How Issa Rae’s ‘Insecure’ Reminds Us That It’s Never Too Late to Find Your Calling in Life

By Jamie-Lee Collman

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Since this television series has made it to Netflix, I figured now would be a great opportunity to revisit some conversations about the lessons that can be found in each episode. Recently, I’ve found myself questioning a lot of the directions I’ve chosen to go in life. Oftentimes, I was wondering if I was behind or possibly no longer aligned with the vision I initially created. 

Was it my vision to begin with or did it belong to someone else? 

Ultimately, I was left feeling stuck, and I'm certain there are others out there who can relate. The pressure can be applied even more so when you were raised by immigrant parents. It’s a struggle that doesn’t always fare well when we decide to alter the trajectory of our lives, particularly in favor of what makes us the happiest rather than the picture we need to paint for everyone else.

I remember the first time I learned about the series Insecure on HBO. It was right after Season 1, Episode 1 was released in 2016. After watching that first episode, I immediately became a fan. There were so many attributes showcased by the main character, Issa, that I resonated with. A lot more than I was willing to admit at the time, because who really enjoys calling themselves out so boldly like that?!

Viewers are introduced to Issa at the start of the series as she is about to enter her 30s but feeling stagnant in her circumstances. She’s holding onto the belief that time is not on her side and she must have her life together by the time she eventually does turn 30 within the next year. It’s evident that deep down somewhere within, Issa knows that she’s meant for more. However, she doesn’t believe that she has the resources or the confidence in herself to make a significant change to pivot her way there.

“How different would my life be if I actually went after what I wanted?”

Following the expression of this thought, Issa goes on to praise her best friend Molly. In this praise, Issa Indicates that, because Molly’s life looks different and “more successful” from hers, she (Issa) must be doing something wrong.

"Everyone loves Molly.”

This statement made me chuckle the first time I heard Issa express it because when you really think about it, it becomes increasingly apparent that Molly doesn’t even love her life let alone herself. She has a romanticized view of what her life should look and be like. While also being burdened by a similar ideal, she should be thinking about marriage and having children by now. She successfully obtained the education, the career goals, and starting a family was all that was left. In this instance, it’s clear that to some degree that Molly doesn’t even hold herself to the same standard that Issa does because she feels inadequate due to her perception of what her life should look like.

That begs the question: Which end of the spectrum is more important? How do people perceive your life? How much do you love the life that you’ve crafted for yourself?

While watching and analyzing this scene, I recognized that there is no “one size fits all” when it comes to the direction our lives can go. Some of you might think “Well, duh!”, but others may not have been raised with this thought in mind. 

Some people may have only been raised on the basis of what the world around us dictated for years of what it meant to have a fulfilling life. Some have never looked at an established life on our own accord where risk is taken to achieve what we want in the name of chasing after what we actually love. Everyone is on their own path and timeline, which has also been a hot topic amongst the new generation even with millennials. We were raised on that belief mentioned earlier, that if you go to college, get a degree, then you would come out and be able to find a solid job working for a corporation to set your life up for success. However, how exactly is success measured in that capacity? It may have worked for our parents, but times are proving to be much different in the span of a 30 year difference.

Many of us have hit 29 and 30 while feeling the same way that both Issa and Molly do about their lives. What makes this even more interesting are the different points they’re at in their lives within the same age frame. Somehow, we’ve been convinced that by now we’re supposed to have it all figured out. We’re supposed to have the house, the career, the partner, and the children. With this pressure continuing to mount on our shoulders, comes a major shift in our thinking. Most of it can also be a testament of how much technology and access to witnessing other people’s livelihoods has challenged that thinking. Our success in life, in this instance, is measured on the basis of how much we love the world that we’ve shaped for ourselves while still paving the way to achieving a successful outcome. 

An outcome that doesn’t have to make sense to anyone else, but us. An outcome that can change as many times as necessary until we find that good spot that works best for us. With the excessive push for adults in their 30s to settle down, many have decided to change that narrative and adopt one that fits their own; regardless if it means starting a new hobby, career, or lifestyle. We are beginning to no longer feel intimidated by the concept of time or that we need to have everything together by 30.

Quite frankly, it appears that 30 is becoming the new 20, where most are beginning to finally find themselves and embrace what they value the most.