From Free to Funded: When to Launch a Paid Subscription on Substack

For those of us who’ve been writing quietly, steadily, for months—or maybe years—it’s tempting to think there’s a clear signal for when to flip the switch to “paid.” Some magic number of subscribers. A moment when everything aligns.

But after talking to other writers, watching the rhythms of my own list, and studying what works (and what fizzles), I’ve r…