My 13 Best Essays of 2022

Greatest Hits, Volume 5.

When 2022 began, I thought I was finished at Medium. Not because I didn’t love the place, or because it stopped being good to me, but because I felt like I ran out of things to say.

That sounds ridiculous to you, but I was dead-ass serious. In 2021, I even penned my goodbye.

I’m famously self-deprecating, but I’d comfortably stack my 133-essay winning streak between February 2018 and July 2019 against the output of anyone else on this platform. That’s not bravado; that’s just facts. No one else did what I did in that span, nor attracted as many eyeballs. Check the tape.

Yet after that seemingly endless content monsoon—everything between “The Art of Intimacy” and “The 7 Noble Pursuits” at this point can be comfortably categorized as my “Classic Period” — I dried up, and I thought I’d peaked creatively.

[Author’s Note: I wrote four of my 10 most popular essays of all time in a row, between January 29 and February 1, 2018. If you want to know when I stopped being anonymous and started becoming a “thing” — on this platform, anyway — it was exactly then.]

For three full years after that, I’d only sparingly hit that level of quality. Highlights were rare, but still high: I never once got as poignant or avant-garde as I would on “We Will Always Have Water”, and never seared as hot as I would on “90 Days, 400 Years”.

But as we rolled in 2022, I was pretty confident I had nothing left. For the first nine months, I wrote less than ever.

But a funny thing happened once I stopped working 70 hours a week. My brain freed itself up to think about things I used to write about under my own name. Life. Liberty. The battle for happiness. The music and mixed metaphors came back.

And then came back September through December. We resumed regular business hours. The draft folder filled back up, then started to empty. Turns out there was some magic left … and no small amount. [If this collection feels backloaded to you, well, that’s why.]

Eventually, the wheezy machine on the fritz rebooted and eventually started humming. Hey, there’s some of my old readers. Hey, there’s some of my penchant for stringing together 150-word sentences that feature 12 clauses, three archaic pop-culture references and a historical analogy. Hey, there I am back at №1 on the Trending on Medium list. The dented, rusted 1983 Porsche 944 rides again.

So for those of you who are new here, or those of you who wonder what the hell I was doing in 2022 before my name reappeared out of the mist like an dead ex-coworker in the LinkedIn “Add to Your Network” reco, I’m dusting off the Greatest Hits machine here.

I used to annually collect Best Ofs, but I didn’t do that in 2021 and don’t feel much like revisiting that year in this collection — it wasn’t all that great and it would feel arbitrary, besides.

But for 2022, a year in which I rediscovered my pure love of writing and started scraping the upper reaches of what I used to regularly do, I think it’s best to assemble a sampler platter of what we talked about, who we were, and how we likely will remember it.

These are ordered chronologically. We start with a eulogy for my cat, and we end with me successfully quitting Xanax after an 11-year dependency. In the middle is a 10,000-word magnum opus that covers the day I got cancelled on Twitter and then Trojan Horses in my entire career. Everything else is pretty much my standard fare. It’s good to have me back.

It’s good to have you back, too. It’s been a pleasure having you here in 2022. Things are looking, if not up, then forward. That’s a refreshing change from the runaway pain and dread of the previous two years.

And you know what?

I’m not fucking leaving.

1. A Man, A Cat, A Lifetime (January 21)

“She went by many alter-egos: kitonka, broccoli, kitler, goblin, Sister Mary Oreo, wap-wap, and apparently also “Daisy.” But she was the same no matter what you called her: a rough-housing meanie with a soft spot for chin scratches, turkey cold cuts, and the warmth of a laptop keyboard or a human’s love.

She died as she lived: on her terms, engulfed in love, unbound by the way we perceive time or the way others perceive us. I’d like to think we’d all love to live that way.”

2. A Note About the Attack on My Hometown (May 17)

“From the West Side to West Seneca, from the hood to the woods, from the Lincoln Parkway mansions to the First Ward split-levels, I knew every one of these people. I knew every kind of joy and pain that people feel when they’re held hostage in an arrangement that’s easy amongst friends and uneasy overall.

Those people in those places and over time all make Buffalo what it is: such a beautiful place to love, and to be from … and a hard place to respect or to wish to remain. That’s how that story goes these days, yet all these stories are the same, and it’d take more time and words than I have to give to tell the full tale properly.”

3. Nothing Is Normal and No One’s Okay (May 27)

“We’re exposed to more data in one day than people during the Rennaissance consumed during their entire lives, and so much of it is so painful. Our brains are literally breaking. No one’s wired to handle this. Not individually, not at this scale, not at this volume.

Once you see it anywhere, you can begin to connect the dots and see it everywhere: department store Karens throwing temper tantrums in Walmart, white nationalists brandishing AR-15s in full tactical gear around seemingly every building of even mild importance, evangelicals leaning hard and fast into rapture-adjacent fanaticism and forced-birth doctrine, Millennials letting themselves go and giving up on usual milestones that once defined American adulthood, a tsunami of Zoomers seeking mental health support for “climate anxiety.” We’re living through billions of stress responses at the individual, institutional, international, and ecological scales. All at the same time. All amplifying each other as they collide.”

4. Your Relationships Matter So Much More than You Think (August 25)

“Taken in total, there’s enough anecdata to suggest that our languishing draws at least some water from or exists in a distressing amplification loop with loneliness at scale. We’re not just grieving, we’ve lost the social bonds, norms, gatherings, and incentives that defined our lives before the pandemic. We feel bad because we miss people and when we feel bad we’re less inclined to do the prosocial behaviors that would alleviate that exact ache.”

