How Olivia Wickstrom Took Her Substack Full-Time (And You Can Too!)

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