Timothy Ratliff is screwed.

While on vacation at a fictional resort in Thailand called the White Lotus (filmed at the real Four Seasons Koh Samui, where the Ratliffs’ “Three Bedroom Residence Villa with Pool” will set you back an astonishing $10,349 per night), our friend Tim finds out the FBI is ransacking his office in connection to his involvement with a money laundering operation. (“And I only made $10 million out of your stupid fucking scheme? Fuck!” he shouts at his co-conspirator from 11 timezones away.) This is one of the subplots of the third season of HBO’s White Lotus, a show which is mostly about power dynamics and rich people behaving badly in beautiful places, a “class satire” about “social climbing” and the necks that typically get stepped on in pursuit of ascension.

For much of our two-week travel bender, my sense of time warped under the influence of changing time zones, producing moments of genuine pleasure. While I had hoped for the purity of an unpunctured pause, I often haggled with recurrent flares of anxiety that everything I had left thousands of miles behind was still playing without me; that when I returned, I’d be on fast-forward until synced up again. (In the words of the paid time off study: “Fear of falling behind.”) But it’s also undeniable that several days of fewer than 30 minutes total screen time produced a startling mental clarity (and the sheepish embarrassment of embodying a cliché): Millennial Woman Finally Turns Off Phone and Knows Peace for First Time.

For our last meal before heading to the airport, we decided to visit the Four Seasons Wailea (where the first season of White Lotus was filmed). The poolside breakfast restaurant was bustling with people who could’ve easily been cast as extras: women with Connie Britton-blond blowouts, wrinkle-free foreheads, a rainbow of Hermès sandals on teen boys and older women alike, and silky swim coverups draped leisurely over taut pilates bodies. Men whose behavior seemed calibrated to project an air of harried importance took calls at breakfast while their families dined and chatted around them; I nearly broadsided one rushing to meet his seated wife and children after bellowing to the host he had been working that morning and needed something quick before he returned.

It was a caricature of the caricature portrayed in Mike White’s world, rendering the presentation of families like the Ratliffs something closer to a docuseries than a drama. Even here, at a beautiful beach resort surrounded by ocean on all sides for thousands of miles where a week-long stay costs the equivalent of six months median rent at a minimum, many still seemed clocked in by choice. It is a strange affluence of Faustian proportions in which one can afford a $2,000 nightly room rate, but cannot afford to eat breakfast without joining a conference call. I wonder what John Maynard Keynes, famed predictor of the late twentieth century 15-hour work week, would say. A life that permits you the most rarefied luxury of time freedom in theory but not in practice presents interesting questions about what “luxury” really means, though sitting at the Four Seasons Wailea, I felt pretty sure it wasn’t sitting by a pool responding to emails.

There’s a glut of research attempting to study the screen time habits of children and teenagers, which is sometimes found to be higher in low-income households—but there’s surprisingly little in the way of studies attempting to parse how adults’ relationships with the worlds in their devices are impacted by characteristics like income or wealth. The digital attention economy is, in many ways, an equal opportunity spiritual vampire, a rare feature of modern life that does not improve with socioeconomic standing. Extreme wealth can buy a room at the Four Seasons, but it can’t buy a less addictive iPhone.

As we wrapped up, our waiter, as if waiting for the meal to conclude before raising the subject, asked if we “had seen White Lotus.” Thomas and I exchanged a brief glance, telepathically negotiating whether we’d try to play it cool or admit it was the only reason we drove 30 minutes out of our way. “We’ve seen it!” Thomas responded, as though we hadn’t just been debating if the infamous Pineapple Suite was real over $37 of bacon and eggs. Fortunately, our restraint didn’t deter him. He immediately began ticking off production trivia: Most outdoor scenes were filmed at the adult pool up those stairs to the left. There’s no “Pineapple Suite” (but you can stay in its real-life equivalent, the “Maile Presidential Suite,” for $31,000 per night!). Jennifer Coolidge ate breakfast in that corner, sealed off from other guests. “There were real guests staying here while they filmed?” Thomas asked. “Yeah,” he replied, “They just blended right in.”

The equations of the “financial independence, retire early” movement translate time to money: The accumulation of investments worth 25x your annual expenses in tax-advantaged, low-cost index funds is, supposedly, the most direct way to buy your freedom. Something tells me that locked tech bag might be cheaper.

For years thereafter, I reordered this same planner, also carefully outlining blocks of time in lime greens or electric blues to denote everything from workouts to meetings. These bright boxes felt like the only suitable way to contain a schedule that increasingly threatened to seep out of the margins, time an unruly opponent that could be circled, plotted, and highlighted into submission. The sight of sparsely populated pages filled me with dread and a sense that some opportunity had surely escaped. Any blank space was a referendum on my commitment level.¹ 

I’d have stress dreams about losing the planner in the same way one might dream about losing a wallet or their front teeth, waking up sweaty, fumbling around in the dark to make sure my emotional support book was still resting on the nightstand where I’d left it. Time was something to be filled, stretched, saved, raced. To waste it was the worst offense. “Time is now currency,” E.P. Thompson wrote in his 1967 essay Time, Work Discipline, and Industrial Capitalism. “It is not passed, but spent,” like money.

The dawn of industrial capitalism utterly transformed humans’ perception of time, and as Thompson wrote, it was a moral shift as much as a technological one: Once time was something that could be bought and sold by the hour, it became a commodity, and commodities can be optimized. “The first generation of factory workers were taught by their masters the importance of time; the second generation formed their short-time committees in the ten-hour movement; the third generation struck for overtime or time-and-a-half,” he wrote. “They had accepted the categories of their employers and learned to fight back within them. They had learned their lesson, that time is money, only too well.” (I wonder what he’d say about the Slack generation and job descriptions that boldly declare noble principles like “work-life integration” and resisting the urge to “punch out.”) 

Industrialization mapped grids onto the undulating topography of our days, weeks, and years, creating the formerly unimaginable concept of “free time” (that is, time someone else has not already bought and paid for). Not everyone accepted this development without pushback: In France’s July Revolution in 1830, rioting Parisians shot at the clock towers. I, however, am much less daring than your average French protestor—and something about this orderly approach always felt inherently safe to me. Never mind that it’s completely at odds with a humanity that is cyclical, seasonal, and ephemeral.²

Even though it’s been years since I’ve owned a physical planner, the sediment from this period calcified my relationship with time: Once I was done buying the physical planners, I simply digitized the color-coded stacks for my Google Calendar, pleased with this rainbow affirmation of my effectiveness. Every six months, I’d realize I hated my system, maniacally drag and drop the boxes around my screen, squeeze in a few more, and issue notices to the people I worked with about my new schedule; the schedule that would finally allow me to transcend the human realm and become one with the Cloud.

