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If you were fortunate enough to be born into a middle-class or higher family in a first-world, western country in the last ~40 years, you are subject to a set of circumstances that would have been unfamiliar to anyone, save a few members of the aristocracy, born before the 20th century: a stable life with financial security is not only attainable, it’s likely.
This isn’t hyperbole: per this 2023 Brookings study, 51% of the lowest socioeconomic quintile of American 9th graders in 2009 were enrolled in college within 18 months after graduation, and 68% of all 2009 high school freshmen attended college after graduation.
Attending college and (assuming you graduate) gaining access to the post-college job market are now table stakes, especially for those who grew up with some means. Of course, the economy is cyclical, you can never fully escape the risk of bad luck, and there’s plenty of room to mess up along the way, but in 2024, with the unemployment rate still near all-time lows, it doesn’t take a Herculean effort for the median American to graduate from college and land a white collar job.
And, as those of us who have spent any time in corporate America know, many of these white collar jobs are excruciatingly simple. To quote myself from a couple of years ago:
If pandemic-induced remote work showed me anything, it showed me how little "work" was necessary to do my job. I legitimately "worked" 5-10 hours per week at times, but I was always pretending to "work", by either moving my mouse to look active or tinkering with files, models, and decks that didn't really need tinkering to pass the time.
It was pretty obvious that if I didn't show up for a day, week, or month, the show would go on. I was playing with an unplugged remote.
The reality of corporate America is that if you follow the rules, do what you’re supposed to do, and maintain pleasant relationships with your coworkers, inertia takes over, and you can make a living wage while coasting through your career by answering a few emails, updating a few spreadsheets, and making the occasional presentation.
But this ability to coast is dangerous.
While our ancestors risked starving or freezing to death, the risks we face today are psychological, not physiological. In a world where survival is all-but-guaranteed, your greatest risk is that you spend your life not really doing a whole lot of anything.
In January 2022, 24-year-old Jack Raines wrote an essay called “The Opportunity Cost of Everything,” which was, among other things, a wakeup call that life is short, and you need to be intentional with your time. I’d like to revisit a quote from that piece:
We don't waste time by making the wrong decisions. We waste time by falling victim to routine and not making any decisions. We see this happen two ways:
Apathy
Hustle
The Cost of Apathy
Tell me if this sounds familiar:
Wake up at 7:30. Roll out of bed, log on your computer at 8:00. Sit around in your sweatpants, make some coffee. Work for thirty minutes, then mindlessly scroll through social media. Maybe you eat some leftovers for lunch. Maybe you pick something up. Back to the computer til five. Then you hit the gym. Come home and shower. Watch football/The Bachelor/Game of Thrones/whatever. Then you make dinner and go to sleep, because it was a long day!
And then you do that over and over and over and over again.
That was my life for a year or so. It has been many of your lives too. And it's easy to fall into this trap of passive routine. You're doing your job, after all. You're doing what you are supposed to do. So you continue to coast on autopilot. Day after day. How many of those dots can you color in with weeks like that? 20? 50? 100? There's no telling.
That's the danger of an apathetic life, life will pass you by before you realize it.
Imagine getting $10,000 every Sunday, but you can't bring any of the money with you to the next week. Surely you wouldn't waste it, right? You would spend every last cent on whatever you want.
Yet we get 10,080 minutes every week. How do you spend those?
The Cost of Hustle
You had a 4.0 in college and landed a great job out of school. You got accepted to a top MBA program. Your goal is to follow the American Dream: Resume filler job that pays well in your early 20s, top MBA, consulting/IB for two years in your mid-late 20s, pivot to private equity around 30, make as much money as possible. The road map to success.
The roadmap to success is like a weird game of Corporate Candy Land.
I was on the road map to success for a while. The problem was that I never asked myself if I liked playing this game in the first place.
I mean yeah, I would have a made a lot of money playing this game. Hell, I probably could have won the game. But was this a game worth winning?
Here's how this game would have gone: Post-MBA, I would have made a ton of money working 90 hours a week for an investment bank/consulting firm. It's not like I would have any time to actually spend that money. But if I did the tedious tasks long enough, I would get promoted to a position where I would work slightly less hours, doing slightly less tedious stuff, and make more money.
