- Trying!
- Posts
- The Importance of Being an Earnest Cynic
The Importance of Being an Earnest Cynic
Sarcasm, irony, and pessimism are easy—too easy for this difficult moment. But what else is there?

You know, I really do have to admire today’s advertiser, 1440 Media, for giving this whole “unbiased news” thing a shot at a moment when most of us crave news either saying ‘that guy is good’ or ‘that guy is bad.’ Maybe give their ad a click and get me $1?
When E., one of the relatively new subscribers to Trying!, reported that she’d signed up for these emails because I “sounded really funny and cynical,” my heart melted. Finally, I thought, someone gets me! Here I am, producing meticulously constructed essays every single damn day—the prose rife with hidden gags, bilingual puns, and the occasional fart joke, the sensibility a venomous distillation of seen-it-all snark—and it turns out there was someone roaming the internet in search of just such a newsletter. Kismet!
Of course, E. is still new around here, so she may be unprepared for what is to come: an unending flood of flailing darkness and only mildly amusing anecdotes with which no civilian reader can keep up. She wants funny and cynical? Oh boy, is she gonna get it!
Or will she? Because as gratified as I was to read her words, I instantly questioned whether I could live up to them. I mean, funny: sure! Obviously. I wear my zany face with pride. Unlike Joe Pesci, I am most definitely a clown here for your amusement. No one can make a joke like me.
No one. Not a single goddamn soul.
Thing is, most of the jokes—like that one just above—are only funny to me, for reasons I often struggle to explain, let alone understand. While I am very happy to make you giggle, I’m even happier to be the giggler myself, to stumble on an absurdity that tickles the deepest parts of my brain. It’s not like I’m guffawing at my computer with enough force to bother the downstairs neighbors, though. I’m laughing out loud on the inside1. I am my own clown.
So, funny: Yes, definitely. But cynical? That’s a hell of a lot more complicated. Because while I have seen a ton of crap in my life, and am thoroughly unimpressed by most of it, and generally expect the remainder of my time on earth—roughly another 50 to 100 years, give or take—to be disappointing at best, I’m honestly quite conflicted about that attitude.
And that’s because cynicism is easy.
More after 1440 Media’s highly clickable ad…
🪨
If you're frustrated by one-sided reporting, our 5-minute newsletter is the missing piece. We sift through 100+ sources to bring you comprehensive, unbiased news—free from political agendas. Stay informed with factual coverage on the topics that matter.
🪨
Look, there’s much to be cynical about right now. As I was writing this essay, for example, the president announced his immigration enforcement personnel would be putting up to 30,000 people in concentration camps in Guantanamo, where U.S. law is more of a suggestion than, you know, the law2. This is, as we say in the media, deeply troubling. But because I am a cynic, I cannot say I did not see that coming. In fact, because this likely crime against humanity was so predictable, it’s actually disappointing. As a cynic, you live life expecting the worst from people, and when they inevitably deliver, you despise them more for meeting your expectations.
For my generation of Americans—X, in case you were distracted and hadn’t already figured it out—cynicism and its siblings, irony and sarcasm, are our natural states of being. We grew up overshadowed by the Baby Boomers, who dominated business, politics, and pop culture, and while we roamed more freely than kids today, we were also constantly aware we would probably be killed at any moment by nuclear war, AIDS, crack, hitchhikers, or some combination thereof. Is it any wonder that we distanced ourselves from these all-enveloping existential threats with wordplay, low expectations, and an instinctive avoidance of sincerity?
The thing about that stance is that it’s an easy one—too easy. Nothing impresses, everything could be better, and geez, why do I have to suffer through this? This kind of cynicism takes no effort, merely a kind of Pavlovian training. And when distancing becomes your default mode, it becomes its own kind of trap. You can’t get out of it because you can see yourself struggling, vainly trying to find a mode of being that’s not even necessarily positive or optimistic but just less caustic, and the cynical persona you’ve cultivated sneers and snarks at the earnest You that’s attempting to emerge.
And so I think a lot of what I write here is that very attempt: to first show off my cynicism, perhaps, but then try to get past it and on to something else. What is that something else? It’s not optimism, I can tell you that. I certainly don’t expect things to get better. I may be a clown, but I’m not a lunatic!