Whenever periodic tweaking, rearranging, and wrestling my capacity into the confines of these two-by-three squares couldn’t make things more sustainable, I blamed a faulty strategy for my failure to accommodate the load. It never occurred to me to ask whether the problem might’ve been the load itself. 

More recently, I’ve been preoccupied with time—how we use it, how we perceive it—following a conversation with a friend who just landed a major novel and film deal. “Now that things are taking off,” she told me in a voice note, “it feels more important than ever to protect my space and thinking time.” This struck me immediately as profound. Where I had understood early career traction as proof I needed to make my time (and myself) more efficient, more available to seize every opportunity while people cared what I had to say, she saw this as a trap. Her instinct—to protect, not maximize—implied a self-trust that left me speechless. 

This new framing rendered my approach almost exactly backward. What if the thing I had internalized as proof of high performance was actually a lack of trust, a self-imposed policing of time and effort that implied things would certainly turn to shit if I allowed any breathing room? Giving myself over to the anaesthetic glory of pinballing through a packed day almost always meant abandoning my physical self entirely, something I only noticed when someone asked me how often I held my pee as a proxy for connection to my body’s most basic cues. I realized I was holding my pee while they asked.

The unfortunate thing about meticulously creating this architecture designed to enable constant motion is that you can’t really hear over the sound of the whirring machinery, so it’s easy to become alienated from the “you” that might choose something else. Space is a prerequisite for stillness, and stillness for listening. Rarely did I consult any such “inner voice” for direction in my decisions. Who needs an inner voice when you have a color-coded G Cal barking orders at you every 15 minutes? 

But this is the implicit operating logic powering most places where we’ve substituted a paranoid surveillance for human instinct, to the point that we hardly notice it as a discrete presence: You should closely budget every penny, because you cannot be trusted to allocate your resources wisely without intense monitoring and restriction. You should count your caloric intake, because without this supervision, your body cannot be trusted to know how and when to fuel or move itself. From this primordial soup emerges everything from fad diets to agitated, high-octane Black Friday benders. How much of this prescriptive complexity and indecision could be avoided if instead we learned how to access and trust the silenced parts of ourselves that know what we want without cost-benefit analyses or crowdsourcing?

“Temporal” is a word with a double meaning: It means both “relating to time” and something that’s “of the flesh”—something earthly, corporeal, real. When humans adopt the invented logic and language of economics in their individual lives too earnestly (“time is money!”), we become alienated from the sort of intrinsic power that can’t be neatly quantified or even explained; the quiet knowing that says when something feels wrong, or right. 

______

¹ “Blank Space” is also the genre-shifting Taylor Swift single that marked her transition from country to pop, but I’ll keep it in my pants.

²I’ll note this is doubly true for women, whose bodies and hormones are literally cyclical, though again, I’ll keep it in my pants!

In his 2018 book Bullshit Jobs: A Theory, the late writer and “anarchic economist” David Graeber articulated how and why this kind of worklife proliferates in a system theoretically designed to prevent such inefficiency in the pursuit of profit maximization. He compares the increasing “bullshitization” of a market economy, in which low unemployment is considered a unilaterally worthy, bipartisan goal (with no qualification for whether that employment is socially useful), to the “full employment” goals of the Soviet Union, and puts forth a compelling case for why private corporations are often no better than big governments** when it comes to avoiding bloat. 

Based on his quantitative and qualitative surveys and studies conducted between 2013 and 2018, he estimated a staggering 35–40% of work in a modern economy fits his “bullshit” definition, defined broadly as work that could disappear tomorrow with effectively no material consequence for humanity—nobody would even notice it wasn’t being done anymore. A critical part of this theory: If you work a job that’s partially or wholly bullshit, you know it. Very rarely is the person in such a position under any grand delusion that their job is something worth doing, and that knowledge is a sort of spiritual violence in itself. (He makes an important distinction between bullshit jobs and shit jobs, the latter of which are critical to the continued functioning of society but usually go under-respected and underpaid, like the aforementioned teachers, nurses, et. al.)

If you’ve ever worked for a giant multinational corporation, you can probably intuit how this bullshit metastasizes out of control: There’s a managerial game of telephone up, down, and across many levels of hierarchy which inevitably trends toward excess and unnecessary complexity, where those on the bottom rungs of the ladder are usually the only ones actually producing anything. He categorizes the jobs in this B.S. ecosystem into five subgroups: duct tapers, box tickers, goons, flunkies, and taskmasters.

The book is both radical (in that it inspired a lot of backlash from bastions of market-based efficiency) and intuitively, primally obvious if you’ve ever had a “full-time” job that could be completed in an hour and a half each day. A particularly industrious friend of mine noticed this a few years ago about his data analytics role and proceeded to accumulate five simultaneous full-time remote jobs at big-name companies. He said the craziest part was how little people checked in on him or questioned what he was doing all day. This went on for years. Each paid in excess of $100,000. It seems hard to believe that an efficient market could produce outcomes like this, which begs the question: Are we finally approaching a crescendo of absurdity? 

Graeber’s book was an expanded version of his original viral essay, published more than a decade ago, and in the intervening years, it seems to me the situation has only accelerated. It’s captured in reflections like Derek Thompson’s recent piece for the Atlantic, “White-Collar Work Is Just Meetings Now,” where top Microsoft execs are quoted saying, “I think we’ve hit the high point of max human inefficiency in white-collar work. It sometimes seems as if the modern worker spends more time talking about work than actually working.” 

The exec said later in the piece that he was “optimistic about artificial-intelligence tools” as the fix (of course), allowing people to “focus on their work” (sure!)—but I think a more cynical read is that the very reason there are so many meetings is because there might not actually be that much work to do—just corporate boats against the current, circling back ceaselessly into the prediction of Keynes’s 15-hour week. 

Graeber’s original premise, that most “knowledge work” is just elaborate corporate theater, struck a chord with the Youth. In general, Gen Z seems altogether more skeptical of big business’s elaborate, bizarre rituals: An Instagram Reel in which a person simply read Thompson’s “White-Collar Work Is Just Meetings Now” article generated 2.3 million views and more than 1,300 comments, flooded with people contributing their own anecdotes of meetings to plan the next meetings. So if much of it’s pointless, and many of us seem to know it, why do we still play along? On this question, we can consult Occam’s Razor: Most of us just need the money.

