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Rule-Maker or Rule-Breaker?

13 min

Golden Hook & Introduction

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Mark: Alright, Michelle. I'm going to say the name of a book, and I want your brutally honest, one-sentence roast. Michelle: Lay it on me. I'm ready. Mark: The Four Tendencies. Michelle: Oh, that's easy. It's the book that tells you why you can't stick to your New Year's resolutions, and then makes you feel both completely understood and slightly attacked. Mark: (Laughs) That is… painfully accurate. It’s a book that holds up a mirror, and you’re not always sure you like what you see. We are, of course, talking about The Four Tendencies: The Indispensable Personality Profiles That Reveal How to Make Your Life Better by Gretchen Rubin. Michelle: And she’s the author who’s all about happiness and habits, right? I feel like she’s built a whole universe around how to be a better human. Mark: Exactly. But what's fascinating is that Rubin wasn't always a self-help guru. She has this incredibly rigorous background. She clerked for Supreme Court Justice Sandra Day O’Connor. Michelle: Wait, what? From the Supreme Court to telling me why I eat cookies when I promise myself I won't? That's a career pivot. Mark: It is! She comes from this world of intense rules, logic, and high-stakes expectations, which makes her exploration of our often-illogical human nature even more compelling. It all started with a very simple, but profound, question.

The Fundamental Question & The Four Tendencies

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Mark: The question that unlocks this entire system is this: How do you respond to expectations? Michelle: Okay, that sounds simple enough. Like, do I meet my deadlines? Yes. Do I floss every single day like my dentist tells me to? …Next question. Mark: Well, you’ve just hit on the core distinction. Rubin breaks expectations into two types. There are outer expectations—things like a work deadline or a request from a friend. And then there are inner expectations—the promises you make to yourself, like your New Year’s resolutions, or deciding to learn Spanish, or, yes, flossing every day. Michelle: Right. The things no one will know if you skip. The things you can quietly let slide until you have a shame spiral at 3 a.m. Mark: Precisely. And how you respond to that inner/outer dynamic is what determines your tendency. The whole idea was sparked by a conversation she had with a friend. Picture this: it's a blustery winter day, and her friend is lamenting that she just can't get herself to go running. Michelle: Oh, I know that feeling. The couch has a very strong gravitational pull on winter days. Mark: But here’s the kicker. This friend was on the track team in high school. She never missed a practice. She was a star athlete. But now, as an adult, she couldn't 'make time for herself' to run. Rubin was puzzled. Why could she do it then, but not now? Michelle: What was the difference? Mark: Accountability. In high school, she had a coach and a team. She had outer expectations. As an adult, running was just an inner expectation. And that friend, Rubin realized, was an Obliger. Michelle: An Obliger. Okay, I’m listening. That sounds painfully familiar. Mark: Obligers are the biggest group, by the way. About 41% of people. They readily meet outer expectations, but they struggle to meet inner expectations. They are the rock of the world for everyone else, but they often let themselves down. Michelle: Wow. Okay, so who are the others? Mark: So, if you meet both outer AND inner expectations, you're an Upholder. You keep your promises to others, and you keep your promises to yourself. You wake up and go for that run, no problem. You make your to-do list and you follow it. Michelle: That sounds… exhausting. And amazing. Mark: Then there are the Questioners. They resist outer expectations, but they'll meet an expectation if it makes sense to them—if they've turned it into an inner expectation. They need to know why. 'Because I said so' is their least favorite phrase in the universe. Michelle: I think I might be married to a Questioner. Every simple request turns into a Socratic dialogue. Mark: (Laughs) And finally, you have the Rebels. They resist ALL expectations, outer and inner alike. If you ask them to do something, they'll likely do the opposite. If they tell themselves to do something, their inner contrarian might just resist that too. Their motto is basically, "You can't make me, and neither can I." Michelle: Hold on, Mark. This is fascinating, but I have to ask the question that I know some of our listeners are thinking. This sounds a little like a personality horoscope. 'You're a Rebel, so you're spontaneous!' How is this different? I know the book gets some criticism for being a bit reductive, for putting people in boxes. Mark: That's a fair and important challenge. Rubin addresses this head-on. She quotes a reader who worried, "When you define yourself, you confine yourself." But her argument is that this framework isn't about confining you; it's about liberating you. She says, and this is a key quote, "The happiest, healthiest, most productive people aren’t those from a particular Tendency, but rather they’re the people who have figured out how to harness the strengths of their Tendency, counteract the weaknesses, and build the lives that work for them." Michelle: Okay, so it’s not a life sentence. It’s a user manual. Mark: Exactly. It's a diagnostic tool. Once you know your operating system, you can stop trying to run software that's not compatible. To really see the power of this, let's look at the two polar opposites on this spectrum. The rule-followers and the rule-breakers. The Upholders and the Rebels.

