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.

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........

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