Obviously, if much of this effort is really as wasted as I’ve made it sound, you’d expect to see signs in economic data. While American gross domestic product may be higher than ever, it’s become a bit of a popular concern in academic journals and media coverage alike that American innovation has been stalled for most of the 21st century. To me, this indicates that while there might be a lot of money sloshing around in the system (and a lot of people working to get that money), much of that frenzied action—this illusion of growth—might not be accruing toward actual progress, or the material state of things improving. In other words, we’re definitely making more, but we might not be making better. (In 2023, that socialist nanny state Sweden, powered by people all hopped up on adequate social services, overtook the American economy for the #2 spot on the Global Innovation Index.) 

A side note: I assume this sense of futility would be especially maddening for working parents. If one or both parents suspects their job falls into this category of well-paid profligate nonsense, it can feel like a cruel twist of modern capitalism that that (unnecessary, superfluous) junk is what they can be paid to do, while the critical work that must be done at home is relegated to nights, weekends, or other people. In 1975, feminist activist Silvia Federici critiqued the way industrialized economies fundamentally ignore the value of domestic labor in Wages Against Housework. She considered this the core exploitation on which all other labor exploitation relied, and believed the only way to rectify it was to compensate people for caregiving work, thereby recognizing it as work—not just the natural activity We Ladies like to do in our spare time that must be subsidized by The Actual Real Work of generating fancy charts for slideshows so your boss’s boss’s boss can more readily comprehend revenue is down without having to read.

Back in 2018, when I felt trapped by the prospect of spending 40 more years in an in-person office job, I became obsessed with financial independence. The equation was simple, the path was clear, and the connection between money and freedom was obvious; a personalized, depoliticized solution to a collective affliction that I had mistaken for unique to me. This was two years after my first boss pulled me aside to bestow her pearl of wisdom, which meant I had long been equating significant swaths of “working” with “high-stakes pretending that I’d give my life to achieve our KPIs (in exchange for my rent).” This seemed like an inescapably bleak way to spend the bulk of one’s time, even if this truth was complicated by the fact that I felt Kool-aid-concentrate levels of love for my company and the people I worked with. 

With no understanding of all that fancy-shmancy labor theory and nary a whiff of skepticism about capitalism, it still made intuitive sense to me that I would necessarily get to do more interesting work with more social value if I were choosing it not on the merits of whether it could pay me enough to service my car note, but if it served a genuine purpose. If I could play by the rules of the game long enough to “win” and buy my independence from its strictures, I could spend the rest of my life working on things I cared about without any regard for my material well-being or the prestige of a title and direct reports. (Granted, whether my former life determining button copy on WhatsApp pop-ups was more or less socially valuable than my “work” now as a chronically online podcast host is up for debate.)

We all know what happens next. I slashed my spending to the bone, started working a parade of part-time jobs, engaged in spreadsheet rain dances, and mainlined podcasts about how to do everything from eat to travel for free. To my shock and delight, it worked. Over the following years, I accumulated tens of thousands—and then hundreds of thousands—of dollars. The punchline, of course, is that the work I ended up doing for fun once I no longer really needed the money became the thing that generated the most money. (Go figure.) The point is, if you game the game for long enough, you may eventually “win”—and your level of desperation commitment (hustling free food out of lunch meetings you weren’t invited to instead of buying groceries, working 80 hours a week, etc.) will determine how quickly.

The more worthwhile question, then, is whether this is the most sensible way for a society to organize itself. My story illustrates the center of the Venn diagram between Graeber’s thesis and FI/RE dogma: If you accept his premise that a solid chunk (35–40%) of all modern work is functionally pointless, it stands to reason that you could eliminate it and still achieve roughly the same amount of real productivity (that is, results) with a lot less languishing. 

Furthermore, if you accept my premise that accumulating a sufficient nest egg is what enabled me to assume the risk of giving up my “corporate career,” and we agree for argument’s sake that my work now is more beneficial than my trafficking in decks to be attached to emails that nobody read, then couldn’t the existing “bullshit jobs” paradigm be viewed as a sort of wasteful purgatory preventing humans from fully flourishing; from reaching their potential? Employment for employment’s sake? Soviet Union-style Fake Email Jobs?

Ten years and one global pandemic after Graeber’s essay was originally published, it feels as though we’re reaching a fever pitch of recognition that something needs to change. Graeber takes pains to explain he wrote the book to explore the phenomenon, not propose solutions. Still, he says a universal basic income*** might come closest to chipping away at the intractable problem of nonsense jobs, because, like FI/RE, a UBI decouples your livelihood from work. A straightforward, “everyone gets the same amount” direct payment of UBI that’s enough to support a dignified existence would “massively reduce the amount of [public and private] bureaucracy in any country that implemented it.” 

While critics suggest this would be disastrous for “productivity” (a dubious claim if you accept that what we quantify now as productivity is people needlessly pushing paper—or money—around from one pile to another), this strikes me as a cynical view of humanity. The notion that a human with enough money to afford their basic needs would be content to sit around all day watching Love Island reruns and inhaling family-sized bags of Cool Ranch Doritos until they die completely ignores just how fundamental the human search for meaning is; how viscerally we crave purpose and seek challenges. 

“The underlying assumption [of critics] is that if humans are offered the option to be parasites, of course they’ll take it,” Graeber writes, “but leave [people] to their own devices, and they almost invariably rankle even more at the prospect of having nothing useful to do.” In other words, most people don’t need more authoritarian oversight and busy work to keep them contributing to the world—they need more freedom. (The great irony of these concerns about people unfairly leeching off society is that our current system enables some of the most breathtaking examples of shameless parasitic behavior not at its depths, but at its heights, where supposedly the most upstanding among us reign—take the former CEO of UnitedHealth, for instance, whose total compensation topped $142 million in 2021 during the largest global health crisis in 100 years.)

I’ve experienced the upside of financially secure freedom: I started Money with Katie three weeks into the lockdowns of 2020 because my full-time and part-time jobs had skidded to a halt, leaving me with effectively nothing to do. It seems like we used to understand that this is how innovation happens: In 2007, Google engineers were given one free day a week to pursue whatever interested them. They invented Gmail, which is, I’ll admit, alternatively a brilliant creation and a scourge of “Bumping this!” messages. (Eventually, the “free day” policy got relegated to its own siloed group, and these days, the company is more likely to generate headlines like this one.)

Another approach that strikes me as more reasonable than whatever economic fever dream keeps producing ever more jobs like East Coast Dynamic Brand Consultant but not enough, I don’t know, teachers and nurses, would be to approach the economy a little bit like modern newsrooms approach their businesses: The fun stuff (games! recipes! celebrities!) generates most of the revenue, which is then used to fund the necessary, hard, and expensive reporting that sponsors won’t touch. Frivolity’s profits subsidize the essential-but-not-profitable core function of the newspaper. What if all the excesses of trillion-dollar companies were spent not on hiring more “box tickers” and “flunkies,” but instead rerouted where the money was needed for unprofitable essential services? (Did we just reinvent corporate taxation? I guess so, but in my proposal, they actually have to pay.)

