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Luvvie Ajayi: Speak Your Uncomfortable Truth – Transcript

Read the transcript of Caitlin’s interview with bestselling author, speaker, humorist, and a self-professed troublemaker, Luvvie Ajayi.
by Natallia Darozhkina | Oct 18 2018

Ben Schuman-Stoler: Welcome to the Simplify Season 4 bonus episode. I’m Ben Schuman-Stoler and I just wanted to drop in and say thank you. Thanks to all you out there who listen to Simplify all over the world. You’ve helped us get on the map and the fruits of your efforts are so visible now. I mean, since we got over a million listeners earlier this year—which still blows my mind—so much has continued to improve: we’ve added Terence, Nat, Ben Jackson, and in the meantime Ody, Caitlin and I still get to keep working on this really incredible thing. I mean, we’ve been shortlisted for the “Podcast of the Year” now by FutureBook, you can check out all the episodes now in Salon. We’ve more and more resources available on the Blinkist Magazine and we’re cooking up a stellar Season 5 with more of what you guys love.

So I just wanted to say: thanks. Thanks for listening, thanks for sending us emails, for your reviews, likes, comments, and for your support. Now quickly to business: today we have another bonus episode. So if you’re new to Simplify—yes, we do say “six episodes, six ways to change your life”—but the bonus seventh episodes are where we feature someone who maybe isn’t as well known as our other guests, but who we think has a smart, important and helpful approach. Someone we think you should know. So today we’re going to meet Luvvie Ajayi, and if you think there’s someone out there we should talk to, just send us an email. We’re at [email protected]. So with that let’s get into the episode with Caitlin and Terence.

Caitlin Schiller: Welcome to Simplify. I’m Caitlin Schiller.

Terence Mickey: And I’m Terence Mickey.

Caitlin: Hooray! Back in the studio again. We’re here today to talk about—or talk about the work of—a lovely person named Luvvie Ajayi. She is a writer, a humorist, an activist, and a self-professed troublemaker — the best of all titles. She has a podcast called Rants & Randomness, which is where I first heard of her. But today we’re talking about her book, which is called I’m Judging You: The Do-Better Manual. Sounds kind of harsh, isn’t really.

Terence: What drew you to her and her work in particular?

Caitlin: Well, I said that I first heard about her from her podcast. The fact is that I first heard her on her podcast, but our awesome production assistant Nat was the person who brought her to my attention.

Terence: Yay Nat!

Caitlin: Hey Nat! Heard about Luvvie from Nat, and I listened to her podcast and immediately was really really drawn to her voice. Her actual sonic voice is very warm and lovely, but so too is the space that she creates. She rants and it can have some kind of vigor behind it, but she also makes this beautiful warm space in which her interviews happen. She often talks to people from the African diaspora in the US doing really, really interesting things. One of the interviews I really enjoyed was with the editor of Essence Magazine—and I recommend that one if you go listen to Luvvie’s work—but I liked her voice in all the senses. And then I picked up the book and thought she’d be a cool person to talk to.

So what this book is about, it’s a lot of stuff: it’s humor essays, she talks about people’s wigs, she talks about bad manners at family dinners, but between all that stuff, there are sections that focus really hard on social issues. And it’s here where she gets to the heart of her message, which is really: get uncomfortable and tell the truth. That it’s our duty and can be a joyful duty to be really real with each other and hold each other to higher standards than we do––and that might involve telling somebody some uncomfortable truths.

Terence: I was really struck by the simple power of her message. You know, we can take for granted the ideal of truth-telling and doing right by ourselves and by others. But if we don’t insist upon these ideals, it’s really easy for them to erode, and so I really appreciated that. And even with the title of her book, she calls that “an obvious but uncomfortable truth,” we judge each other. And since nobody likes discomfort, she uses that powerful tool of humor to kind of coat the discomfort. And that reminded me of the—I think it’s Flannery O’Connor—but “the darkest truths are best told with a punchline.” And I think she’s kind of epitomizes that message.

