In short
Issa Rae discusses her essay collection and her reading habits, using books to explore self-improvement, confidence, collaboration, friendship, and identity across decades (20s vs 40s). She also touches on creative process and writing for TV.
Guest backgrounds
Issa Rae is the guest; she’s a writer/producer known for creating and starring in Insecure. She’s also a longtime reader who recently made time to read more consistently, using a “30 minutes a night” habit.
Key claims
Mondays and New Year’s feel like “fresh starts” and resets; goals should be repeated and tailored to what feels authentic. Needing to be liked/praise can trap you in living for others. Changing how you speak and act matters—words and presence carry weight. Turning 40 brings a “blank page” mindset and more confidence.
Notable examples
The Courage to Be Disliked (approachable philosophy in conversation form); Playing Well with Others (navigating feedback in creative collaboration); Great Black Hope (work/identity and coming-of-age); The Wilderness by Angela Flournoy (close-friend group intimacy); an Insecure writers’ room example about filling perspectives beyond “people who think like you,” plus Melina’s “it doesn’t look like black people” set critique.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOReading Habits and New Year's Resolutions
0:44 to 1:24
Issa discusses her love for reading and how she incorporates it into her life.
Loving Mondays and New Beginnings
1:24 to 3:08
Exploration of how Issa finds motivation in Mondays and new beginnings.
“I was like scrubbing my kitchen cleaning while I was, because I'm also like you describe a multitasker.”
The Courage to be Disliked Book Discussion
3:08 to 5:01
Issa shares insights about her reading of 'The Courage to be Disliked' and its impact.
“Well, one of the books that you've bought is The Courage to be Disliked.”
Creative Industry Challenges
5:01 to 7:24
Issa talks about the challenges of working in the creative industry and collaboration.
“And so in that way, I was kind of just approaching it from the perspective that they're just, again, things that I need to shed or I want to shift how I'm thinking.”
Reflections on Turning 40
7:24 to 11:28
Issa shares her feelings about turning 40 and the newfound wisdom it brings.
“and how they react to your sort of feedback or opinions.”
Navigating Friendships in Your 20s and 30s
12:30 to 14:01
Discussion on the challenges and dynamics of friendships in changing life stages.
Dating Perspectives in LA vs. London
14:01 to 15:01
Explore the differences in dating culture between LA and London.
“We just mesh really well, but we're all from LA.”
Insecure's Impact on Love
15:02 to 16:00
Discussion on how the show Insecure influenced personal relationships.
Angela Flournoy's 'The Wilderness'
16:01 to 18:02
Insights into Angela Flournoy's new book and the power of friendship.
“I knew she was a writer and she was, I think, going for her MFA in New York.”
Sisterhood and Friendship Dynamics
18:03 to 19:16
A deep dive into the differences between friendships and sisterly bonds.
“And it takes, it's everything that you want in a novel.”
Show all 25 chapters
Childhood Memories and Creative Spaces
19:17 to 21:34
Reflection on childhood spaces and their influence on creativity.
“Like there's one section where a character who's had a baby has like a prolapsed situation.”
The Writing Process and Personal Reflection
21:35 to 24:24
Insights into the struggles and processes of writing from personal experience.
Navigating Real-Life Anecdotes in Writing
24:25 to 27:08
Discussing the challenges of sharing real-life stories in writing.
“And when I do want to hear a good job, I rarely hear it.”
Exploring Identity Through Literature
27:09 to 28:00
The impact of literature on identity and societal contributions.
“And so like that, just knowing that there's, you know, there's a light at the end of the tunnel.”
Exploring Identity and Work in Great Black Hope
28:00 to 29:48
Discussion on the themes of identity and work in the context of Great Black Hope.
“questions that we don't often ask about like kind of black privilege and also are in class in a way that was really, really compelling to me.”
Generational Differences in Expectations
29:48 to 31:18
Insight into the pressures faced by different generations regarding identity and success.
“I watched so many movies where I couldn't help it.”
Auntie Love and Family Dynamics
31:18 to 33:00
Discussion on the joys and challenges of being an aunt and family relationships.
“Like, oh, I'm drawing on things that I also know and am familiar with.”
Anticipating New Beginnings with Family
33:00 to 35:16
Conversations about pregnancy, expectations, and family growth.
“Whenever people are like, do you want kids?”
Adapting Literature: Eleanor Oliphant
35:16 to 38:14
Discussion on the adaptation of Eleanor Oliphant and the unique voice of the character.
“I kept thinking, oh, I want to see an Issa Rae adaptation of this.”
Unexpected Friendships and Growth
38:14 to 40:08
Sharing experiences of unexpected friendships that influence personal growth.
“Have you ever had a sort of unexpected friendship with someone that's like pushed things in an unexpected direction?”
The Pressure of Creativity and Perfectionism
40:08 to 42:01
Discussion on the challenges of perfectionism in creative work and the fear of judgment.
“In LA, do a lot of people just have scripts that they're all, like, writing?”
Overcoming Cringe in Creative Work
42:01 to 42:48
Learn how to navigate the fear of judgment and embrace early creative work.
Diversity in the Writer's Room
42:49 to 44:07
Understand the importance of diverse perspectives in storytelling.
“Now we need like these other perspectives to like fill it and fill the other characters.”
The Value of Conflict in Collaboration
44:08 to 45:29
Discover how disagreements can strengthen creative partnerships.