The fact that a modern industrialized economy has a bottomless thirst of well-compensated headcount for “digital marketing SEO ninjas” but relatively little demand for artists, educators, musicians, and builders who do work that makes the human experience feel worthwhile is a signal that whichever McKinsey consultant is pulling the strings behind the scenes of our economy with their latest $100 million government contract has been given way too much power to define “value.” Maximum total possible wealth is not, it’s worth stating explicitly, the same thing as maximum shared prosperity, and a society committed to the former will find it impossible to achieve the latter. It seems more and more people are coming around to the idea that this is a foundational, organizational mistake.

There is more than enough money—more than enough real productivity—to accommodate such a shift. And while not every necessary job is glamorous in the traditional sense, things like construction, cooking food, and caring for others are useful to humanity, and thereby inherently meaningful in a way that Graeber’s bullshit jobs, by definition, can’t be.

When people are free to pursue work that is meaningful and interesting to them unbound by the practical limitations of things like keeping a reasonable roof over their head or access to basic medical care, they thrive, and so do the rest of us. This is a somatic truth; I feel it in my bones. As we saw in 2020, when people have more financial breathing room, they are less easy to exploit—and wages for essential jobs rise. Though I didn’t know it yet in 2018, my decision to reorient my entire life around self-insuring my material existence was actually an attempt to expand my autonomy and create more safe options. In doing so, I bought the time, space, and freedom necessary to realize it would probably be more generative to question the systems that structurally limited those options in the first place. 

That’s the paradox of the nebulous monolith that is “corporate culture”—it is enormously powerful and seemingly inescapable, and yet, entirely reliant on unquestioning cooperation from the masses. As Grace Blakeley put it at the end of our show last week, “If we all stop obeying, that’s it.” The challenge, of course, is that disobeying costs money, at least at first. In the meantime, there’s always FI/RE. 

*I have only ever worked for corporations with tens of thousands, if not hundreds of thousands of employees, so I’ll concede working for a four-person startup is—obviously—a radically different experience, but still not immune to BS.

**In fact, a comparison of the growth of “administrative” jobs at public and private universities suggest this sort of Fake Email Job has grown faster in private institutions than public ones, something Graeber explains by pointing to the rich boards of trustees steeped in the logic of the corporate world that are less inclined to question the necessity of layers of coordinators and specialists than the public officials who are more likely to feel pressure to crack down on waste.

***If you listened to last week’s episode of The Money with Katie Show, you know that my guest, Grace Blakeley, doesn’t think universal basic income is a good long-term solution, and is more in favor of universal basic services for the things all humans need to survive. I don’t feel strongly one way or the other, and I think both arguments are worth entertaining.

Dear reader, this was a seismic miscalculation. It turns out Americans hate insurance companies more than Zuck hates our attention spans. Instagram’s built-in insights told me the video was shared nearly 3,000 times in a few days. It accumulated 798 comments of commiseration, frustration, and confusion. That type of engagement is usually reserved for Ballerina Farm or political controversy. 

We crowdsourced creative approaches in the comments. Billing department employees, physicians, and chronically ill folks alike chimed in with their favorite workarounds for navigating this dystopian labyrinth; call the medical provider first and ask for the cash-pay rate without divulging you have insurance; no, call the insurance company first and request an estimate; no, that won’t work, because they’ll tell you they don’t know; no, you need to find the secret Excel file with the procedure codes; no, not THAT Excel file; no, let the bills go to collections and then commence mob-boss-style hardball negotiations.

The comments section felt like a collective effervescence, and also, this meme:

Finally, one commenter snapped us out of it: “We shouldn’t have to do this for something we pay thousands of dollars a year for.”

Historically, the FI/RE (financially independent, retire early) community hasn’t had much to offer in the way of advice for these concerns in the US. More often, questions about how to fund healthcare in early retirement are met with shrugs of resignation at best, and naïve, eugenics-y health platitudes at worst (“Just eat right and exercise and you’ll never have to worry about healthcare expenses!”). 

I know this because I used to respond this way (with the shrug, not the eugenics). When people would reach out and ask the eminently reasonable question of how to account for $1,000 monthly premiums and $15,000 out-of-pocket maximums in their financial independence number after untethering from corporate benevolence, I’d find rambling ways to conceal the fact that I had no idea. The solution was always the same: Just save more money. Pete Adeney, the prolific Mr. Money Mustache, has famously opted out and doesn’t have insurance at all, opting instead for a direct primary care model.

In the best cases, you’ll find advice for how to negotiate medical bills (to varying degrees of success), but funding your own insurance in a system designed to sop up as much liquidity as possible from whatever’s sloshing around in S&P 500 benefits reserves is astronomical even for the worst plans, and they’re only getting worse. 

There are no good answers for individuals, because this is a universal problem in need of universal overhauling. The only real solution is to burn the whole thing down and start over. The sooner we can collectively get onboard with this reality, the better for everyone. We could start by dropping the phrase “socialized medicine,” propaganda that prominent ex-insurance executive Wendell Potter admits was dreamed up in a Cigna boardroom. (There is an embarrassing amount of evidence that a single-payer system would be $450 billion cheaper each year. A society that believes a small number of people should be permitted to get rich off the financing of medical expenses has lost its way.)

In the absence of systemwide changes to the rules (and the banding together that would require), people are left to individually perfect their level of game play. Much like the FI/RE community jumps through loopholes to navigate this playing field, similar attitudes are present in another community preoccupied with winning the game of life: the biohackers. In both, a deep but scarcely acknowledged sense of structural precarity fuels an obsession with extreme optimization. Derek Thompson recently pointed out a crucial aspect of this pursuit of efficiency:

To save you the 47 seconds of what I can only describe as “American Psycho produced by Andrew Huberman,” a beefy, chronically shirtless man awakens sitting upright, gazes into his own eyes as he removes his mouth tape, brushes his teeth, puts on a sassy little outfit, pulls his Rolex out of a grayscale Louis Vuitton box, drinks espresso, lights a candle, journals, takes supplements, enters a red light chamber, meditates in a different red light chamber, starts his Lamborghini, of which we get eight (8) gratuitous angles, goes to the gym, works out (shirtless again), cold plunges, swims, and then reads a book (my money’s on Atomic Habits or something by Mark Manson) in a sauna in his backyard. This is, allegedly, the “routine that saved his life.” 

