Editor’s note, September 20, 8 am ET: We’re bringing you some of our best-loved Your Mileage May Vary columns while Sigal Samuel is on parental leave. The one below was originally published last September.

This unconventional advice column offers you a unique framework for thinking through moral dilemmas. It’s based on value pluralism: the idea that each of us has multiple values that are equally valid but that often conflict with each other. Submit your own question here.

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The Jewish High Holidays are coming up, and that includes Yom Kippur. It’s a holiday that encourages people to reflect on their behavior and make amends. That’s all well and good, but I’m someone who struggles with scrupulosity — constantly worrying about my morality and if I’m doing The Most Possible Good™.

In practice this is far more paralyzing than motivating. Fixating on the ethical implications of all possible decisions makes it harder to take any action, and I’ve lost hours scouring my memories of my past behavior for immorality like a football player watching footage of their games to analyze what they could do differently. Guilt simply isn’t serving me, but I worry that saying to hell with all that means I’ll stop striving to be a better person and become morally complacent.

I’ve observed Yom Kippur for decades, and don’t want to simply avoid the day. But the holiday is a moral scrupulosity trigger. How do you think I should approach this? I want to stop feeling guilty for letting guilt get in my own way.

Dear Scrupulous, 

Have you ever heard the story about what happened when God decided to give the Bible to flesh-and-blood human beings? According to the ancient rabbis, the angels hated the idea. They argued that humans were deeply flawed mortals who didn’t deserve such a holy scripture; only angels could be worthy of it, so it should stay up in heaven. 

It fell to Moses to rebut the angels’ argument. He asked them: What do you angels need the Bible for? The Bible says not to murder, not to commit adultery, not to steal — do you have jealousy or other emotions that could lead you to do those things? The Bible says to honor your father and mother — but you don’t have parents, so how could you ever do that? And the Bible says to sanctify the Sabbath — but you never do any work, so how could you even honor the Sabbath by resting? 

The angels saw that Moses was right. Angels are really great at one thing: being perfect. But perfect creatures are static. They don’t experience painful challenges, they don’t grow, and they don’t make choices that add beauty to the world. We humans do those things. God gives the Bible to humans not to make them into angels — but to make them better at being the unique thing they are: human animals, with feelings, flaws, and all, that can learn to use their capabilities in more beautiful ways.

I think there’s a lot of wisdom in this story. And I want you to notice how far it is from demanding that humans do “The Most Possible Good™.” That language suggests a maximizing ethical theory like utilitarianism, which says that we have to do the action that produces the greatest good for the greatest number. In other words, we have to optimize. 

Moral optimization may be possible for angels, but not for humans. We each hold multiple values, and sometimes those values are in tension with each other, forcing us to strike a balance as best we can. We’re not omniscient beings who can know with certainty how best to strike the balance. 

What’s more, sometimes different kinds of moral good straight-up conflict with each other. Think of a woman who faces a trade-off: She wants to become a nun but also wants to become a mother. She can’t balance between those options — she has to choose. And what’s the better choice? We can’t say because the options are incommensurable. There’s no single yardstick by which to measure them so we can’t compare them to find out which is greater.

Given that this complexity is baked into the human condition, it’s impossible to be a perfect optimizing machine. And the more you try to force yourself to be that, the harder it’ll be for you to actually help others, because you’ll just be so burned out. As you’ve already discovered, the optimizing mindset is exhausting — you end up expending a lot of precious mental resources that you could be spending on something else. It can even lead to paralysis. And a lot of the time, there’s no knowably best decision.

So instead of trying to optimize everything, you can adopt a goal that’s humbler but more realistic: to live in line with your values as best you can. 

I know that can feel scary. Optimizing makes being human feel less risky. It provides a sense of control, and therefore a sense of safety. The unspoken premise is that if you optimize, you’ll never have to ask yourself: How could I screw up that badly? 

But there’s another way to feel safe. It’s about leaning into the fact that we are imperfect and vulnerable creatures and that even when we’re trying our hardest there will be some things that we do not do optimally.

