Passing Judgment

On how to better surf a tidal wave together

I love ideas. The piles of half-read books scattered by my bedside are large and growing. I love the thrill of sudden insight, the sense I now understand something I did not. We named one of the core cultural principles at our last company “Joy of Learning.” For who are we—what are we—if we are not learning?

And yet this part of me, like everything, casts a dark shadow.

At their best, our minds, those intellectual razors with which we cut open, peer into, and reorganize the reality of our experience, enable us to navigate, explore, and improve the world.

Yet, as the proverb goes, minds make wonderful servants and terrible masters. And they often do not serve the best within us. In fact, it seems that, even at their best, our minds are always partly serving our need for control and comparison.

It is worth reading Scott Alexander’s obituary of Scott Adams in its entirety. I was never a fan of his cartoon, Dilbert, but the arc of Adams’ life echoed painfully for me. It is the arc of a nerd who feels both empowered by and trapped within his mind.

Adams is both smart and deeply, deeply insecure that he isn’t smart enough. He can solve engineering problems and analyze culture and politics better than most, but his intelligence doesn’t provide him with the love and safety and belonging that he, like all of us, so desperately desires. To protect him from the pain of that insecurity and disconnection, his mind crafts stories of his superiority (“I don’t belong because I am better than them, because I know more than them.”) He makes his mind serve his insecurity and it becomes a cruel master that fuels his isolation and makes our collective life a little harsher.

I have been that nerd. I have been desperate to prove that I am smarter than what society has recognized and terrified by the truth that I am not that smart or special, that I will not find a path out of my lonely mortality as some genius hero, that I will die and all that I have ever done will soon be forgotten. And to protect against the pain of being judged, I have defined myself as superior to all the sheep who can’t see what I see. I have been an arrogant prick over and over and over again.

Following the maxim that hurt people hurt people, nerd culture has often had a vein of arrogant cruelty. Think the comic book guy in the Simpsons sneering at the lesser minds who enter his shop. As our society and economy has increasingly deified the ungrounded intellect and those who wield it best, this tendency has become less funny.

It is not just us nerds who fall into this trap. I spent my 20s and 30s running around with many smart, compassionate people of all stripes reminding ourselves of how much better we were than everyone else at saving the world. I challenge anyone in our highly educated, globalist tribe to claim that they haven’t at times defined themselves by their superior knowledge and thought.

The natural first response to revealing this pattern is: “wait, are you saying that I should drop all skepticism and judgment and accept everything anyone says or does?” It was certainly my first response. I was terrified that the choice was binary – either I was my current arrogant, judgmental, incisive self or I would be a kinder, more accepting pile of mush that would blandly smile at any policy or individual no matter who they helped or hurt.

That fear of losing all that my mind brings me was like a thick suit of spiky armor—protective, separating, and not easily shed. And heavy, so exhaustingly heavy. It was that fatigue that finally led me to step out from the armor to explore what lay beyond.

There is a scene in The Big Lebowski in which Walter returns from one of his blunders and barks “am I wrong, am I wrong?” To which the Dude responds: “No, Walter, you’re not wrong, you’re just an asshole.”

I found myself increasingly responding in this way to the voice in my head, to the snarky conversations I have relished, to the societal discourse I have followed. You’re not wrong, but you aren’t right either, and aren’t you tired of being an asshole?

Our minds are like Walter, obsessed with the question “is this right?” It is a vital question. We need to ask it to live and thrive. Without it, we too easily believe the stories our emotions and bodies tell us. That can lead us into dangerous territory indeed. But it is a small question, a sterile question. I realized it was a question I needed to live through, but not a question I could live for.

We’re not wrong…

Accepting our Unknown

We are mirrors for each other. The things we judge in others are always the things we judge most harshly in ourselves. At core, I, like Scott Adams and so many others, judge others for not understanding because I fear and hate the parts of myself that don’t understand. None of us understand what this life is, why we are here, and where we are going. Embracing that truth means embracing terror, loneliness, and helplessness. So our minds resist, construct armor plated with reason and righteousness, convince us that we know and are in control and are better than all those who suggest we are not.

We all repeat this pattern, some more, some less. Aren’t we tired of being assholes—to ourselves, to others, to reality? Don’t we want to find another way to walk through this bewildering life together? Like the character in Robert Frost’s poem New Hampshire, aren’t we tired of standing before a beautiful, dark forest and only allowing ourselves to fearfully see it, as Frost biographer Adam Plunkett writes, with a “self-certain, disengaged abstraction?”

I am only interested in one question these days: how does this help me love more deeply? Every idea, every action, every solution is flawed. Pushed far enough, they all eventually collapse into harm, even this view of the middle way itself. The binary view that leads us to cling to our protective judgments so tightly is not real. We can hold our knowing judgments within and beside a sea of unknowing nonjudgment.

Let’s ask “is this right” as we are allocating limited budgets and designing airplanes. But then let’s mostly ask whether the stories our minds are telling us truly help us love more deeply. If an answer does not help me love this brief life, how much does it matter if my mind claims it isn’t right?

I, of course, don’t mean a simple, romantic Hollywood love. I mean the root love that most traditions around the world are designed to help us remember and that Joe Hudson characterizes as manifesting in four forms: peace, care, enjoyment, and, most importantly, deep acceptance. The acceptance that no matter how painful, how infuriating, how irrational, this situation and all the people in it belong here. That love contains gentle kindness, and it contains arrogant skepticism. They are all part of the story.

Love in the Age of Judgment

Alan Watts has a memorable answer to my fear that relaxing my judgmental shell would dissolve me into bland, useless mush. Well yes, he says, you will become goo. You always have been, you just pretended you weren’t. You are prickly, judgmental goo. And those people over there whose sneering judgments of you hurt so much are too, even if they won’t admit it. If we remembered this truth, maybe we would be a little less certain of ourselves and a little less cruel to each other.

We need our judgments more than ever. The looming tidal wave of AI will soon test the depths of our minds, our hearts, and our souls. Those who cannot adequately judge are already getting swept away by the flood of possibility, illusion, and manipulation (reports of AI fueling spirals down mental health and quasi-spiritual rabbit holes will surely grow). But we can surf the wave without sneering down at all the others trying to find their own way beside us.

Like Scott Adams, many of us have spikes sharpened by our education and our modern, materialist worldview. For us, navigating this wave will require remembering what lies beneath all our judgments. As Adams feared, that part of us recognizes that we aren’t that smart or special, that we don’t know what this is or what will happen next, that we will leave this world soon and be forgotten.

And it is okay with those truths. For that part of us does know one thing—that it is loved and it can love it all.