I’m two years alcohol-free, but the vacant precision of the self-improvement in this video makes me want to go on a bender fueled by intravenous espresso martinis just to restore balance in the universe. 

Obviously, nobody in their right mind is actually living this way (and I can begrudgingly admit to enjoying a cold plunge), but it’s telling that this brand of lifestyle content codes as aspirational to a significant subset of young people. And Derek’s observation—that this hyper-optimized brand of self-obsession all but requires the metaphoric or literal absence of the needs of other people—is a critical component. This is a worldview that teaches happiness is found via meticulous construction of a life you can frictionlessly glide through, all your rough edges sanded down. It’s a life in which you are accountable to nobody but your two-hour morning routine and arduous “self work,” the more burdensome and relentless, the better. 

The idea that we all must be constantly “working on ourselves” is the undergirding assumption of so much of modern life, personal finance included, and it’s a covertly appealing one: It prescribes giving a shit about nobody but yourself. But optimization is a response to things getting worse. We don’t usually experience the impulse to optimize when we feel we have plenty. If you’re guaranteed a month of paid vacation each year like the French, you probably aren’t stressing about how you’ll spend each and every hour of your down time.

Optimization is often a reaction to a life that’s both too full and too empty, and the subconscious awareness of a seemingly bottomless pit of risk. There’s a reason the people who live in the countries with social safety nets are chain-smoking Camels and drinking espresso at 4 pm to gear up for a cheese plate tour of the town square instead of “biohacking.” When you feel like the rug could be pulled out from under you at any moment, there is no room for error. This is a feature, not a bug, of the American status quo, which is most adept at creating problems for which it can sell you solutions.

The other day, a friend who outside of Portland texted me to express concern about the people who go to her gym, whom she described as “the raw meat types.” “They all walk around barefoot,” she whispered to me in a voice note from the parking lot, “so I’ve been spreading light paranoia about athlete’s foot.” 

Apparently, four of the four people with whom she raised the issue assured her that if you “just don’t think about it,” you’ll be fine. The mind has control over the body, they lectured her, so to remain healthy, she should think healthy thoughts. “I don’t think that’s how fungal infections work,” she said. She sounded disoriented.

This is the reassuring, mystical logic of self-optimization: That if I am healthy, natural, perfect, streamlined, I will not suffer. Transcend your own human form and all its pesky co-pays via Thinking Positive Thoughts and drinking raw milk. It is, at its core, a deep desperation for control; an every-woman-for-herself ethos that says there are “superior” people, and with enough obsession and focus, you, too, can become superior, and if you’re superior, who cares if our healthcare system is a too-big-to-fail, vibes-based cartel? The inferior people deserve their fate. (I promised you eugenics, and now I am delivering.)

The self is the final frontier of this optimization effort, which is how we ended up with influencers like this guy:

I know you’re not going to believe this, but if you’re ready to “acquire valuable datasets,” do “group workouts,” and “raise your collective consciousness,” you can join his Mastermind, Leveraged Lifestyle. This can all be yours for the low, low price of $1,997.

To a person who feels protracted overwhelm, this rugged individualism can feel like salvation (after all, it certainly narrows your focus via “the complete absence of other people”). But this prescription insulates you from the type of connection with others that would allow collective recognition to take place. Reducing your life to an enormous checklist of physiological maintenance implies that our shared symptoms can and should be managed with more concentrated individual effort. This fracturing distracts from the reality that everything from lax food regulation to ever-rising insurance premiums drives all of us further into our siloes of escalating self-work, saving, and stressing.

As a former group fitness instructor who bears an alarming and readily searchable internet record of enthusiastically endorsing “optimization” of all sorts, I am guiltier than your average person of investing too much faith in the promises of a #streamlined existence. It assures you deliverance from risk, suffering. Who doesn’t want that? The feeling that provides the thrust for this worldview—a desperation for control and a better life—is legitimate and deeply human. It’s the solution that ultimately proves hollow. 

Resist the insistence that you are a commodity to be optimized. Luxuriate in your human inefficiency! Streamlining yourself into oblivion has the same resigned pitch as the healthcare advice to “save more money,” and it’s ultimately futile for the same reason: You will never arrive. The human cost will continue to rise for as long as it is permitted to do so.

I wasn’t yet a self-proclaimed personal finance nerd, so the lifestyles surrounding me were often confounding. There was the entry-level executive assistant who drove the brand-new Lexus and lived in a one-bedroom apartment with humongous walk-in closets, the couple who owned a gorgeous home in our city’s upscale suburb despite neither holding a job that could explain such a purchase, and mostly, there was a lot of discretionary spending at bars, restaurants, boutique gyms, and shops. The most challenging to parse were those on the cusp of plausibility: Yeah, he’s an electrical engineer…but a penthouse and a doorman? A lot of it didn’t add up. 

Over time, an uncomfortable disorientation seeped in. My lifestyle looked nothing like theirs, yet I knew enough to deduce we were in relatively similar pay bands. I was fumbling for different ways to ask the same awkward question—How are you pulling this off?—which was usually a translation of an even more uncomfortable itch: I must be doing something wrong.

Now that I’m loosely aligned with a network of folks who hustle in their free time to speed up their wealth accumulation process, I know what “normal person” quick progress looks like—and this wasn’t it.

In my confusion, I concocted theories.

“Maybe they know which hot stocks to invest in.”

“Maybe they found a really talented lender and accountant. Do I need an accountant?”

“Maybe they have some of that ‘passive income’ I keep hearing about on Instagram.” 

Having no idea how investing worked at the time, my imagination filled in the gaps with increasingly unlikely explanations. Of course, now I look back and know better. The real answer is the world’s oldest riddle: What’s great if you can get it but absolutely befuddling if you can’t? Family money.

This knowledge has been one of the greatest side effects of learning how saving and investing works. It lifts the mysterious mathematical fog shrouding illogical situations, simplifying and ventilating feelings of shame or inadequacy. You know Jennifer earns $54,000 but owns a $900,000 home in the part of town with the best walkable coffee shops? It’s not a secret, hard-to-find mortgage product that you’re too unsavvy to access or a first-time homeowner program for which you missed the application period. It’s—say it with me!—family money. We shouldn’t begrudge Jennifer; though, of course we’re human, so we might. I know if I were offered a three-bedroom hand-me-down from some wealthy relative, I’d gladly accept, too. 

Still, it’s good to know: If a person is inexplicably well off, someone who came before them must’ve put in the time and compounding on their behalf. This is great news. It means you can adjust your comparison standard for the inflation of rich parents and quit blaming yourself. 

