MONSOON SEASON

Join our cozy Substack community for free guided meditations, daily wisdom, podcast breakdowns and weekly newsletters that I don't share anywhere else.→ https://asayee.substack.comAbout this EpisodeHow do you rebuild your life after addiction? What does it actually take to become a full-time writer online? And why do so many talented people struggle to grow on Substack even when they're creating great work?Today I'm welcoming Olivia Wickstrom to Monsoon Season. Olivia is a full-time Substack writer, coach, and the creator behind Petal + Hearth, now living in the south of France. But before building a creative business around slow living, writing, and helping thousands of writers grow, life looked very different.We begin with a viral article she wrote over a decade ago in college, on Portland's most notorious strip clubs before tracing the path that led Olivia to sobriety, moving back into her grandparents' backyard apartment to rebuild her life, and eventually creating the freedom she once believed was impossible. We also dive deep into Substack strategy, discoverability, creative positioning, and the biggest mistakes new writers make when trying to grow online.This conversation is both deeply personal and incredibly practical—a reminder that the life you want often begins on the other side of the hardest season you've ever lived through.Chapters00:00 | Welcome02:10 | Grounding Meditation04:53 | Introduction to Monsoon Season06:06 | Meet Olivia Wickstrom07:22 | Tarot Card Pull10:18 | Portland Strip Clubs & "Stripparaoke"15:08 | Choosing Sobriety23:03 | A Message to Her Younger Self25:04 | Main Character Energy29:25 | Taking the Leap into Entrepreneurship32:41 | Borrowing Courage37:16 | From Cottagecore to Teaching the World How to Grow on Substack43:05 | Finding Your Three Content Pillars50:18 | The Biggest Mistakes New Substack Writers Make53:35 | Discoverability vs. Talent59:17 | Money, Abundance & Creative Business1:06:36 | "I Want to Live More Than I Work"1:10:33 | Flowers 🌸1:14:20 | Olivia's New Course1:15:16 | Final Thoughts1:16:03 | Outro*This episode was recorded live on Substack on July 9, 2026.This episode is for you if:🫆 You're dreaming of building a creative business but don't know where to begin🫆 You're starting a Substack (or thinking about it) and want to grow intentionally🫆 You're navigating sobriety, recovery, or rebuilding your life after a difficult chapter🫆 You're afraid to leave the security of a job to pursue something that feels more aligned🫆 You want to create meaningful work without sacrificing the life you're buildingWe talk about...🫆 Olivia's unforgettable college story visiting Portland's notorious strip clubs🫆 The moment she decided to get sober and the season that changed everything🫆 Rebuilding her life while living behind her grandparents' house🫆 What "main character energy" actually means—and how to embody it🫆 Why your failures may actually be leading you exactly where you're meant to go🫆 The biggest mistakes new writers make when starting on Substack🫆 Discoverability, positioning, and why packaging matters just as much as talent🫆 Choosing your writing pillars without overthinking them🫆 Building a creative business that supports your life instead of consuming it🫆 Why Olivia's goal isn't to work more—but to live moreConnect with Olivia Wickstrom✨ Website: https://www.oliviawickstrom.com/✨ Substack (Petal + Hearth): https://substack.com/@petalandhearth✨ Instagram: https://www.instagram.com/oliviawickstrom/✨ LinkedIn: https://www.linkedin.com/in/olivia-wickstrom/✨ *NEW* Course: How to Take Your Substack Full-Time: https://substack.com/@petalandhearth/p-203592308Connect with Monsoon Season✨ Subscribe on Substack: https://asayee.substack.com✨ YouTube: https://youtube.com/@asa-yee✨ Instagram: https://instagram.com/asa.yee

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About this Episode

If you've ever felt the pressure to show up the same way every single day, force yourself into formats that don't fit, or follow a system that was never built for you and wondered why you keep burning out, this conversation is for you. Today I'm welcoming Michelle Breana to Monsoon Season. Michelle is a The Rhythm Architect who helps soul-led creatives break free from rigid ways of working and find their own natural inner rhythm. She gets real about the night she deleted Instagram with no plan, just a quiet voice that said you don't have to be here and how that one choice cracked open seven years of healing she didn't know she needed. We get into what it actually means to find your rhythm, why jealousy is data not a character flaw, and the difference between consistency as devotion versus consistency as punishment.