Of course, we should still try to live in line with our values. But in those moments when we fall short, we shouldn’t berate ourselves, thinking, “I sinned!” In Hebrew, the word we typically translate as “to sin” (lachto) actually means “to miss the mark.” It’s the same word we’d use to describe someone with a bow and arrow who’s targeting the bullseye but misses it slightly. This is a useful image, because it reminds us just how normal it is to miss the mark. Just as the archer’s arrow is buffeted around by the wind, we’re buffeted around by all the physical and psychological conditions acting upon us — naturally we won’t always hit the bullseye! And when we do miss the mark, we deserve compassion.

I know what you’re thinking: What if adopting this mindset means you’ll become morally complacent and let yourself off the hook too easily? This is one of the most common objections to practicing self-compassion. But research shows it’s not well-founded. In fact, psychologists have found that more self-compassionate people are better able to acknowledge when they’ve made a mistake. They’re more likely to want to apologize and make amends to others when they mess up. And they try to do better the next time around. Why? Because, to them, mistakes don’t feel so psychologically damning. That allows them to take more — not less — responsibility for their actions.

Yom Kippur can feel terrifying when any mistake you’ve made over the past year seems damning. But according to the ancient rabbis, Yom Kippur is not meant to be a somber day — it’s one of the happiest days of the year! After all, it was on Yom Kippur that Moses descended from Mount Sinai carrying the second set of tablets inscribed with the Ten Commandments, ready to gift them to the people. 

You probably know what happened to the first set of tablets: Moses shattered them after seeing the Israelites engaged in idol worship. What’s less known is that, according to one rabbinic story, God’s response to the shattering of those tablets was to actually congratulate Moses. Why did God think breaking them was the right move? And what was different about the second set? 

While the first tablets had been fashioned by God and God alone, the second tablets were a human-divine collaboration: Moses carved the stone and God inscribed the words. And while the first tablets contained only the words of the Ten Commandments — a black-and-white, rule-based morality — the rabbis tell us that the second tablets contained within them all the stories and interpretations that Jewish sages would later develop.

In other words, God recognized that you can’t just give humans a list of moral rules and call it a day. Maybe that would work for angels, who live in a simplified, disembodied world, but our ethical life is just too messy and multifaceted to be captured by any single set of universally binding moral principles. Yet God chose people over angels anyway, inviting us into the collaboration and embracing our humanness rather than rejecting it.

So, to the rabbis, Yom Kippur was a happy day because they fully expected that God would accept and embrace messy humans. 

Please, don’t try to be more zealous than God.

When you’re taking action, by all means, aim your arrows as true as you can — try to hit the bullseye, the place that captures as much of what you value as possible. But once you’ve released the arrow from your bow, let it be. 

If it turns out that you missed the mark, that you acted suboptimally, I put it to you that that is okay. You are not an angel. You are not a perfect optimizing machine. You do not have access to a magical mathematical formula that can consider countless incommensurable variables and spit out the very best move with certainty. You are human and you do the best you can with what you’ve got. 

The wisdom of these millennia-old stories is that that’s good enough for God. Let it be good enough for you, too. 

Bonus: What I’m reading

• Writing this column reminded me of The Mindful Self-Compassion Workbook, written by the psychologists Kristin Neff and Chris Germer. It really helped me develop a self-compassion practice, which has in turn helped me get a grip on my own scrupulosity. I also strongly recommend the eight-week self-compassion course run out of Neff and Germer’s nonprofit, the Center for Mindful Self-Compassion.

• I’ve always associated the philosopher Thomas Nagel with questions about consciousness, but I recently learned that he’s also super interested in questions about religion. In a great essay called “Secular Philosophy and the Religious Temperament,” Nagel asks: What, if anything, does secular philosophy have to put in the place of religion? More specifically, can it answer the question: What is the underlying nature of the universe, and how can the human individual live in harmony with it? 

