Thinking Well

Appreciation for mindful process

I’ve noticed the folks I most admire seem to think well.

This doesn’t mean they’re always right—I think it’s their process I’m drawn to. How they absorb information and apply critical thinking, minding their blindspots, navigating bias and nuance, and how they express the often-complicated perspectives that emerge. I’m compelled by their mindful effort, and their being cognizant of human tendencies, incentives, and their own silos. It’s a lack of rigidity, a willingness to ask “What if I’m wrong?”, and an eagerness to own up to a changed outlook. Tyler Cowen, Ezra Klein, Julia Galef, and Scott Alexander come to mind here.¹ Friends as well, but you wouldn’t know those names.

It’s a rare quality and one I aspire to.

Big Sur tide pool, yesterday.

We are—I am—burdened by the narrow prism of a singular experience. But that doesn’t stop me from often defaulting to the idiotic presumption that my perspective is correct. Feeling right is comfortable. And being uncertain (or worse, wrong) is scary. Plus, humans are particularly adept at clocking patterns and as valuable an engine as that’s proven, it can also be detrimental. Combine a maladaptive pattern fixation with some confirmation bias and an egotistical death-grip on being right and—speaking from experience—we nearly want to steer down the wrong alleys as we leap quickly and cling tightly to our shoddy conclusions with nary a second thought. Our evolutionary skids are well-greased to slide into poor modes of thinking.

Simply being aware of this slant is tough enough. Actually battling the tide and applying perspective is a constant course correction. So I’m always impressed by those who stick with it over the long haul, keeping calcification at bay in an ever-less-relatable world, dodging the deepening ruts of I’m not wrong, society is.

Stewart Brand, Lloyd Kahn, Kevin Kelly, and John McPhee² come to mind.³ Those folks are also successful, so it’s even more admirable to see them retain these qualities. How difficult must it be to clock fallibility if you’ve been proven prophetic in other arenas?⁴ (Maybe it’s that none of them have pivoted to a podcast empire, where they’d literally be surrounded by yes-men in their headphones, unchallenged for hours each day.)⁵

Pushing back against our lesser instincts is a muscle that has to be worked. The thoughtless drift back towards certainty⁶ is not just innately gravitational, but one that’s socially reenforced. I frequently think about proverbial water cooler talk—bitching about how the boss doesn’t know what he’s doing, the mayor doesn’t know what she’s doing, and the baseball team management are all clueless morons. Shitting on agreed-upon-morons is an age-old path to common ground and—speaking from experience—nearly everyone snatches that low hanging fruit. The softer grasp of actual honestly is harder. Nuance is tricky. “It’s complicated” is a flaccid reply that few want to attach themselves to—it asserts little identity and offers no comfort blanket of “Hell yeah, brother” affirmation.

So how do those I see as thinking well manage it?

The folks I most admire are voracious readers and consumers of other’s experiences. I have to assume this global perspective helps shape the critical thinking they’re ever-honing. I appreciate General Jim Mattis’ quote about his reading habits:

“By reading, you learn through others’ experiences, generally a better way to do business, especially in our line of work where the consequences of incompetence are so final for young men. Thanks to my reading, I have never been caught flat-footed by any situation, never at a loss for how any problem has been addressed (successfully or unsuccessfully) before. It doesn’t give me all the answers, but it lights what is often a dark path ahead.”

Seems smart. Forming opinions based solely on our narrow experience—literally the default for most of us—is a shortsighted embrace of our blindspots.

Studying human nature and the ways we’re likely to trick ourselves also seems commonplace for those I admire. Kahneman’s books Thinking Fast and Slow and Noise come to mind as frequently referenced. Tetlock’s Superforcasting as well. And I recently read a few books on statistics and the logical fallacies we can all fall into with big numbers, which came recommended from some of the above thinkers.⁷ (They were great; it’s amazing how much stupider we get, proudly empowered by misinterpreted data.)

I like to play devil’s advocate and far better thinkers than I do as well. I’ve borrowed from their processes. (For me this is sometimes out loud and at the expense of others who didn’t consent to my thought exercise, which is something I need to work on.)

What’s the other way to think about this? What are my blindspots?

What am I or others likely predisposed to think here and how do I counter that tilt?

What’s the person across from me experiencing? How would I steelman the opposing argument?

How do I honestly feel about this? I hear the story I’m holding onto, but what if I dig deeper and sincerely examine the underlying drive.

If this egregious error were committed by me, my friend, or someone on my side of the cultural divide, what generous latitude would I grant and how would my opinion look different? What lessons should I draw from this inverted perspective that might inform future leaps to judgment?

What if I’m wrong?

It’s an imperfect system. Very frequently the way that I’m wrong is that I’m literally not thinking clearly, or at all, and am falling victim to my own basic inclinations with staunchly held (yet poorly informed) views—and I’m not even aware of it. So catching myself is a work in progress. But that’s kind of the point, even for the greats.

mental clarity

It’s not easy to say “It’s complicated” and un-quenching to offer “I don’t know.” (Also difficult: simply resisting the desire to have an opinion on something.) And harder still to concede “I was wrong.” But all the minds I admire most do so with regularity.

That isn’t to say they lack clarity or moral conviction or opinions. They’ve got those a plenty. (And I seek them out.) But I see those as softly held positions. Ones that are open to change and to new information. And these folks keep at the steadfast work required to maintain that open mindfulness.

Not unlike meditation and the exercise of constantly bringing the mind back as it wanders off with a thought, it’s about the process—that practice—one that demands rigorous self-examination and a constant course-correction back toward flexibility and curiosity.

Ideally, anyway.

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1. I love Chuck Klosterman and his often-counterfactual prodding and he literally wrote a book titled But What If We’re Wrong? but he’s probably too much of a post-modern deconstructionist to include here—his logical train of thought can be so impressive, but will also keep going right past the station to Never Never Land. I’d probably add early Emily Oster (her pivot to parenting advice I can’t speak to), Brian Potter (in a particular lane), Matt Levine (also in a particular lane), Noah Smith (sometimes), Cremieux (on the right topics), Aella (with her caveats), Steve Rinella (but he’s slipping… podcast empire problems), and maybe Michael Pollan. I guess I didn’t include them up top because they didn’t come immediately to mind and because of caveats. Though ultimately everyone has them… it’s a hard target to hit.

2. I had to double check as I hadn’t heard anything from McPhee in a minute and he’s 95. But he’s STILL on staff at The New Yorker and helping on projects!

3. Vaclav Smil has been recommended to me as well, but I haven’t read his work.

4. Looking at you, Elon.

5. Looking at you, Bro Jogan.

6. Growing up Catholic I found much of that religious appeal stemming from moral clarity and existential certainty. Knowing What this is and How this ends is a whole lot safer than the ambiguity of the ether. Embracing and exploring the unknowable complexity of it all is downright frightening. That’s not to say that rigorous critical thinking is wholly incompatible with faith, but the global majority (75%) gravitating toward the shelter of prescriptive truth seems testament to the fact that a full reckoning with uncertainty is a challenging discomfort.

7. Millions, Billions, Zillions. Everybody Lies. How to Read Numbers.