5 Lessons I learned from Insecure

Chisa Pennix-Brown
7 min readDec 29, 2021

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Many things can be said about the groundbreaking show by the Chocolate Gawdess Issa Rae. She shared 5 years on screen, plus her creation and development time, to bring us a black cinematic masterpiece.

At a time when we knew we needed unapologetic black assness on the screen, but didn’t know that this show was going to be a defining moment in history…it came, it saw, and conquered.

I missed the first season and was tardy for the party because I did not have HBO. I was one of those people that was like, I’m not getting a station for just one show. However, all the social media attention made me cave in from my FOMO when the online cousins kept telling the world how good the show was.

I caught up when the second season started and the rest is fangirl history. Now that it’s over and I have cried through the last episode, plus the entire documentary that followed the course of the show and how dynamic it was, I can clearly articulate my lessons. Just FYI…if you’ve read what typical things everyone has said, then know that this is not that!

Lesson 1 Wear a Good Ass Bra!

Damn it if Kelly didn’t have them girls SITTING! (Ya Heard?) As a plus-size woman, it was refreshing to see someone that is beautiful inside and out who dressed so impeccably. Not only did she give me kimono envy, but the way those TATAS were showing up on the screen was nothing short of #bigtittylife!

Kelly exuded confidence in every scene. She was smart, daring, and the “tell it like it is” friend that we all need. She was always down for a party, but made sure that business was taken care of.

She is not body positivity…she is Positive Body! I needed to see this Queen grace my screen. Personally, I would not be mad if there was a documentary on JUST KELLY and her clothing, drinking, and work journey. As a matter of fact, Natasha, where do you get your bras from? #preguntas

Lesson 2 Fuck Them Kids

Issa was like, “we not throwing hands, we throwing babies!” When she kicked Condola in the hospital…I hollered! I had to rewind three times before proceeding through the rest of the episode.

I loved that scene, and as comedy goes, it was too real. I know plenty of people who wish a baby mama would!

Past relationships and situationships can truly ruin your future if you let them. I know we were all sick at the end of Season 4 because Condola seemed hella selfish. However, what Condola knew is that her baby was going to be several things: cute, probably tall, and well cared for, regardless of her relationship with Lawrence.

I fully understand the dilemma that Issa had to undertake, but she realized that she “could” handle it and adapt to create a new version of her life. I would love to explore the dynamics of that story, but unfortunately, we jumped several years into the future. In my version, Issa and Condola become very cordial and can even collaborate on some dope-ass event.

The moral of the story is that you have to see yourself in the position and accept it for what it is. I’m glad that they were able to work it out and upgrade to a bomb-ass house!

Lesson 3 Find Your Truth

There were many people who expressed discontent with Tiffany’s character. While I couldn’t personally identify with some of the things she experienced, I understood the drain of depression and anxiety. When she left to get that hotel room and have time to herself, I felt that in my spirit. We don’t take enough time for ourselves all the time and we need to do better as a society and specifically as black women.

The overwhelming pulls of society and the expectation we put on ourselves can be crushing. Reaching out to friends and admitting that you need help is a sign of strength.

Her husband, Derek, was a PROVIDER in more ways than one. He was there as a husband, father, and as a friend to her friends and his. He is the Real MVP for the men in this series.

I do wish we got to delve into her character and background more, but I appreciated her struggle and what I assume was ultimately a triumph since she was pregnant again in the end.

Lesson 4 Be Teachable & Build a Team

I adore the fact that Issa learned from Condola and stepped her game up. People do not give her the credit that she deserves because of the Lawrence situation, but I believe that she was a force that made Issa level up. It’s all a dream until you see someone else that looks like you achieving success. The connections, relationships, and leadership that provided the blueprint were laid all the way out.

Once Issa had that, the road was paved with more than good intentions as she built her team with Quoia as her trusty, get it done, ready to pop off assistant. She provided comic relief and treated the business like it was hers. That dedication and talent enhanced the vision.

Quoia gets three snaps in a Z formation because she made the BLOCC hot!

Lesson 5 Change Plans & Be Flexible

It’s one thing to have a plan and stick to it. However, if that plan is not working and neither are you, then it’s time to change the plan, but not the goal. I thoroughly enjoyed the venture of seeing Issa find her path. As a woman who hosts events, and has done it for a long time, she showed me that I was personally thinking too small. I am super motivated to get into that corporate bag and have the life that she dreamed about when she was on stage with Elaine Welteroth. I was on the couch like….yassssss bih!

Molly learned this lesson the long way. I have been a Molly in my rigidity to stick to what I want and not try alternatives. Once she learned that she was the one keeping herself from experiencing all that life could offer her, she blossomed.

I loved the storyline with her and Tauren and I truly appreciated how he was there for her when she had family issues. As a person who has lost both their parents, I understand what it’s like to have someone there to be strong when you can’t. I applaud the easy love that was developed between these two Legal Eagles.

I completely loved the scene with them eating ALL the snacks. Can someone pass me one of those mozzarella balls tho?

*Bonus Lesson

Black Love Wins! It wins in real life and on the screen. I did like Issa and Nathan together as an idea, but she was not equipped to deal with a person that is bipolar. It's not the easiest thing to handle on a day-to-day basis. Issa needed someone to care for her in a way that he may not have been able to. I am glad that he recognized that and walked away but still loved her as a friend. Nathan is definitely self-aware and on some grown man shit.

On the flip side, this image of Issa and Lawrence as perfectly imperfect love will forever be something that allows us to be ourselves and stop harboring what other people think. As a matter of fact, stop focusing on what old you thought life would be like. The growth and time apart were necessary for the independent maturity that each person needed.

What was so magical about their love was that they could both be successful alone. They didn’t need each other, but they realized they wanted each other. The future could be so much brighter if we have the courage and tenacity to make it so. Our love is stronger than we know and that’s on “Give it to the People”. Thank you to Issa Rae for allowing blackness to be so beautiful.

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Chisa Pennix-Brown
Chisa Pennix-Brown

Written by Chisa Pennix-Brown

Chisa Pennix-Brown, MBA Life Stylist, Podcaster, Mental Wealth Advocate, NC's #1 Small Business Facilitator #Author of The #90DayFocus (http://t.co/9CCgwjwrj4)

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