How She Built a Full-Time Creative Business on Substack, After Rebuilding Her Life
Five years sober, 24K+ subscribers, and the life Olivia Wickstrom never thought was possible.
This is the companion article to the latest episode of MONSOON SEASON—a five-minute read capturing the biggest ideas, memorable moments, and key takeaways from the conversation.
▶️ Listen or watch the full episode wherever you podcast
About the Episode
How 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?
Last Thursday, 161 people joined us live on Substack for this conversation with Olivia Wickstrom, a full-time writer, Substack coach, and the creator behind Petal + Hearth. Over the past year, she’s grown her publication to 24,000+ subscribers, built a community of 700+ paid members, generated more than $56,000 a year through Substack alone, and now helps writers around the world build sustainable creative businesses through her coaching and courses.
But none of that is where this story begins.
It begins in Portland, hopping between notorious strip clubs for a college magazine assignment. It winds through addiction, moving back into the apartment behind her grandparents’ house to get sober, and slowly learning how to become someone she could finally trust.
“Everything I have today, the emotional maturity, the relationship, the life in France, the stable business, the financial freedom. It’s all because of my sobriety.”
From there, we move into the practical side of building a creative business. We unpack the slow burn of growing on Substack, why discoverability matters just as much as good writing, the biggest mistakes new writers make, and how to build something that supports your life instead of consuming it.
This isn’t just a conversation about Substack. It’s a conversation about rebuilding your life from the inside out, and a reminder that the life you want often begins on the other side of the hardest season you’ve ever lived through.
*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've been posting for months, and you're continuously doubting yourself.
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 aligned.
You’ve ever wondered whether it’s too late—or whether it’s even possible for you.
3 Key Takeaways
If the things you wanted had worked out, you wouldn’t be here.
One of my favorite moments in the conversation is when Olivia reflects on the relationship that ended, the digital nomad coaching business she poured herself into, and all the versions of her life she thought were supposed to happen. At the time, each ending felt like failure. Looking back, they were redirection. Had any one of those plans worked, she never would’ve built the life she has today. It’s such a beautiful reminder that sometimes the thing we’re grieving is the very thing making room for what’s actually meant for us.
Becoming the main character isn’t about confidence. It’s about authorship.
Social media has turned “main character energy” into an aesthetic. Olivia offers something much more grounded. It’s the willingness to stop living a life someone else wrote for you. She assumed adulthood would follow the familiar script—partner, marriage, house, children—until sobriety gave her enough space to ask a different question: What do I actually want? Some seasons you’ll feel bold. Other seasons you’ll barely recognize yourself. Neither determines whether you’re the main character. You become one the moment you start making choices that are actually yours.
Great work deserves to be discovered.
As someone who spent fifteen years in creative direction and brand marketing, this part of the conversation lit me up. We spend so much time questioning our talent when, often, the real problem is clarity. Olivia reminded me that discoverability isn't about becoming more generic. It's about becoming more unmistakably yourself. Your writing can be brilliant, but if a stranger can’t tell who you are, who your work is for, or why they should care within a few seconds, they’ll keep scrolling. That’s not a talent problem. It’s a communication problem—and one you can absolutely solve. She dives into practical tips in the episode.
"If the things I wanted would've worked out, I wouldn't be here."
— Olivia Wickstrom
Meet Our Guest
Hey there! I'm Olivia, a full-time Substack writer, originally from California, now living in the south of France. My publication, Petal + Hearth, explores life abroad, what I dub main character energy, and what it really takes to build a creative business you love. When I'm not writing, I'm coaching other writers on how to grow their own Substack publications. And outside the "office" I'm almost always cafe hopping, reading, or dreaming up my next creative project.
Connect with Olivia:
✨ Website
✨ Substack
✨ *NEW* Course: How to Take Your Substack Full-Time
I ask every guest to choose a song they're currently obsessed with, and I listen to it on repeat as I prep and research for our conversation. Olivia's pick: "Lost Boys" by Phoebe Bridgers.
FLOWERS 💐
FLOWERS is a signature MONSOON SEASON tradition. Before each interview, I reach out to someone who knows my guest best—their biggest cheerleader, closest friend, or loved one—and invite them to give them their flowers.
This week’s flowers came from Olivia’s mom, Tamara Wickstrom.
“The nurses were the first to see it. They kept telling us, ‘This one’s a fighter.’ And she was... Being Olivia’s mom has meant the big stuff comes, and my heart drops, and I worry. And then I watch her find her way through it and come out the other side better than before. Every single time.”
It was one of the most emotional moments of our conversation.
To hear the full message—and Olivia’s reaction—you’ll have to watch the episode.
About Your Host
I'm Asa Yee, a Bangladeshi-American meditation teacher, writer, and host of MONSOON SEASON.
Before this chapter, I spent over 15 years in creative direction, editorial, and brand marketing, helping shape stories, build brands, and lead creative for some of the beauty industry's most recognizable companies. Today, I bring that same lens for storytelling, identity, and human nature to conversations about self-mastery, culture, creativity, and the courage to build a life on your own terms.
I believe vulnerability is the most powerful thing we have. Not as a tactic, but as the actual portal to building a life and a business that feels like yours. The more honest we are about who we are and what we struggle with, the more we give other people permission to do the same. That is the whole philosophy behind everything I create.
Born and raised in Queens, NYC. Living in Charleston. I am a cinephile, a mango connoisseur, and a chai addict. So glad you are here — make yourself at home. 🤎
Stay soft,
🥭 Asa