• In this Aeon essay, philosopher Elad Uzan argues that AI will not be able to solve ethics for us, despite what some people hope. Drawing on the mathematician Kurt Gödel’s famous incompleteness theorems, Uzan writes, “just as mathematics will always contain truths that lie beyond formal proof, morality will always contain complexities that defy algorithmic resolution.” 

Over the years, Julianne Holt-Lunstad has fielded many requests from startups looking for her help. These entrepreneurs came to the Brigham Young University professor with the well-meaning goal of “solving” loneliness; they believed their app or company could help consumers build genuine connections, and wanted Holt-Lunstad’s opinion on this feature or that business tactic. 

Across the pond, University College London professor Noreena Hertz was getting the same calls. They wanted her to join their boards, to advise them, to give their proof of concept a stamp of approval. 

“Of the many startups who’ve approached me, and it’s probably about 50 or 60 in the space,” Hertz told Vox, “there hasn’t been one where I felt convinced by their business model.”

That CEOs and founders were clamoring to pick the brains of these two women is entirely predictable — their work may have been the basis on which these startups were founded. Holt-Lunstad is among the most cited academics who study loneliness and social connection. The commonly repeated stat that loneliness is equivalent to smoking 15 cigarettes a day? That came from her research. She was the lead science editor on the Surgeon General’s 2023 advisory on loneliness and isolation. As for Hertz, in her 2020 book The Lonely Century: How to Restore Human Connection in a World That’s Pulling Apart, she coined the phrase “loneliness economy,” at the time, a fledgling market of niche services, like friends for rent and professional cuddling.

In the years since Hertz gave it a name, the loneliness economy has only ballooned. As public attention to loneliness has mounted — despite the fact that research doesn’t consistently show whether a loneliness epidemic exists in the first place — the market stepped in to offer solutions. No longer are the lonely limited to joining a running club, they can now rent friends and cuddlers. They can hire a coach to help vanquish loneliness and build a community. (One charges $3,000 for a three-month program.) They can attend a $1,000 weekend-long summer camp to make friends (with the option to pay in installments via Klarna). They can buy a $250 pendant that listens to their every word and can communicate back via voice or text. They can join a coworking space meant to quell loneliness with a nearly $300 a month price tag. They can enroll in a bootcamp for how to be less shy, hop in a group travel excursion with other solo venturers, download an app where AI pairs you with other strangers for activities. Loneliness is no longer a societal issue with mental and physical costs and structural solutions but one businesses hope consumers can buy their way out of.

But is it possible to disrupt the slow burn that is making a friend? To outsource the intimacies of friendship to AI? To put a price tag on human connection? 

“I would caution developers to really critically evaluate their business model and the barriers to who they’re actually reaching,” Holt-Lunstad told Vox. “Think about ways that [connection] can occur organically without monetizing it.”

The cottage industry of loneliness services is just another example of capitalism wrapping its tentacles around human desire. But in most cases, the cost of the app, or product, or experience is going to be much higher than the possibility of eliminating loneliness.

One person’s loneliness is another’s business opportunity

Since the early 2000s when Harvard political scientist Robert Putnam warned of the decline of civic and social spaces in his seminal work Bowling Alone, we have witnessed the “privatization of community,” according to Sam Pressler, a fellow at the Harvard Human Flourishing Program who studies community, connection, and class. Gathering spaces shifted away from places of worship and union halls to boutique fitness centers and private, members-only clubs. “There was already this dynamic in place where you could, at a premium level, sell people on community,” Pressler said.

The pandemic pushed the loneliness economy into overdrive. Widespread social isolation enabled researchers to study perceived levels of loneliness during lockdowns. Media coverage of loneliness outlined its harms. Although Vivek Murthy, the US surgeon general during the Obama and Biden administrations, first referred to loneliness as a “health epidemic” in 2017, his 2023 report opened the door for other iterations: the male loneliness epidemic, the Gen Z well-being slump, a worsening midlife crisis. Over the past five years, search interest in the loneliness epidemic grew over 600 percent.

