I recently read and then re-read Amazon Original Stories’ “I Should Be Smarter By Now” by Issa Rae. If you don’t know, back in the early 2010s, my friends and I fell in love with the Awkward Black Girl YouTube series. We would always find time and watch the latest episode at work, on the lab computer. I want to say that we all have moved on to different careers, and I hope the statute of limitations for HR to write us up has passed. We would ensure all our work was done and did not interfere with our duties. It was the highlight of our day when a new episode dropped. This led one of my friends and me to attend a talk by Issa Rae at a local college about her current and future endeavors. From 2011 to now, I was here for everything Issa Rae did.
When I saw that Mrs. Rae had written six short books with her blend of humor, how-to advice, and pitfalls of achieving success, I was ready to clear my day and read all 6. Over the mini- Christmas break, I read all six books and can say, if you are trying to launch your creative project, honestly, any project, these six books will help you prepare for setbacks, the pitfalls of not planning, and why having paperwork will save your money and career.
“The Business of Being Me” is the first book in the series. It set a firm foundation for part of her journey from web creator to HBO success with the show “Insecure”. Mrs. Rae reflects on her work ethic from her youth, which helped her find her path into writing and creating shows. Her missteps in understanding her worth led to a loss of money. I loved that Rae kept pushing, turning missteps into lessons learned. Using the leverage of her collaborators to help move projects forward, and in addition, understanding the creative system for networks and writing. One lesson I took away from this book is that resilience is key. You will get more noes than yeses, and you need to be able to pivot and keep moving forward. Collaborations and mentors are key to her writing process. Working with people like Shonda Rhimes and Larry Wilmore helped Issa Rae find her voice as a writer while working in high-pressure situations. Each stage of her path taught Mrs. Rae a valuable lesson about her talents and how to use them to further her dreams and business. I would recommend this book to anyone who wants an overview of what is needed to succeed in TV or content creation.
“Playing Well with Others” is the second book in the series where Issa Rae learns what playing well with others truly means. The book opens with someone calling her “particular,” and she ruminates on whether it is a good or bad thing. Mrs. Rae lands on it’s a good thing to be particular, when you have a specific vision in your mind. As Mrs. Rae goes through the process, she acknowledges misconceptions that she had to do everything herself. In this book, Issa Rae’s lesson in understanding how diverse backgrounds work to strengthen the vision. Typically, people say they want diversity, but they really wish to be yes-men. Creating a safe space for collaborators allows for better critiques, openness to change, and working with people who understand and see your vision. These types of people will create the vision and challenge you to pursue a better one. Playing well with others, Issa Rae describes times when not having the creative buy-in or equity within films and projects leave you at the whims of others creative vision, and with little to no say over the direction. I love the final paragraph of the book that states, “being particular isn’t about rigidity. It’s about refining your vision and holding yourself accountable.” I can see a lot of creatives needing these words of wisdom to ensure the world sees their vision. Issa Rae also offers a bit more insight: being particular helps elevate collaborations and storytelling. When you are working with the right people, your vision goes from 20/40 to 20/20 in high definition.
“The Geography of Creativity- this book was the one book that did not fully resonate with me, but also gave me the best insight into location, location, location. In this book, Issa Rae discusses how her misconceptions about where she lived hindered her from forming creative partnerships. As she realized, choosing the right school helped her build connections and improve her creative process. Living in New York made it harder to launch her career, but in California, she was able to expand it and tap into resources more readily. The Geography of Creative asks people to consider whether they are in the right place to grow their dreams. If you are trying to become a journalist, you may want to be in the Media capital of the world and not a small town. If you are trying to become an investment banker, you may need to start your career in New York City and move once you have established connections and a network. Please pay attention to your location, as it may be the difference between how much success you achieve.
“I See You Seeing Me”- this is another book, where I learned more about Issa Rae’s life, and teaching people that you never know who is watching you. She starts with how she was manipulated into a fight over a new student, and she ended up losing a friend. Throughout the book, she pointed out that in the late 2000s, more people became critical of celebrities online for old tweets. She had to let go of a part of her life to prevent people from taking her statements out of context. In the end, she was still criticized for a statement from a book she wrote. I remember that drama, and I was like, “This is weak; people are holding this against her.” I, too, read the OkCupid data paper and felt her statement was both her opinion and satire. I also, in the late 2000’s, tossed my hat in the ring for Asian men. Not many Asian men gave me the time of day. Most of them politely rejected me, but that’s another essay for another blog.
I will review the last two books next week. So far, this series feels like a mini-masterclass in how to launch your projects without losing your voice, make effective use of resources, and prepare yourself for success. I loved reading this series. I read it twice to ensure I got every gem and nugget of knowledge.
Until Next Time,
Che Michelle
Below is a link to Amazon if you want to read any of these books.
Che-Michelle Tales 
Leave a comment