The Two Extremes: The Upholder and The Rebel

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Michelle: Alright, the ultimate goody-two-shoes versus the ultimate non-conformist. This should be good. Let's start with the Upholder. Who is the quintessential Upholder? Give me a character everyone knows. Mark: Hermione Granger. Without a doubt. Think about it. She loves rules, she loves schedules, she gets anxious when Harry and Ron break the rules. She meets every deadline, she does all the reading. She meets all the outer expectations of Hogwarts. Michelle: Totally. She’s the one reminding everyone about their homework while they’re trying to save the world. Mark: But she also has powerful inner expectations. She doesn't just follow the rules of the Ministry of Magic when they become corrupt. She follows her own internal code of justice. She starts S.P.E.W.—the Society for the Promotion of Elfish Welfare—because her inner voice tells her that house-elf slavery is wrong, even when everyone else accepts it as normal. She has "rules beyond the rules." Michelle: That’s a great distinction. So it’s not about being a mindless drone. It’s about having a strong internal compass that aligns with the external one, most of the time. What’s the downside, though? They sound kind of perfect. Mark: The weakness is rigidity. Upholders can have trouble when plans change unexpectedly. They can get very upset by mistakes. There's a story in the book about an Upholder woman who was in labor, on the way to the hospital, and she insisted her husband not speed and park in the correct lot. Michelle: No! While in labor? That’s commitment. Mark: That’s Upholder-tightening. They can struggle to see when it’s not only okay, but necessary, to break a rule. Now, let’s swing to the complete other end of the pendulum: The Rebel. Michelle: The person who would not only speed to the hospital but probably take a shortcut through a golf course. Mark: (Laughs) And they'd do it because they want to, not because of the emergency. The Rebel motto is, "It’s so hard when I have to, and so easy when I want to." They resist being told what to do. There's a great, simple story in the book about a Rebel who was told that a nearby greenway was dangerous and that people get mugged there. Michelle: So they stopped walking there, right? Mark: Nope. They started walking there more consistently. The warning was an expectation, and their immediate impulse was to defy it. Michelle: Wow. That is… a special kind of wiring. I know people on both ends of that spectrum. My college roommate was a total Upholder... her planner had its own planner. And my brother is 100% a Rebel. You ask him to take out the trash, and suddenly it becomes a philosophical debate about the social constructs of household chores. Mark: That is a classic Rebel response. They resist the expectation of the task. The moment you ask, you've created an obligation they feel compelled to push against. Michelle: So what happens when these two types have to live or work together? An Upholder and a Rebel. It sounds like a sitcom premise doomed for cancellation after two episodes. Mark: It can be a disaster, or it can be a superpower, which brings us to the whole point of the book: using this knowledge to your advantage.

