“I read your latest newsletter.”

If you write one of these too, you may be familiar with the sinking feeling a statement like this evokes. What’d I do now? Am I in trouble? Once, someone called me in tears about something I’d written in the Maven Game…

“When I read it, I get the impression that you’re not too worried about the point you’re making,” my friend continued.


But this wasn’t just a bit of apropos-of-nothing cruelty at a socially distanced backyard picnic. My friend reads a lot in the realm of business and advice. Much of what he finds there is so focused on its agenda, on making its point, that it becomes a true chore to read.

“I’d rather have good writing that’s a little bit pointless,” he concluded.

In a perfect world, I’d strike a balance between the two. But I’m OK with a slight tilt in the direction of readability, particularly since my day job leans so heavily in the other direction. My clients have no patience with pointlessness. Justifiably! They have book contracts and agents and editors and things kind of have to line up. So I reign myself in, keep myself on task, drive toward that conclusion and subconclusion and subsubconclusion. Thematic unity. Consistency. Coherence. It’s exhausting. The mind is discursive. It resists.

This is why I love shows like James Burke’s Connections, movies like My Dinner with Andre, books like Moby-Dick. (I know, I know. There are no shows, movies, or books like these. It’s sad.) Take me on a ride. Digress. Life’s too short to hew so closely to the outline. The brain itself is a web of odd and unexpected connections. The best writing helps us form new ones.

I always tell authors: the reader is both more intelligent and less knowledgeable than you think. You will have to explain concepts that seem fundamental to you as an expert. But as long as you do so, the reader will follow you almost anywhere—as long as you keep things interesting along the way.

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