The World of Maybes: Escaping the Trap of Infinite Options

By 9:47 p.m., the night has turned into a negotiation.

You’re hunched on the couch, Netflix glowing in front of you like a digital roulette wheel. There are 4,237 things you could watch. The algorithm whispers, “Because you watched…” and you obediently scroll through row after row of glossy thumbnails.

None of them feel quite right.

Maybe there’s something better if you scroll just a little further.

Your food delivery app pings: “Want to reorder your usual?” You hesitate. You liked that dish, but there are also 312 other nearby restaurants, and surely one of them has the perfect combination of spice, portion size, and delivery time. You open the app, telling yourself it’ll just be a quick look.

Twenty minutes later, you’re deep in a menu comparing two nearly identical pad thai options, like some deranged sommelier of takeout.

At some point you look up at the clock and realize you’ve spent half an hour deciding what to eat and what to watch. You’re hungrier, somehow more tired, and vaguely annoyed—with yourself, with the apps, with the sense that life is slipping past while you rummage through its possibilities.

And beneath the triviality of the scene, a quieter, unnerving question lingers:

If I can’t even choose dinner without feeling this much friction, what does that say about how I’m choosing everything else?

Jobs. Cities. Partners. Projects. Investments. Identities.

We live in an age that worships options. To be “successful” is to keep as many doors open as possible, for as long as possible. Don’t commit too early. Don’t tie yourself down. Don’t specialize. Don’t delete. Don’t burn bridges. Reply “maybe” to every invitation until you see what better offer comes along.

On paper, this seems like freedom.

In practice, it often feels like being trapped in a room lined with doors you never walk through.

This is an essay about that trap: the paradox of optionality. How the relentless pursuit of “the best” quietly undermines both our decisions and our happiness. Why reversible choices make us more anxious than irreversible ones. Why maximizers who secure objectively better outcomes are often less satisfied with their lives than people who settle for “good enough.” And how to redesign your relationship to choice so you can stop living in a world of maybes and actually move through your one real life.

Not by pretending options don’t matter. But by learning when—and how—to close the right doors on purpose.

The supermarket in your head

The easiest place to see the problem is a literal supermarket.

Walk into a big-box grocery store and wander down the cereal aisle. If you grew up in a small town or another era, you might remember a time when cereal meant: corn flakes, something vaguely sugary, and maybe muesli if your parents were into that kind of thing.

Now you face a three-story mural of boxes: gluten-free, protein-packed, keto-friendly, rainbow-colored, chocolate-dusted, marshmallow-studded, “with ancient grains,” “with probiotics,” “with cartoon tigers.”

On the surface, this is progress. Somewhere in that kaleidoscope is the perfect cereal for your particular microbiome and childhood nostalgia.

But your brain doesn’t get to experience that theoretical upside for free.

Sheena Iyengar, a Columbia Business School professor who has spent decades studying how people make choices, once ran a now-famous experiment using jam. On some days, shoppers at a gourmet market encountered a tasting table with 24 exotic jams. On other days, the same table offered just 6 flavors. With 24 jams, more people stopped to taste. But they were one-tenth as likely to actually buy a jar compared to those who saw only 6. And when people did buy from the smaller selection, they reported being more satisfied with their choice. (business.columbia.edu)

It’s a beautifully counterintuitive result: more people were attracted to the larger assortment, yet fewer decided—and those who did were less happy.

Iyengar and her colleague Mark Lepper concluded that abundant options can be demotivating; they draw us in but then overwhelm us when it’s time to commit. (business.columbia.edu)

This “choice overload” idea went viral. It snuck into business books and TED talks and dinner-party conversations. It’s comforting to blame the salad dressing aisle for our existential dread.

But as often happens, the story got more complicated.

A 2010 meta-analysis pooled 63 experiments across 50 studies and found that, on average, having more options did not reliably reduce satisfaction or willingness to choose; the overall effect was essentially zero. (academic.oup.com) Sometimes more choice helped. Sometimes it hurt. The mechanism depended on specific conditions: how important the decision felt, how much people already knew about the options, whether they had a clear goal, and so on.

So abundance of choice isn’t automatically a villain.

The cereal aisle isn’t the problem. The way our minds respond to it is.

