HBO’s Insecure: A Look into the Intentional Season

One thing “Insecure” did secure, is a spot in television history, for showcasing and honoring Black love, creativity, art, and talent in a show that now sets a new standard for the future of media. Part of what made “Insecure” so dear to viewers’ hearts, is the fact that many of us grew alongside the characters and the show, in general. We’ve watched Issa Dee go from deciding to leave her job at a non-profit, to taking a chance on herself to truly do the kind of work that she wanted to do. We as the audience aren’t in the same place we were when the show debuted in 2016. In fact, I’m sure many of us realized so much about ourselves through the cast’s amazing acting and storytelling from the writers. And although saying farewell feels bittersweet now, it’s amazing to look back upon the journey up until the final episode and to realize what powerful legacy has been left behind by Insecure.

If you are familiar with Creative Flow Alchemy framework, then you can probably guess which season Issa Dee is in when Insecure ends. If not, let me give you a quick rundown. You see, when one begins their creative journey, they more than often begin in the dark; asking questions and looking for inspiration. Issa Dee knows she wants to uplift her community, but she has no idea how to do this other than by working in the non-profit world. She didn’t have the answers yet, which is why it’s called the Inquisitive season. Next is the Inspired season, which was the stage in Issa’s career when she begins to dream about highlighting her community on her own terms, and takes the plunge to quit her position at We Got Y’all. Meeting and networking with Condola? That would be Issa in the Intuitive season, allowing communication and connection with like-minded people who ultimately share the same hopes and goals. And finally, Issa takes her career into her own hands and starts her own company, the Blocc. Although we see her struggle between sticking to authenticity or playing it safe to avoid conflict, we see Issa Dee finally able to do the work she’s been wanting to; with the intention to showcase and uplift Black people, art, talent, and communities and to be remembered for doing so. This is the Intentional season.

Funny enough, this framework can be can applied to almost any character in the show. Molly’s personal transformation? Lawrence’s career journey, anyone? While there are multiple examples of characters and relationships that match the seasons in this journey, it’s important to note that the lessons these characters learn along the way are often difficult, but made possible through a community of people who want the same things as the end-goal. You can even apply these seasons to Issa Rae and the show itself, as it has evolved from a web series to a full-length show that has intentionally left behind an incredibly transformative legacy. The documentary special revealed that Issa Rae and the incredible team behind the show had a larger end-goal when it came to their Intentional season. They not only wanted to make sure that Insecure was a damn good show on its own, but they also made it a priority to use their resources to create space for Black talent to grow and gain experience in writing, directing, and acting.

It’s safe to say that the cast and crew of Insecure will forever feel honored and blessed to have put in work to create a piece of revolutionary art. There is a beautiful sense of pride that is apparent on the set of Insecure, knowing this show has changed so much, from the lives of the people working on it to the kinds of Black stories we see on TV. So while we rewatch our favorite episodes and mourn the end of an era, we must also take time to appreciate and applaud the many ways in which Insecure intentionally created a cultural shift in our lives, and allowing us to grow along with the show - both of us navigating the world in our authentic, awkward selves.

Insecure reminds us what it is to be a heart-centered millennial and why it is so, so important to follow what sparks your soul in this life. It reminds us to lift each other up and give each other a voice, and to never forget that what we are doing is for the sake of creating a better right now, and an even better future.

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