5. The Open Secret to Gaining A Massive Online Following (August 30)

So, how do you keep people coming back? Post after post, day after day, and breathlessly sharing your content with their friends? Because, lemme tell you something: your polo-and-khaki ass ain’t gonna cut the mustard when it comes to brand cachet.

A bunch of popular jawns on this platform are empty, vapid columns that remix and remaster the same tired cliches that have dotted every advice essay since before Dale Carnegie was dead enough to roll over in his grave.

Like, you could spit that shit if you want to — quote the stoics or Tony Robbins, or even find new ways to insert “if you don’t see the problem, you are the problem” into a Very Important social justice missive — but you’re just going to be spitting jargon. You’re doing it; you’re middle managing.

6. I Was Cancelled in 2016. Then My Career Took Off. (September 12)

“I walked into Dell on July 9, 2016. I apologized to everyone for failing to protect the brand. I even retrofitted the appropriate Michael Jordan line, stuttering, “Republicans buy laptops, too”. They graciously, silently, let me go on with my work. Still, I didn’t feel right in the office for a while.

As for the general public, well, the hardened corners of the Internet had their fun, too.

It was all over by the following day. The mentions disappeared. The texts subsided. There was a new enemy of the state, a new trending topic, and a new non-Jewish person to loudly brand a Jew.”

7. 40 Years Well Spent (October 5)

“After 40 years, I’m certain I haven’t always built the best sandcastles. I bet there are people reading this, right now, who wish I could’ve given them more, and better. People I wish I could’ve given more, and better, too.

But goddamnit if I never gave up trying, never stopped building, and never stopped to reflect on how to make each next offering a little better than the last. That’s all I can do; that’s all any of us can do.

Beyond all of that, though, I think our real legacies, the real sandcastles, are the people we meet along the way. The way we treat them and change them and love them. The way they do the same to (and for) us. That’s the real work, the real joy, the real sand the sea can’t take, no matter how quickly or thoroughly the waves lay claim to it all.”

8. Then They Came for the White Men and Boys (October 6)

“David Brooks — my dude — you don’t lead off the top of the first with, “You probably have some inkling that boys and men are struggling, in the U.S. and across the globe.” That whooshing sound you hear is some brush-back high-heat ratio’ing you to death because you’re crowding the fucking dish. Take a step back, sell the plate-front property, and enjoy the outer boroughs of the batter’s box.

I won’t sear his wafer-thin silliness line-by-line — because I have a very nice life and I’m casually riding a cresting wave of good vibes — but I’ll begrudgingly play his hits for you.”

9. Who Can F**k At A Time Like This? (October 29)

We were told finding jobs and homes in thriving cities were a ticket to wealth creation, yet increasingly, homes in desirable metro areas aren’t affordable, wages remain stagnant, and trying to secure dignified work commensurate with education or experience has become a Kafkaesque Hunger Games at the mercy of increasingly fickle and selective employers, aided and abetted by labyrinthian Applicant Tracking Systems that reject resumes from qualified applicants who don’t know that gratuitous keyword matching is what gets you through the first of 800 doors. Good luck buying a home if you’re an MBA-holder who assistant manages a Starbucks, unless you moonlight on OnlyFans or spend your remaining waking hours shuttling strangers around as an Uber driver.

10. Elon Musk is a Threat to Civilization (October 31)

“History is no impartial oracle imploring us to learn from our pasts as we forge a better future. It’s sponsored content with a quiz at the end, and if you fail it, there goes the full ride to Stanford. All history is a reconciliation project, but ultimately the voices we pass on to our young and to each other tend to echo the worldviews of the people who were best at killing or gobbling up land and money.”

11. How to Craft A Killer Personal Brand (November 4)

“Ever notice how most mid-level Instagram and LinkedIn influencers look and sound like carbon copies of each other?

Like they all rolled off a Metroplex assembly line with 12 pre-programmed messaging settings and a photoshoot starter kit?

[Like a]n endless sea of calls-to-action, VC jargon, hustle porn, LinkedIn broetry, humblebrags, anonymous mid-level professional honors, divine masculine/feminine psychospiritual babble, Brene Brown quotes, and occasional ham-fisted performative activism when the real world gets a little too real?”

12. The Long Goodbye (December 5)

“So much changed for me, and changed in the world, between 2011 and 2022. I’ve aged out of my 20s and my 30s. I’m on my fourth different mailing address. I started and ended my corporate career and even changed jobs after that. I’ve run 15 half-marathons and a full marathon.

The Buffalo Bills are good now and have been for a while. A pandemic showed up and killed over a million Americans. The disastrous Donald Trump presidency — a surreal 30 Rock joke in 2011 — started and finished, but now he’s running again. The World Cup is in Qatar.

But all the while, the core of what I did each day remained the same: I woke up. Took my inhalers. Took Xanax. Went to bed. Now I do just three of those things.”

13. The Vibe Shift Was Real After All (December 7)

“As the last vestiges of Deep Covid lifted, many of us were let out into a vaguely unrecognizable world — suddenly IRL felt like the Uncanny Valley. The trajectory we found ourselves on in the 2010s ran its course. What followed was a devolution, in a way. I wholeheartedly admit to devolving.

As 2022 started, I was still fighting with reality. I sucked wind through all the survival-prompted things I did and became to fill pandemic space and time. At the same time, I wanted to “get back out there.” But “out there” wasn’t out there anymore, and there was little left to get back to. 2019 me wouldn’t make it in 2022. Neither would 2020 or 2021 me. Still, there I was, trying to live three timelines at once, trying to be three people in one and finding out they were probably better off not meeting.”