When You Know You're Impressive, Just Be Impressive. Please.

I have once again appeared on Jacks of No Trade to rate beers; unfortunately, this time it was Octoberfest beers, which I really don’t like. (These ones were so, so malty.) Also I am deeply disturbed to see how my side delts have simply disappeared since I tore my shoulder and am unable to lift. Oh well.

I am, somehow, 43 years old. (I don’t like it any more than you do.) I am therefore at a stage of life in which some lucky and plucky people from my immediate generational cohort, the people I grew up with, are now reaching the genuine upper rungs of wherever they work; a girl from my high school that I haven’t seen in twenty years apparently just became the youngest female VP in the history of her financial services company. There’s others who are just barely holding on, still waiting tables or working retail, and hey man, everybody’s on their own journey. (I’ve personally been that a lot more often than I’ve been financially secure.) And, of course, there’s the great big mass in the middle, a lot of my old peers who settled into comfortable grooves and have mostly stayed there, I’m sure with varying levels of comfort regarding their positions. A lot of people have bought houses and had families and achieved comfort. Though I know it always disappoints some people to hear this, it’s worth saying that the most popular kids at my high school have almost all gone on to lives of success and happiness. Everybody chases their own version of the good life and while nobody ever reaches it fully many people get the good enough life.

What varies a great deal, even among the successful, is the degree to which success prompts certain kinds of status anxiety. And, for people in Gen X, the Millennial cohort, and Gen Z, there’s the eternal question of how to both reach impressive heights of aspirational success while appearing not to try or to care.

That youngerish people would often prefer to maintain a certain affective distance from their success is a well-worn notion. I take it as given, though of course plenty of people maintain an unapologetic attitude towards the grind. We lived through this long drift in the latter 20th century that ironized conventional success in general and career success in particular, from the beatniks to the hippies to the grunge era, from the jaded youth of Freaks & Geeks to Office Space to Beck’s “Loser” to the early Silicon Valley skewering of Microserfs to the ironized career indifference of the characters on Seinfeld. Of course, plenty of people went right on along chasing the dream and valorizing hard work, such as in the “greed is good” Wall Street culture of the 1980s. Certainly, though, in popular culture traditional metrics of life success have been relentlessly critiqued and ironized in the past half-century-plus, largely because our visions of a successful life really have been rotten. The depiction of the white collar workplace as a site of relentless boredom and meaninglessness, whether in Workaholics or Fight Club (book and movie) or the British Office, did not come from nowhere. Meanwhile, again for good reason, elite culture has adopted a lot of cynicism about meritocracy; that our success is everywhere influenced by the fickle whims of fate, and that structural inequality is built into all of our systems, have become too hard to ignore. And so cultured people learn to view career success with a certain level of distaste.

The trouble of course is that people still need money and want to look successful. So you have a lot of mannered attitudes, among a certain strata of society, towards adult achievement, particularly career achievement. Which, usually, is fine. It’s fine to feel conflicted about one’s own flourishing; it’s healthy to both want to do better financially and professionally and to also understand that the systems of financial and professional reward are fundamentally broken and unfair. This is something that many people deal with, and if you confront it all with a little humor and self-awareness, it’s not a big deal. You may ask yourself, how did I get here?

What gets to me is the way that certain people clearly see appearing not to try as a way to try, who need to aspire to never appear to be aspiring. They never stop trying, but part of their trying is making sure no one thinks they try. They work relentlessly, but they want you to think they’ve never sweated a day in their life. They, like, got into a great school, but they don’t take that stuff too seriously? I mean, yes, they got that promotion. Yes, they live in that brownstone. Yes, Dakota and Maddissonn go to a $75,000/year preschool. Yes, they bought in, hook line and sinker, when they were in elementary school, and have spent the vast bulk of their lives never not striving, never slowing down, never allowing themselves to let a few things go. Yes, they always said yes to everyone with authority or connections or a gradebook. But they don’t take it too seriously! Haha! They may have climbed over a ton of bodies to get to the top, but they don’t, like, think it’s a big deal or whatever. “What, this objectively very impressive career and life, this old thing? Oh, geez, I’m a little embarrassed by it! Funny you even noticed. Haha. I’m the high-flying overachiever who gets it.” It drives me fucking nuts. It drives me nuts.

There are few things that annoy me more than a particular species of striver: the ones who hustle and grind white-knuckled through the early part of their lives, striving to get into the best college and then to get the best internship and then to get the most enviable job and then to get the most fuckable partner and to make the most money and earn the most accolades, and as soon as that status is secured, to act as though it was all a joke, no big deal, not something worth taking seriously. It’s a type of weaponized self-deprecation that ultimately does the exact opposite of deprecating the self. All of it is done in the service of being not just successful, but also with it, cool, laid back, sensible, with a good head on one’s shoulders. In other words, it’s a deeply perverse exercise because it’s the habit of denying the importance of success or one’s interest in achieving it as just another way to achieve success. It’s continuing the grind by pretending to reject the grind, advancing in meritocracy by denying the legitimacy of meritocracy, striving by insisting that you’re not into that whole striving thing. The point is to end up looking not just rich and stylish and successful and Instagrammable but also wise and approachable. To have it all while pretending to be the kind of person who would never try to have it all.

I’m not a fan of ambition, in general, but I think it’s even worse when the ambitious deny their ambition as a way to achieve their ambitions. I would much, much rather someone just say “I’m successful, and I know it, and you know it too.” I’ve never been in that position, and I’m sure it’s complicated to sort through those feelings, but I’d like to think that if I had climbed to the top of the achievement heap I wouldn’t be so vulgar as to act like I just tripped and fell into my success, which makes it so much worse for everyone else. And, no, you don’t have to adopt some regressive just deserts philosophy of economic success to be straightforward and unapologetic about your achievements. You can understand that success is always buttressed by luck and subject to the whims of fate, and that you are the benefit of any number of structural advantages that helped you along the way, and that what we define as success is frequently morally bankrupt, and still be direct and honest about your accomplishments and what they mean to you. You can understand all that and still be thankful for where you’ve landed and think in an uncomplicated sense that your hard work and talent have played significant roles in where you’ve gotten. And doing so will be much less annoying than trying to add “Person Who Gets It” to your list of awards.

Let me put this in a pull quote, for proper emphasis:

Past a certain level of accomplishment, the affect of being unimpressed with one’s self, of not taking one’s own success seriously, becomes worse than arrogance, righteousness, self-promotion, or bragging.

The rest of us should get to just resent your white-knuckled climb up the ladder of achievement, OK? It’s literally the least you can do. Don’t try to add virtue to everything else that you’ve achieved; don’t strive and grind to put “Doesn’t Go in for Striving and Grinding” on your already-loaded resume. Please.

This is definitely a much broader thing that definitely sucks, and I see it all around me all the time, but also yes, this is also about specific people. Two specific people, actually.