Sure, I probably still wouldn't enjoy the work. But I never cared about enjoyment, fulfillment, or any other irrelevant metric, because those weren't the objectives of the game.
Money. Power. Prestige.
Those were the objectives. I just wanted to win the game. Opportunity cost be damned.
Yeah, I might be miserable. But at least I'd be rich. And people would know it.
Hustle and apathy are two sides of the same coin.
You are either too disinterested to pursue what you want out of life, or too vain to realize you are pursuing short-lived things.
And the opportunity cost of both? Your life.
The thing about life is that you don't get a do over. You don't get to go back. You don't get to reach the mountain top, realize that you can't hold on to those fleeting feelings of success, and try to reset your life. Because those dots in your calendar can't be erased.
I still believe this passage is directionally true, but, looking back, I drew a false equivalence between apathy and hustle. Both have their issues, of course, but the former is far more damaging than the latter.
I would characterize hustle as “misguided ambition,” and the risk with hustle is that your priorities might be determined by external influences, leading you to pursue career paths and life choices that you would not have otherwise pursued on your own. Apathy, however, is far worse than misguided ambition. Apathy is a complete lack of ambition that results in you not pursuing anything at all.
They say that necessity is the mother of invention, but the luxuries of modern life have cured us of necessity, rendering the invention of oneself (through improvement, exploration, and/or the pursuit of a higher self) unnecessary. No longer needing to struggle to survive, many of us relax, defaulting to the apathetic life.
We all know what this apathetic life looks like:
You take an “email job” out of college and spend the next few years getting pretty good at moving around numbers in spreadsheets and logos on PowerPoints. You spend something like 30% of the work day working, and 70% of it zoned out, available to work, of course, while the day passes you by. Your Slack icon is active, though you likely aren’t.
You do this for a few years, then, assuming you hit a few KPIs, you get promoted, and you manage a few folks doing the same tasks you just graduated from. Maybe you switch jobs after five years, where you’ll move slightly different numbers around on slightly different spreadsheets, but nothing really changes. Life becomes a spectator sport where you trade time spent idling on autopilot for a decent paycheck, because your current situation is “good enough.”
The following tweet sums up this entire phenomenon:
“Good enough” might be the optimal strategy for your 401k, where you want to set your money in the S&P 500 and forget about it, but your life isn’t an index fund, and the purpose of life isn’t to optimize for some minimum viable income that pays you enough to cover your mortgage as you sleepwalk to your grave.
The point of life is to live, and living isn’t a spectator sport.
Living means taking risks, pursuing your interests, embarrassing yourself, attempting difficult things, setting ambitious goals, trying, failing, and trying again. Living means pushing your mind and body to their limits, just to see what you’re capable of. Living means fighting back against the inertial forces that draw all of us toward the apathetic life. Living means being the protagonist of your own story, not a passenger whose outcomes are at the mercy of their environment.
The irony of modern life is that those of us with the means to really, truly live, who can afford to take risks and strike out on our own and blaze our own paths, are the least likely to do it, because we are seduced by the comforts of the apathetic life, and we don’t have to go above and beyond to make ends meet. So we continue existing, not living, and the clock keeps ticking.
The most dangerous aspect of the apathetic lifestyle is that you don’t notice the time you’re wasting while you spend your days scrolling TikTok or Instagram, firing off the occasional email while absorbing whatever slop the algorithm pushes to your timeline. It’s only 10, 20, and 30 years later, when the time is gone, that you think, “Shit, maybe I should have done more with my life."
So, what, on the other hand, does the intentional life look like?
The apathetic life expresses itself as maintenance of some status quo, where an individual does precisely what is needed to maintain inertia’s trajectory, and nothing more.
The intentional life expresses itself through actions that change one’s default trajectory, leading to outcomes that would have otherwise been unattainable.