Comparing yourself to others is almost always fraught, but in the uncertain throes of early adulthood, it can be an irresistible (and somewhat practical) measuring stick. Comparison is how we make sense of ourselves in a world without absolutes. It’s natural. But to be helpful, it must first be calibrated accurately.

In 1% of scenarios, you’ll encounter that adolescent freak of nature who, at age 12, cornered the lawn-mowing market in their suburb and funneled the proceeds directly into pre-stock split AMZN, and her million-dollar home at 25 years old is merely evidence of her prodigious entrepreneurial acumen and ability to allocate capital. But this is, far and away, the exception to the rule. 

Here, people will point to surveys about inheritance and claim that “fewer than 20% of people inherit their wealth,” but we must take a wider (and less literal) view: I wouldn’t check “yes” on a survey asking if I inherited my wealth, but my parents allowed me to graduate debt-free, gave me a car, and paid for most of my wedding. Just because their contributions to my bottom line prevented it from becoming negative rather than boosted it into six-figure territory doesn’t mean I didn’t benefit from the choices they made. Does someone whose parents put down the money for their first home report an inheritance on a survey? 

Self-reported data about how and why someone has what they do isn’t a reliable gauge of the phenomenon I’m describing here, which relies less on giant, one-time cash transfers and more on a consistent pattern of compounding small advantages over many years—from receiving rent stipends to covertly using a parent’s AmEx for groceries, insurance, and gas or accessing your dad’s Delta miles for semifrequent first-class international trips. For all our talk about generational wealth, it’s fairly challenging to quantify where a relative’s benevolence ends and a young person’s self-sufficiency begins. 

Still, some of it is quantifiable: The 25-year-old in Manhattan whose parents foot the bill for all fixed expenses such that a meager entry-level salary can be spent entirely on discretionary whims is providing a boost that, to an outsider, would appear nonsensical. If you didn’t know any better, it’d be easy to assume that you must be uniquely failing at capitalism, rather than simply having been dealt a hand that looks more like a foot.

But one of the first lessons you learn in any personal finance education (at least, that which doesn’t come from someone trying to sell you a crypto arbitrage course) is that there are no shortcuts. You must either earn a lot of money, invest consistently for a long time, or some combination of the two. In the absence of both, you can assume a third path:

Maybe she’s born with it. Maybe…oh, wait. Yeah. She’s born with it.

Regardless, the promise of a tabula rasa in the future feels like purification. But when you’re staring that promise in the face? When you open the glistening, unblemished page in your new $29 Moleskine and it’s time to write your first entry? Planning to be somebody and being somebody are different jobs.

Part of the voluntary shame of this process is the pesky memory of all the first pages that came before: the budgets carefully manicured then discarded the moment we discovered our desires didn’t fit inside them, the earnest devotion to reasonable screen time limits bypassed in mindless, repetitive 15-minute increments, the pledges to meditate every morning promptly abandoned as soon as the first frantic 6am Slack message of the new year arrived. 

It’s humiliating and endearing, the way we return to the altar of our goals and plans, ready to suffer our penance and re-up. The cynics among us gave up on this ritual long ago, but the naive optimists? We can’t help ourselves.

To call my typical end-of-year review process “achievement-oriented” would be generous. It’s been focused—narrowly and obsessively—on money and career progress since 2020. I’d go through the motions of setting personal goals (screen time! meditation! books!), but my heart wasn’t in it. 

“I don’t know,” I’d write in the spiritual or family or relationships sections, “Maybe I’ll call my parents more. Anyway, back to Forbes 30 Under 30!” I’d write, reanimated and foaming at the mouth over a meaningless list and its honorees, many of whom were cautionary tales so possessed by ambition that their drive turned them into felons. 

While the self-imposed pressure to make the annual turnover meaningful is uncomfortable, I think we feel it because we accurately judge the stakes to be high. We might get a fresh start every year, but our years are not unlimited. The desire to do right by ourselves is natural; healthy, even. 

Part of this onerous ritual for me each year involves rereading all of my journal entries from the last 365 days. Since my birthday is on December 22, I get the double-whammy of turning another year older right before the calendar changes over (I like to think I was early to Capricorn season because, well, you know). It’s a valuable exercise to digest a full year’s worth of the things I felt strongly enough to write about in the moment, because themes tend to emerge.

During my review of 2023’s goals, I noticed something: At the beginning of the year, I had intended to avoid corners of the internet that made me feel shitty, like Elon’s radioactive social experiment. I had intended to start my day more thoughtfully and to avoid catastrophizing and spiraling. I had intended to spend more time making things, and less time consuming them. Compared to my financial and career goals, these were footnotes. Asterisks. On your way to making a million dollars, I seemed to write, can you also cut down on doom-scrolling?

So imagine my surprise in reading back through the journal and finding entries about my phone creating anxiety, waffling about how to start my day (“Kinda wanna work out, kinda wanna just start working, I don’t know. Maybe I’ll shower;” girl, just pick one), and—what else?—some good, old-fashioned spiraling. 

This was, strangely, comforting. It was like staring at a roadmap to myself. Oh, I thought, I’m sitting here making lists of income and net worth goals, when the real needle movers are right in front of me. On a day-to-day basis, there were strikingly few entries about money. For how much emphasis the subject received in my goals, it was almost entirely absent from my journal entries. There was plenty of hand wringing about my creative process and business decisions and long-term dreams, but the dollars and cents of it all never really entered the plot. 

Maybe it’s because it had been a focus for so many years that there wasn’t much else to say, or maybe it’s because once you reach a certain satiation point, further focus feels beside the point. Or maybe it’s that the dollars and cents of it all were never really the point. 

It didn’t take a close reading to reveal that brute-forcing my way through more work, rather than creating the space necessary to make that work good—might’ve been self-defeating. (After all, as I reviewed my 2023 treatise, manic in its loftiness, I couldn’t ignore that I’d met neither the net worth nor the income goals I had set. All that emphasis—and for what? Even the approach that prioritized financial and career success above all else didn’t produce the intended results—financial or otherwise—so maybe the approach wasn’t serving me as much as I had thought.) 

Of course, I’m still Money with Katie—so that’s not to say I don’t have any financial or career goals for 2024. Just that their weight has been right-sized among the things that I’d historically ignored, the things that clearly had a larger influence on my day-to-day satisfaction than the second decimal point of a savings rate or an arbitrary net worth threshold.

And I don’t know—maybe it’s the optimism <> narcissism cocktail talking, but something tells me my approach this year might be the one that Finally Changes Everything.