Naturally, the startup world began to see a business opportunity, Pressler said. WeWork founder Adam Neumann launched a new residential real estate company with a goal of “solving loneliness” and $350 million in funding from Andreessen Horowitz. The app 222, which uses AI to pair strangers for group activities based on personality-based questions, raised $10 million in funding. “You then get this anchor within startup land that really has an approach of solve customers’ problems and pain points, in that loneliness is a customer problem or pain point to be solved, through productized market solutions,” Pressler said.

Brian Choi had heard of the male loneliness epidemic, but luckily didn’t feel like he fell into that category. He grew up in the Los Angeles area, where he still lives, and has plenty of friends, but he signed up for 222 several years ago as a way to supplement his social life and meet people who might be interested in activities his existing friends aren’t.

“Dance, for me, means a lot,” the 34-year-old video game character artist, told Vox. “For my best friends, hard to sell them on that. So 222 is a good angle on sharing that experience with other people who are presumably also open to dance.”

But most of the platform’s events, Choi found, were centered around dinner and drinks, which didn’t appeal to him. If there was a meetup with an interactive element, like brunch and a pottery class, he was more likely to engage. But despite attending about a dozen 222 events over the years, Choi hasn’t fostered any serious friendships. “It’s dependent on individuals to be proactive about inviting folks into their lives after the 222 event,” Choi said. “And that can be scary for a lot of people.” 

Once a market emerged for loneliness-adjacent services and products, influencers started promoting them. Over the last few years, the content creator Zaid Khan observed his peers hosting “community” events that seemed well-meaning enough until a few common themes emerged: The events seemed to be furthering the creators’ brands, they often came with a ticket price, and they were attended mostly by young, white people. This widespread commodification of community is what Hertz refers to as “WeWashing” — like greenwashing — because an occasional knitting club with a $50 fee does not a community make. 

Charging any sort of premium for a social event or service runs the risk of exacerbating inequities. According to Holt-Lunstad’s research, people with only a high school education or less or those who made less than $75,000 a year were less socially connected than those with higher education and incomes. People who stand to benefit the most from interventions to build relationships often can’t afford a $200 a month gym, or lack the time to swipe for friends. These spaces can then become, like Khan observed, homogenized by race, class, and ability. “I’m sorry, but young, attractive, white, straight, 20-somethings living in New York will have no issue. … You can walk into any West Village bar and meet those people,” Khan said. “It’s excluding the people who, I think, genuinely could need it.”

“Masking” a symptom

There is a contradiction at the heart of the loneliness economy: the need for human connection in the modern world is difficult to solve, let alone value and commodify. In order to make money, companies either have to charge top dollar for their social club or camp, or, they need their product to be used by as many people as possible, as often as possible, which inherently flies in the face of how relationships are fostered. 

“The ethical problem begins when a company intentionally exploits a consumer’s loneliness, insecure attachment, or fear of missing out to pressure that person into purchasing.”

Cindy Rippé, Terry College of Business at the University of Georgia

Relationships are projects of patience. They unfold after repeated interactions in a physical space, after slow revelations and disclosures and laughs. The loneliness economy isn’t built on unhurried bonding. Instead of consistently showing up to a community event and slowly building connections, some apps are effective at connecting users with strangers for one-time events, but are less focused on encouraging users to exchange numbers and hang out again. “We know from the research that relationships take time to develop, and that there needs to be consistency also over time. When you get to know someone, it takes time,” Holt-Lunstad said. “If you’re only doing it sporadically or once, that’s going to be less likely. If it’s all virtual, that’s going to be less likely.”

Just like hunger and thirst cue you to eat and drink, loneliness is a sign to interact. Swiping for friends may feel productive and occupy time, but without actually hanging out, it may just be a distraction, Holt-Lunstad said. “What I worry is that [apps] may be effective in masking that symptom without actually fulfilling any social needs,” she said. “It would be like no longer feeling thirsty, but we’re not actually drinking any water.”