This episode is for you if:

• You've been following someone else's system and wondering why you keep failing
• You've burned out chasing discipline and secretly want permission to do it differently
• You're somewhere between who you were and who you're becoming and the in-between feels heavy
• You're ready to stop performing a version of yourself that was never actually yours

We talk about...

• The night Michelle deleted Instagram, her Saturn return, and why 2019 changed everything
• How to build a healthy relationship with social media without sliding back into old patterns
• Why your resistance to certain formats isn't laziness, it's information
• The borrowed systems problem: why most creatives are running someone else's operating system
• What jealousy is actually trying to tell you
• The difference between devotional consistency and punishing yourself into showing up
• Why knowing your natural rhythm matters more than any productivity hack
• Identity, and what it means to finally take up space unapologetically
• What this audacious season of life is asking of you

Connect with Michelle Breana:

• Instagram
• Substack
• The Rhythm Audit

Connect with Monsoon Season:

• Subscribe on Substack
• Follow Asa on Instagram
• Watch on YouTube

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This week I did the thing I've been too scared to do. Not because the fear left, but because staying stuck finally cost more than the fear did. In this solo episode I talk about what happens when you shoot your shot anyway, the external momentum it creates, and the internal clarity that opens up underneath it. Turns out shooting your shot was never really about the outcome. It's proof you're someone who moves.

Sign up for our newsletter: https://asayee.substack.com/ What if the best way to build your life, business, or creative work is to think less like an influencer and more like an undercover agent? Inspired by the film Dhurandhar, this episode explores vigilance, patience, identity, and the quiet power of moving through the world without needing everyone to know your next move.

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A raw and honest solo episode where I open up about the chaos of building in real time, from repricing my coaching offer and navigating my first hate comment to refining my story and figuring out what is actually on my list this week. 🧡

Join the Monsoon Season newsletter: https://asayee.substack.com/About this episode:We don't want what we think we want — we want the feeling underneath it, and until we learn to name that feeling, we will spend our whole lives chasing the wrong things.

Subscribe to the newsletter on Substack for weekly podcast breakdowns, free guided meditations, and vulnerable weekly newsletters.https://asayee.substack.com/ 💌 About the episode:A dented candle in a cluttered garage looks like trash. Place the same candle in a gallery with intention and it becomes art. The candle did not change. The context did. In this episode I am talking about why so many talented creators and entrepreneurs stay invisible, not because their work is not good enough, but because nobody taught them to build the room. Inspired by the late Virgil Abloh, we explore the difference between perfecting your craft and building the cultural context that lets your work actually land. I share three practical ways to start building your room today, including the What I Am and What I Am Not exercise that will change how you think about your brand, your content, and everything you create.

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The most dangerous place you can be as creator or someone building a personal brand is almost committed. Not checked out, not fully in. Almost. Because almost gives you just enough activity to avoid confronting the fact that you have not actually decided yet.

In this solo podcast episode I am pulling back the curtain on every content mistake I made over fifteen years and what they all had in common. They were all half measures. Posting inconsistently. Creating on platforms I hated. Sharing watered down versions of my real opinions. Spending months on branding before I had said anything worth branding. This one is for anyone who feels like they are showing up but not breaking through.

The half measure is why.

And going full measure is the only way out.

About this episode: I spent decades identifying as someone with zero discipline who could not be consistent. That was my story and I wore it like a badge. This year that all changed. In this solo episode I am pulling back the curtain on what actually made the difference, and it has nothing to do with motivation, willpower, or getting your life together. It starts somewhere much quieter than that.We get into the real reason consistency feels so hard, why starting small is not giving up, what meditation taught me about joyful effort, and the one phrase that changed everything for me: suck but don't skip.If you have started over more times than you can count, this one is for you.Subscribe on Substack for episode breakdowns, essays and free guided meditations: https://asayee.substack.com/ Need more 1:1 support? I coach creatives and entrepreneurs to help clear inner blocks so they can tap into their authentic encoded gifts and build what they were meant to build. Book a discovery call to connect and figure out if we could be a solid match. https://calendly.com/asa-yee/private