What I learned sending 3 million emails

Since I started this newsletter, people have now read my emails 3 million times. That’s about 11 years of reading!

What do my best emails have in-common?

I uploaded my best and worst performers to Claude, and discovered my best emails do five things:

1. Grab my reader’s attention early with curiosity and a promise of value

2. Hold attention through the email by telling a story

3. Respect my reader’s time and intelligence

4. Leave them with a simple action they can use right away

That’s four things. (See, I’m holding your attention, because #5 is my secret sauce)

5. Acknowledge and resolve a contradiction

As Claude explained:

"Your readers see gaps between what makes sense and what’s happening. You call out those gaps and unpack them. If you're doing your job, readers feel ‘you’re not crazy’ validation, and get a path forward.”

Those gaps show up in four ways:

1. Acknowledge a tension they live with but haven't named – “A list is not a strategy"

2. Resolve a false dilemma – "OKRs don’t cause problems, they surface them"

3. Address an uncomfortable truth they already suspected – “Save time is not your value prop"

4. Show the hidden structure beneath a messy problem – "How to prioritize the 6 marketing channels"

So, yes, my best work follows a pattern, but it comes from years of obsessively watching teams work through challenges, not a process I could hand off – not even to Opus 4.8.

Simple next step

If you’re trying to develop useful engaging content – acknowledge and resolve the unspoken paradoxes that haunt your audience using stories, not advice.

I hope this helps!