#191: The curse of the try-hard
Morning!
After I received the below reader question, it kept popping back in my head for days. The asker’s perspective was pretty convincing (and puzzling), but eventually I started to see it as a story worth retelling, so that’s what I tried to do. Comments are open for additional interpretations!
Thanks for your amazing questions as always. Link to the submission form is here (it’s also in the footer of all my emails).
Dear Baby,
How do I get myself to care about and invest in my life and dreams when trying almost never works out for me, while half-assing it and following along the path indicated to me has perversely brought tremendous results? The Less I Try The More It "Works." This issue mostly manifests in dating and in my professional and academic lives. I have never once truly succeeded at something I cared deeply about or really wanted, but this is something I try to keep to myself, because I've succeeded plenty without really trying (privilege) at things that society deems valuable (mainly graduating from really good schools and getting a well-paying, stable, "prestigious" job), so I feel like a spoiled jerk even just writing this letter.
Dating-wise: When I go on dates with guys I am not attracted to, not interested in, or bored by, I am incredibly at ease just being myself, not thinking about trying to come off well, and very often they think I'm great and I end up in a relationship without really trying just by virtue of continuing to see them because they want to and I am "giving them a chance." Also because I’ve absorbed conventional meme-wisdom that heterosexual relationships work better when the guy likes the girl more. But I always feel a little dickish, like I am using them for attention or passing the time, knowing that if someone I considered "better" came along, I would drop them in a second. So I end up breaking up with them and forgetting they even existed. I'm obnoxiously arrogant. It isn't that I treat them poorly, but their feelings and well-being are never top of mind for me. I am secure in the knowledge that they would never leave me because "of course I'm the best they'll ever do" and this gives me a sort of fuck-it confidence, which guys weirdly seem to really be into. As soon as any little thing bothers me, I cut it off immediately and am ice-cold to any emotional appeal. I've unfortunately gained a reputation of being a bit of a fuck-boy.
On the other hand, the few relationships I've been in where I've been deeply attracted to my boyfriend and thought they were The Best, I've had constant low-level anxiety about them leaving me, I suddenly become a jealous insecure woman who sees a threat in every other woman who interacts with my boyfriend. I start to see myself as a hideous flaw-filled worm whom no one could love or even want to be loyal to. I start to overthink outfits, I make conversation topic lists, I am anxious about every little nuance in every text I send, I try to "read" them and become their "ideal woman." And my crushing anxiety about when he will lose interest in me becomes this subconscious pressure that I think ends up driving them away. These men break up with me probably because my need for reassurance and my performance of “perfection" is exhausting (even to me!), and I pine for months, even years.
Work-wise: I ended up in an entire career on a sort of "watch me fail at this" teenage dare with my parents. Turns out the job path my parents had in mind for me came incredibly easy to me: I didn't really study for any of the entrance exams, was incredibly calm at every step because I had nothing riding on the outcome and didn’t really want it for myself, threw together applications, half-assed a lot of the academic work and got decent grades anyways, didn't second-guess anything, was borderline cunty in the various interviews, and it has continued to just unfold really well for me, a decade later. My take-it-or-leave-it-I-don't-give-a-shit energy is off the charts.
Meanwhile, programs/jobs/career paths where I've labored over the exact right wording in the applications, tried to strategize my approach, tried to network and meet the right people, researched and rehearsed and tried to do everything "right," have been rejection-central. Papers where I've tried to shine and distinguish myself academically for my "brilliant thoughts" (LOL) have ended up being mediocre at best. I always feel embarrassingly like I am trying too hard to be liked and accepted in a cringe way. A new acquaintance of mine actually observed that I was way over the top and frenetically enthusiastic when talking to someone about a topic I cared about.
I think that these various experiences have taught me that my caring is somehow a curse. Every time I try hard at something because I care deeply about the outcome, it’s almost like my effort is the very reason it ends up not working out. But the result is that I feel disconnected from my life. Like my intentions, wishes, and efforts don't matter anyways and I am simply floating along. My life has somehow created itself around me with barely any input from me.