How have your goals changed this year? Send us an email at moneywithkatie@morningbrew.com and let us know.

If you just had the discipline to work longer hours, you’d earn more.

It’s compelling because it feels fair—if someone works harder, they should achieve more.

We buy into this “meritocracy messaging”: that if we want to achieve great things or experience success, it has to feel like work. A healthy body, an overflowing bank account, an amazing job…surely these aspects of Adulting Porn are only available to those with the self-control and work ethic to arduously strive for them, right?

But successful people are not more disciplined—they’ve just found approaches they enjoy.

Take exercise and healthy eating, for example: I don’t enjoy wandering around a big box gym, poking at a few smelly machines, and indiscriminately curling dumbbells. So guess what? I don’t. If my only option for exercise were this hypothetical poorly lit big box gym with bad ’80s music and zero structure, I’d probably never exercise. 

At my most fit, I was going to 7–9 fitness classes per week. I loved the format of the classes, I loved the music, I loved the instructors—I thoroughly enjoyed my time in these classes, even if we were doing four straight minutes of burpees at 5:45am.

It wasn’t discipline that pulled me forward—it was joy. As soon as it became genuinely enjoyable, it was easy to work out. It actually required very little discipline.

This is the secret that productivity experts already know: It’s why they encourage “getting into flow state,” the magical, psychological zone wherein time collapses, the work becomes fun, and you derive a deep sense of satisfaction from whatever you’re doing.

So often we assume it’s the person who, regardless of the environment, determines the outcomes. We don’t give our environment enough credit.

But it’s easy to make good decisions when the good decisions feel good. Rather than trying to change yourself, try changing your environment instead.

Hard work ≠ guaranteed higher income

Similarly, working really hard doesn’t guarantee you’re going to make a lot of money. 

Most low-wage workers are busting their asses. People with money are often no harder working than those without it. But the paradoxical relationship between work that feels “easy” and the amount of money I earn used to confuse me: How is it that I enjoy what I do more and earn more now? 

This two-hour-long interview with MrBeast encapsulates it well: MrBeast, aka Jimmy Donaldson, has been making YouTube videos since he was a kid, raking in more than 24 billion views on his channel and 100+ million subscribers. When he’s asked how he’s achieved so much by age 25, he has a simple answer: He’s obsessed with it. Working on videos for 18 hours a day is what he wants to do. 

The idea that you have to be intensely exerting yourself or displaying herculean feats of discipline day after day to achieve outstanding results is perhaps the biggest con of all. The best results usually come from the things that make us forget to eat because we’re so engrossed. It takes more effort to pull ourselves away than to keep going.

This is why it’s crucial to pursue alignment in your life (and work, and health, and all the other things that impact your quality of life).

When the things you’re doing (your habits, your thought patterns, etc.) are in alignment with the essence of who you are, how you learn, and what you’re good at, successful results follow naturally. No need to strong-arm or force yourself to do the things you think you’re supposed to do—ease is the real goal. 

Sure, there are people out there who eat dry grilled chicken with plain brown rice every day and work “boring” data entry jobs, but I’d venture a guess that the repetition and predictability of those choices is just what works for their personality types. 

The next time you’re tempted to look at someone else who seems to have it all and think, “Gosh, it just seems so easy for them,” you’re probably right! They probably are doing something that feels easy to them, and that’s why it’s going well. That’s how they manage to do it. 

They’re not harder working or smarter or better than you—they’ve just stumbled into alignment.

It’s 3 PM on a Tuesday, and I look up from my computer between meetings and realize I haven’t eaten or consumed water since breakfast. I’m suddenly aware of how hungry I am—and as an extension, cranky. 

In an effort to be as effective as possible with my “deep work” (thanks, Cal Newport), I block off Monday, Wednesday, and Friday each week to maximize sustained focus and minimize interruptions from the outside world. As a result, my Tuesdays and Thursdays usually become back-to-back marathons, often beginning before 8 AM and leaving me crawling across the finish line past dinner time. 

And as anyone who’s tried to cram a bunch of work into a shortened week will tell you, it rarely goes according to plan.

This meant that—on this particular Tuesday—my aspirations for the day had long been left in the dust of meetings that ran on too long or unexpected roadblocks that stymied timelines. Not only had I not finished the work I knew I needed to complete, but a few new urgent items had found their way onto my list. I hadn’t exercised, eaten lunch, or prepped dinner as I had planned to do. A load of wet laundry sat damp and mildewing in the washing machine.

A sense of overwhelm descended swiftly, blanketing my mood in a self-indulgent pity party. Normally, I’d let this mood carry me out to sea and ruin the rest of my day. I had imagined my husband coming home from work, and how I’d lay my corporate sacrifice at his feet: Look at how much I had to do today, I’d tell him, Let’s order Popeyes chicken sandwiches and melt into the couch, ignoring my own goal for workday dinners to be “cooking nights,” excused by my own poor planning. 

Worst of all, this all-too-common ordeal didn’t initially prompt me to interrogate my own ability to set boundaries or stay focused on the right things. It left me feeling sorry for myself. The experience of falling short—at the end of a day that felt unreasonably busy—was (and is) the perfect cocktail for externalizing blame.

But then I was reminded of something my BOSSY co-host Tara said a few weeks earlier that had buried itself in my subconscious: “I can’t be around people who aren’t actively designing the type of life they want to live. If you aren’t happy, do something about it.” 

The quote, which seemed to materialize in response to my spiraling, was telling me: You need to take some accountability and interrupt this well-worn pattern.

With an arsenal of tools at my disposal, I started with my favorite: I closed my laptop and went for a walk around the block. Finally away from my desk, I was able to engage in my go-to neurotic pastime of wearing headphones while manically talking to myself, so passersby would assume I was regaling a human on the other end of my AirPods with an incredibly detailed version of my to-do list. 

It finally occurred to me that what was bothering me was the way I had allowed the chaos of the day to supersede my other goals: I hadn’t responded to texts. I hadn’t exercised. I was already resigned to the $30 UberEats delivery instead of the chicken breast and brussel sprouts waiting patiently in my fridge. Ultimately, I had created this situation I was now excusing myself for being in, and I needed to stop enabling it to continue.

Might it have been true that I had too much on my plate that day? Sure. Could I have excused my bad mood? Of course. But believing the outcome was my fault—and therefore within my control to fix—appealed to me more in that moment. Sometimes, this control is a delusion, but one with a valuable outcome: radical accountability. It doesn’t mean you’re necessarily going to retain ownership of every item on the to-do list—sometimes delegating is a way to take control, too.

