How Issa Rae Blazed Her Way to the Top

Issa Rae at BET's Black Girls Rock show.

Issa Rae and the word trailblazer pretty much go hand-in-hand. The multi-hyphenate talent has gone from YouTube to HBO to starring in Hollywood feature films, all while starting a music label (Raedio), a production company (Hoorae), and investing in a coffee shop (Hilltop Coffee).

Building a media empire from scratch isn’t an easy thing to do, so it’s pretty much impossible to have anything but respect for Issa’s game. Of course, it hasn’t always been an easy ride to the top. Here are some of the top business, financial, and life lessons Issa’s shared about hustling harder when the hustle gets hard.

Chart Your Own Course

Since Insecure debuted in 2016, Issa’s been taking advantage of seemingly every opportunity that’s been thrown her way, branching out just about everywhere. She had to pave her own way, chart her own course. As she said in an interview with Glamour magazine, “There was no blueprint to do this. There was no one I could look to and be like, ‘Oh, so-and-so made some videos and then had a television show, and then did movies.’ You kind of just do it.”

Follow Your Passion (but it’s okay to have a backup plan)

Not many Hollywood stars get their start at Stanford. Most students jump into tech, finance, law, medicine, or another advanced field but not Issa, she knew she wanted to go into a more creative field. As she shared with Bustle, “I’m a Capricorn, so I always have a plan or something to fall back on. Even if I had attended business or law school, I was still always going to be creative and continue to write. I’m a firm believer in acquiring a skillset, but I always knew what I wanted to do.”

In other words? Don’t give up on your daydreams. Do what you’ve got to do to pay the bills, but don’t forget about carving out time to make that side hustle your main hustle.

Find a Way to Get Out of Debt (and stay there)

HBO may be bankrolling Issa’s hit TV show Insecure today, but her YouTube series Awkward Black Girl was solely on Issa’s dime. While the show started with a crazy low budget of just $5 for the debut episode, costs quickly ramped up to $1,000 an episode – without paying anyone.

Issa ended up maxing out her credit cards to pay for equipment and other expenses, an experience she told left her feeling “devasted” because she wasn’t sure she’d ever get out of debt. Her solution? She ran a successful Kickstarter campaign that raised over $56,000 to help produce a season of the show. While Issa’s story shows the value of investing in your future – even at a steep cost – it also shows that sitting on debt isn’t good for anyone!

Know Your Worth and Claim It

Issa’s role as a producer exposed her to a different side of the business: salary negotiations. Along the way, she realized that men who work for her “have no problem asking for what they’re worth,” compared to women, who are less likely to bring up their salary needs or wants.

This eye-opening experience charged up Issa’s own confidence when negotiating. As she said in one interview, “If I’ve generally been working hard, and have been an asset to the company, why would I not ask for my worth? If a company does not value you, you don’t belong there. And if you don’t feel comfortable asking, know that the person next to you does.”

We couldn’t say it better ourselves. Speak up when you feel like you’re worthy of a promotion or raise to set yourself up for the future. Look into what other people with your title are making, highlight what you’ve given to your company in your role, and make the money you deserve.

Lift Each Other Up

Issa is notoriously commited to the Black community and that goes well beyond her screenwriting. “I’ve learned that black women have been running things for a while,” she told Forbes. “We don’t necessarily get the credit, but there are a lot of black female entrepreneurs. I’m proud to be one of them, and I think it’s important to showcase that.”

Issa is quick to point out that lifting each other up benefits the entire community. As she told Bloomberg, “We can support these businesses by amplifying them. Just because they’re Black-owned doesn’t mean they’re only for Black customers. If you love the business, spread the word and support it as much as you can.”

Focus on the Long Game

For Issa, sustainability is a key part of her game plan. We all know Hollywood can turn a cold shoulder to celebrities in a heartbeat which is why Issa’s been working to diversify her portfolio rather than banking solely on the success of Insecure.

The lesson here is simple: When you find success or something that works, don’t expect it to last forever. Always be on the lookout to keep your finances healthy and your career path growing.

Get in Control (and stay there)

So, what’s the secret sauce to Issa’s success? She hasn’t been afraid to step up and take control. Whether it’s controlling her debt or controlling the opportunities available to her by creating her own, the brightness of Issa’s future is on her and the work she’s put in. What are you doing to control your future?

Photo of Issa Rae at BET's Black Girls Rock show (cropped)
Bam0822, CC BY-SA 4.0, via Wikimedia Commons