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Why Are We So Certain About Our Mistakes?

A technique to avoid future regret

Photo by Andre Guerra on Unsplash

OOne of the most painful parts of the writing profession is reviewing your own published work. It’s a bit like the uncomfortable experience of listening to your own voice being played back to you, except instead of finding that you don’t like the sound of your own voice, you often find you don’t like what that voice is saying, nor, as a result, the person in possession of it.

As Frederick Buechner wrote, we cringe at what we wrote long ago, wondering how on earth we could have been so “callow and wrongheaded, so alternately glib and pontifical.” Seneca, a wonderful writer and observer of the human condition, made it more universal: “When I think of all the things I have said, I envy the mute.”

So what do most of us do? Well, we try our hardest not to think of all the things we’ve said. We preserve our ego by keeping our mind as far as possible from the idea that we’ve ever been glib or callow or guilty of pontificating. And of course, as a result, we go on being precisely those things longer than necessary.

Those of us blessed or cursed not to have been born perfect will find it impossible to review anything we’ve published without being overcome by an urge to cringe — and the longer ago the words were written or said, the stronger the feeling. It’s undeniable. The trying way too hard. The undeserved superiority.

I’ve recently had the unpleasant privilege of reviewing and updating my first book. I say privilege because it’s gratifying to find that something you wrote when you were 25 years old still has an audience and a publisher interested in keeping the material current. I say unpleasant because that’s the nicest way to describe what it’s like to look seriously at anything you wrote at that age, and then to read it again over the course of many hours in a recording studio for the audiobook.

When reviewing these pages — pages I’d hurriedly written and edited in my excitement to publish my first book — I wonder who the hell I thought I was. I’d studied and sat with the topic for how long? And here I was, printing words that could never be unprinted. I’m embarrassed by the certainty of it. As if it had never occurred to me to hedge my bets or entertain the possibility that subsequent events might prove me wrong. Why couldn’t I have said simply that this is what I thought at the time and knew to be true to the best of my ability? There’s a pervasive overdone-ness to so much of it. If there’s any proof of the ego’s insecurity, it’s there — in the fact that I have to put two sentences where one would clearly do, a big word where a simpler one would have sufficed.

And I didn’t just publish it, I promoted it.

One of the most haunting things about this kind of reflection is the gulf between then and now. What was once inconceivable becomes not just obvious but glaringly so. In the case of Trust Me I’m Lying, I went through dozens of drafts as I was writing the original manuscript. I not only read the audiobook in a New Orleans recording studio in early 2012, I distinctly remember reading it out loud to my dog in late 2011, and editing it line by line as I did so. My intention was to see my own work clearly and solve for any problem within it. And yet, here they are.

And here I am now, regretting it, as I inevitably will regret parts of this article, and parts of the article I wrote last week and the one I will publish next week. It’s interesting that we know this is true — that we will almost certainly reject a good portion of what we think, what we say, and did. Yet, how many of us live our lives understanding this fact in the moment?

How many of us, when we pick up a shirt in a store or consider a new haircut, give much thought to whether this will be the one that, some years down the road, we regret? Again, every one of us — no matter how conservative, no matter how much we stick with the staples or believe ourselves insusceptible to trends — knows the inevitability of this shame. (Again, I am no exception if this video will convince you.) Yet each time we try to tell ourselves that this — whatever we’re doing or saying or thinking or deciding on — will not be one of those examples.

Which is why it’s precisely the kind of exercise we should do more often. Many people practice regret minimization in their financial lives, perhaps with a pile of gains from cryptocurrencies: “Would I regret selling, knowing, and discovering it has continued to go up, or would I regret not selling and losing everything I have?” But to do this in broader life, with our opinions and life decisions, is rarer: How many young people who danced with the alt-right in 2016 and 2017 (before the movement turned deadly serious) might have saved themselves the regrettable experience? How many radicals in other eras might have done the same? How many of us stop to think about how the tone of an email will come off in the future? Or weigh the immediacy of a temptation or a passion against the feeling that so often overcomes us after we’ve indulged?

The economist Tyler Cowen dispensed this advice. “Treat yourself like a piece of your writing,” he says, “which you set aside for a week so you could look at it fresh.” In other words, give yourself distance from yourself. Put your thoughts, your drives, your attractions up for review and see if time — whether it’s a week or a month or a year — is kind to them.

I vividly remember how intolerable this kind of review was to me with Trust Me, I’m Lying. Even with all my editing, I made deeper reflection impossible. I rejected one potential publisher who was interested in engaging in a longer editorial conversation about the book’s direction. I pressured the publisher I did work with for a shorter timeline. I resisted changes in some places that would inevitably have required me to consider changes elsewhere. The book needed to come out. There was no time. This was my window. Reservations be damned. The result was not only regret about a handful of missed typos and errors on release day. Over the next few years, I experienced the slow and humbling realization that my ideas were a wee half-decade early.

We need the review process most when we’re young. Any reader of one of the fuller editions of Anne Frank’s diary can see this. Even within two years in that attic, surrounded only by her family and locked away from the outside world, Anne changed and matured. She writes repeatedly of her horror at the tone of earlier entries and takes substantial pains to edit and refine her thinking. She’s appalled by her judgments of other people and the statements she made while upset or exhausted. In reviewing and reflecting, she is able to see their side of things and identify concrete improvements to be made in herself as well.

She had the courage to inspect her own most private thoughts and examine the record. She asked herself if this was the person she wanted to be. Where the answer was no, she worked to improve.

This is a process we should all engage in, writers or not. It shouldn’t fall to Facebook’s Memories feature to get us to put our past up for inspection — whether it’s been nine years or nine days. Nor should it fall to our actual memories, which are filled with biases and flaws. No, we need to look at the actual evidence. We need to look at ourselves critically, as we would some other person. It will at times be painful, but we’ll grow from it.

Our world moves faster now, especially for young people. Instagram and Twitter and Snapchat in the pocket — prompting, prodding, addicting us to say what’s on our mind and act on our urges, to form our identity in real time, with no delay. Not simply in the form of youthful indiscretions that look bad to college recruiters, but comments and opinions that will not stand the test of time. (Though this is true not just for the young. Ask Donald Trump, who seems to have managed to tweet something at one time or another that perfectly undermines whatever policy or narrative he’s pushing today.)

Right now, each of us is forming the self we’ll face in the mirror in a year — and for many years thereafter. Each one of us is accumulating the record of acts and beliefs and statements that will come dribbling back to us in the future in one way or another. It is unavoidable that some of these will be regrettable, but it’s by no means fated that we’ll cringe at all of them — because we can prevent them from happening.

Cowen’s advice on doing it in the moment, on seeing our own desires with freshness and perspective, can prevent regret before it happens. We can give ourselves time to reflect now. There will still be room for spontaneity and impulse, for if we are honest, most of us are far more reactive than we are deliberate. The point is to drop the certainty and the ego — the blissful ignorance where we do whatever we want, we do what feels right but never question why — before these impulses curdle. We can know that the thoughtless, slavish devotion to trends rarely ages well.

And most of all, we can remember that less is almost always more. We can resist the urge to put two words where one will do — where none will do — and reduce with equal measure our knowing certitude of all those things that are, inevitably, never fully knowable.

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’

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