“And it was fun and it helped enrich the characters.”
Reflections on Collaboration and Growth
45:47 to 46:34
Explore the nuances of working with mentors and collaborators.
“So what I got is that you hated the courage to be this guy.”
Transcript
Automatic transcript. May contain errors.0:00Did you know Lululemon's iconic Flow Y bra also comes in tank top styles and even a dress? Now in new fun summer colors, Flow Y brings a racerback shape to streamline styles you can wear anywhere. Our buttery soft Nulu fabric feels nearly weightless with sweat wicking four-way stretch for comfort you'll want to keep on after practice. Flow freely on and off the mat with light support and refined design. Shop Flow Y now at lululemon.com. nobody really cares about you in your 20s you're kind of dismissed as a but you don't know that you think everyone expects you to just i've arrived and i'm here and i'm i i know everything nobody expects that of you and if i knew nobody expected that of me then i would have fucked up so much more isa ray welcome to bustle one night stand thank you so much we're thrilled to have you you've chosen some incredible books for us to talk about today um as well as your own new collection of essays have you always been a big reader yeah I mean I've always loved reading but I haven't had the time and more recently and it's always my new year's resolution I'm like a big new year's resolution person and I read more as always like at the top of the list but these last couple of years I've just made more time and then I try to do the 30 minutes a night thing and I always fall off but I've been more consistent I loved that chapter in your essay collection about how you love Mondays and love New Year's.
1:26Talk me through that. I was like scrubbing my kitchen cleaning while I was, because I'm also like you describe a multitasker. I'm always doing one thing. You have to, you have to feel productive. I felt very validated when I got to that chapter. I'm glad, I'm glad. I wrote it for you. Yeah, when school ended, I started loving Mondays. Actually, when school ended and my job was something that like I woke up loving to do, then I started to love Mondays. and Mondays in particular, they just feel like a fresh start. I'm always like trying to have a new diet. I'm always trying to have a new plan and Mondays are like, oh, a fresh start for me.
2:02And so loving Mondays means I absolutely love the first of the year because that is the ultimate reset. That is like my chance to be the person I've always wanted to be. It just feels like everyone's on the same page about starting over. And so it feels more attainable. Yeah, sometimes I shy away from the like, not the self improvement, but the idea of like new goals and stuff like that, because it makes me feel a bit bad about myself. Yeah, no. But you feel very like. No, and I'm fine with like repeating the goals. Like I didn't do this the last time, but I'm definitely going to do it this time.
2:33And then maybe I might add one new one that feels genuine, authentic, like something that's that's come to me that I'm kind of already on the way of doing and dedicating to. So like even the decision to read more this year, I was like, how do I actively do this? And I was able to use it for a role that I played where I was like, oh, I'm going to find books that I think relate to this character. And so now I have an excuse where reading is work to help me get in this character. And so that was huge for me. And it's just about trying to find ways to work my goals into what I'm already doing. So it doesn't feel as daunting.
3:09Well, one of the books that you've bought is The Courage to be Disliked. which I hadn't read before. Tell me what you love about this book. So this was a book that was a January read. Let me tell you, the most I read is generally in January. And I thought it was a great New Year's resolution book. I knew I was going to be turning 40 this year or two. And so everyone has always told me about your 40s, how you have a newfound sense of confidence and you kind of stop giving a fuck. And this book jumped out at me. Maybe I saw it in a recommended reading list. And I was like, oh, OK, this the title alone resonates just, you know, as a former people pleaser.
3:47And I was just I wanted to see what it was about. And then it just was super gripping in that it was like approachable philosophy. Sometimes philosophy is by nature very heady. And sometimes the thinking feels a bit too circular for me. And this is like in the form of a conversation. And it was just I read it at the right time. that's interesting I was um so I went to buy it from McNally Jackson on Prince Street and they had it in the self-help section which I think is wrong like and at the end of the book I was like people should not do this but once I understood that it was like philosophy we were more like musing on different theories of things I was like okay but yeah I wouldn't put it in the self-help section but it could I see both ways yeah I think it should be in multiple sections yeah so I hope that someone who is just like, I don't know, someone who's like imprisoned by their trauma, which I think this book is really good for because it's, it almost frees you of the burden of your past defining you, which I find really powerful and obviously easier said than done.
4:51But just the notion that that's possible, I think can help someone to at least try to overcome whatever it is they're going through. So in that way, sure, self-help. But there, like you said there's so many things where you are like the student we're like no you just can't no do that that won't work that's impossible and you can't live that way but i think if you're in a if you're in a period of your life where you are determined to just shed and and change then this this is for you there were also so many moments where i was like kind of angry after the first few chapters and then i got to a point where it was like felt like it really like got me right there and I was like oh you were literally the student in this book this is your story you were the pupil got it I mean because I just thought the perspective because he was talking to someone who was unhappy right and I saw I was like I wonder if a happy person would agree with these kind of maxims do you know what I mean yeah I guess maybe I do identify as a as a happy person yeah right and so I think again it's easier said than done I don't I've I'm blessed where I haven't had any massive traumas.
