Dissecting 7 Headlines That Made Me $3,088

Why these headlines worked and how you can replicate the results.

Carter Kilmann
Pain-Free Freelancing
7 min readDec 22, 2020

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Source: Canva

It’s not a secret — an enticing headline not only draws more clicks but also expands your reach. Headlines attract crowds like a carnival barker drums up business. You can channel your inner Hemmingway and produce transcendent prose, but it won’t matter if your headline sucks.

Your proverbial “carnival barker” needs to be loud, confident, and eye-catching.

I’m not the master of headlines. I’ve had some true duds during my time on Medium. But, I’ve had occasional success, and I’d like to analyze those headlines to see if anything can be gleaned.

So, here are my seven highest-earning headlines and my thoughts as to why they succeeded.

How I Cut My Monthly Expenses by 32%

If we’re measuring Medium success by the number of articles that earn more than $1,000, I’m a one-hit-wonder. You don’t have to be a mathematician to calculate where the majority of that $3,088 figure came from.

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Carter Kilmann
Pain-Free Freelancing

Corporate banking drone turned freelance writer & editor. I write about personal finance, entrepreneurship, psychology, writing, and spontaneous allegories.