Caitlin: She totally does. And it’s “I’m judging you,” but it’s “I’m judging you with a smile and an elbow in the ribs” that lets you know, that not she might be judging you and telling you something that you don’t want to hear, but she’s judging you and telling you something that you don’t want to hear because she thinks we can be better than that, which is what real friends do. So without any further ado, should we just listen to the interview?

Terence: Let’s do it!

Caitlin: Cool.

Caitlin interviews Luvvie Ajayi

Caitlin: Hi, Luvvie. Thanks so much for taking the time to come on Simplify. Could you introduce yourself, please?

Luvvie Ajayi: I’m Luvvie Ajayi, I’m a writer, I wrote a book called I’m Judging You: The Do-Better Manual, I’m a speaker on all types of topics related to pop culture, media, race, and business. And I am a professional troublemaker. I have a podcast called Rants And Randomness. Essentially, I am a Jill of all trades, master of few.

Caitlin: Cool. I think that’s probably one of the best things to be in this day and age, honestly, gives you some flexibility.

Luvvie: Absolutely!

Caitlin: What is your way of helping people to do better? It seems like it’s to just call them out, let them know someone’s watching them.

Luvvie: I wrote this book in a way where it felt like you were at brunch with your best friend who was telling you that like, “Yo, I think, you’re better than what you’re currently doing.” So a lot of the feedback that I’ve gotten about the book is like people don’t feel scolded. You literally feel like you’re talking to a friend of yours, who’s just like, “Girl, let me tell you how you can get it together because I’ve been where you’ve been. I was this person. I’m not judging you without love, like this is with love, but I want you to be a better person.”

For us to fix any major problems as happening in the world, we’re going to have to get uncomfortable. Like, people are so afraid of discomfort – it’s crazy. People would rather sit in injustice than discomfort. So it’s like, how about we all just get used to the idea that some things are not going to feel comfortable and harmonious? But for things to get better, for the greater good of the world, we’re going to have to like, get prickly and feel the wincing times of having weird conversations with the person you love, who’s telling you, “That thing that you did was not OK.” Or being told, “Hey, the group that you’re a part of has been a part of like the global web of oppression for centuries.”

And just being able to understand that like, discomfort will not kill you. It will not kill you, but it’s necessary for growth. It’s like, how like, when babies are teething, how they’re crying for two months because the teeth are trying to poke through their gums. Same thing! And they get teeth, and they’re all good, they can chew food. But they have to go through that piece before they can get to the other side. So people are just so afraid of that piece that they’ll back out of anything before it gets uncomfortable.

Caitlin: Have you been in a situation where you’ve confronted someone from… Or you’ve called someone out on bad behavior and they weren’t receptive to it?

Luvvie: Some people will not always be receptive to your loving criticism or critique, and that’s OK. But I think our jobs is less to worry about like, “how will they receive it?” And more to figure out, “how do you want to make sure it comes across?” Like, I think, our jobs is less about the landing and more about like making sure we’ve done our part in the way that makes most sense. Because if we’re always worried about how people will receive it, we will do very, very few things.

So that’s why I always say that like, I use my checkpoints. Like, whenever I want to ask somebody something, or say something that feels scary, or do something that’s going to make something a situation uncomfortable, somebody uncomfortable, I always ask myself… My three checkpoints is: Do I mean it? Can I defend it? Did I say with love? And if the answer is yes to all three, I say it. And hopefully the person that you’re talking to receives it in the way you intended it to be received.

Caitlin: That’s like really good practical advice actually. What do you think people’s trouble is with receiving criticism?

Luvvie: Because it makes you stop and say like, “Oh wow! Actually I have to adjust something that I already do.” So it’s that adjustment, like having to make any adjustment as a person is not comfortable and it’s not easy. Like, usually when somebody calls you out on something or, you know, says, “Hey, you could do this thing better.” It means, you have to make a certain shift like, “Oh this thing that I’m doing, I haven’t been doing it perfectly right, which means I have to change the way I’ve been doing it.” And it’s not easy.

Caitlin: What have you been called out on and made a change?

