Olivia: Jackson, if Mindy Kaling's book Is Everyone Hanging Out Without Me? were a food, what would it be? Jackson: Oh, easy. A box of assorted, high-end donuts. Some are brilliantly funny and insightful, some are just sweet and fluffy, and one of them is filled with a surprisingly dark revenge fantasy. Olivia: That is a perfect description. And it's that mix of sweet, sharp, and surprisingly dark that made Mindy Kaling's 2011 memoir a massive bestseller and a nominee for the Goodreads Choice Award for Humor. Jackson: It’s so interesting to think about when she wrote this. She wasn’t the mega-producer she is today. She was still in the thick of it on The Office. Olivia: Exactly. And what's amazing is that Kaling wrote this while she was on the show, where she started as the only female writer at just 26. That experience of being a young, South Asian woman in a male-dominated comedy world is the engine behind so much of the book's humor and insight. Jackson: It really sets the stage. The book feels like it’s written from the trenches, not from the top of the mountain. Olivia: And it really starts with this core, universal anxiety that gives the book its title, this feeling of being on the outside looking in.

Olivia: That title, Is Everyone Hanging Out Without Me?, is so painfully relatable. Kaling builds her entire philosophy from that feeling. She doesn't just write about it as a passing phase; she presents it as a fundamental part of her identity, starting from childhood. Jackson: Right, she has that whole chapter, "I Forget Nothing," which is such a great title for a look back at your youth. It’s not a rosy, nostalgic view. It’s a detailed accounting of every slight. Olivia: It really is. And the most powerful story in that section, for me, is about a boy named Duante Diallo. He was the handsome, popular star of the basketball team at her private school. She describes herself as a "competitive, bookish nerd." One day, he comes up to her and says, "You would actually be really pretty if you lost weight." Jackson: Ugh, that is the most devastating, backhanded thing you can say to a teenage girl. It’s a compliment wrapped in an insult. Olivia: Precisely. And it works on her. She becomes obsessed. But then it gets worse. As she gains a little more weight, he escalates. One day, in front of all his friends, as she walks by, he says, "Speaking of whales…" Jackson: Oh, that’s just brutal. High school can be such a minefield. Olivia: It’s pure cruelty. And it leads her to adopt this extreme diet where she just eats half of whatever is on her plate. She loses thirty pounds in two months. But here’s the kicker, the part that really defines Kaling's worldview. After she loses the weight, Duante doesn't stop. He just changes his taunt. He says to his friends, loud enough for her to hear, "Remember when Mindy was like a whale?" Jackson: Wow. So the lesson is, bullies don't have a code of conduct. There's no winning by their rules. Olivia: Exactly. And Kaling takes this a step further in her chapter "Don't Peak in High School." She argues that this experience of being the "overlooked kid" is actually an advantage for a writer. She says while the popular kids are busy being popular, the outsiders are observing. They're collecting material. Jackson: That’s a great reframe. Is she saying that you need to have a miserable adolescence to be a successful adult? Because I think a lot of people would co-sign that. Olivia: She almost does! She uses this example from the movie Waiting for Guffman, where a character says he became a great observer because he "sat next to the class clown, and studied him." Kaling’s advice is to be that person. Don't worry about being the star of the school play or the prom queen. That stuff is fleeting and, as she puts it, makes you look "kind of pitiful" if you're still talking about it at thirty. Jackson: It’s a powerful idea. The anxiety of being left out, the pain of being bullied—it doesn't just have to be trauma. It can be training. It’s your superpower in disguise. Olivia: That’s the core of her Outsider’s Playbook. She also applies this to her physical self, not just her social life. She has this whole chapter called "I Am Not an Athlete," where she details every single failed attempt at sports, from learning to ride a bike to a traumatic diving board incident. Jackson: Oh, the diving board story is terrifying! The camp counselor, Scott, forces her to jump off the high dive when she’s only six. Olivia: And she gets a huge gash on her leg! She reflects on it as an adult and says the lesson is, if you're scared of something, it probably means you shouldn't do it. You should call your parents. It’s this anti-Nike, "Just Don't Do It" philosophy that’s so funny and refreshing. Jackson: It all ties together. Whether it's body image, sports, or social status, she finds strength in admitting what she's not, rather than trying to be something she isn't. Olivia: And that becomes the foundation for how she approaches her career. Because if you're already comfortable with being an outsider, you're much better prepared for an industry that is designed to make you feel that way every single day.

