Issa Rae meets many people’s definition of a successful person.
She graduated from Stanford University in 2007 and is an Emmy-nominated actor and television showrunner, New York Times bestselling author, and serial entrepreneur. She founded her own production company, Hoorae Media, in 2020 and co-owns companies such as hair care brand Sienna Naturals and California-based coffee shop chain Hilltop Coffee and Kitchen.
But she struggles to feel successful because she doesn’t have any shows actively producing new seasons or movies in theaters, she said on the Nov. 12 episode of her podcast, “Not My Best Moment.”
“Do you consider yourself successful now?” host Kevin Fredericks asked Ray.
“I know I look like I’m successful to other people, but right now I’m not. I feel really stagnant,” Ray responded. “The only time I feel successful is when my work gets aired.”
The 40-year-old created, executive produced and starred in HBO’s “Insecure,” which aired for five seasons and won multiple awards. After the show ended, she created two other series for HBO and appeared in films such as “Barbie,” “Vengeance,” and the Oscar-winning “American Fiction.” She produced the film One of Them Days, which was released in January and grossed $11.6 million in its opening weekend in North America against a budget of $14 million, according to Variety.
But with no TV shows or movies actively airing or being released in theaters, Ray said with a laugh on the podcast that he feels like he’s “emptied out again.”
“(Screen entertainment) is my love. Like, I could have (multiple) businesses… and those are great passion projects, like, but the things that I’m excited about, the things that I’m excited about, aren’t happening right now,” Ray said. “No, I don’t feel successful. I’m optimistic. I’m not successful right now.”
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I’m sure many of you can relate to the feeling of “Now what?” After experiencing a moment of career success. For example, getting a promotion or finally completing a multi-month project may not feel as successful as you expected.
According to workplace performance coach Hena Pryor, even top performers can get stuck in a loop where they achieve career victories, then become anxious about not being able to repeat those successes and become demotivated as a result.
“For high performers, the goalposts are always moving…When they’re willing to try something new or take that risk, there’s more at stake because they have the potential to win,” Pryor told CNBC Make It in July 2024. That anxiety can “corrupt your motivation over time” and prevent you from trying new and exciting things, she said.
In times like these, Prioritize process over results, Pryor says. Reflecting on the steps you’ve taken to achieve your big goals, the lessons you’ve learned along the way, and even the challenges you’ve faced can help you feel more fulfilled and feel more comfortable in the moments when you’re stagnant.
According to Shigehiro Oishi, a happiness expert and professor of psychology at the University of Chicago, you can also cultivate “psychological well-being” by intentionally giving yourself experiences that change the way you think and see life.
If you’re feeling stuck in your career, perhaps traveling, reading a good book, watching a movie, or picking up a new hobby could help increase your sense of happiness and fulfillment, Oishi said on the Oct. 27 episode of the podcast “10% Happier with Dan Harris.”
Oishi said you can also push yourself to find signs of hope in your frustrations. Sharing your thoughts with others or writing them down also makes it easier to remember and think about them.
Oishi said, “I want them to experience something interesting and tell a story about it.” “It’s really important to write about it and talk about it.”
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