Issa Rae said she feels like she hasn’t reached the level of success to where she feels like retirement is in the near future, but when the innovator does, she plans for that era to be full of rest.

During Blavity Inc.’s annual AFROTECH Conference, the writer closed out the fireside chat portion of the event as the keynote speaker. Excited about her appearance, attendees gathered at the Hilton Austin and packed the room to hear what gems the self-made media titan would drop. While talking to Simone White, Senior Vice President of AFROTECH and Talent Infusion, she spoke about her career journey, business practices, and her future in Hollywood.

Many people in and outside of the industry would deem the multitalented creative as a very successful individual who has shattered glass ceilings and reached heights many haven’t. Despite the actress creating HBO’s award-winning HBO hit series Insecure, founding a media company, co-owning a coffee shop in her hometown, launching Raedio, an “audio everywhere company,” and recently releasing Viarae Prosecco, she confessed she doesn’t feel like she’s had the “you did it” moment yet.

When she does reach her pinnacle, although the sky is the limit, she plans to kick back and relax because “it’s hard being an entrepreneur,” “it’s hard pursuing what you love,” and “it’s hard doing something where there isn’t a blueprint.” A compliment she hopes to receive 10 years from now is praise for being able to relax after tirelessly working.

“Girl, you stopped, you chilled. Wow. You’re chilling. Good for you. Wow. You retired. Wow. Good for you,” Rae said as she mimicked an ideal comment that would flatter her.

The 38-year-old then admitted she never envisioned herself working for a long time.

“I don’t have a desire to work forever. I want to do things that I wanna do forever,” the entrepreneur told White. “But the work part of this is hard, you know? It is. And the anxiety and the windows that you feel like you have…I definitely wanna reach a point where I feel satisfied ’cause there is a thing of constantly moving the goalpost and adjusting what success means, and I just want to be at a place where I’m satisfied and it just has not come yet.”

This led to the Standford University alumna being transparent about the insecurities she faced, and still faces, in her career when she has moments of uncertainty about her work and business decisions.

“I for sure doubt myself,” Issa explained. “I know, you know, that I’m not the smartest person in the room that I enter. I know that, again, there’s so much that I don’t know and I want to accomplish. And I’ve had a lot of moments, the imposter syndrome moments where I’m just like, ‘Oh, is this all that I have? Is this, all that I’m meant to contribute? Is my purpose, this portion of my life?’ And then maybe it’s meant to inspire someone else and this is kind of all there is.”

She continued, “It just comes back down to deciding what I have to say. Like, and it goes back to the creative root in me of just like, what do I need to get out of my system? And thankfully I have the freedom and an incredible team that is encouraging.”

The producer then shared she often wonders how long she’ll have a career in the film industry since it’s unpredictable for creators.

“I just doubt my longevity all the time,” she said. “I doubt my ability to be here. It’s just…it’s competitive and our industry is changing. It changes so much and it’s so fickle, and you know, you guys have seen it and will see it. But there [are] constant waves of when we’re relevant to the powers that be and that can be discouraging and frustrating because it’s just like, we know ourselves and we know our stories and we know how valuable we are, and how much we create culture and impact culture.”

The Golden Globe winner did reveal that lending her hand to ensure the Black community has a bigger voice and platform in Hollywood and media would play a major role in her feeling the ultimate success.

“To be told when we can have our moments, it’s incredibly frustrating,” she continued,  “So, that’s something that keeps me up at night and I wanna change, and I feel like part of my satisfaction will come from that.”

As heavy hitters make their way to AFROTECH Conference Stages, more gems are expected. Don’t miss out on your chance to be enlightened! Purchase your tickets here.