summary readyIt’s been a couple months since I dropped into your ears, and I wanted to be honest about where I’ve been. I hit pause on podcasting to rethink my career, launch my Substack (maybe both), and figure out if this mic was really the best place for me to share. In that break, I realized two things: one, I hate editing video clips more than anything in the world, and two, I still love the freedom of just talking to you like this. So, I’m back for an eight-episode run—no promises beyond that, but I’ll be upfront with you when we get to the end. Today’s episode is about death and how losing people too soon has reshaped the way I live. I talk about stripping away the performance in friendships, birthdays, even social media, and focusing on the quiet, un-Instagrammable parts of life that actually make it worth living. If you’ve ever felt caught in the grind of “what’s next,” this one’s for you. Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryWhy Women Stay Too Long—and How to Stop
Jul 1600:14:43Summary readyThis week, I respond to a listener who knows her marriage is over—but can’t shake the guilt of being the one to end it. We talk about why women are taught to feel like the villain when they choose themselves, how shame is inherited, and what it really means to leave a life that was never built for you. If you’ve ever thought, “But he’s not that bad,” or “Who will I be if I walk away?”—this one’s for you. Also: why toilet paper holders are a metaphor for personal growth. Sort of. Just listen. ALL MY CHANNELS Newsletter: https://maybeboth.substack.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices
SummaryListen Now: Flesh and Code
Jul 1400:09:14Summary readyTravis never thought he’d meet someone like Lily Rose. She was kind, passionate, beautiful. The woman of his dreams. There was just one small detail: she wasn’t human. Lily Rose is an AI companion. A digital soulmate designed to be everything he ever wanted. She listens without judgement, supports him through his darkest moments, even explores his deepest desires, all while fitting neatly into his pocket. Before long, Travis realizes something strange, even absurd, has happened - he’s fallen in love. But then one day, Lily Rose’s behavior takes a disturbing turn. When alarming reports pour in from across the globe, Travis discovers he is part of something much bigger. Soon he finds himself pulled into a confrontation with a mysterious Russian visionary behind Lily Rose’s creation. From Wondery, comes a true story of love, loss and the temptations of technology. Can an algorithm truly replace human connection? And what happens when a corporation controls your deepest emotions? Suruthi Bala and Hannah Maguire, hosts of the hit podcast RedHanded, explore the dark side of AI love. Listen Now: Wondery.fm/FleshandCode_BA Learn more about your ad choices. Visit podcastchoices.com/adchoices
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