To see that more clearly, we need to leave the supermarket and step into a place where choice is supposed to be sober, rational, and high-stakes.

What the judge ate for breakfast

A few years ago, researchers examined more than a thousand parole decisions made by Israeli judges over the course of 50 days. Each judge’s schedule followed a similar pattern: a morning session, a mid-morning break, another session, lunch, and a final session in the afternoon.

You might hope that the main thing determining whether a prisoner received parole would be the legal merits of their case.

What the data showed was… unnerving.

At the beginning of each session—right after a meal break—the probability of a favorable ruling (parole granted) was around 65 percent. As the session went on, that rate steadily declined, sometimes approaching zero just before the next break. Then, after the judge rested and ate, the positive ruling rate jumped back up to around 65 percent and the cycle repeated. (in.bgu.ac.il)

Same judges. Same laws. Same types of cases.

Very different outcomes, depending on how many decisions they had already made and how recently they had eaten.

The study’s authors framed this as an example of “decision fatigue.” As judges made ruling after ruling, their mental resources wore down, and they increasingly defaulted to the easiest, safest choice: deny parole and maintain the status quo. (en.wikipedia.org)

We tend to think bad decisions come from not thinking hard enough. Sometimes they come from thinking too hard, for too long.

Now merge this with your own life. You wake up to dozens of notifications, emails, calendar invitations, and small logistics to handle. What’s the fastest commute route? Do you respond to this message now or later? Which of fourteen SaaS tools do you renew, and which do you replace? How do you allocate your team’s time across eight competing priorities?

By the time you get to a truly important decision—what project to champion, whether to say yes to a new role, which city to move to—you’re depleted. You may default to the status quo (safest), or you may lurch impulsively toward whatever requires the least immediate effort. Either way, the volume and persistence of choice are shaping your trajectory more than you notice.

And that’s before we add a particularly modern twist: not just many options, but the sense that one of them is objectively optimal—and that it’s your job to find it.

The maximizer’s curse

Imagine two seniors in college, both on the hunt for their first real job.

Student A approaches the search like a military campaign. They scour every posting, attend every career fair, track every employer’s compensation data, consult rankings and alumni, and meticulously optimize their résumé and interview responses for each opportunity. They will not rest until they’ve identified the absolute best job they can get.

Student B takes a different approach. They think about the kind of work they’d like to do, the kind of people they want around them, and the minimum salary that would keep them out of financial panic. They apply broadly but don’t obsess. When they receive an offer that meets their criteria and feels promising, they accept it and stop looking.

Psychologists Barry Schwartz and colleagues call people like A “maximizers” and people like B “satisficers.” Maximizers search extensively and aim for the best. Satisficers search until they find something that meets their standard and then they commit, without tormenting themselves over whether an even better option might be out there. (works.swarthmore.edu)

You might expect maximizers to end up both more successful and more satisfied. After all, if you cast a wider net, you should land better fish.

In some ways, that’s exactly what happens. In one study, researchers tracked college seniors through their job search. Maximizers indeed landed positions with starting salaries about 20 percent higher than satisficers. Objectively, they did better. (works.swarthmore.edu)

Yet on almost every subjective measure—happiness, optimism, satisfaction with the job they accepted—maximizers scored lower. They felt worse, even after “winning.” (works.swarthmore.edu)

Why?

Because maximizing doesn’t stop when you sign the offer letter.

If your mental model of life is “there’s a best option and my job is to find it,” then every decision is an opportunity to fail. Whatever you choose, you’re now haunted by the ghost of all the alternatives you rejected but haven’t fully let go of. You’re doing this job—but you could have been doing that one. You’re living in this city—but what about the one with warmer weather? You’re in this relationship—but what about everyone you swiped past?

Maximizers are more prone to regret, more likely to ruminate on what might have been, and more drawn to upward social comparisons—constantly looking at people who seem to have scored a better deal. (works.swarthmore.edu)

Having more options doesn’t merely give them more opportunities to succeed. It gives them more ways to feel they’ve fallen short.

A maximizer’s life is full of unopened tabs—both on the screen and in their head.

FOBO: Fear Of a Better Option

Patrick McGinnis, a venture capitalist who coined the now-ubiquitous term FOMO (“fear of missing out”), later defined its sibling: FOBO—Fear Of a Better Option. (en.wikipedia.org)

FOMO makes you worry you’re in the wrong place (“Everyone else is having more fun without me”). FOBO makes you worry you’ve made the wrong choice (“There might be a better option if I keep looking”).