Harnessing Your Tendency

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Michelle: Okay, so you can't just tell a Rebel to be more like an Upholder. That would be like telling a cat to act like a dog. It’s not going to happen. Mark: It will absolutely backfire. You can't change your fundamental tendency. But you can change your circumstances. You can learn to speak the language of other tendencies and, most importantly, your own. This is where the framework becomes a practical tool, not just a theory. Michelle: So how do you do that? How do you manage these different personality operating systems? Mark: Rubin shares a fantastic story from a teacher of four- and five-year-olds. It was nap time, and as you can imagine, getting a room full of kids to settle down is a challenge. But instead of a one-size-fits-all approach, she used the Four Tendencies. Michelle: For four-year-olds? That’s advanced. Mark: It’s brilliant. For her little Upholders, she’d say, "It's nap time now. The rule is we rest quietly, and when you wake up, we'll play the game I promised." She appealed to their love of rules and schedules. Michelle: Okay, that makes sense. What about the others? Mark: For the Questioners, she wouldn't give a command. She'd ask a question. "Why do we need to take a nap? Is it because our bodies get tired from playing so hard?" She let them arrive at the logical conclusion themselves. Once they agreed it was a good idea, it became their idea. Michelle: That is so smart. You're giving them the 'why' they crave. Mark: For the Obligers, she’d lean on external approval and their desire to help. "You were such a good napper yesterday, you really helped the whole class rest. Can you be my great helper again today?" Michelle: Aww. Appealing to their role as the good, reliable person. I see the pattern. So what on earth do you do with a Rebel toddler who doesn't want to nap? Mark: This is the masterstroke. You give them freedom and choice. She’d say, "You can choose not to sleep. That's your decision. But the rule for everyone is that you have to stay on your cot and be quiet so your friends can rest." Michelle: Ah! You reframe it. The choice isn't 'nap or don't nap.' The choice is 'nap or lie quietly.' You give them a way to resist the main expectation (napping) while still achieving the overall goal (a quiet room). That is brilliant. It's not about forcing everyone into the same mold. It's about speaking their language. Mark: Exactly. And it works for adults, too. For the Rebel in your life, you don't give them a command, you give them information, consequences, and a choice. You don't say, "You need to save more money." You say, "Here's the data on retirement savings. People who save this much can retire at 60. People who don't, often have to work until 75. The choice is yours." Michelle: You let them be the hero of their own story, making their own free choice. Mark: You empower their identity. A Rebel won't follow a diet because a doctor told them to. But they might follow it if they decide, "I am a healthy, athletic person, and this is what healthy people do. I want to do this." It becomes an expression of their freedom, not a submission to a rule.

Synthesis & Takeaways

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Michelle: You know, this framework, which seems so simple on the surface, is actually a profound tool for empathy. It’s a decoder ring for human behavior. Mark: It really is. It's not about judging someone for being a 'Rebel' or an 'Obliger.' It's about understanding their operating system. When you know your partner is a Questioner, you stop getting frustrated that they need a reason for everything, and you just start giving them the reason upfront. Michelle: And when you know you're an Obliger, you stop beating yourself up for not having 'enough willpower' and you start building the external accountability you actually need to succeed. You get a gym buddy or sign up for a class you have to pay for. Mark: Exactly. You stop fighting your nature and start working with it. Rubin quotes the writer John Gardner, who said, "Every time you break the law you pay, and every time you obey the law you pay." Michelle: That’s a heavy quote. What does she mean by that in this context? Mark: Whether the 'law' is an outer rule or an inner goal, every choice has a price. The Upholder pays a price in rigidity. The Rebel pays a price in instability. The Obliger pays a price in resentment. The Questioner pays a price in analysis-paralysis. There's no perfect tendency. This framework just helps us understand the price we're willing to pay, and why. It gives us the self-knowledge to navigate those trade-offs wisely. Michelle: It really makes you think... which one am I? And more importantly, which one is my boss, my partner, my kids? It feels like a key that could unlock so many frustrating interactions. Mark: That's the journey. And we'd love to hear about yours. Once you figure out your tendency—and Rubin has a quiz online you can find easily—drop us a comment on our socials. Tell us the most 'Upholder' or 'Rebel' thing you've ever done. It's always fascinating to see this in the wild. Michelle: I’m already mentally cataloging every frustrating group project I’ve ever been in. It all makes sense now. Mark: This is Aibrary, signing off.

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