Writing Logistics

Mark Duggan writes about the planning fallacy over on the Pinstriped Bible:

The world is a complicated place full of random chaos and your brain works by grouping clusters of that chaos into an easier to understand model. In my model of the morning, there were only a few things going on.

I am definitely running into that fallacy head on with my writing right now. In my mental model of the morning, I walk my daughter to kindergarten, walk home, eat breakfast, and then write for about three hours until it’s time to go pick her up.

I don’t plan for common but irregular things, like the kids leaving a mess that needs to be cleaned up, or ants invading my kitchen after a rainstorm, or a doctor’s appointment, or an email that needs a quick response, or a news event that interest me, or a friend who pings me and wants to chat.

Nor do I plan for black swan events, like my mom calling me from Sweden last week and telling me that my brother had a stroke. (He’s fine now, it turned out to be a minor one, thank goodness.) I’m 6,000 miles and nine time zones away from that, and it’s really out of my hands and nothing I can do, but something like that completely fills my available mental capacity.

But the one big thing I really don’t plan for in my mental model is the time it takes to think. Just to think things through, make associations, build mental models for solving a problem.

I think this is a particular problem for me because of the kinds of things I like to think about and say and write. If I have a strength as a human being, it’s my ability to think about things more deeply and broadly than others. If I only write about shallow things (hello, Twitter), or pursue something deeply but narrowly (hello, Catfish Stew), I feel like I’m limiting myself. Part of what I want to accomplish in my experiment as a writer is to figure out what is the best combination of width and depth that works for me.

Duggan has a suggestion:

The problem is almost always oversimplification. If you want to know how long it will take to get ready in the morning or how long it will take to drive home during your lunch break, don’t make a list of tasks and guess, time yourself when you do it. Measure the act itself, not your mind’s recreation of a simplified version.

I’m having trouble fitting the writing task into my three-hour window. I need to adjust my model of writing to fit the data. Either I need to get more narrow and/or shallow in what I think and write about to be able to fit my writing into that window, or I need to give myself permission to not publish something every day.

Or a combination. My “Quantum Moneyball” article yesterday, for example, gave people headaches:

Thinking broadly and deeply about something is fine, but probably what I need to learn most is how to do better is to bring that deep and broad thought back into a narrow context so people can relate to it more easily. Because people learn most effectively when that learning is only slightly different from what they already know and believe. As Ben Casnocha recently pointed out, you learn most from people who mostly agree with you:

In order to even have a coherent conversation with someone, you need to share a language, basic values, assumptions, conversational norms. … If these basic table stakes aren’t met — 98% of the game, in my view — there’s no productive conversation to be had.

. . .

Want to learn and get smarter by talking to people? Seek out those who agree with you on 99.9% of things, and then push, push, push at the niche-y, hyper-specific areas of disagreement. It’s not about groupthink; it’s not about confirmation bias. It’s about learning on the margin.

So maybe the model for me is something like this: pursue one deep and/or broad topic per week. If that topic takes me more than one day to write about, so be it, and I won’t publish that day. But then, after that topic is explored broadly, pursue that or other topics narrowly and or shallowly for the rest of the week.

Let’s see how that goes.

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