Issa Rae meets many people’s definitions of a successful person.
She’s a 2007 Stanford University graduate, an Emmy-nominated actor and TV showrunner, a New York Times bestselling author, and a serial entrepreneur. She founded her own production company, Hoorae Media in 2020, and co-owns companies like haircare brand Sienna Naturals and Hilltop Coffee and Kitchen, a California-based coffee shop chain.
But since she doesn’t have a show actively producing new seasons or a movie in theaters, she struggles to feel successful, she said on a Nov. 12 episode of the “Not My Best Moment” podcast.
“Do you consider yourself successful right now?” host Kevin Fredericks asked Rae.
“I know that I appear successful to other people, but right now, no. I feel really stagnant,” Rae responded. “I only feel successful when my s— is on the air.”
The 40-year-old created, executive produced and starred in HBO’s “Insecure,” which ran for five seasons and won multiple awards. After the show ended, she created two other series for HBO, and starred in movies like “Barbie,” “Vengeance” and Oscar-winning “American Fiction.” She produced the movie “One of Them Days,” which released in January and grossed $11.6 million in North America in its first weekend against a $14 million budget, according to Variety.
But with no TV shows or movies actively on air or in theaters, Rae feels like she has “nothing again,” she said on the podcast, laughing.
“[Screen entertainment] is my love. Like, I can have [multiple] businesses … and those are, like, great passion projects, but like, what I do and what I get excited about isn’t happening right now,” Rae said. “So no, I don’t feel successful. I’m optimistic. I’m not successful right now.”
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A lot of people can probably relate to the feeling of “Now what?” after experiencing a moment of career success. You might get a promotion or finally finish a months-long project, for example, but you don’t feel as successful as you expected.
Even top performers can get stuck in a loop — achieving a career win, worrying that they can’t replicate that success again and feeling unmotivated as a result — according to workplace performance coach Henna Pryor.
“For high performers, the goalpost is always moving … When they go try that new thing or go to take that risk, more is at stake because they have a scope of wins behind them,” Pryor told CNBC Make It in July 2024. That anxiety “can erode motivation over time,” keeping them from trying new, exciting things, she said.
In these moments, prioritize the process over the outcome, Pryor said. Reflecting on the steps you took to meet a big goal, the lessons you learned along the way and even the challenges you faced can help boost your sense of fulfillment and make you more comfortable during stagnant moments.
You can also try developing your “psychological richness” by intentionally giving yourself experiences that could shift your mindset or perspective on life, according to Shigehiro Oishi, a happiness expert and professor of psychology at the University of Chicago.
If you’re at a bit of a standstill in your career, perhaps traveling, reading a good book, watching movies or picking up a new hobby can help boost your happiness and fulfillment, Oishi said on an Oct. 27 episode of the “10% Happier with Dan Harris” podcast.
You can also push yourself to identify silver linings in your frustrations, said Oishi. And if you share your thoughts with others or write them down, you’ll be able to recall and reflect on them easier.
“Experience some interesting things, but make it a story,” Oishi said. “Writing and talking about it is really important.”
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