5:53And so in that way, I was kind of just approaching it from the perspective that they're just, again, things that I need to shed or I want to shift how I'm thinking. I want to shift how I define myself because I have lived the first 34 years of my life, like thinking of myself in a certain way. So what does it look like to try to change that and to not define myself by my past and so it just felt empowering to do so and just just something to to keep in my subconscious but I'd imagine if you do identify as like an unhappy person and you want to be happy this could be the first step to yeah to try to get there yeah how do you identify I think I identify as a happy person as well most of the time but I also like I struggle sometimes with books that feel like they lean a bit into self-help because I if I feel like they're shouting at me oh absolutely which to be fair did there were only a few instances where I was like back in your box my friend but not often you say it out loud I was literally I'd just be like pause or like put the book away and be like enough of you for now yeah um but no I did it is provocative and I think especially the stuff about needing to be liked and how when you especially the stuff about needing praise was like and how you're basically living to someone else's life goals I thought that was really powerful.
7:15Yeah. I think in your chapter of essays, the one called Playing Well with Others, you write really beautifully about the sort of challenges of like caring too much about what other people think and how they react to your sort of feedback or opinions. Can you tell me a little bit about that? Yeah, it's hard to work in a creative industry and collaborate with other people if you can't be completely honest with them. And you also just as a creative myself, I know what it's like to get my feelings hurt when you feel like I'm delivering what I think is the best parts of myself and my creative work.
7:51And you don't like it. And now I don't know how to do that. I don't know how to I don't know how to move about. But now my confidence is kind of crushed and I recognize that can alter someone like that can hurt someone that can alter someone's career, my negative feedback. And so I'm really sensitive to how I deliver news that I don't appreciate something. I don't understand something. And I've learned over time how to navigate that. But it's a constant dance because, again, I'm thinking of myself. But, yeah, even in other scenarios, like when you're collaborating with someone, I just try to, like we kind of talked about, like give the bigger picture of things.
8:30And I work really hard to show what I appreciate, but I still have a lot of work to do on that front. Like I just worked on something where I was like, I don't like this for me, but I recognize that this was good. And so how do I marry the two? Yeah, that's difficult. Yeah, it is. Does that change the way you think about your career moving forward? All the time. Yeah. And it's just it's kind of part of the game, but I haven't figured out a solution yet. Yeah, I know that I'm like, I should change something and I got to figure out how to navigate this part. but I don't I don't know what to do about that quite yet so when you talk about turning 40 there's there's the a few lines in this book one that I wrote down that the life that lies ahead of you is a completely blank page there are no tracks that have been laid for you to follow there's no story there how do you feel about that with the context of turning 40 does that feel like does that feel true to you does it feel empowering or yeah it does I'm already doing things that I just never imagined what kind of things they're more embarrassing things I don't want to talk about yet but things that i said that i wouldn't only like 30 and 20 year old me would be like girl what like why are you this is me with this microphone right now this is like i'm like what am i doing but here i am we're so proud of these uh did y 'all see that we changed we have new but yeah there's just stuff where i'm like oh i'm i'm trying new things i'm challenging myself in new ways and um i like that and i want to see what else i want to do and you know younger me you do think that your life is supposed to be a certain way and kind of wind down in your 40s and I'm like what are you talking about there's so much to do and there's so much that I don't want to fall into and it's not about like being afraid of getting older I want to age gracefully I want to do all the I want to do so much more but I'm just so much wiser than I was and I do have more confidence that's amazing I sort of really love that idea although I also think it's nice like when you've had such big successes like you've had I do feel like it's nice to carry that forward like I remember in my early 20s you're just like am I get like am I actually gonna make it or like am I actually gonna like I certainly had these moments where I was like interning for free at magazines being like like told my parents I think this is gonna work out but you have that fear and like when you get a bit older you're like okay I've got some like wins on the scoreboard yeah you feel it and you feel like just a bit more rooted yes you know there's something you're so you're flailing in your 20s and in so many ways in your early 20s and you literally don't know what you're doing you're you just got here in so many ways and you feel like there are all these expectations placed upon you but like also nobody really cares about you in your 20s like it's really nobody cares you're you're kind of dismissed as uh but you don't know that you think everyone expects you to just i've arrived and i'm here and i'm i i know everything and it's just nobody expects that of you.
11:25And if I knew nobody expected that of me, then I would have fucked up so much more.
11:53These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure, or prevent any disease. Class is now in session. And the UPS Store is here to help you ace arriving on campus. Our certified packing experts can pack everything you need, from desktops to decor. Plus, when you pack and ship with us, you get our exclusive pack and ship guarantee. Your items arrive safe or your money back. Restrictions and limitations apply. to get a 20 % off packing coupon and for full details visit the upsstore.com slash packing happily 20s are really difficult i was thinking about this the other day i was like you have all this freedom more freedom than you've had before but also like not that much freedom because you have any money you don't have like you're sort of setting up your oh my god it's so difficult like the highest highs and lowest lows in your 20s i think yeah yeah yeah because also what else do you know the definitely highest highs because it's like it's the first time you're kind of like living for you exactly i was like out all the time like yeah and then oh the next day it was way more rough in your like 30s and 40s you know like god what happened to me i used to be better but also just the community that you form in the form of friendships the relationships that you build in your 20s are so they seem like everything i may are they are but um you know as you start to refine who you are and what you're looking for in your friendships and relationships there is like a in some cases quiet devastation of like oh I'm growing apart from these people and we're not and I thought we'd be friends forever it's a weird feeling that isn't it and you sort of I noticed that when I was living in London at the time there was suddenly this like decamping out the city of all my friends that got married and those of us that were single it was like we were just like left in our little apartments like cool yeah you made a big you left London to come here which was better because I feel like being I moved when I was 31 I think it's better to be a single 31 year old in New York than it is in London really yeah why because everyone in London was just like getting shacked up and leaving the city it was very suburban the existence suddenly okay so yes being single yes because you don't have to watch everybody be in relationships whereas out here everybody's pretty much single everyone's just and even my friends that are in relationships they're in the city still they're still going out whereas my friends in london are really like you know i'm good i'm set yeah exactly life's over what's the vibe like in la in your 30s you know i i guess a little bit like new york but with less proximity of people like i was thinking about that my friends we're we're all mixed in relationship status married single, engaged.