Maybe it’s “hopeful pessimism,” as this recent article in The Atlantic termed it, borrowing from the title of philosopher Mara van der Lugt’s new book. The idea is that when things are bad—as they are right now, god they are so fucking bad—it’s better to be a pessimist than an optimist. Because while an optimist assumes things will improve, and therefore may not act to improve them, a pessimist’s pessimism may push them to work to change the future. If, of course, they have some sense of hope. That hope, van der Lugt explains, can come from uncertainty: “Things might get pretty bad, but there’s no telling if things could at some point get better again,” ven der Lugt told The Atlantic’s Gal Beckerman. “Similarly, things might be pretty good; they could also get pretty bad again. So it’s never ever a closed story. The open-endedness of the future means that there’s always ground to stick with things that are worth fighting for and worth being committed to.”
I do like that point about uncertainty, partly because it reminds me of me. And I also like the idea of holding on to our values in the face of failure. Because if the worsening is what we all should expect, then it doesn’t matter whether we choose to crumble and fold or to stay true and fight. So why not choose the righteous path, the earnest path, the virtuous path? When defeat is all but certain, you might as well stand for something. You certainly don’t need to grind yourself down before the bastards get a chance. Don’t make it any easier for those jerks.
This is harder. This is hard. It requires us all—yeah, including me—to shed our cloaks of irony and embrace a directness and an earnestness that frankly can seem a little cheesy. Or a lot cheesy. Part of the difficulty is not crossing the line into sentimentality and nostalgia, which have their own pitfalls. We want to see clearly, think clearly, speak clearly, and act with determination. Christ, that’s exhausting. But it’s what we have to do if we’re to have any hope of a better future, or at least a slightly less awful one.
Here’s a lovely irony: This earnestness, this direct approach to values and virtues, is what defined the original Cynics, the 5th- and 4th-century Greeks who were followers of Diogenes of Sinope. The O.C.’s shocked the world they lived in by dropping out of society—but remaining in public. They begged for money, they dug through trash for food, they shat and screwed in full view of everyone, not for attention for themselves but to point out the failings and hypocrisy of others:
The Cynics were careful observers of human nature and could not abide what they saw there, in others and in themselves: namely, a tendency to luxury, ambition, stupidity, cruelty, and greed. They responded to this realization by dropping out of polite society. They sought to be liberated from the shackles of social expectations and tried to see life as it really is, and things as they really are. Their public stunts thus served the serious purpose of heightening awareness of what is truly virtuous and worthwhile and what is merely conventional.
The Cynics, Usher points out in that article, were frugal fellow-travelers, dedicated to radically reducing their impact on the world while highlighting the wastefulness of the rich and powerful. (Diogenes himself slept in a terracotta urn—the kind used to bury the dead.) But as ascetic as they were, they were not anhedonic. They simply found pleasure where others didn’t or couldn’t (and not just by screwing in the street):
“Even the despising of pleasure is itself most pleasant once it’s become a habit,” Diogenes was keen to point out. “Just as those who’ve gotten accustomed to a pleasant life become miserable when they pass over to the opposite condition, so those persons whose training has been the opposite from theirs enjoy despising pleasures with more pleasure than the pleasures themselves.”
Sound like any kvetching writer you might happen to know?
I’m hesitant to suggest we fully bring back the Cynical movement of Ancient Greece. For one, you can’t épater les bourgeois by begging3 and fucking in the street the way you could 2,500 years ago. Nowadays, it’s likely to get you put on a plane to Guantanamo. For another, embracing poverty and hard labor today feels like a tasteless stunt, especially if you have a choice in the matter. Comfort is not a sin. Nor is upgrading your Trying! subscription to one of my paid tiers.
But we can adopt something of their mentality. The Cynics tried to live on less to prepare themselves, to toughen their bodies and minds for the struggle that is life, and for a life of scarcity. They considered themselves citizens of the world, obligated not to any nation but to one another, to the alleviation of human suffering. And they did it with good humor, employing just enough irony and wordplay to make their point, without getting trapped by the pose4.
If we cynics of today, in shedding our pessimism and loping toward virtuous earnestness, wind up emulating the Cynics of yore, I think they’d find that highly amusing. We’re all clowns, after all. 🤪🤪🤪
The Trying! Awards Are Open for Nominations
Who gave it a good shot last year? Who failed miserably? Who just half-assed it? Submit your picks now for the 2025 Trying! Awards!
Notes
Hilarious!
Not that this president cares much about U.S. law on U.S. soil, either.
Their begging is what earned them the name cynic, which means “doglike.”
They were definitely weird about a lot of things, especially in their eschewing of society overall and their embrace of “nature,” which sounds like they’d be drinking raw milk and going anti-vax.
Reply