Luvvie: You know, like there are times when I’m more blunt than people are used to. So, I mean, a lot of times I stick with what I say, but I’ve been called out for… I think, like once I was called out for like how I said a particular statement. And I was like, “OK, I see how that could have not worked for you, and I will make sure I’m even more thoughtful moving forward.” But getting to that point is making sure you can’t take ego out of the thing, right?

Like, you have to be able to kind of check yourself too and be like, OK, make sure it’s coming from not trolls online, but people who actually love you and respect your work. Really have to pay attention those times, when those people are the ones who are giving you criticisms. And just understanding that life is about making adjustments along the way. Critiquing you is not being like, “You’re a bad person.” It means you made a misstep. And hopefully, you see that, take it on, and then make an adjustment, and keep it moving. Learn a lesson and keep it moving.

Caitlin: I think that people get so focused on succeeding that they forget that part of what succeeding is failing.

Luvvie: Yes, like you can’t expect to succeed without making any fails. Like, I don’t know anybody, who’s successful, who’s never failed – that’s kind of crazy. Like, failure is part of life. It’s just a thing that you have to deal with.

Caitlin: Part of the way that you self-identify is as a troublemaker. What does that actually mean to you?

Luvvie: You know, I think troublemakers are disruptors and people who kind of shake the table a little bit. And I feel like I’m a disruptor. Because, you know, I’m often the person who says what people are thinking, but dared not to say. So even that makes me a troublemaker. So it’s kind of like, “Oh, OK.” But it’s not like, my goal isn’t to make people uncomfortable, funny enough. My goal is to say what I feel in the way that I feel it, in the way that I mean it, intentionally. And what I find is people who tell the truth, who are very super committed to telling the truth like me, end up coming across as troublemakers. Because people would be like, “Oh my God, I can’t believe you said that!” But you were thinking it, you just happened to not say it.

Caitlin: Have you heard of this Buddhist concept of fierce compassion?

Luvvie: No, but I get it immediately when you say it.

Caitlin: It’s this concept that sort of changed my life. It’s the thing that’s given me any relationship with my Dad, whatsoever. But it’s kind of another way of finding yourself into this very Christian idea of loving your enemy which can be really hard. But the idea of fierce compassion is that you create justice not through revenge, or inflicting cruelty, and like equal measure upon your enemy, or somebody who’s done you harm, but by holding them to account, asking them to be better than they have been. And I felt like that was the place that you were coming from in your book.

Luvvie: Yeah, like I’m somebody who considers herself an optimist. So when I see the world going to hell in a handbasket, I’m always like, “I expected better of us. So, how do I make sure that I’m doing my part to make sure we’re expecting better of ourselves?” And for me essentially, this book—which is why I called it The Do-Better Manual—the importance of it for me was to kind of tell people like, “Look, things can be better, but we kind of have to make it our business to make things better.” I think, if we all told more truths, we’d be in a better world. If we told more truths to each other, to ourselves, we’d be better for it.

Caitlin: What is one thing that you would like people to do better at in general? What’s an idea that you’d like to leave listeners with?

Luvvie: You know, it’s just a simple idea of… It’s so funny. You’re going to be like, “You already said that!” But I mean it! Like, making it a point to just tell more truths. Like, it means challenging yourself to always say what you mean.

So, people start honoring your word more, if they realize that you’re impeccable with your word. Like, you’ve been able to stand by your word means a lot. So yeah, I do my best not to lie. I’m not saying, I am a perfect truth-teller. But I do my best to make sure that I am not walking through the world misrepresenting myself, misrepresenting my ideas, and being somebody that I am not. I do my best at it, and that’s all we can do.

Caitlin: Thank you so much for taking the time to talk today. It’s been really a pleasure to hear your thoughts.

Luvvie: My pleasure. This has been a great conversation! I love having interesting chats with people who ask interesting questions. And you just asked me some really good ones. So thankful for that!

Caitlin: Oh, thank you. Have a great one! Enjoy your day in Chicago.

Luvvie: Thank you so much.

Caitlin: OK, bye!

The Bookend

Terence: Welcome back to The Bookend where we end with books.