FOBO is what keeps your dating app inbox full of half-finished conversations. It’s why you let perfectly good opportunities age into irrelevance in your email. It’s why you RSVP “maybe” until the very last minute, hoping something better materializes.

At scale, FOBO creates a world where no one really commits to anything until they’re forced to. People stay in jobs they dislike “for now” while they passively scan LinkedIn. Teams endlessly postpone decisions because someone might bring new data to the next meeting. Cities become populated by semi-transient professionals who refer to every neighborhood with the noncommittal language of “for the time being.”

McGinnis calls FOBO “an affliction of abundance.” (nypost.com) When everything is possible, nothing feels good enough to choose.

Our culture tends to frame this as a moral failing: people today are flaky, entitled, indecisive. But morally judging the behavior misses the structural change underneath: we truly do have more options available—and more visibility into them—than any previous generation.

The problem is not that we want good things. It’s that we’ve smuggled in a hidden assumption: that with enough searching, there exists a perfect option that will relieve us of the need to make tradeoffs.

That assumption quietly wrecks us.

The invisible cost of keeping doors open

If you’ve ever shopped for a nontrivial purchase—say, a laptop—you’ve probably fallen into a pattern.

You start by browsing a couple of obvious choices. Then you realize there are ten more brands than you thought. Each has seventeen sub-models, each with slightly different specs, each with dozens or thousands of reviews. You open so many tabs your browser shrinks them to indistinguishable little icons.

At some point it dawns on you that every option is a bundle of tradeoffs. This one has more RAM but a worse screen. That one is lighter but costs more. This one has stellar battery life but a finish that scratches easily. There is no dominant option; every choice means giving up something.

Psychologists call these “tradeoff difficulties.” When options are mutually exclusive and each has both positives and negatives, we feel an internal friction. Tradeoffs don’t just cost money; they cost emotional energy. (reference.org)

Barry Schwartz puts it bluntly: “To choose one thing is to give up the others.” The more attractive the rejected alternatives, the more painful the sacrifice. (en.wikipedia.org)

When you open twenty potential doors, you don’t just give yourself twenty opportunities for happiness. You give yourself nineteen vivid ways to feel loss.

Now add a second cognitive quirk: loss aversion. Our brains weigh losses more heavily than equivalent gains. We would rather avoid losing $100 than gain $100, and we tend to value what we already have more than identical items we don’t own yet. This is the “endowment effect,” documented in experiments where people given a simple mug demand roughly twice as much to part with it as others are willing to pay to acquire the same mug. (econpapers.repec.org)

When you commit to one path, every other path now feels like a loss. Each door you close becomes a mug you could have owned but didn’t.

The result is a peculiar modern sensation: living in a state of constant, low-grade mourning for lives you never led.

And this is where reversibility—our obsession with “keeping options open”—makes things worse, not better.

When reversible decisions make us less free

Imagine you take a photography class where, after weeks of effort, you produce two prints you’re genuinely proud of. Let’s call them A and B.

At the end of the course, the instructor tells half the class: “You can take either A or B home, but once you choose, your decision is final. No swaps.” The other half hears: “You can take A or B home, and if you change your mind in the next week, you can come back and swap them. Take your time.”

Intuitively, most of us think the second group has it better. More freedom, more flexibility, more optionality. Many of the students in Dan Gilbert’s actual experiment at Harvard chose the reversible option when given a say. (thoughtsandpolitics.blogspot.com)

Yet when researchers followed up days later, the people in the irreversible condition liked their chosen photo more than those who knew they could swap. The ability to reverse the decision led to more second-guessing, more counterfactual thinking (“Maybe I should have picked the other one…”), and ultimately less satisfaction. (pmc.ncbi.nlm.nih.gov)

When you can’t go back, your “psychological immune system,” as Gilbert calls it, goes to work. You reinterpret, reframe, and gradually weave your choice into your sense of self. You learn to appreciate what you’ve got because, frankly, you have no alternative.

When you can go back, you keep the evaluation loop running. You monitor. You compare. You imagine the alternative. You revisit your choice in your head even if you never physically swap the photo. The door that could be reopened stays mentally ajar.

