Boyz II Men was on to something when they first crooned their hit song, “It’s So Hard To Say Goodbye.”

Get your tissues ready the culture is about to bid farewell to what has been deemed as one of the best series of our generation.

In October 2016, the world was introduced to Issa Dee and her crew on Insecure. For the last five years, they have been like an extended family, they’ve caused division on Twitter timelines, and most importantly, they’ve shown an authentic experience that comes with growth during life’s journey. 

Not only has Insecure done an amazing job at reflecting the everyday struggles that come with the insecurities of figuring out what life is all about, but the series has jumpstarted the careers of Black creatives like creator Issa Rae and a host of cast and crew who made the show possible.

Now, after five years, several Emmy nominations, a win for single-camera Editing at the 72nd EMMY Awards, NAACP Image Awards and several other accolades, Issa Rae prepares to say goodbye to the series that seemingly changed her life forever. Ahead of the season premiere, Shadow and Act and spoke to the multi-hyphenate about season 5 and ending the shows.

The final farewell

During the process of creating Insecure, Issa Rae knew exactly the type of journey she wanted for her central character. Yet, over the years that path has shifted.

“I started off knowing what journey I wanted to take our main character on and where I wanted to have her end up,” she said. “As far as the specifics, they’ve changed so much over time. I’m extremely happy with the way that this show has ended on many levels, but it was definitely not what I thought it would be.”

The journey

The thing about growth is that oftentimes, social media and the things we see reflected on on-screen are nothing like the actual process. But not for Insecure.

We’ve witnessed firsthand the ugly truth that comes with growing pains. From Issa’s relationship with Molly (Yvonne Orji) to her relationship with Lawrence (Jay Ellis), viewers have been taken on a roller coaster and it’s not over just yet. 

“This was always a story about growth and the journey from insecurity to acceptance and that’s exactly what we wanted to showcase,” Rae added. “I wasn’t interested in telling a show where each character stays the same, that’s more of a sitcom vibe. So this journey of figuring one’s self out and evolving with intention was something that we set out for each character.” 


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She also notes that if you reflect on everyone in season one and soon by the end of season five they’ve all stayed the same, then they’ve failed at the show’s intention of showing what it’s like to truly grow as a person.

Reaping the rewards

For many people, Insecure has become the show that is an accurate depiction of this thing that we call life.

As this chapter closes, Rae understands that the experience that Insecure has provided her with is something that doesn’t come along often.

“I will never be able to fully articulate what it means to me where people I love so much believed in me and really came through,” she said, holding back tears. “I know that this doesn’t come along often and I won’t get that experience again.”

Prepare to begin the journey to goodbye with the final season premiere of HBO’s Insecure on Sunday, Oct. 24.