This opportunity arises a lot, I think—with disproportionate outcomes in money and career. I needed radical accountability to manage my own stress and mood, but Tara had intended it as a management technique: “If someone on my team is underperforming, I take responsibility for that. That’s on me. Where am I not communicating clearly enough about my expectations?” 

Surely there are people who truly underperform, though, right? I pressed her. 

“Well, sure,” she replied, “but the final ‘that’s on me’ is keeping them around once I know that’s the case.” 

Something told me that if I had called Tara up that afternoon and complained about my self-inflicted predicament, she would’ve been straight with me: “I don’t get it. It’s 3 o’clock. What’s stopping you from doing a 20-minute walk and getting a second wind? Go eat a protein bar, drink some water, and get back at it. And next time, don’t schedule yourself the same way. You shouldn’t have been in this position to begin with.” 

Sometimes, the “truth” won’t be as useful as the delusion that returns your agency to you. Maybe the challenge in your life, finances, or career that’s souring your outcomes really isn’t your fault. 

But if believing it’s within your control allows you to change it, this approach says, that would ultimately generate a more favorable outcome, no? If you don’t like something in your life, it says, do something about it.

As we talked through my approach (earn, invest, ball out), she shared her own: Rather than deriving confidence from an ever-increasing nest egg that can produce predictable income in the future, she explained that she prefers to devote her energy to developing relationships, businesses, and habits that reinforce her confidence in her own ability to create income. I’m paraphrasing: “I’m not optimizing for stability, I’m increasing my confidence—the confidence that I can turn on that money spigot at any time.”

While these might sound like two sides of the same coin, the implications about the types of choices we’d make according to these worldviews are very different: Where I might walk down a dead-end path today simply because it has a dollar sign attached to it that I can funnel directly into VTSAX, Tara might choose the longer, meandering road with no certain paycheck…that eventually leads to six more. It’s the difference between short-term and long-term thinking.

As I reflected on her ideas about the various ways to reliably produce future income, I was reminded of classic stories about early employees at startups that eventually made it big—they turned down the lucrative six-figure consulting salary to take a risk on a new venture because they believed in the mission, and ended up cashing out to the tune of millions of dollars in equity just a few years later (I know a couple of people for whom this was true, and while their decision looked foolish at the time…they definitely got the last laugh). 

Rather than memorizing the rules of the gameboard and carefully maneuvering one square at a time, these people flipped the whole damn table—risking utter destruction in the hope that their tiny metal Top Hat might land on Boardwalk.

That’s not to say either approach is better than the other, just that they reveal a lot about what, exactly, you’re comfortable placing your faith in: Do you want to rely on the storied success of the public markets, or are you interested in placing a leveraged bet on yourself? 

Take my own example: By selling Money with Katie to a larger media company at the end of Year 1, I took the first stable exit on offer. A bird in the hand, right? It’s obviously worked out well for me, but we don’t know what would’ve happened in a parallel universe in which I had said, “Thanks, but no thanks.”

Still, it’s easy to venture into romantic territory here; in the United States, we love the rags to riches story of The Little Hustler Who Could who french braided their bootstraps, bought some lemons from a black market wholesale dealer, and turned them into gourmet lemonade at a 400% markup. But “betting on yourself” is a lot more charming in theory than in practice, when your mortgage is on the line and the little mouths in your home need to be fed. 

This belies a contradiction within the fantasy of the American dream: The type of stability we’re taught to chase (the W-2 job, the starter home, the 2.5 children and golden retriever named Max) is directly at odds with the risk-taking required to place the type of entrepreneurial bet on yourself that our culture so devotedly celebrates. 

When a single 24-year-old sharing a fifth-floor walk-up uses their nights and weekends to build a company and strikes it rich, it’s inspiring; brave. When a 35-year-old sole breadwinning parent quits their stable accounting job to hang out their own shingle, it’s risky; foolish. 

Counterintuitively, the less you have, the bigger swings you can take. Stability might cap your downside (or, at the very least, create the illusion of a capped downside), but it often places a limit on your upside, too. 

(A brief aside: You can always build a business on the nights and weekends as a parent so that you don’t have to quit the job that supports your family, but as many parents of young children have told me, that often requires an unreasonable sacrifice of time you’d probably like to spend with *checks notes* the aforementioned children…all for an uncertain payoff. And while there’s a bewildering strain of hustle porn that effectively claims, “having children made me grind harder and made me more successful,” I’ll give you one guess as to which gender that type of rhetoric comes from. Hint: It’s not the one who’s statistically more likely to bear the burden of caring for those children.)

Bigger swings become riskier as your lifestyle, business, and family grow, because you simply have more on the line. In my own rush to secure a stable situation (secure income, a nice home, a relatively “safe” investment portfolio), I didn’t notice the opportunities I was forgoing. Being too preoccupied with “responsible” choices often led me down predictable paths with equally predictable outcomes—and while predictability can be great, it’s also inherently limiting. It’s indisputable that the Katie who shared an apartment with a friend for $800 per month could afford to take more chances than the Katie who pays $5,000 per month for shelter.

Funnily enough, I remember thinking at the time that I could never quit my job to pursue my side hustle full-time. It felt “too risky,” despite being a single renter with no dependents and very low overhead in a robust job market where it would’ve been a piece of cake to get another paycheck job if things went bust. Even in my relative “freest” state of adult existence, I didn’t feel comfortable betting on myself—and while I told myself at the time it was because I was just too responsible to take chances, I know in hindsight that sometimes fear often masquerades as maturity.

Of course, I’m thankful for how the last few years have gone: Despite my preference for the safe and stable path, I’ve had (what I consider) fairly outsized returns, both in business and in life. But Tara’s words have rung true in a way I hadn’t expected: She’s inspired me to have a little more faith in my ability without the safety net of a big name institution or someone else’s stamp of approval. Because at the end of the day, short-term thinking communicates something very specific: I don’t believe that I can generate another, better opportunity, so I’m gonna take this less risky one that’s right in front of me—whether it’s a job offer that’s not quite right, or an investment that feels “good enough” but not “great,” or a life path for which the most compelling benefit is stability. 

And hey, sometimes that is the best opportunity you’re going to get—in which case, you should probably take it. After all, if you grew up in a home that was often chaotic and unpredictable, or you’ve experienced dire financial insecurity, sometimes stability is what you crave most (or what you crave most right now). 

But for me, I’m not sure I ever thought twice about what I was optimizing for—or if stability was the most inspiring thing I could aspire to. It was just the most obvious thing. Fortunately, on that path, I still meet people like Tara, who help me think about money and opportunities just a little bit differently…and in those moments of coming together, new opportunities can arise. And the next time they do, I know who I’m betting on.