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The “brilliantly wry” (Lena Dunham) and “lovably awkward” (Mindy Kaling) New York Times bestseller from the creator of HBO’s Insecure. In this "delightfully deadpan" (Essence) bestseller named for her wildly popular web series, Issa Rae waxes humorously on what it’s like to be...

In this comically insightful collection, Issa Rae charts her journey from digital storyteller to cultural force, redefining modern success. Through refreshingly candid essays, she takes readers behind the scenes of building her creative empire, sharing hard-won wisdom about staying true to your vision while navigating Hollywood’s ups and downs. It’s a master class in turning authenticity into achievement.

It’s a gamble to bet on yourself in Hollywood. But Issa Rae placed it. Charting her evolution from struggling writer to media mogul, she pulls back the curtain on her ever-evolving career in an always-changing industry and reveals that the best investment she made was her belief in herself. As she reflects on weathering storms and lessons learned, Issa moves forward with renewed purpose.

From the imagination stage to actually making the magic happen, writer-producer-actress Issa Rae is a multitasking phenomenon. She’s also an inveterate procrastinator. But even that’s part of her creative strategy. Blending personal anecdotes with practical insights, Issa explores the challenges of having to constantly deliver, the importance of “workations,” and the value of embracing a unique creative rhythm in an increasingly demanding world.

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.