14:39We just mesh really well, but we're all from LA. I can't imagine being a transplant looking for love in LA. It feels like it would be a night. I wouldn't do it myself. Interesting. I don't think LA is a good dating city. And I for sure romanticized it in Insecure, knowingly. I was like, I'm deceiving people. I don't care. This is what I want it to be, but sorry it's not but i think new york is a is a fun everybody says it's terrible but everybody is very attractive here yeah yeah i think it's fun i mean yeah it's definitely better than london but i also feel like oh yeah you're also you not being from here yeah you have an exotic accent wow i'm gonna use that to my advantage it's like our one thing we've got going for us talking of insecure when um jay ellis came on a one night stand he talked about how one of of the books he recommended was bell hooks all about love oh yeah and he read it after filming season one of insecure and he was talking about love and said you know i felt like i need to worry about that kind of thing and then after that first season he wanted to go deeper which i thought was really sweet so him getting married and serious about his relationship is all because of insecure and bell hooks and i'd like to think he probably read that because of natasha because natasha rothwell who plays kelly on the show she talks about how she revisits that book over and over again and one of my favorite jokes that she improvised um in the first season was bitch I'm gonna call bell hooks on you and so that's yeah insecure is yeah um to credit for his love life I also loved um Natasha by the poppycock yeah I still say taco like her all the time it's so good so good well talking of another book that really has an incredible group of friends because you know we were just talking about what it's like to sort of find your friends in your 20s there's an incredible book that's not yet out on shelves but the wilderness tell me about this book which I know is written by one of your friends yeah I love Angela Flournoy I actually met her in my 20s when I was in New York she was friends with my roommate one of my roommates because I had two and yeah she wrote a book it's so interesting like we were both trying to become who we are now and And I had no idea.
16:58I knew she was a writer and she was, I think, going for her MFA in New York. And I had a bajillion jobs, but I didn't know that she wanted to be a novelist at all. And so I read her first book, The Turner House, when it came out. And I just remember just being blown away like, this girl, because we only knew each other in the club brunch dinner scene. Club brunch dinner. You know, and so it was, I didn't know the extent of her talent. and so the Turner House blew me away and then there's still a show that she wrote a drama for HBO set in LA that was about a family that was so good set in the 90s that HBO ultimately didn't pick up but it was I think about it every other week and so I've been waiting for her follow up and the Wilderness is her follow up and it really does follow her close friends and she's been through so much and just the way she writes people you feel like you know them and And yeah, I'll read everything she writes.
17:57I think she does such a beautiful job of creating this sense of like, everyone has their own path. Yeah. Which is really lovely. And the writing is so beautiful. Yeah, it's vivid. And it takes, it's everything that you want in a novel. And I want to say, you know, I primarily read nonfiction. And this year, I've been more intentional about reading fiction books. And I want to say that Turner House, her first book was also my first foray back into fiction. And so I don't know how much I can say about what she's been through in her personal life. But that informs so much of this storytelling and also makes it more all the more raw.
18:39It's so raw is exactly the word I was going to describe. And you think and seeing the way that these friends, I mean, I've got sisters. and I think that way that you talk to sister that like these girlfriends really talk to each other in that way with that like intimacy and that shorthand of like that closeness yeah which is like wait you said you have sisters an older sister and a younger sister okay okay I was gonna say there there's definitely a way that you talk to your sisters I don't know yeah do you talk to your sisters the same way that you speak to your close friends is it completely different I I would say I'm more honest with my sisters, like more unfiltered.
19:17Like there's one section where a character who's had a baby has like a prolapsed situation. And she's like, can you have a look at what's going on? I would more like to do it with my sister than my girlfriend. Yeah, okay, that's fair. I think I'm the... Are you the other way around? I am the other way around because my sister and I are six years apart and I still feel protective of her. And there's some things that I've gone through that she doesn't know about and that she's gone through that I don't know about. And so I think there's just a difference there. Yeah. Whereas like my friends know they've been there for so much of what I've gone through.
19:49But yeah, I'm more unfiltered with my sister, but there's still a desire to preserve. I think that's, you're actually right. Cause I was just thinking now, there's a lot of stuff my sisters don't know. But there's some that my girlfriend, I'm like, we'll cut that bit. But no, that my girlfriends definitely do know about. But yeah, it's just, it's interesting. And those like spaces where you feel you can be completely honest, I just like. oh my god yeah they're just they're safe spaces literally and i want to say that angela i'm like i know she's an only child and so like obviously like the her girlfriends do mean everything to her and so this is without a doubt a love letter yeah to them i loved the um chapter in your book where you talk about your childhood bedroom um with your sister and it was just so lovely um Was it fun to like dive back into some of those memories?
