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To Paywall or Not to Paywall? That is the $5 Question

How many of us struggle with doubt? No one will pay for my work. Yes, they will!

Harry Hogg
4 min readFeb 4, 2025
Image: Author — -tell me what you really think, Jenny

Friends, Romans, and newsletter subscribers — lend me your inboxes. I come to you today with a dilemma of Shakespearean proportions. Do I fling open the doors of The Hogg Pen Newsletter like a literary Oprah, screaming, “YOU get a free post! YOU get a free post! EVERYBODY GETS A FREE POST!”?

Or do I slam the gates shut, fold my arms, and declare: “No money, no words.”

This question keeps me up at night (well, that and an ever-growing stack of unread books, but let’s focus). Substack offers two paths: the generous Free Spirit Route or the Monetized Genius Avenue — and I am stuck at the crossroads, clutching my metaphorical map.

The Case for Free: Winning Hearts, Not Wallets

There’s something noble about giving away my words for free, like a modern-day storytelling Robin Hood (except I’m not robbing anyone, and my Merry Men are just me and my cat). Free content builds trust! It says:

“Hey, come on in! The literary water’s fine. Read, laugh, cry (preferably at my humor, not my life choices).”

Starting free means more readers, more shares, and more engagement. It’s the…

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