{"id":177287,"date":"2025-08-26T14:55:16","date_gmt":"2025-08-26T14:55:16","guid":{"rendered":"https:\/\/www.europesays.com\/us\/177287\/"},"modified":"2025-08-26T14:55:16","modified_gmt":"2025-08-26T14:55:16","slug":"issa-rae-is-learning-to-chill","status":"publish","type":"post","link":"https:\/\/www.europesays.com\/us\/177287\/","title":{"rendered":"Issa Rae Is Learning to Chill"},"content":{"rendered":"

Issa Rae has built not just a career but an empire by keeping her head in the clouds, her nose to the grindstone, and her personal life protected. The writer-producer-entrepreneur-actor-director-comedian-activist-memoirist-podcaster-executive-all-around-badass burst onto the scene in 2011 with a scrappy YouTube series, The Misadventures of Awkward Black Girl<\/a>, which she shaped into a cultural phenomenon and, eventually, into the trailblazing and critically acclaimed HBO series Insecure<\/a>. At just 27, Rae wrote her first book, which took its name from her web series and its material from her personal life. Soon after the book\u2019s release\u2014when her family members expressed shock at how prominently they were featured and readers shared sections out of context as social media ragebait\u2014Rae came to regret just how much of herself she had revealed in those pages. It was then that she put the memoirist\u2019s pen down and spent the next decade picking up just about every other baton in the entertainment industry. In a few short years, she became a verified mogul, with a production company, music label, and\u2014yes\u2014coffee chain to her name.<\/p>\n

It wasn\u2019t that Rae disappeared behind the scenes. If anything, she became an even more recognizable public figure, appearing, fittingly, as President Barbie<\/a> in Greta Gerwig\u2019s blockbuster 2023 film Barbie and as herself as one of the voices of Google\u2019s Assistant. But since her days of early stardom, she has learned a lot about managing her image, deftly threading the needle of a life in the limelight and out of the headlines. \u201cI try to be really, really careful about what I do share,\u201d she told me over Zoom. \u201cAnd sometimes alcohol gets in the way of that, and I\u2019m like, Oops, damn. I shared under the influence.\u201d <\/p>\n

But today, of sober mind and clear heart, she is publishing her second book: I Should Be Smarter by Now<\/a>, a collection of six personal essays, released through Amazon Original Stories, that offer an intimate and vulnerable look behind the scenes of her breathless rise through the creative ranks. I sat down with the 40-year-old star to hear about the lessons she\u2019s learned, the myths she\u2019s let go of, and why giving herself permission to pause might be her boldest move yet.<\/p>\n

It\u2019s been a decade since you published your first book, the brilliant and best-selling memoir The Misadventures of Awkward Black Girl<\/a>. What inspired you to write about your life again, and why now?<\/p>\n

A decade is crazy. First of all, thank you, and also eff you for aging me. My last book was written in my 20s, so actually I take back that curse-out. I\u2019m not that old. <\/p>\n

I recognize that I\u2019m just a different person now than I was then. Part of this project was about wanting to reestablish myself in this decade and in this iteration of myself, while also following up with my previous work. So much has happened since I published that book, and my life has changed so much for the better. I get asked all the time about my own journey, especially by creatives and entrepreneurs, like they want to know the blueprint. And I\u2019m not claiming that this is that, but it definitely has a lot of advice and stories that can help kick-start your journey if you\u2019re a dreamer.<\/p>\n

What do you see as the biggest difference between the \u201cawkward Black girl\u201d of Misadventures and the woman you are now?<\/p>\n

I just feel way more secure in myself. You know, I\u2019m definitely still awkward, but there\u2019s more of a confidence. Professionally, I can say I almost know what I\u2019m doing, which is the name of a chapter, but I also feel confident in who I am and who I\u2019m going to be in my core. I have the foundation built, whereas before it was so rickety and I was kind of finding my place.<\/p>\n

If you could go back and tell your younger self anything, what would it be?<\/p>\n

Just, like, stop comparing your journey to others\u2019. That\u2019s been huge for me. Even now, I\u2019m competitive, but I\u2019ve taught myself that it\u2019s not that I want to do better than you; I want to do better than me. That really matters to me. So sometimes I still look over and I\u2019m like, Damn, that person topped themselves again. They\u2019re killing it, and they just did this in two years\u2019 time. Why is it taking me so long? And that\u2019s just unhealthy.<\/p>\n

