Issa Rae Shares 5 Ways Courage Can Help Advance Your Career

Amidst record layoffs and fears of a recession, Issa Rae shares advice for entrepreneurship and career success.


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Issa Rae launched her career with a YouTube series—and since then, she's created and starred in the hit HBO series Insecure, starred in two major motion pictures, and made the Time 100 list of the most influential people in the world, twice. Naturally, a lot of different factors have played into Rae's success, but the multi-hyphenate recently discussed one common theme at the core of her positive career trajectory: courage.

On Feb. 1, Rae sat down with television host and former NFL player Nate Burleson for a virtual Black History Month fireside chat to discuss the entrepreneurship challenges Black small business owners face in the U.S. and Canada. The chat, which was hosted by Intuit QuickBooks + Mailchimp, went beyond basic business advice or sage wisdom exclusive to BIPOCs. Rae shared universal lessons that can be applied to anyone looking to grow their income this year. She explained how courage has been a key tool in her personal success—and how she recommends others utilize it in their own lives. Below read up on the five key takeaways that can be applied to your life right now to grow your psychological and financial security this year.

Have the courage to recognize when people-pleasing is blocking your success.

When Rae started her hit series Insecure, she had to learn to stand up for herself to make sure her vision was brought to life as she intended. “Generally, I’m a non-confrontational person and I found that I was often a people-pleaser to my own detriment,” she admits. When she saw results that missed the mark, because she didn’t have the courage to push back on certain decisions, she blamed herself. Now, she knows that it's imperative to stand up for the integrity of the projects she leads.

Whether at work, home, or in-between, it’s important to recognize when staying quiet or playing small is devaluing your time, earnings, or savings. This might mean stepping up to take on more decision-making responsibility in the office, or fighting back when you realize you’re being overcharged by a vendor or underpaid by a customer. It can be intimidating the first time you communicate your concerns, but overcoming the fear of confrontation can seriously pay off. Know that if you don’t stand up for yourself, no one else will.

Have the courage to tap into your network. 

One of Rae’s first sources of funding was her brother’s friend’s dad. He needed someone to film talent shows at his school and, for a nominal fee, Rae did the job. She negotiated with him to use the camera outside of the school, so she could do her own work. And soon, she found herself getting help from people in her community who saw how hard she was working and wanted to aid her journey.

It's a common tendency to hide creative passions or keep goals to yourself—especially if things are still a work in progress. But, there's value in opening yourself up to the community around you and having faith that others also want to see you win. Hopefully, you'll find that there are many more supporters than there are naysayers. And the people around you may have a wide range of resources, materials, and ideas to advance your goals—you just have to ask. Don't be afraid to put yourself out there and engage with the communities around you. Some friendly bartering could give you the kickstart you need and foster a network of support.

Have the courage to build a team of mutual support.

When Rae was in her early days writing her web series, she quickly “realized how challenging it is to build something from the ground up." Although she always wanted to be a leader, she knew she needed help. As she was looking for a way to support herself, Rae built a team of like-minded individuals to get her ideas off the ground. She even bartered services with her team when she didn’t have cash to offer.

Whether in entrepreneurship or a hard-charging career, it's important to realize that you’re never in it alone. No matter what, it’s crucial to build a trustworthy team of people who you rely on and who rely upon you. Rae says it's a priority to make sure that “the people you’re working with can see their future in your vision and also trust that you're going to help them get there.” 

So, be transparent about your limitations, celebrate wins as a team, and set a plan in motion that helps individuals on your team grow in the ways they want to. This looks like setting milestones to deliver on services or benefits that they really need in addition to pursuing your personal goal posts. Keep in mind, their success is your success too.

Have the courage to slow down and prioritize rest.

“As soon as you get that first wind of success and the promise of your business booming, you want to say ‘yes’ to every opportunity and ‘yes’ to every meeting,” Rae says. The first few years of a new business or career can feel like a rat race. But there will come a time when your success will bring enough psychological safety that you have to hit pause.

Rae says that after reading Shonda Rhimes’ book Year of Yes, she implemented the “year of no.” Now, Rae makes sure to account for at least one rest day per week (which also functions as her “procrastination day") and she found that she was more creative after slowing down.

Take a page from Rae’s playbook by recognizing when you need to rest. Don’t take meetings on those sacred rest days, and carve out time to be empathetic towards yourself. While we've often been conditioned to think that overwork will be rewarded with a promotion or recognition, it usually just leads to burnout. So, have the courage to slow down instead. You may even find that strategic focus allows you to identify better paying opportunities that still align with your skills and interests.

Have the courage to charge more.

No matter how much you’re making right now, chances are someone else out there is doing the exact same work and making more than you. Research shows that this is especially true for women of color.

Rae shared her own experience with undervaluing herself, explaining that she used to do college tours, showing her work around the country, and charged only $100 plus travel expenses for her time. A helpful administrator put the bug in her ear that the university paid thousands of dollars to other visiting speakers—and that she needed to charge more.

While keeping up with the competition isn’t the only reason to demand better compensation, it’s still a valid one. Charging more can also make your work more sustainable. It's hard to offer your skills or products to everyone who needs them if you don’t have the income to support scaling your business.

If you want to see your success grow, chances are you’ll have to charge more for what you’re already offering, so that you can finance that growth. The extra income can be used to pay for more advertising, drop shipping, or services that reach new markets and clients.

The same advice applies to those in 9-to-5 jobs. If you’re just making ends meet, chances are you’re so focused on survival that you do not have the bandwidth to take on innovative projects that could raise the bar or secure a promotion. Worse still, you probably don’t have the energy to look for a better paying gig altogether. So have the courage to ask for that raise, charge more this year than last, and increase your prices. Not only do you deserve it, but financial security is important to keep your family, business, and career afloat for the long haul.

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