The loneliness economy also fails to take into account the barriers preventing people from making friends in the first place. In recent surveys, the results of which have not been published, Holt-Lunstad has found both internal and external obstacles to connection, including anxiety, a fear of rejection, physical and mental health limitations, the economic cost of participation, and the time investment required with joining a club. “It might be, that’s a great program, but it’s too far away, or that’s a great program, but it costs too much,” Holt-Lunstad said. “And then, of course, there’s the internal barriers where there’s so much shame and stigma associated with this that many people don’t want to feel like I have to have an app or a program to make friends.”

These potentially lonely consumers may be more vulnerable to companies’ marketing efforts, even though the products are unlikely to solve the underlying issue. According to research, when people feel like they are lacking close, intimate relationships, they are more likely to buy themselves things. “One of the things, for instance, could be spending money to go on group activities rather than individual activities,” Aulona Ulqinaku, an associate professor of marketing at Università Carlo Cattaneo LIUC in Italy, told Vox. People could spend money to join a club you aren’t particularly interested in just to feel a part of something. 

Shopping can also serve as a social experience in itself, Cindy Rippé, a senior lecturer in the Department of Marketing at the Terry College of Business at the University of Georgia, told Vox in an email. Employees and other patrons can become familiar and friendly faces, effectively turning a retail space into a third place. A paid social experience, such as a club, could theoretically achieve the same fulfilling effects as shopping, Rippé said. But spending money isn’t what makes people feel better; it’s repeated social interaction, familiarity, belonging.

Because companies can track your activity online, users who search for local clubs or interact with these groups on social media may be repeatedly served ads for other community-centric businesses and thus spend more money on services that may not be effective.

“I hope that we are looking at a world where marketing can be looked at as an instrument for helping people rather than exploiting people,” Ulqinaku said. “The aim should not be, ‘I make money [off] of you.’ The aim should be, ‘I want to make you feel better. I don’t want to exploit you.’”

Putting a price tag on relationships

The pairing of lonely consumers who might be willing to spend money and businesses that definitely want to make it may be good for the bottom line in the short-term, but perhaps not for social health or for revenue in the long-term. (After all, if these products don’t work, people will stop paying for them, and if they do work as promised, people will also stop paying for them.) Friendship isn’t a product you can advertise or put a dollar amount to, Pressler said, and we shouldn’t apply market solutions to non-market goods.

“You can approach it with a consumptive mindset where it’s like, ‘Well, I just need to consume more relationships, and if I consume more relationships, ergo, I will not be lonely or disconnected,’” he said — but that’s not how real-world interactions work. The power imbalance between the companies earning money and the consumer spending it to fulfill a core human need may veer on exploitative, too, Rippé said: “The ethical problem begins when a company intentionally exploits a consumer’s loneliness, insecure attachment, or fear of missing out to pressure that person into purchasing.”

Which isn’t to say communal gatherings with a price tag are inherently exploitative. Live music and events, like concerts, successfully bring people together for shared experiences, according to Hertz, the professor and author. (Of course, tickets have become so expensive that seeing your favorite act perform is becoming a luxury.) Groups centered around an activity have the potential to connect people, too. But buying your own yarn and needles to bring to a weekly craft night at your local knitting shop is different from paying $50 to join a one-off “knitting club” organized by a VC-backed friendship app.

Because social health touches so many aspects of life — the physical spaces we inhabit, the technology that both facilitates and inhibits socialization, the costs of interacting — the path toward connection is more complex than marketable products or individual purchases. It involves government investment in public spaces and low- or no-cost community events; policies that allow everyone to lead a dignified life, which includes the space for leisure activities; and a societal shift that prioritizes slow, intentional relationship building instead of instant connection. 

“The need is real,” Hertz said. “The purported solutions are many. Some of them I think can be part of the solution. Some of them may well end up making us lonelier as a society.”

This story was originally published in The Highlight. To get access to member-exclusive stories like this every month, become a Vox Member today.