20:40Once I started to like remember them, yes. You know, it's so hard. I find, I love writing about characters because I can just make stuff up. You get to reach the part of yourselves that feels the most accessible. That's kind of almost a bit shallow. But when you're writing something like this, I'm like forced to dig deep in a way where I'm just like, I don't feel like it or I don't, I'm not prepared to. And it does take a lot of work to remember. So yes and no, like when I finally was like, when I discovered what I wanted to write and I could reach the memory where it opened up and I was like, oh yes, my childhood bedroom actually did inform so much of my perspective and made me dream in ways that I'm kind of waking up in it now.
21:32Like that feels beautiful, but it's such an arduous process to like do the digging interesting did you talk to your family members about stuff to help i did i called my little brother um just to see what he remembered about like our joint restaurant hamburgers everywhere because there was a part that i had to make up in the phone and i hated that word because we used to play with that that stupid phone all the time and i was like what were the other characters and he he was like i don't know bro I remember doing it I remember you were bossy it was fun yeah but I don't remember he remembered the this is daddy what are you doing because we became an inside joke for us but yeah and then of course talking to my sister about certain things but for the most part it's so like isolating yeah yeah interesting I love the details of like you having the like house computer in your bedroom went like 1994 and it being like this freedom yes because my mom didn't know anything yeah about computers she was kind of just like here okay you're playing number munchers a math computer game great sure yeah get out my face but um there is something so lovely about like childhood bedrooms as being this first like space of your own where you get to be creative and i really related to you talking about the desk and i remember my desks being like this is where i do things and it being like this incredibly kind of empowering space yes oh my gosh the desk is when's your birthday october 1988 libra yeah i'm a triple libra oh wow i know oh that makes sense okay you're comforting but yeah there's just something about yeah feeling official and having a desire to do things because you have a desk like i have to live up to this desk literally because I have it so what am I gonna do what am I gonna write and that's so funny because it really does all start with the desk and then I'm a big hand writer and so it's so much better I feel like my brain doesn't work fast enough for the computer it does not at all I can't ever yeah I can't catch up to the computer I feel like the computer is when where I go when things are like official and they're forming and then I know that I'm going to be in edit mode but I love the messiness of writing and then the organization is what the computer is for did you go on any workcations while you're writing these chapters because i love that chapter too i was like what i need to do absolutely i went so many places i went to paris i went to mexico i went to mauritius i was writing this book for a really long time and not writing this book yeah it's like most writers yeah i was not writing for a really long time um because yeah part of it is like even though i wasn't digging into anything too too personal it was still like digging into you know myself and and so i had to kind of just be by myself to let things marinate yeah at least that's what i told myself while i was you know walking the streets of italy who's your um first reader that you give stuff pages to to look at it's so funny i'm not you don't no only who has to read it interesting sometimes um sometimes i'll show stuff with my husband but he's too supportive yeah he's like great job you're like was it though yeah you don't you don't even know it yeah it's fine because i don't want to hear a good job i just want to hear what i need to fix And so that's why I give it to the people who need to read it.
25:00And when I do want to hear a good job, I rarely hear it. I know, right. Yeah. Did you worry with any of the anecdotes about like, oh, God. I mean, I thought the story you told about when someone called the wardrobe for these background actors skanky. I mean, can you tell me a little bit about that? Yeah. I mean, I don't want everyone to throw anybody under the bus. But this was something that also like, you know, defined. When you ask the question, like, how am I going to move? what am I going to do moving forward and not what I'm going to change. That is something that I've actively changed moving forward.
25:30And I have more of an awareness around the weight of my own words and my own presence and what speaking up can change. And so in that way, like that was, that was a pivotal moment for me. And it was the first time that I had felt like kind of an antagonist on something that I was supposed to be a team player, which I felt like I was until So I felt like we were treating everybody on the team the same. I think also there's those moments sometimes when people look at you and you're like, okay, but which team are you on? Yeah. And it was, which team are you on is a great way to put it because like, this was also like a racial thing for me.
26:08And I was like, oh, this kind of comes, this comes first. Like, I feel an obligation here to say something because this is not something that I would tolerate. I can't like sweep this under the rug. And so it doesn't feel good to be a part of this right now. No, I think that's the thing. Whenever you're writing about real life, it is scary, like people reading it, who are involved and stuff. But you handle it really beautifully. Thank you. And so, yeah, to kind of answer your question, I was worried about that. And there were a couple of instances where I talk about things that have happened throughout my career that, you know, still hurt.
26:42Whether that's like friendship breakups through working together and collaborations and the like. And it's just like, I don't mean to vilify anyone or anything like that. It's more about like, again, the learning lessons and hoping that other people who've gone through it, who are so deep in it now. And some of these things depressed me so heavily. And I was just like, oh, I don't even want to do this anymore. I don't want to do this if I don't have this person in my life. I don't want to do this now that I've failed miserably. And so like that, just knowing that there's, you know, there's a light at the end of the tunnel.