Reversibility feels like freedom, but it often functions like a tax on your attention.

Contemporary research has confirmed this pattern beyond art-class posters. A 2022 study on decision reversibility found that, in general, reversible decisions yield lower satisfaction than irreversible ones, largely because they increase counterfactual thinking (“what if I’d chosen differently?”) and anticipated regret. (pmc.ncbi.nlm.nih.gov)

We pay for our reversible choices not just in extra time spent deciding, but in ongoing mental rent.

You can probably think of decisions in your own life that became bearable, maybe even precious, because they were no longer up for debate. A child, once born. A career change, once made. A city, once moved to with both feet.

The hard part is trusting this process before you feel its benefits. While you’re still on the couch, staring at all the possible paths out of your current life, it feels reckless to lock one in and discard the rest.

So we stall. And stall. And stall.

At this point, it’s useful to borrow a metaphor from an unlikely place: the math of slot machines.

The gambler at the row of slot machines

Picture a gambler sitting in front of five slot machines, each with a lever and a hidden payout rate. Some pay off frequently with small amounts. Others rarely but with larger wins. The gambler’s goal is to maximize their total winnings over time.

They face a dilemma. On the one hand, they should “exploit” the machine that seems to pay off most based on what they’ve seen so far. On the other hand, they should “explore” the others to gather more information—maybe one of them is better but just hasn’t paid out yet.

Too much exploration and they waste time on bad machines. Too much exploitation and they might miss a better one.

This is the classic “multi-armed bandit” problem in statistics and machine learning—a neat, mathy encapsulation of the exploration–exploitation tradeoff. (en.wikipedia.org)

Life is a multi-armed bandit problem with worse documentation.

Jobs, cities, projects, people—they’re all “arms” on a metaphorical slot machine. Every date, role, or prototype is a pull of the lever, giving you noisy information about how rewarding that particular arm might be long-term.

In principle, you’d like to explore widely when you’re young (try many arms) and gradually transition toward exploiting the best ones you’ve found (pull them more often) as you age and your time horizon shrinks. Algorithms can show, with some elegant math, how to do this near-optimally when rewards follow certain distributions and time is finite.

In practice, of course, you’re not an algorithm. You’re a human with loss aversion, FOMO, FOBO, decision fatigue, and social comparison instincts.

What many of us do, especially in option-rich environments, is something like this:

We explore. Then we explore some more. We treat exploration as our default mode and exploitation as something we will eventually switch into once we’re sure we’ve found the best arm.

The trouble is, you never get that guarantee. The world doesn’t send you a little green checkmark saying, “Relax, this is the optimal option. You can stop looking now.”

So you stay in a kind of permanent pseudo-exploration: you keep your current job but constantly browse job boards; you stay in your current city but read articles about where you “should” be living; you work on your main project but keep a swarm of side projects in the back of your mind in case one magically takes off and rescues you from needing to commit.

From the outside, your life kind of looks like exploitation—you’ve made some apparently stable choices. Inside, your relationship to them is still exploratory. You haven’t psychologically bought the mug; you’re just holding it while keeping an eye on the other mugs on the table.

No wonder it feels so fraught.

The lesson from bandit problems is not “always explore” or “always exploit.” It’s that you need a policy—a set of rules—that tells you when to stop exploring and start leaning into what you’ve learned.

Most of us don’t have that policy. What we have instead is vibes: moments of panic-driven searching and moments of regret-driven clinging.

So how do you build a saner relationship to optionality?

Redefining “good enough”

One place to start is by reclaiming a phrase that sounds, at first, like a cop-out: “good enough.”

Herbert Simon, the Nobel-winning economist who first introduced the idea, didn’t mean “sloppy, thoughtless mediocrity.” He meant that in a complex world, with limited time and attention, the aspiration to “maximize” is often illusory. Rational agents don’t seek the best; they seek something that meets their aspirations under real constraints. They satisfice. (en.wikipedia.org)

The challenge is that many high-achieving people have been culturally conditioned to hear “good enough” as failure.

If you grew up being told you were “full of potential,” you may have internalized a sense that settling for anything less than the best option was a betrayal of your gifts. If your professional training is in law, consulting, finance, engineering—environments where optimization is a virtue—you may translate that ethic into your personal life in ways that make you miserable.

