This week’s question comes from Gregory Stock’s “The Book of Questions”: When was the last time you stole something? Why haven’t you stolen anything since? Is there anything you’d steal if you were certain you wouldn’t get caught?

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I’ll be honest with you—this question made me squirm a little when I first read it. There’s something about the word “stole” that immediately puts us on the defensive, isn’t there? We want to say, “I’m not a thief!” But Stock’s genius lies in how his questions force us to examine the gray areas of our moral landscape, the places where our high-minded principles meet messy reality.

So let me start with my confession: I may have swiped a roll of toilet paper from work once. I had a cold, desperately needed something to blow my nose, and the supply closet was right there. No tissues in sight, but plenty of TP. I grabbed an extra roll, used some at work, then took the rest home to get me through the worst of my cold. There it is—my life of crime laid bare.

Now, you might be thinking, “That’s it? That’s barely even stealing!” And that reaction itself is fascinating. It reveals how we instinctively create hierarchies of moral transgression, how context shapes our understanding of right and wrong. A roll of toilet paper from a corporate supply closet feels different from shoplifting a candy bar, which feels different from embezzling money, which feels different from stealing someone’s identity. But why?

The Evolution of Our Moral Compass

When I was a kid, the rules seemed clearer. Taking something that wasn’t yours was wrong, period. I remember being about seven years old and pocketing a piece of candy from a friend’s house without asking. The guilt ate at me for days until I finally confessed to my mom and made her drive me back to return it and apologize. The shame was overwhelming—not because I’d been caught, but because I knew I’d crossed a line.

But as we grow up, we discover that the world operates in shades of gray. We learn about corporate tax loopholes, wage theft, price gouging during disasters. We see how “legal” doesn’t always mean “moral,” and how “illegal” doesn’t always mean “wrong.” Remember Robin Hood? He was technically a thief, but we celebrate him as a hero because of who he stole from and why.

This complexity changes how we think about theft. That toilet paper incident? In my mind, it barely registers as stealing because the context makes it feel reasonable. I was sick, I needed help, and taking something worth maybe fifty cents from a company that wouldn’t miss it seemed like a victimless transgression. But if I’d taken that same roll from a friend’s bathroom, I would have felt terrible about it.

The Social Contract We All Sign

What we’re really talking about here isn’t just individual morality—it’s the invisible social contract we all participate in. We agree not to take things that belong to others partly because we expect the same courtesy in return. It’s a system built on mutual trust and shared vulnerability.

But this contract gets complicated when we factor in power dynamics and economic inequality. Is it the same moral transgression when someone steals bread because they’re hungry versus when someone steals a luxury item they simply want? Most of us would say no, even if the law treats them similarly. Our moral intuitions recognize that desperation changes the calculus.

This is why Jean Valjean’s theft of bread in “Les Misérables” resonates as tragic rather than criminal, why we root for Aladdin despite his pickpocketing, why many people felt conflicted about prosecuting parents who stole baby formula during shortages. Context matters enormously to our moral reasoning, even when the law tries to apply universal standards.

The Power of Conscience

Which brings me to the third part of Stock’s question: Is there anything I’d steal if I were certain I wouldn’t get caught? My immediate, visceral response is no. Not because I’m particularly virtuous, but because I’ve realized something about myself over the years: I would know, and that knowledge would be its own punishment.

This might sound sanctimonious, but I think it’s actually quite practical. My conscience—that internalized voice of moral judgment—has proven to be remarkably persistent and unforgiving. It doesn’t care about external consequences; it cares about the story I tell myself about who I am. And “person who steals things” isn’t compatible with that story, even in a hypothetical scenario with no external consequences.

But I recognize this is a privilege. My conscience can afford to be uncompromising partly because I’ve never been truly desperate. If my family were starving and I could steal food with no consequences, would my moral calculations change? Probably. Would I judge someone else for making that choice? Absolutely not.

The Gray Areas We Navigate

The more I think about this question, the more I realize how much of our daily lives exist in moral gray areas that we rarely examine. When we use a company’s Wi-Fi for personal browsing, are we stealing? When we take extra napkins from a restaurant, use a student discount we no longer qualify for, or fudge our taxes just a little—where exactly is the line?

Most of us have internalized rules that help us navigate these situations without constant moral anguish. We develop intuitions about what feels acceptable and what doesn’t, often based on factors like:

• The relative power and resources of the other party
• Whether anyone is actually harmed
• The social norms in our community
• How the action aligns with our self-concept
• Whether we’d be comfortable if everyone did the same thing

These aren’t perfect guidelines, but they’re how most of us actually make moral decisions in real time, rather than through rigorous philosophical analysis.

What Our Answers Reveal

Stock’s question is clever because it doesn’t just ask about our actions—it asks about our reasoning. Why haven’t you stolen anything since your last transgression? What does that reveal about how you’ve changed, what you’ve learned, or what you fear?

For me, the answer isn’t fear of consequences but rather an evolution in self-understanding. I’ve learned that my peace of mind is worth more than anything I might gain through questionable means. I’ve also developed a more nuanced understanding of how small compromises can erode our moral foundations over time. It’s easier to maintain clear boundaries than to constantly negotiate with myself about what’s acceptable.

But I also recognize that this stance comes from a position of relative security and privilege. It’s easy to be principled when you’re not facing impossible choices.

The Invitation to Reflect

Perhaps the real value in Stock’s question isn’t in the specific answers we give, but in the self-examination it prompts. When we think about theft—whether we’ve committed it, avoided it, or might consider it—we’re really exploring fundamental questions about morality, society, and human nature.

We’re asking: What do we owe each other? How do circumstances affect moral judgment? What role should empathy play in how we evaluate others’ choices? How do we balance individual needs against collective agreements?

These aren’t academic questions. They shape how we vote, how we treat people who’ve made mistakes, how we think about economic inequality, and how we navigate our own moral decisions every day.

So I’ll turn Stock’s question back to you: When was the last time you took something that wasn’t yours? What stopped you the next time you had the opportunity? And if consequences were truly impossible, what would that reveal about the moral boundaries you’ve drawn for yourself?

Your answers might surprise you. They certainly don’t have to match mine. The goal isn’t to reach the “right” conclusion but to better understand the moral reasoning that guides your choices—and perhaps to develop a bit more empathy for others navigating their own complex moral terrain.

After all, we’re all just trying to figure out how to be good people in a complicated world. Sometimes that starts with admitting we once stole a roll of toilet paper.

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What’s your answer to this week’s question? I’d love to hear your thoughts in the comments below.