the moral weight of a mistake

interrogating badness

Welcome to debrief! This newsletter is on pause and will be sent out semimonthly while I finish writing my book. But you’re in luck this fortnight—because I’m in between drafts! Enjoy this new essay on why sharing my manuscript with beta readers triggered my basest fear: that I am a bad person.

A portrait of a bad person at brunch (Paumanok Vineyards in the North Fork, Long Island)

Have you ever written something—a text, an email—in a blaze of cathartic glory, hit Send, and regretted it five seconds later? That’s how I felt sending my book’s manuscript to beta readers.

At first, I was giddy with excitement—almost a year to date since I created the document Big Bad Law (wt) (BAD FIRST DRAFT).docx, I was finally showing my words to someone other than my editor. My book was gaining sentience!! It was off to its first playdate! What wondrous, exciting times!

Only for a wave of nausea to hit. It was as if my stomach experienced gravity for the first time.

What have I done?

“What, are you afraid of being wrong?” a friend asked me as we strolled Prospect Park, his tiny dog barking at children and anything with wheels—his dog’s only two fears.

“No,” I replied, envying his dog. “I’ve been wrong plenty times before. I think there are much worse things in life than being wrong—like being a bad person.”

These days, we are more likely to call a person “bad” than a dog. And at my core, I believe myself to be bad.

This fear isn’t purely hypothetical. I was called a “bad person” by my childhood god—my mom—more times than I can count. Family members, even those who love me in large, smothering ways, have made clear to me the lines which, if crossed, lead to disownment.

Badness is always pushing up against my organs and pores, threatening to burst forth, spill over, consume me. Sometimes I wonder if this abstract anxiety is what fuels the physical symptoms commonly associated with anxiety—vomiting, gastrointestinal issues, body-focused repetitive behaviors like picking skin and pulling hair—the body trying to excrete, expel, eject a nonexistent poison of which the mind is nevertheless convinced exists.

The pernicious part of this abstract anxiety is that sometimes, it is reified. Toxic authority figures, whether parents, teachers, bosses, or online commenters,¹ are the first in line to make sure you know that a mistake isn’t simply a mistake—it’s a moral failing.

How could you do this to me/us?

Whenever authority figures respond to mistakes with blame and shame, how could you not impute morality into your actions, yourself? We have so few examples of how to respond to mistakes without moral implications. The first time I saw it happen, I was nearly 30.

What was it about Big Bad Law (wt) (SLIGHTLY BETTER SECOND DRAFT).docx that could paint me as a bad person?

For one, it’s not a final draft. When I sent it, I hadn’t yet read the manuscript myself—only written it. That’s unacceptable for junior employees in most settings; not proofreading your work is a luxury reserved for senior execs who communicate solely through surprise phone calls and email subject lines. To emulate even a fraction of the execs’ stream-of-consciousness working style is to be a “bad employee.” Hell, the law firm Covington & Burling has specific lingo for what it expects of associates: “Covington Perfect.” Is this memo Covington Perfect? Is this email Covington Perfect?

It should come as no surprise that my second draft isn’t Covington Perfect.

Which shouldn’t scare me—none of my beta readers expect Covington Perfect (or at least I don’t think so)—but it does. Because I still expect Covington Perfect. I still believe anything less than Covington Perfect is a moral failing. And that expectation, that belief—no matter now unrealistic—was continually rewarded for 26+ years of my life and is still rewarded now in most corporate settings.

One of my friends told me that when she was on leave, recovering from burnout and overwork, she’d crochet and practice making stitches that were too large—and then just looking at them and leaving them like that. Practice living with mistakes, in the smallest, most inconsequential form. Practice living with the nonexistent poison that the mind so adamantly insists exists.

But being “bad” goes beyond form—one can be “bad” in substance, too. What if the events I wrote about—the personal disclosures made—paint me as a bad person, irredeemable, unworthy of even attempts by others to understand?

I think about Kristi Noem not infrequently. She’s the Governor of South Dakota. Earlier this year, she published a book—a requirement for all modern politicians, it seems—which includes an anecdote carefully calculated to showcase her ability to make “difficult, messy and ugly” choices when the need arises. The only hiccup: the anecdote was about killing her dog, Cricket, because Cricket had behavioral issues (e.g., biting attempts, attacking chickens) and wasn’t taking well to hunting dog training.

Cricket was 14 months old.

Now, this isn’t admission that I’ve killed a dog—I haven’t—but I have done things which I’m afraid make me a bad person. And writing about it—and sharing that writing—is as close to public judgment as it comes. I’ve been getting stomachaches ever since I sent my manuscript off to beta readers, and I know it’s because I’m worried they will read my thoughts—my true thoughts, not the ones I understand my conversation partner wants from me and therefore reflect back to them—and conclude, beyond a shadow of doubt, that I am a Bad Person.

I read on How to Glow in the Dark (a great resource for those interested in querying agents and/or traditional publishing, btw) that the achievement of publishing isn’t the writing or publishing itself—it’s acquiring the emotional skills to navigate the demands of doing so. It’s “learn[ing] how to get hurt and keep going down the same path anyway.”

It’s a skill I didn’t have to obtain in school or as a lawyer, simply because I never loved anything enough in school or legal practice which would require me to get hurt and keep going. If I got hurt—got rejected from a Goldman Sachs internship, got rejected from MBB, got an average grade, got shut out of certain opportunities at a firm—I simply gave up and tried something else. Did you know that I decided a career in STEM “wasn’t for me” because I initially failed to test into AP Chemistry? I was 15 and already preventing myself from loving something. I never cared about anything (or anyone, for that matter) enough to venture further, grit my teeth through humiliation to try again.

On one hand, diversifying and pivoting frequently is extremely helpful—it helped me avoid sinking too much effort into something that wasn’t going to pay off. But on the other hand—it also means I didn’t have anything worth sinking, nay, enjoying effort on. I didn’t enjoy anything. My life was filled with telic pursuits instead of atelic joy. There’s a lesson to be learned here about balance—pivoting most of the time, but committing to hurt and humiliation some of the time—that I’m still learning, page by painful page.

Most days, I’m convinced I’m a bad dog and someone should just put me down. But other days, I try to tell myself that every dog deserves a chance, even one some have called “bad.” ◆

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1. Yes, I do consider online commenters to be authorities. I probably shouldn’t. But I do.