About this episode

Olivia Wickstrom shares her journey of transforming her Substack from a cottagecore blog into a successful platform through experimentation and strategic changes.

Season 4, episode 3 is here! Olivia Wickstrom didn’t set out to build a Substack. She set out to make affiliate income from a cottagecore blog. What happened instead was a slow, sometimes frustrating, eventually life-changing discovery of what the platform could actually do for a writer willing to experiment. We covered a lot of ground in this one. What we discussed: - How Olivia’s Substack started as something completely different and gradually found its identity across three very distinct content pillars. - The nine months where almost nothing happened, and the specific change in her Notes strategy that finally broke the plateau. - Why she sometimes makes her best, most actionable content completely free, and what that counterintuitive decision does for her paid tier. - How she’s driving major Pinterest views to her Substack and what she’s still trying to figure out about it. - What romanticising your life actually looks like in practice. - The cultural differences between American and French attitudes to work that have subtly started to change how she thinks about her own life. - A brand new year-long series she’s announcing here for the first time, and why it might be her…

People in this episode

Host: David McIlroy

Guest: Olivia Wickstrom

Topics covered

• Substack
• content creation
• affiliate income
• cottagecore blog
• personal projects
• cultural differences

Keywords

• Substack
• affiliate income
• cottagecore
• content strategy
• Pinterest
• cultural differences
• personal projects

Mentioned in this episode

Organizations: Substack, Pinterest

Places: American, French

More episodes of How to Write for a Living

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• 406: Becoming a world builder (with Nathan Baugh) · May 17, 2026 · 46 min
• 405: He deleted every social media account and built a thriving community anyway (with Seth Werkheiser) · May 10, 2026 · 54 min
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• 401: Welcome to Season Four (let's build it together)! · April 5, 2026 · 16 min

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