27:15There's hope on the other side. totally it's brilliant I mean I loved all of your essays they were also sort of like as I was saying to you before I'm definitely going to share one of them with my colleagues at work thank you about collaboration one of your other books that you recommended uh fiction great black hope by Rob Franklin which I loved um and like tore through tell me about your love for that book oh my gosh it was recommended to me by um an exec I work with and I speaking much for 20s and thinking thinking about like New York and I love ensemble stories but this in particular was just so fresh from a perspective that I was familiar with in a way but like it just felt like it was asking questions that we don't often ask about like kind of black privilege and also are in class in a way that was really, really compelling to me.
28:11And it was just juicy. It was a coming of age story that felt like unique, but also like something that I might see in an elevated CW show, which I love. Do you ever read with the goal of optioning things to adapt? Yes, I think more recently, if anything. But I love a good mystery. And these characters stuck with me, but it was also about, you know, so much more than that. And this young man's journey in identity. yeah I also think it has really interesting things to say about work and work as part of your identity same as the courage to be disliked which sort of I mean the courage to be disliked sort of offers the idea that you know your whole identity can't be work which I think is obviously true and then the idea that it's only by contributing things that you sort of sometimes to the wider society that you can feel valuable and I think you sort of see the characters in Great Black Hope wrestling with that in the sense of like what to do for work and I think I saw this with some of my friends from university who had a lot of money like in their 20s they drifted more than the rest of us because they weren't like pegged down by the same imperative to just like figure it out figure it out and like and that does give you some purpose but I don't know I thought it handled it so beautifully that sense of like they're all trying to work out who they are and even if you don't land on exactly who you are but you are able to sustain yourself there's real pride in that you know when you don't have much so I don't know I thought it would just handle it beautifully yeah agreed and it also feels and that's the timeliness of it when i think about even this generation and like how they may be going to to school for something that may not exist like imagine deciding what your purpose would be but also not being able to to achieve that and there's such a scariness there and this generation in particular feels more more uncertain in a way of who they should be but also more determined to live their lives while while they can because of that uncertainty so it was relatable but it was also really good insight into um something I feel a little bit more removed from now do you ever like fictionally cast books in your head when you're reading them I don't um anymore I think I did that more when I I was like reading in high school and I was like, so I was obsessed with like the actors in a different way.
30:31And so like, that's all I could do. I watched so many movies where I couldn't help it. I don't see a face. I see an essence and it's, and I'm, I'm fine with that. You see faces? I think I do sometimes see faces. Yeah. Not always. You know what I think about? Do you watch Love is Blind? Yeah. Whenever someone's like, oh, I didn't imagine what they look like. I tend not to believe them, but then I'm like, oh, I do that when I read. I don't. Yeah. I don't physically see them outside of like oh they have a pointy nose and their hair is a certain way but I can't like put them together and I like it that way that's interesting so are you like a visual thinker then in that way when you're like ideating for your own shows or your own I'm definitely a visual thinker I see yeah I see things vividly for my own work but that I'm like Like, oh, I'm drawing on things that I also know and am familiar with.
31:23But for other people's writing, not so much. That's interesting. You really have a sense of the weight of different generations of stories as well, which I thought was really sort of like beautifully handled. And the pressure of like a parent's generation come up with one set of needs and one set of goals and one set of expectations. And then things have changed for their kids, but they find it hard to watch them do things differently. Oh my gosh, I was just having a conversation about that. There's just, yeah, there is such a pressure to like let your kids be who they are and allow them to flourish.
31:58But like also that feels so impossible to do. And you really take their failures and the things that they go through so personally. Whereas I feel like my parents were just like, yeah, you live it, you fucked up, you live and you learn. And these set of parents just really, really feel so like kind of invested in a new way with their kids like they just feel like it's a personal attack if their kids don't do well or don't go down a specific path they take more blame for it in so many ways it's interesting that isn't it like that that sort of shift do you have nieces and nephews i do yes like being an auntie i love me too oh my god you do how many do you have four oh well done the way yeah congratulations likewise I have five um and yeah it's the best oh my gosh yeah I want to spend more time I think about that all the time like I want to just be there especially sisters kids are different than but I love my brother's kids I love both of my brother's kids they're amazing but when my sister had um her most recent daughter I was like oh I now i want this like i this is because she looks like her and she's so i never thought i wanted girls but my my my sister's daughter made me want like a girl it's amazing what's the age range for yours 10 8 5 and 1 you're so good what about you no but it is it's 11 it's 11 9 7 five and now she just turned two oh okay so i got that yeah you've got it down you've got it down because it's two years apart so yeah it helps yeah it's um it is so fun and it's such a sort of like i don't know you feel so like protective of them but also i'm happy to give them back immediately but you're about to have a baby on the way like you have a new baby coming i was just thinking like oh i miss babies are the best it's so fun oh man my younger sister who's pregnant she her first child evelyn she had through ivf after trying for many many years to get pregnant and um successfully had a baby through ivf and then like at like 10 months after evelyn she they just got pregnant completely oh my gosh that happens all the time i just had that happen to a mutual friend yeah where it's just like the less you think about it then it's like oh and i suddenly and she was like i know i should be so happy and she's like i am happy i want my baby but she was also like she's gonna have 220 months oh and she knows the the gender no she's is she gonna surprise herself yeah that's so funny yeah yeah my sister did that the first time too it's sweet i don't know if i can handle that really do you think you'd want to know i think so yeah i'm i think so yeah i don't know i'm not sure i'm not sure i want kids so i don't know you're going back and forth well i mean you have you're not even going forth no exactly i'm just I'm back.