The most obvious expression of an intentional life is one’s career. While luck plays some role in the magnitude of our outcomes, there are no “accidental” successes. Some industries, such as medicine, law, aerospace engineering, and hedge funds require outsized effort just to get one’s foot in the door, and, in any field, ascension beyond the middle ranks is reserved for individuals who differentiate themselves.
That being said, professional outcomes are far from the only signals of intentional lives. As Naval Ravikant once said, “The only real test of intelligence is if you get what you want out of life.” “What you want” is subjective.
If “what you want” isn’t correlated with a particular career path, then a low stakes job with high flexibility could play a critical role in helping you achieve that. I remember, for example, meeting a few digital nomads in Budapest in 2021 who took full advantage of the lax return-to-office requirements at their California-based tech jobs by living abroad and traveling across central Europe. Sure, they may have temporarily sacrificed some degree of career advancement opportunities, but they certainly made the most of it. (Have you been to Budapest? It’s an incredible city, really.)
Making that same career sacrifice to doom-scroll TikTok from your living room for hours because you don’t like the office, however, is not great! If you’re optimizing for ambitious career outcomes, awesome. Do the work needed to make it happen. If you optimize for flexibility, excellent. Take advantage of that flexibility by doing something, anything, with your time. Maybe you have non-work interests that you want to pursue, like learning a foreign language, writing a book, volunteering at animal shelters, or building a niche artisanal clothing brand. Maybe you want to work on an independent business venture, and a low-stress job subsidizes your ability to work on the side hustle in your free time. That works too!
What I’m saying is that you should be intentional with your life and have a little ambition about something, otherwise you’re just wasting your own time. Wasting anyone else’s time is incredibly disrespectful, why would you tolerate doing that to yourself?
- Jack
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Jack's Picks
RARE BUT RELEVANT VENUE SHOUT OUT: For my fellow New York residents, I had the pleasure of checking out Jean’s off of Lafayette Street a couple of weeks ago for a buddy’s birthday, and it’s my new favorite night spot in the city. My best description is that Jean’s is what Acme wants to be: a quality bar/club with good vibes and 10/10 music that isn’t overrun by wanna-be TikTokers trying to be “in the scene.” I will be running it back to try out their dinner soon. Anyway, the place slaps, and if you’re sick of running back the Spaniard for the 12th time, it’s a much-needed improvement. (Not an ad, but one of the owners, John, is a friend of mine. The least I can do is show a little love).
On to non-venue recs: Scott Heiferman is a successful entrepreneur who has sold two startups for God-knows-how-much money, and 24 years ago, he took a job working behind the counter at McDonald’s to “get back in touch with the real world.” Here is his blog about the experience.
I really enjoyed Josh Brown’s recent blog post on the difference between having “fame” and having “influence.”
My favorite thing about this piece is just how exactly you made the case.
I mean, we've all read the "you should get off TikTok," and the encouragement to be more ambitious, and the "our jobs suck now." That stuff.
But the way you made the case was much more compelling - like, you have made it look absolutely silly and depressing to sit around wasting one's time. Which is a good thing.
In my own case, I'm not an ambitious person by nature. I'm just terrified, to my core, of waking up a year from now having done nothing. Therefore, I refuse to waste my time. I insist on trying interesting stuff.
Cool piece.
Not to be dramatic, but I think this is the article I was looking for when I started subscribing to Substacks.
Desk-job induced apathy is such a struggle for me right now and it is so hard to find people writing about it. One reason might be reluctance of people who have easy, high-paying jobs with a nice-enough boss, to say that it can still be a miserable experience. A lot of people might dismiss that as whiny when there are people who can barely afford rent and food.
I have tried leaning into doing the bare-minimum at a job I don't care about but that gives me a healthy salary and benefits. But the expectation that I be accessible most of the normal 8-hour day even if I'm not doing any real work means that I still don't have the brain space to pursue my interests. It is hard to really engage with a book if I've got an ear open for a Slack notification. I work in tech and there are not any part-time developer jobs but I would absolutely kill for one.
It's interesting you mention index funds -- having money set aside for retirement is a major reason I stick with the career I've got, plus health insurance and housing costs. My tech job isn't UBI, it's got a 40 hours of availability and ~15 hours of work requirement attached.