It has occurred to me that maybe I'm just that meme that’s like: "Someone's lack of reciprocation is not a challenge to convince them of my worth" and I need to just start giving up on jobs/careers/people whom I desire who do not want me, and just get comfortable in my own lane? Is the answer just: Get over yourself, be grateful that some things are really easy for you, stop being a dissatisfied bitch for no reason, re-adjust your romantic and unrealistic expectations from life, let yourself be adored by a dude and let go of your weird resentment that you're "out of his league," and just be happy???
WHY TRY, BABY?
You’re a compelling storyteller. I like this narrative you’ve constructed about your life—how you only ever fail upward, are only ever rewarded with what you don’t want. It’s funny and tidy, and makes a memorable character out of you: tragic, impressive, and a little cruel. But I don’t think it’s exactly right, about your life or about you, so now I want to try to deconstruct it.
There are a few different ways to reframe what you’ve told me. Here’s one: You’re not sure what you want yet. You’ve had a few vague ideas and tried to pursue them, but nothing worked out right away, so you’ve coasted along on your privilege and charisma and now you have a reasonably nice life but feel lonely and unfulfilled. You’re embarrassed that you’ve achieved so much through so little and ashamed that it still hasn’t made you happy, both of which stifle your attempts to change things because how dare you be ungrateful? On top of that, you’re stuck in a trap of dating to appease your own demons rather than to connect: either with men who make you feel safe because you know they’ll never leave you, or with men who make your heart race because you think they might. In both cases you feel flattered initially (flattered to be adored; flattered to be given the time of day by someone you deem “above” you), and then eventually unloveable (because you’re an ice-cold bitch; because “better” men see you as expendable), which in a way quiets your mind, because now you don’t have to wonder anymore.
In neither case are you truly connecting with someone, allowing yourself to be seen by a person you care about, or attempting to see that person for their full humanity. The highs and lows of these dating patterns are an intoxicating foil to the familiarity of them—they offer the drama of romance without the risk. Sometimes you really do try: to date differently, to branch out professionally, to let the mask slip to reveal your true over-the-top enthusiasm. But your only association with these experiences is rejection, so then it’s back to apathy or anxiety, whichever most efficiently delivers you from true presence and vulnerability. As time has worn on, you’ve lost whatever optimism initially inspired you to try to find more meaning in your life. If the game is rigged, why bother with sincerity? Why try at all?
Maybe that’s not exactly right, I took some liberties. But what I find useful about this framing is that, despite sharing the general facts with your own framing, it leads to a very different conclusion than the one you suggested. You say your results have been “tremendous”—but have they? Financial stability is nothing to balk at, but you otherwise describe yourself, in so many words, as unhappy, lonely, anxious, powerless. You feel like your only option to regain what little agency you have left is to embrace the life you’ve found yourself living but never wanted, to recast your tender disappointment as rugged nihilism, and to dissolve the scaffolding of your personality for the sake of progress that doesn’t come at the cost of your dignity. I know what you meant about tremendous—that other people have more material problems than you or aspire to your lifestyle—but what you’ve described isn’t enviable on a deeper level. I would bet there are a few people reading this who have less money than you and still don’t think your life sounds all that tremendous. I say that not to be mean but to release you from feeling crazy for feeling dissatisfied. You’re allowed to want more out of life than golden handcuffs.
The first idea I think you need to discard is that the less you try the more it works. Just because these jobs and men want you doesn’t mean they’re working—reciprocity is what you’re after. And just because you didn’t spend energy trying to please them or actively shape their idea of you doesn’t mean they brought out your best or most authentic self, either. In a way, they actually allow you to hide your true self behind cold indifference. You contrast these experiences with how you approach more desirable ones—torturing applications, ruthless networking, pre-planning conversation lists, trying to seem smart. This side of you, while driven from a more earnest place, is hiding too. In both cases you seem to define success by whether you can sneak into places you think you don’t belong. You say you’re obnoxiously arrogant, but I’m not so sure. I think you could like yourself a lot more.