34:53Back on my own. Exactly. Whenever people are like, do you want kids? I'm like, who the fuck wins?
35:01Understood. Yeah. I'm not sure whether I'd find out or not. I think it's probably quite a fun surprise. That's when my sister was like, this is the only thing I have to look forward to. Yeah. Is this surprise. So I was like, you know what? It's true. Get it. Those first few months, you really are in the trenches. But yeah, no, I loved Great Black Hope. I thought it was so fun. I kept thinking, oh, I want to see an Issa Rae adaptation of this. oh thank you okay all right yeah from your lips yeah got it but and i lied i lied i read another book recently that we're not talking about today but luster and i saw an actress in mine for that and that was like um i was obsessed with with raven this raven leilani right yeah who did you see playing i kind of want to say yet because i'm okay i'm gonna try i'm on a mission but i think it's taken so maybe i should just say but i won't yeah i don't want them to steal it yeah good idea Your fourth book, Eleanor Oliphant is completely fine, is being adapted by Reese Witherspoon.
35:54I know. Yeah. And I'm fine with that. Yeah. A director from Fleabag, I think, is on board, which I think is an interesting. Oh, yeah. I did hear that. Yeah. And I feel confident that it'll be done well. But she's such a specific character. I hope that they go with someone new. Oh, interesting. Who did you have in mind for it? I don't think I really had any. I read this book a long time ago, so I had to just sort of brush up on it this weekend. But who do I think I could see? I don't know. Yeah, that's what it is so specific. And that excited me where I was like, OK, I hope in hearing that Reese was adapting it or producing it.
36:35Yeah, I had that desire of like a breakout. But then what's scary about a breakout potentially is like, I guess as an actress, will people only see you as that? Yeah. But it was she was one of those characters I just couldn't get out of my head for a while. What did you love about the voice in particular? I mean, the humor. There was her clearly being on the spectrum in some way. And like the way that she was so blunt about things in almost Amelia Bedelia-esque way. And yeah, it just it made me laugh so many times unexpectedly. Yeah. She reminded me actually of my grandma a little bit. She was a bit definitely a bit spectrum.
37:15me and a comment about i think when she runs into her hairdresser and the hairdresser's like your hair looks nice and she's like several people have told me that so that leads me to leave you've done a good job i was like that's exactly the kind of thing why that would have said yes it managed to have that tone but still be really really heartfelt and i found myself like crying at parts in the book and i i just i wasn't expecting that i really felt for i wanted her to be happy i know And the stuff with when you get to the end and you actually find out what happened. Oh, God, it's just awful. Yeah, there's for sure a lesson in trauma there, obviously, and how we tend to cope.
37:54And that was tragic, but also it didn't weigh the book down. And the fact that you knew that there was something crazy and tragic, but it was still a page turner. And I just wanted the best for her. Have you ever, I mean, the book sort of, what propels Eleanor out of the norm in a way is partly this relationship with a work colleague, this sort of like unexpected friendship. Have you ever had a sort of unexpected friendship with someone that's like pushed things in an unexpected direction? Yeah, working out here, actually, pushing things in an unexpected direction. Yes, I've had a couple of those friendships.
38:28My first working out here, I worked in a theater company, at a theater company by day. And then it was all theater and theater company by day. And then I would sell tickets for another theater company at night. And I befriended like the guy who did all the tech and sound for one of the productions. And one of the productions we worked on was, or he worked on, wasn't great. And he was just like someone who just I wouldn't typically be friends with. I wouldn't ever meet him. And we just immediately clicked. And now he's in LA with me. He's married. And we just, we have such a, we don't get to see each other all the time where we're so bonded by kind of the trenches of, of where we started.
39:16And I think he knows so much more about parts of me than maybe even other friends do. Cause I was so isolated in my New York. Like I didn't have my core friends here and I was also like a really shy person. And so he was kind of the first person that I met on my own as my own friend. Oh, that's so lovely. Yeah. Is he the same age as you? He's like one year older. Yeah. From Seattle. I love those friendships. They're the best. They really, really are. And we've seen each other through so much. I would say that he encouraged me in so many ways to like kind of pursue beyond writing. I didn't care about holding a camera.