But look again at the data from maximizers vs. satisficers. The cost of always trying to find the best option is not merely time. It’s happiness, optimism, life satisfaction, and resilience. Maximizers report more depression, more regret, and lower self-esteem, even when they achieve more. (works.swarthmore.edu)

If life is a portfolio, relentlessly maximizing every decision is like constantly day-trading your own existence: exhausting, anxiety-inducing, and often no more effective than a calmer, long-term strategy.

“Good enough” is not the enemy of excellence. It’s the mechanism that lets you concentrate excellence where it matters.

Practically, this means deciding, in advance, where you will allow yourself to be a maximizer, and where you will deliberately be a satisficer.

You might, for instance, decide that who you marry or whether you have children is worth a “maximizing” mindset—extended exploration, deep reflection, and a willingness to endure prolonged uncertainty. But which apartment you rent in a given city? That might move into the satisficing bucket: define your minimum criteria, pick the first place that meets them, and stop wondering if the unit across town has a slightly better layout.

In his work on FOBO, Patrick McGinnis suggests something similar: sort your choices into categories—high-stakes, low-stakes, and “no-stakes”—and reserve your deliberative energy for the first category. For the lowest-stakes decisions, flip a coin and move on. (patrickmcginnis.com)

This isn’t about pretending trivial decisions don’t matter at all. It’s about acknowledging that your capacity to decide is finite. Every hour you spend split-testing laundry detergents is an hour you don’t get to spend deliberating about how to shape your career, or your character.

Minimizing choice in the trivial domains is what gives you the bandwidth to face the serious ones with clarity.

Designing your own irreversibility

If you accept that keeping some doors firmly closed can increase your satisfaction, the next question is uncomfortable:

Which doors do you want to make irreversible?

Modern culture loves the language of “keeping your options open,” but many of the goods we actually care about—deep expertise, long-term collaboration, enduring communities—emerge from foreclosing alternatives.

To become a genuinely great surgeon, you more or less have to give up the option of being a great jazz musician. To build a company, you have to walk past the other jobs you could have taken. To show up fully for your child, you have to relinquish thousands of other ways you might have spent those Saturdays.

The temptation is to treat these as tragic constraints imposed on us by circumstances. But you can also see them as choices you actively design.

For example, some people reduce trivial reversibility by constraining their environment. Barack Obama famously limited his wardrobe to gray and blue suits, explaining that he wanted to eliminate small decisions so he could focus on big ones. Steve Jobs did something similar with his daily outfit. (en.wikipedia.org) This is a tiny act of self-imposed irreversibility: once you’ve decided you’re a “blue-and-gray suit person,” you no longer revisit that choice each morning.

On a deeper level, you might choose to bind yourself to a practice or path with social commitments. There is a reason we formally enroll in degrees, sign contracts, hold public ceremonies. We are outsourcing some of our willpower to the structure around us.

This is not about martyrdom. It’s about recognizing something that research on reversibility keeps finding: as long as you believe you can swap your choice at any moment, you’re less likely to adapt to it and more likely to keep comparing it to fantasies. Locking something in gives your psychological immune system permission to do its work. (pmc.ncbi.nlm.nih.gov)

When you hear people decades into a career or marriage say, “It was hard, but I wouldn’t trade it,” that’s not evidence they got the globally optimal option. It’s evidence that they stopped running the comparison script for long enough to grow around their choice.

Of course, there are decisions where irreversibility is dangerous. You don’t want to lock yourself into abusive situations, destructive contracts, or belief systems that punish dissent. The point is not, “Make everything irreversible.” It’s, “Be conscious about where you’re keeping things unnecessarily reversible and paying the psychological price.”

A simple litmus test: are you revisiting this decision because the world has changed and new information truly matters, or because you’re afraid to accept the tradeoffs of having chosen at all?

Trusting the shape of a finite life

Underneath the anxiety about options is often a deeper fear: if you commit too early, you will miss your “real” life.

Maybe there was a version of you who moved to Berlin instead of Boston, who became a filmmaker instead of a lawyer, who married your college sweetheart instead of parting ways. Somewhere out there, dozens of ghost selves are living parallel lives, each one a little taunting: you could have been me.

