How Insecure’s Issa Rae is inspiring a generation of content creators

Author’s note — this piece was originally written for #paid on December 29, 2021.

Ladies and gentlemen — her.

I’m literally obsessed-like.

It has been five years since the premiere of the HBO tv series, Insecure. The show, which was written and produced by and stars Issa Rae, has gained massive media attention and a loyal following of fans that tuned in to new episodes every Sunday at 10 PM. With the series recently coming to an end, fans are not only praising Insecure for its writing but also for the relatability of its characters and the real-life topics that were brought to the forefront of its plot. From struggling with mental health and navigating complicated relationships — both romantic and platonic — to celebrating Black culture and creativity, Issa Rae has managed to give life to a creation that makes other creatives feel seen and heard.

In a tweet from Jasmyn Lawson, a content executive at Netflix, she shared that Insecure has become a standard for creators, both veteran and new. “#InsecureHBO has been a transformative show, not just for Black culture, but the entire industry. As a comedy exec, there’s not a day that goes by that I don’t hear it talked about or brought up in a pitch. Both new and veteran creators use it as a reference. It’s a new blueprint.”

Fans of both Insecure and Issa Rae are now wondering what the future holds for the writer and what she will create next. In May, it was announced that she had secured a $40 million deal with WarnerMedia, where she’ll produce film and television content across WarnerMedia’s brands over the next five years. If you’re not familiar with WarnerMedia’s portfolio, these brands include but are not limited to HBO, TNT, Adult Swim, and WB. While it’s not shocking to fans who have followed Issa’s career since her YouTube debut of The Misadventures of Awkward Black Girl, it is very clear that Issa’s price has gone up, and truthfully, we love to see it.

Her career, thus far, can be seen as a standard for creators and creatives across industries and areas of focus. From designers to writers to filmmakers, Issa has changed the game in the world of entertainment and has made an impact on what it means to be a content creator. While she has much more work to do, she is already leaving a legacy that is inspiring seasoned creators that have been doing creative work for years and a new generation of creators that are on a path to solidify their own voices in this space.

If there’s anything we know for sure it’s that Issa will never have any issues securing a bag. Throughout her career and in every project that she conceives, she always finds a way to ensure that she showcases the work of other women and people of color, especially when they are creators. This is no different in her recent partnership with MasterClass, an online learning program that boasts having the best instructors in the world. Issa Rae is now one of those world-class instructors sharing her personal insight into how current creators and creators in the making can “create outside the lines” and reach their full potential without taking “no” for an answer.

This is one of many recent projects that Issa has put into motion to put the spotlight on content creators however, she has been laying the groundwork since 2014 when she built ColorCreative — a management company that specifically caters to supporting diverse creators and producing content that is inclusive. In an interview with The Cut, Issa shared, “Collaborating with creatives I admire — that’s what I’m made of. I’m really proud of how it all came together.” Issa is a multi-hyphenate that has continued to open the doors for other creators and it appears that she has no plans on stopping. Through her media company, HOORAE, which serves as the umbrella banner for both ColorCreative and Raedio, Issa is tapping into the creator economy to source talent with the sole purpose of being creative.

Hella Inspiring

It takes doing the work of a creator to truly understand the time, energy, and, occasional self-doubt that goes into producing creative content. While creators have been around forever, it seems as though content creation has only recently gotten attention as a career path. Today, creatives are defining their own lanes and showing through their work just how valuable they are to brands; so much so that there’s a whole economy that revolves around them. This is something that Issa and other creators know well and the reality is that individuals who do content creation full-time or as a side hustle are just figuring it out as they go. That’s why it’s more important than ever for creators to have leaders in the space to look to for their knowledge and insight. For many, Issa Rae’s career has become a master guide on how to make money as a creative without sacrificing authenticity.

While she has made a name for herself as an actress, writer, producer, and activist, Issa’s real power is in her ability to show up as herself. In a world where 7 out of 10 people experience imposter syndrome, visibility and understanding are everything, and making creators feel seen is something that Issa excels at. In interviews, she has even described her own style of networking in which she builds relationships with the individuals that are working right next to her rather than immediately trying to connect with everyone at the top. Oftentimes, those people are creators themselves or fans of creators that are just a referral away from a new opportunity. This is a sentiment that resonates with many creators on the rise, like Kar Logan a writer and producer for Situationships on BET.

“​​When I was first moving to New York in 2012 I got introduced to Awkward Black Girl and I want to say that was my first Black web series. From there, I went on to watching Black&SexyTV where I found even more web series and this made me want to create and produce my own with other like-minded individuals. The journey we’ve been invited on with Issa, on and off the screen, is what fuels and inspires me because she makes it look so effortless. She’s a testament to what someone can do if given the opportunity. Issa shows people what networking across as opposed to always reaching for the top can do for creatives, and it’s gotten me through so much. Building a tribe of people on the same page with the same aspirations gives you a different kind of energy because you’re with people who ‘get it.”