Jackson: Okay, so being an outsider gives you material. But you still have to get your foot in the door. And Kaling is brutally honest about how many times she failed at that. It’s not a glamorous story at all. Olivia: Not in the slightest. Her chapter "Failing at Everything in the Greatest City on Earth" is a masterclass in creative struggle. She moves to New York after college with her friends Brenda and Jocelyn, and it’s a series of letdowns. Their apartment is a cramped railroad in a sketchy neighborhood, and her career is going nowhere. Jackson: The audition stories are the best. The one for the Broadway musical Bombay Dreams is just peak cringe. Olivia: It's so vivid. She shows up, sees she's one of the few Indian women there, and gets overconfident. She aces the singing part, but then comes the dance call. She has zero dance experience. She's wearing completely inappropriate clothes. She tries to follow the Bollywood choreography and it's a complete disaster. She just walks out in the middle of it, utterly humiliated. Jackson: I think everyone who's ever pursued a creative field has a story like that. A moment where your ambition writes a check your skills can't cash. Olivia: Absolutely. And she has another one that's even more telling. Years later, after she's a successful writer on The Office, she gets invited to be a guest writer at Saturday Night Live. This should be a victory lap. Jackson: Right, it’s the dream. Olivia: But she describes it as a total failure. She feels completely out of place. She says she contributed nothing. She tries to write a sketch about a pregnant cat played by Bill Hader, and it bombs at the table read. She feels so inadequate and isolated that she almost leaves after the first week. Jackson: This is where some of the mixed reviews of the book come in, isn't it? Some readers found it hard to sympathize with, you know, 'oh, my two weeks at SNL were so awkward.' But I think that misses the point. Olivia: I agree. The point isn't the specific situation; it's the universal feeling of imposter syndrome. It doesn't matter how successful you are, you can still feel like a fraud who doesn't belong. And the story has this beautiful resolution where Amy Poehler sees how uncomfortable she is and just says, "Hey, we're all going out. I'll wait for you." Jackson: That small act of kindness changes everything for her. Olivia: It does. It gives her the courage to stay. And it leads to her central piece of career advice, which she learned from her experience creating the play Matt & Ben with her friend Brenda. When you feel helpless and like the industry won't give you a shot, you have to "write your own part." Jackson: That play was their big break, right? It was this absurd premise where the script for Good Will Hunting just falls from the ceiling into Matt Damon and Ben Affleck's apartment. Olivia: Yes, and they starred in it themselves, with Mindy playing Ben Affleck. It was a huge hit at the New York Fringe Festival and went Off-Broadway. It was a direct response to the frustration of auditioning and failing. They stopped waiting for permission and created their own opportunity. Jackson: It’s the ultimate example of 'failing upwards.' The rejections and humiliations in New York fueled the creation of the very thing that launched their careers. It’s a much more honest, and frankly more useful, blueprint for success than the polished stories we usually hear. Olivia: And once she found that success, she started developing this incredibly specific, hilarious rulebook for how to navigate the world she was now a part of.

Jackson: This is my favorite part of the book. It’s less a philosophy and more a series of personal amendments to life. It's so specific and funny. Olivia: It really is. She's not offering broad, generic advice. She's giving you her personal, highly detailed, and often unconventional code of conduct. The chapter "Best Friend Rights and Responsibilities" is a perfect example. Jackson: Oh, it's genius. It’s like a hilarious, unwritten social contract. We all know these rules, but she’s the first one to actually write them down. Olivia: The rules are so good. For example: "A best friend is required to hate who you hate." There's no neutrality. If you're feuding with someone, your best friend must also be feuding with them, even if they don't know why. Jackson: My favorite is the rule about your friend's new boyfriend. You have to try to like him five times. You have to give it five solid, good-faith efforts before you're allowed to officially declare that you hate him. That is so specific and so true. Olivia: It is! Another one is about borrowing clothes. You can borrow anything, but if you ruin it, the owner gets to "talk shit about you to your other friends for one calendar year." After that, it's forgiven. It’s a statute of limitations on friendship grievances. Jackson: It’s hilarious, but it's also about creating clarity. She does the same thing in her chapter on the term "hooking up," where she's so frustrated by the ambiguity. She just wants to establish a clear definition for everyone. Olivia: And her solution is so simple: "From now on, let’s all agree that hooking up equals sex. Everything else is ‘made out.’" It’s a plea for linguistic order in a chaotic romantic world. Jackson: And then there's the "Guys Need to Do Almost Nothing to Be Great" list. It's so funny because the bar is set so incredibly low. Olivia: It's shockingly low. The advice includes: own one well-fitting peacoat, have a signature drink that isn't complicated, and know how to make one great dish. That's basically it. She’s saying that a tiny amount of effort from a man reads as incredibly thoughtful and impressive. Jackson: The peacoat one is my favorite. She says it makes you look like a "put-together Obama speechwriter." It’s such a specific and aspirational image. Olivia: But it all comes back to this central idea of hers. In a world of confusing social signals and unspoken expectations, maybe we're better off with our own clear, if quirky, personal rules. She even has a list of her ideal level of fame, which isn't about being universally adored, but about specific perks, like being able to skip the line at brunch. Jackson: And having a stand-in who gets plastic surgery to look like you. Let's not forget that one. Olivia: We can't forget that one. It's all part of her manifesto. It’s a guide to navigating life not by following society's vague rules, but by creating your own very specific, very funny ones.

Jackson: So when you put it all together—the outsider anxiety, the public failures, the quirky rules—what's the real message here? It feels like more than just a collection of funny essays. Olivia: I think it is. I think Kaling is arguing that the most authentic life isn't about achieving some perfect, frictionless ideal. It's about embracing your specific, weird, sometimes insecure self and building a life, and a support system, that works for you. Jackson: So the humor isn't just for laughs. Olivia: The humor is the mechanism. It's a tool for survival and self-definition in a world that often wants you to be someone else. She dissects her own insecurities about her weight, her career, her love life, but she does it with such wit that it becomes empowering, not self-pitying. She’s taking control of her own narrative. Jackson: That makes so much sense. She’s not just telling you it’s okay to be flawed; she’s showing you how to make your flaws your most interesting and powerful features. The book is a testament to that. Olivia: It really is. It’s a reminder that you don't have to wait for an invitation to the party. You can just start your own, with your own rules. Jackson: It makes you wonder what your own "Best Friend Rights and Responsibilities" would be. Mine would definitely include a clause about not making me watch horror movies. Olivia: Absolutely! And that's a great question for our listeners. What's one non-negotiable rule in your friendship code? Let us know on our social channels. We'd love to hear them. Jackson: This is Aibrary, signing off.