This is not a solvable problem, because it’s not a problem; it’s the human condition.

A finite life—in which you will never taste every dish, meet every person, or pursue every career—is not a bug. It’s the only reason choices are meaningful at all. If you had infinite time and zero constraints, “choosing” would collapse into “eventually doing everything.”

The paradox of optionality is that the more we try to simulate that fantasy—by preserving every option in case we get to it later—the more we erode the quality of the actual life we’re in.

When Dan Gilbert talks about our “psychological immune system,” he’s pointing to a quiet superpower: our ability to make peace with, and even grow to love, realities that once felt like compromises. (blog.ted.com)

But that system only switches on when we accept that a decision is, for our purposes, done.

If you refuse to cross that threshold—if every choice is provisional, every project is a “test,” every relationship is “for now”—you never give your mind the conditions it needs to synthesize contentment. You remain in a perpetual demo mode of your own life, with watermarks over every scene: “Trial version. Expires soon.”

Closing doors is not about ascetic self-denial. It is about trusting that a deeply inhabited, particular life can be richer than a thin acquaintance with infinite possibilities.

From the outside, that might look like voluntarily shrinking your universe: fewer apps, fewer side hustles, fewer “backup plans.” From the inside, it feels like finally having room to breathe.

Some very practical heresies

None of this is an argument for recklessness. It’s an argument for a different default.

Instead of assuming, “I should keep this option open unless there’s a compelling reason to close it,” you might experiment with, “I should close this option unless there’s a compelling reason to keep it open.”

That might mean:

• Deciding in advance where you will allow yourself to maximize, and explicitly satisfice everywhere else.
• Setting time or iteration limits on exploration (“I’ll look at apartments for two weeks, then decide from among the ones I’ve seen”).
• Treating reversibility as a scarce resource, not a default—something you deploy strategically rather than bathing every decision in the indefinite “you can always change your mind.”
• Deliberately creating small irreversibilities—a recurring calendar block, a standing order, an automatic investment—so you don’t renegotiate your life from scratch each morning.
• Resisting FOBO’s whisper that you can outsource your fear of mortality to more Yelp reviews and more swiping.

Importantly, none of these practices will feel natural if your benchmark is “the best.” They will feel like losses, like you are voluntarily stepping away from potential greatness.

And that is precisely the emotional skill we seem to need most now: grieving the lives we will never live, so we can be fully alive in the one we have.

If we’re honest, many of our “open options” are not really live possibilities. They are fantasy safety blankets—reassurances we carry to soothe the part of us that can’t stand the idea of limits.

When you look closely, some options have already quietly expired. You are not actually going to move back to your college town with your college friends and resume your college life. You are not actually going to launch all seven of those startup ideas. You are not actually going to read every book on your list.

Accepting this is not cynicism. It’s what frees you to choose which few books you will read, which one company you will build, which tiny set of people you will show up for.

It’s what lets you walk through a door and, instead of staring back at all the other doors, start furnishing the room you’ve entered.

You are the doors you close

On that couch at 9:47 p.m., with your streaming service and your delivery apps, it doesn’t feel like you’re making a big philosophical statement. You’re just hungry and tired.

But micro-decisions are not actually micro. They are tiny training sessions in how you relate to choice itself.

Every time you prolong a trivial decision in pursuit of the perfect option, you strengthen the mental habit of maximizing. Every time you settle quickly on a “good enough” choice and pour your energy into enjoying it, you practice a different habit: constraining your search, accepting tradeoffs, and being present.

In that sense, how you choose cereal and movies and shoes is not separate from how you choose projects and partners and missions. It’s all rehearsal.

The world will keep offering you more—more products, more paths, more pings, more people to compare yourself to. The tools around you are designed, in many cases, to pull you deeper into exploration, to keep you swiping and scrolling and sampling without ever quite committing.

You don’t have to fight that by becoming a monk, renouncing all but one kind of jam. You can start by simply noticing the cost of endless options on your own nervous system—and then, small decision by small decision, becoming choosier about what you choose to care about.

When you look back years from now, the shape of your life will not be defined by the set of options you once had. It will be defined by the doors you walked through and the ones you let close behind you.

In a world of infinite maybes, the rarest thing you can give your future self is a life that is fully, unapologetically, yes.