Issa Be Working, Okay?!

While creators are looking to Issa Rae for inspiration on how to navigate the industry and their careers, they aren’t the only ones that should be taking notes. Issa Rae is a real-life example of how brands can partner with creatives on campaigns and initiatives that spread awareness of their brand story and introduce their brand to audiences that may have never even known existed. Earlier this year, LIFEWTR partnered with Issa for the launch of their Life Unseen campaign which advocates for fair representation in the arts.

The campaign consisted of several key initiatives, all of which were designed to amplify the work and stories of diverse creatives. The Life Unseen Study, spearheaded by the Institute for the Quantitative Study of Inclusion, Diversity, and Equity, unpacked the systemic disparities in the fashion, film, music, and visual arts industries that directly impact marginalized individuals; while The Life Unseen Artist Collective featured a group of 20 creators that were selected to submit their own artwork which was later featured on LIFEWTR’s largest bottle collection. Brand collaborations like this not only amplify the work of creators but it gives them the courage and drive to continue their work. In a press release for the campaign, Issa shared “LIFEWTR understands that creativity literally doesn’t exist without diversity of culture, perspective, and interpretation. Together, we’re inviting everyone to help shine a light so the work of unseen artists can be seen.”

If there’s one thing about Ms. Issa Rae it’s that she is always working on something. LIFEWTR wasn’t the only brand she collaborated with this year. She also teamed up with the global sneaker brand, Converse, to produce her first-ever collection of customizable sneakers. Dubbed “Issa Rae By You,” the collection was inspired by Issa’s own creative process and her use of affirmations to keep her inspired and encouraged. The Creator that helped bring her vision to life? Nick Fulcher, also known as “Nicky Chulo” on Instagram and Twitter, a Haitian American designer and art director based in Los Angeles. In a statement, Issa shared that her partnership with Converse “was all about empowering the next generation to get up and DO what it is they aspire to do.” Whether you’re a fan of sneaker culture or not, it is clear that each shoe was designed with self-expression in mind.

It’s uncertain whether being an inspiration for a generation of creators was included on Issa’s 2021 vision board but because of her efforts to share the stories and visions of creatives everywhere, she has become a leader in the entertainment industry and a role model; or as some would say, “the Beyonce of creatives”.

Lowkey Thankful

While I haven’t met Issa Rae, the legendary businesswoman, or Issa Dee, the awkward yet relatable character that Insecure is based on, I would like to think that they both would share similar advice to creators who are doing their best to gain more exposure and access to opportunities — just do you. Creators are constantly being told to find ways to stand out and for marginalized creators, especially those who are Black women, that can be a challenge. Just this summer, TikTok was under fire after Black creators shared grievances that the platform’s algorithm perpetuated anti-blackness and allowed white creators to profit off of their original content. If creator spaces like TikTok, YouTube, Clubhouse, and Discord don’t feel safe for creators of color, where can they go?

This is why Issa’s work to champion talent across creative fields has been critical to the future of content creation. The time for creators to thrive is now and there are so many stories to be told.

Whether she recognizes it or not, her passion for and vocal support for creation is inspiring other creators to lean into their own visions and carve a path for themselves. Clarissa Laskey, a content creator and founder of, is doing just that by making her presence known in the travel blogger space.

“There have been so many challenges I have faced as a creator over the years but the biggest challenge for me has always been imposter syndrome. Can I actually do this? Do I deserve to get this opportunity? Am I really worth this amount? Issa’s career has inspired me as a Black woman to remember that no matter what, to always show up as your true, authentic self — in your content, words, and work. When you have put in the work and it’s your time to shine, you will, and you will also create opportunities for others to thrive and succeed too.”

Although Issa has shared the obstacles she has had to overcome in order to accomplish the many firsts she has had as a Black creator in the entertainment industry, she has been able to do so with grace, style, and humor all while creating spaces and opportunities for creatives to work alongside her. Whether it’s featuring new artists in her shows, bringing on creatives to collaborate with for brand partnerships, or speaking to students in the early stages of their careers, Issa is leading the way as a pioneer in the creator space.

With the final season of Insecure wrapped up, it is no wonder why fans are heartbroken and disappointed. Yes, we know that she will be working on other projects and is already bringing some to life, but to many creatives, Insecure is a visual and artistic representation of what can happen when you dream big and that will be hard to let go of. As we know, all things must come to an end but for many, the closing of this chapter is the beginning of a legacy that will redefine what it means to be a content creator.

You’re iconic as fuck, Issa.




content creator writing about marketing, travel, wellness, weed, culture, and other stuff. find more parts of my brain on twitter and instagram—@jaydeipowell.

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Jayde I. Powell

Jayde I. Powell

content creator writing about marketing, travel, wellness, weed, culture, and other stuff. find more parts of my brain on twitter and instagram—@jaydeipowell.

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