Caitlin: I like it. You’re perfecting your own kind of Bookend rhythm.

Terence: I got it right this time.

Caitlin: Not that it was wrong last time. We have to ask Ben for his honest opinion on how The Bookend intros are.

Terence: That’s true. He can give us a little grade.

Caitlin: That was cool, I really enjoy talking with Luvvie.

Terence: Yeah, like you said, she’s got a great voice, great energy, really lively and a really simple but powerful message.

Caitlin: Definitely. And to interlock with some of the things that we talked about in the conversation there, one of my favorite concepts I guess––which is such a cheesy thing to say––one of my favorite ideas is the idea of “fierce compassion,” which I think that I might have mentioned on a previous episode, but it’s a Buddhist concept of exactly what Luvvie’s talking about: fiercely holding one another accountable in a loving way because you believe in their inner goodness and ability to be their absolute best.

I first heard about it from an episode of On Being—endless shoutouts to Krista Tippett all the time. I heard this episode on fierce compassion—I think that the episode’s called Love Thy Enemy—and it really is the thing that has given me a relationship with my Dad. He and I have had a difficult relationship—and if you’re listening, Dad, you know that I say this with love too—it’s been tough. And what this idea of fierce compassion brought to me was that it was OK for me to tell him that I wasn’t satisfied with how our interactions were anymore, and that I wanted more, and always had.

And the fact of the matter was that once I got brave enough to do that, it came to light that he did, too. And we had this long really honest conversation in which tears were shed on both sides, and we both pledged to do better by each other. And I think that, you know, at 33 I have a better relationship with my dad now than I ever had before. And it’s because I was given this tool to understand our relationship could be different and come from a place not of anger on either one of our parts, but on belief that we could be better than we were.

Terence: Were you afraid to hurt his feelings by being honest?

Caitlin: Absolutely. Yeah, and I was afraid of being uncomfortable.

Terence: What was it about fierce compassion that you felt like give you a tool to kind of overcome your own fear of hurting his feelings and make you feel like you could be honest without it coming across angry, or misinterpreted, or escalating into something worse?

Caitlin: I think because it put me in touch with my own… The compassion portion of it put me in touch with my own desire to make everything better all the time. And to make things better through empathy and being kind rather than being angry, angry or something that I guess I’m a wussy about a lot of times. And it gave me a way to channel my anger into an emotion in a way of being that was more productive for me and made me better able to communicate with him.

Terence: That makes sense. And I think that fear of hurting somebody is the biggest barrier to truth-telling. So what books did you pick that were relevant to Luvvie.

Caitlin: Relevant to Luvvie? Alright. I’ve got two. The first one is Why I’m No Longer Talking to White People About Race: Understand Racism and White Privilege by Reni Eddo-Lodge. It’s an excellent book. It’s by a black British journalist, her name is Reni Eddo-Lodge. It takes you through the history of black Britain, starting with a London race riots of the 1980s and it dismantles the myth of race blindness. It talks about concepts like positive discrimination which is a way of creating opportunities via looking purposely to include people who are unlike yourself rather than remain blind to them or exclude them. And it’s just informative, it’s detailed, it’s fair, and it’s full of information that we all either need to learn––white people like myself––or see reflected to us in today’s cultural climate.

Terence: Sounds great.

Caitlin: It’s really, really, really, great. How about you? Why don’t you do yours?

Terence: I picked Trickster Makes This World: Mischief, Myth and Art by Lewis Hyde. He’s most known for a book called The Gift. But this one is about the myth of the trickster in like Scandinavian, African, American Indian culture. And I picked it because Luvvie introduces herself as a troublemaker, and I think of her method as almost trickster-like in that she’s holding two opposing ideas, not dissimilar from your fierce compassion. And Lewis Hyde kind of looks at those figures in our culture: everyone from and to Allen Ginsberg as people in the culture who are kind of making people feel uncomfortable and creating ambiguity in the service of some kind of larger truth.

Caitlin: That sounds awesome.

