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Remember a mortifying moment that made you self-aware? Honestly, Issa Rae remembers a few. In this illuminating essay, Issa follows her shoulda/coulda/woulda journey from awkward schoolgirl to a Hollywood life under the spotlight. Along the way she offers unfiltered insights into unwittingly courting controversy, curating a cautious but always authentic identity, and navigating the gap between private truth and public perception.

From writer, actress, producer, and New York Times bestselling author Issa Rae comes I Should Be Smarter By Now. In these essays, she shares her journey from internet creative to a multi-hyphenate career in Hollywood. Read or listen to them in a single sitting. Either way, they’re insightful, hilarious, and unapologetically authentic.","format",{"_28":103,"_27":104,"_105":106,"_107":70},"publisher","Amazon Original Stories","page_count",19,"duration","published_date","August 26, 2025","pub_date","August 26","isbn","9781542036955","asin","B0F54MD4FN","hex_code","#669c35","language","English","purchase_links",[],"playlist_links",[],"cover","https://cdn.blackauthored.com/books/12217i/0ce47833-ba31-47bb-9255-20d0a9cb3dc5/1790950640.jpg","thumb","https://img.blackauthored.com/?preset=poster_thumb&image=https%3A%2F%2Fcdn.blackauthored.com%2Fbooks%2F12217i%2F0ce47833-ba31-47bb-9255-20d0a9cb3dc5%2F1790950640.jpg",3,"Kindle","type","digital","audio","order",{"_28":42,"_27":43,"_44":45,"_110":-5,"_111":-5,"_31":112,"_113":114,"_46":47},"biography","image",2,"roles",[115],"author","isLoggedIn",["P",117],"result",{"_15":126,"_17":127,"_13":128,"_129":130,"_19":131,"_132":133,"_21":134},"user","themePreference","light","storedTheme","gaId","G-Z1HVZ17GZ3","Blackauthored","%s","Find your next Black authored read and connect with readers with the similar taste.","handle","@blackauthored","https://blackauthored.com","robots",{"_145":70,"_146":70},{"_23":24,"_25":135,"_27":126,"_136":137,"_138":139,"_19":131},"Organization","logo","https://cdn.blackauthored.com/images/og-image.png","sameAs",[140,141,142,143,144],"https://twitter.com/blackauthored","https://facebook.com/blackauthored","https://instagram.com/blackauthored","https://youtube.com/blackauthored","https://tiktok.com/@blackauthored","noIndex","noFollow"]