Issa Rae Made Us Feel Less Insecure About Our Careers: Read the Q&A

“Let’s Talk Bizz” is a digital roundtable series hosted by Bumble Bizz. Users can win an online mentoring session with some of the world’s most prominent entrepreneurs and leaders.

This month, we chatted with writer, producer, and lead actor of HBO’s hit show, “Insecure”: Issa Rae. With her infectious sense of humour, she had plenty of advice for our users when it came to turning their passions into a career.

Q: What is one challenge you did not expect to face while pursuing your passions full-time?

Issa Rae: One thing I did not expect was the extent of collaboration. I knew I always wanted to bring the people who helped me along for the ride, but I neglected to consider that the people I would ultimately work with may not want that.

It’s been such an uphill battle sometimes to include the people who have started on this journey with me in future projects. I’ve had to develop a backbone by seeing other people go to pursue a different path. Everyone is important to my journey, so they matter and can always be a part of it.

Q: How do you get constructive feedback when you’re just starting off, or when you don’t have a huge audience behind you?

Issa Rae: Oh my God, I need constructive feedback for me to operate! It only helps you to get better and improve. I think where I struggled was in balancing all the criticism or all the feedback. For me, it was about trying to please people like, “Oh, they said that they need more of this character even though that is kind of counter to my instinct, I should do it because they mentioned it,” as opposed to trying to figure out what the feedback’s larger message was.

It’s about balancing feedback with your voice and the story you want to tell. You get smarter about figuring out what pieces to apply and what pieces to drop as you continue to hear it. Feedback should just be a conversation, and you shouldn’t be afraid to ask questions if you do not understand the feedback you’re getting.

Q: How do you keep the hardships of your career from negatively impacting or outright killing the joy that you originally found with your passion? Especially when you’re on a deadline, or becoming creatively exhausted?

Issa Rae: For me, it is just about taking breaks and not being afraid to call them “creative breaks.” I am one of those people who needs to have multiple projects, and sometimes all those projects make me feel like I need to focus on one passion over another. That will then help me get back to work on a different passion, and then another one.

I take upright stretches and I tell myself to breathe, too. Being creative is so hard sometimes when the stuff that you love feels like work, and when people are expecting so much from you. But it comes with the territory, and you really can’t be down on yourself.

You have to be able to take a step back and allow yourself to breathe. Because sometimes you are killing yourself thinking, “I have to keep going, I’m not going to get these opportunities in my future, so I have to take advantage of them now.” Honestly, what is meant for you is gonna be yours, so you have to remember that at all times.

Q: How did you go about choosing the people you chose to hustle with and in turn, trust that your network and those people would carry through your business and your passion?

Issa Rae: Well, I was very prideful so I did not ask for help for a long time. I don’t know what it is, but as a creative — especially early on — I felt like I had to do everything by myself. I had to get the credit, or say that I did this alone, and I don’t know why I saw that as a badge of honor. But after a while of doing it and taking on so many tasks, people around me could see that I needed help and that it just took saying “yes”.

So like my friend from high school, Tristan, he was an actor and asked if he could be part of my projects to get acting experience. And I was like, “Yes! Because I need actors, please.” And then another friend was like, “Girl, you need a producer because this shit is good, but it’s like, not. So let me help you get it together.” So I was like, “You know what? Yeah, sure, thanks.”

A lot of people started coming in that way, and it was just a matter of me saying, “Yes, I need you,” but also making sure that along the way that their careers were progressing in the way that they wanted, too. Because you can take and take and take — but when people are helping you, you should ask how you can help them, too. It’s like exchanging services with one another while helping each other grow.

A special thanks to our Bumble Bizz users for their thoughtful questions and to our partner, AfroChic. AfroChic is an annual cultural arts festival based in Canada and provides a safe platform for black Canadian performance and visual artists to bring awareness to a variety of issues related to African-Canadian women including hair, health and politics. Learn more at