Terence: You know, Lewis Hyde goes down so many rabbit holes and does such a comprehensive look at the idea of the trickster. It’s one of those like amazing reads where you feel like you’ve read 10 books in one.

Caitlin: That sounds so great. Every time you have a book recommendation, I just want to take it from you immediately—Terence makes the mistake of bringing his physical copies and I just want to yank them.

Terence: I’m not going to let go of this one. This is one of my favorites.

Caitlin: I’ll get it myself. Very cool. Thanks for that one. We’ll give you one more to round it off. And this one is a little bit more office world. We can totally go there with this topic, I think. It’s called Radical Candor: Be a Kickass Boss Without Losing Your Humanity by Kim Scott. Have you heard of this one? It’s fairly new. It advocates for being radically honest—not brutal, but radically honest—because this fear of hurting people that we’ve talked about can create the most suffering.

There’s this example of how when Kim Scott was working as a manager at Google. She had just given some sort of presentation and taken questions from the audience after. And her supervisor approached her later and said, “Hey, you know, you did really well with this, this and this, but you just undermined yourself via all those ‘uhms’ you used. Somebody who is as smart as you are shouldn’t be doing that so find a way to fix it. It’s going to make you way more powerful.”

And she was kind of blown back by it, but then she went and she worked with a public speaking coach and found that her talents improved immensely. So she advocates for giving people the gift of being really, really honest in a kind way because it allows them to work on something in themselves that they don’t necessarily see.

Terence: I think people appreciate you more when you’re honest with them if it does improve their performance or, you know, any part of their life.

Caitlin: Yeah, because it also makes you feel safe with them.

Terence: Yeah. I mean when you’re with someone who is dishonest, you feel extremely unsafe and you don’t really know what’s true or not. So even a compliment is kind of worthless because you’re questioning whether it really means what it means.

Caitlin: Absolutely. I actually think that that has a lot to do with why it was so wonderful to talk with Luvvie and to read her book and the space that she creates in her podcast, you know that because she’s being honest with you, it’s safe to just be yourself and make a mistake. And that is so so critical because it’s not that she’s holding you in judgment negatively forever, it’s that she’s going to tell you what’s wrong and then wait for you to fix it, because she believes you can and should.

Terence: Yeah, that’s a great combination.

Caitlin: Cool. I guess that’s it. Should we take it out?

Terence: Yeah, let’s wrap it up.

Caitlin: As you probably already know—but if you don’t, here it is—Simplify is brought to you by Blinkist which is an app. We pick out the key ideas from the world’s best nonfiction books and distill them into smart effective overviews that you can read or listen to in about 15 minutes. We made a voucher code for this episode. You can go try Blinkist and read at least two of the books that we just recommended, Radical Candor and Why I’m No Longer Talking to White People About Race, on Blinkist. So go to and type in the voucher code troublemaker. And you can try Blinkist for free for 14 days, which is more than long enough to read both of those books and more.

This episode was produced by me, Caitlin Schiller, Terence Mickey, Nat Darozhkina, Ben Schuman–Stoler, Ben Jackson and probably Ody Constantinou in there somewhere. We’re not really sure he’s totally back from his Cypriot vacation yet. He got stranded on an island. It’s a really long story.

As always we love to hear from you: you can tweet me at @CaitlinSchiller, Ben at @bsto and Terence—if you want to talk to Terence about his book recs—

Terence: @Terence_Mickey.

Caitlin: Yep, or write to us at [email protected]. We live for those emails—or I do. It means so much to hear from you and to hear what we’re doing wrong, and what we’re doing right, and what you want more of—so write to us.

All right. That’s it. That rounds out Season 4! Thank you so much to everybody for supporting us, for listening, for recommending, for giving us your ears—we know that you could be listening to other things and we’re so glad that you spent your time with us. And thanks to everybody within Blinkist without whose support the show wouldn’t get made. Yeah, so I guess that’s it.

We’ll be back with Season 5 and more adventures for your ears in early 2019. So, in the meantime, write to us, say hi, and till then this is Caitlin checking out!

Terence: This is Terence checking out!

Read the show notes from this episode here!

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