Before I read this book, I would have had a hard time believing that you could feel jealous of anyone professionally. From the outside, your career looks like an unending series of wins, but in this collection, you are very transparent about your many professional setbacks and disappointments. How did and do you maintain your confidence and work ethic in the face of rejection? <\/p>\n

I always lean on the fact that I create. I love making things, whether I have an audience or not. I can always lean back on myself and my imagination and my work ethic. So, when things aren\u2019t going my way, if I\u2019m getting no\u2019s, I get excited in some ways to go back to the drawing board. It\u2019s frustrating at times, but I know I can make what I want to see, and there\u2019s nothing more confidence-inducing than that.<\/p>\n

In recent years, there\u2019s been a bit of a backlash to so-called \u201chustle culture,\u201d with many people reconsidering their relationship to work and constant productivity. In some ways, you could be the hustle culture poster child. You wake up at 4 a.m., you went more than a decade without taking a real vacation, you run a production company and record label, you co-own a coffee chain and haircare company, you have nearly 100 film and television credits\u2014I could go on and on. Has your relationship to work changed over the years or with the culture?<\/p>\n

For a long time, it didn\u2019t feel like hustling, because I had a tunnel vision for a particular career that I wanted to have, and so everything that I did was feeding that. Now I recognize that I need breaks. I\u2019ve gotten a lot better about setting time aside. I still need to be better about just taking vacations and not labeling them \u201cworkations.\u201d But I have gotten better at delegating. I recognize what I\u2019m not good at, what takes all my energy, and what I\u2019m not looking forward to. I\u2019m working with people who enjoy those things. And then refining. I\u2019ve refined a lot. I think before, I was doing all those things you named because I was like, These doors are open, I want to try it, and I\u2019m not going to have this opportunity again. Whereas now I\u2019m like, I\u2019m good. I don\u2019t want to try it. I don\u2019t need to scratch that itch.<\/p>\n

Do you ever experience burnout?<\/p>\n

Hell yes! I mean, the end of Insecure season 5 was really, really hard for me. We were shooting it during COVID. It felt depressing to have to release it in this, like, mask-y manner. I was like, I\u2019m doing all these things, and this show that I worked on for so much of my life isn\u2019t even getting the proper send-off that I want, and that sucks. And I\u2019m tired. And I think I got married\u2014oh yeah. And then after that, I did another show, and I was just like, I\u2019m going to take a month off. I had to promise myself that I was going to do that, because otherwise, I knew I would kill everybody. And myself.<\/p>\n

I\u2019m also still mourning the end of Insecure. I was surprised in the book that you write about how you struggle to start things. What was it like to turn a page after such a monumental and all-consuming project, and do you have any advice for how others can embrace new beginnings?<\/p>\n

Be very, very clear about what your expectations are and do not set them too high. Just like, Okay, my first step is that I\u2019m going to write this two- to three-page treatment for this idea that\u2019s been floating around in my head; let me finally just jot it down professionally. If I can get that done, I am the shit. It\u2019s not about selling it. It\u2019s not about making my next hit. It\u2019s just this idea. And so my advice is: Start really, really, really small where you can be proud of yourself. It\u2019s like putting \u201cwrite a to-do list\u201d on your to-do list and checking it off. I love that.<\/p>\n

In writing about your creative process, you reference how Michelangelo said he could see the angel in the stone before he started carving away at it. Similarly, you could always see the life you wanted inside your current situation and you were just working to get there, bit by bit. What does that life look like, and have you arrived at it?<\/p>\n

Unlike Michelangelo, mine is morphing for sure. It looked one way at one point, and then I was like, It could be prettier, or The features could be a little more relaxed. Right now, I\u2019m in the \u201cfeatures could be more relaxed\u201d stage. I don\u2019t care if my face is a pile of mush as long as it\u2019s chilling. That\u2019s where I am right now. I do want to chill. The future that I want is just to be satisfied, without the internal pressure to do more and more.<\/p>\n

I Should Be Smarter by Now by Issa Rae<\/p>\n

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Charley Burlock is the Books Editor at Oprah Daily where she writes, edits, and assigns stories on all things literary. She holds an MFA in creative nonfiction from NYU, where she also taught undergraduate creative writing. Her work has been featured in the <\/a>Atlanti<\/a>c<\/a>,<\/a> the Los Angeles Review of Books<\/a>, Hyperallergic, the Apple News Today podcast, and elsewhere<\/a>. You can read her writing at charleyburlock.com.\u00a0<\/a><\/p>\n