39:54I didn't want to do any of those technical things. and because he was on the technical side and so gifted, I think he still is, so gifted of a visual storyteller, he made me challenge myself in the way that I tell stories. But he's not, like, pursuing it as much as I want him to. Yeah. Which is to his detriment, I think. I love that you called him out. I am. I'm calling you out, bro. Get it together. Write that. Finish your fucking script. Finish your script. In LA, do a lot of people just have scripts that they're all, like, writing? because I mean all my friends have like novels that they're working on yes included I always joke about like you live in LA and someone's like oh yeah I'm working on my script and you're like where is it oh yeah I'm still finishing it in New York I'm working on my script where is it here it is and here's the treatment here's like people just have a different hustle mentality and I think coming here helped me and moving back to LA it helped me to bring some of that kind of hustle energy with me where it like made me stand out because I was a person of my my word like I was about it and um I don't think I would have been that I would have been one of those people I was like I'm worried I'm still writing it if I had stayed in LA yeah I liked one of the lines that I wrote down from your book is efficient perfectionism which I think is like no but that is the that's such a good way of putting it like and that's kind of what you have to strive for yeah you do i mean otherwise it is a waste of time it's a waste of time and perfectionism can really bog you down and a lot of stuff that doesn't matter i've seen that with so many people it didn't really just it is kind of an excuse it's it's procrastination it's fear it's rooted in fear like no you don't want it to be perfect you're scared of putting it out yeah i saw um like something on instagram or something that was like your don't make your identity contingent on the thing that you're trying to make in the sense like because then it always feels too scary like the idea of like so like just write something you don't like have to think of being a novelist as something that's like this thing over here yeah and i always wonder like who are you thinking of like who's the worst person what's the worst thing someone can say to you like you know who is preventing you theoretically from yeah from putting it out whose judgment do you fear i guess someone could say like this is the worst thing i've ever seen but if they don't matter to me yeah then it doesn't matter that's that's a good way of thinking about it I thought I was talking to my team earlier today because I was talking to everyone about social and posting more and I was like we are climbing cringe mountain guys and we're gonna do it together but that's sort of what it feels like you'll sort of you have to really move beyond cringe and I've read people say that so many times but you sort of especially when you're creating early work because the first draft world you will feel a bit embarrassed yeah i miss those days though like the luxury of climbing cringe mountain when people have no expectations is great and then you lose that luxury when you when you when people have seen your stuff then it's just like interesting so what does it feel like now just now there's way more pressure on you and now like you can get the perfectionism syndrome but i've i've also just had to be like your audience in your head has been the same forever it's your friends and family this is who you're making it for this is who you're thinking of and you can't think about anybody else no i love that um part in your one of your chapters where you talk about filling the writer's room and how um you were like sort of pushed in the direction of getting not just you know people who have your perspective but also different perspectives i think it's such a great metaphor really you know you want to keep your dna and you also want to push yourself a little bit outside those lines yeah but that was yeah that was Prentice, who was a showrunner at Insecure, like he really, really, like again, one of the best collaborations I've ever had, but he really helped me to think about how to do that because I may have had a bunch of people who thought like me in the room and in him telling me like, we already have the you, like was like, whoa, we already have the person who thinks like you.
43:54We already have the you in the room. Now we need like these other perspectives to like fill it and fill the other characters. And that was just so mind blowing to me because I would have filled the room with people who think like me and who share my perspective. And it would have been like, just us saying exactly, exactly, exactly in the room the entire time. Yeah, for sure. So it really helped. We got into so many arguments. So many arguments. We got into gender wars in the room. We got into classwork. We got into so many. And it was fun and it helped enrich the characters. Yeah. And I loved also the detail, the anecdote you tell about when you work with Melina.
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44:31and she walked in on the set and you were like this set doesn't feel right but you couldn't quite articulate why and then she was like it doesn't look like black people yeah yes which is so helpful people always ask like why it's important to have the other black people behind the scenes if you know they're on camera and it's just like because I can't articulate everything I can't like you know that's just I'm not there are levels of expertise that I I just don't have um and yeah it's really refreshing when someone else can articulate something that you just you just can't but it's always like on your team and knows your goal and it's going to help you like find the best route there yeah and also conversely like even with her where that was the best example of working with her in in a way of like oh we're on the same team there were also other moments where I was like I we will fight I will like we're gonna come to blows but I respect you so much and I respect your opinion and I respect like the way that you think and that should that should happen i should be able to be like you know i want to be your ass right now like and you want to be mine yeah and we're still gonna work together and it's gonna be fruitful that's i mean that's also like the cornerstone of all the female friendship in these books where it's like i'm gonna hate you sometimes but i'm gonna tell you the truth yeah yeah which is all you can ask for yeah well i loved your essay collection so much in your book so it's available on amazon right it is it's available on amazon audible i really recommend listening to it that it's so funny when in the first chapter where I think you talk about who's the guy that you're working on the first version of the tv project with oh Larry Wilmore Larry you're like what the fuck do they need Larry for because I read part and I just fast forwarded to that part and I just press play and I was like whoa she's like in my head it was so good um thank you I love Larry and I missed him yeah it's very good well thank you so much for doing this thank you so much for having me like Yeah, I had a great time.
46:26So what I got is that you hated the courage to be this guy. I actually, I genuinely, well, I hated the first chapter about the trauma stuff because I was just like...
From the publisher
In One Nightstand, celebrity readers and writers join us at The Blond in 11 Howard to discuss their favorite books.In this episode, writer, producer, and actor Issa Rae sits down with Charlotte Owen to discuss her new book, I Should Be Smarter by Now. Issa shares why life is better after your 20s, the book she’s desperate to adapt, and what she “romanticized” in her hit HBO series Insecure.
The Courage to Be Disliked: How to Free Yourself, Change Your Life and Achieve Real Happiness by Ichiro Kishimi and Fumitake Koga
The Wilderness by Angela Flournoy
Eleanor Oliphant Is Completely Fine by Gail Honeyman
Great Black Hope by Rob Franklin
I Should be Smarter by Now by Issa Rae
Issa’s new collection of essays, I Should Be Smarter by Now, is available now on Amazon and Audible.
Credits
Director/Director of Photography: Marshall Stief
Assistant Camera: Jasmin Velez
Post Supervisor: Delia Kelly
Post Production Manager: Mateo Delgadillo
Editor: Alex Viola
Producer: Aubree Lennon




