Obsessing about being a good person can backfire. There’s a better way.

Your Mileage May Vary is an advice column offering you a unique framework for thinking through your 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. To submit a question, fill out this anonymous form. Here’s this week’s question from a reader, condensed and edited for clarity:

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.

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