The Quiet Confidence of Issa Dee

So, I’m back to watching Insecure like I always do every year. And every time I watch, I notice something I didn’t before, learn some kind of lesson or have a change of opinion. This time around, watching the series I’m realizing Issa was actually very grounded. Despite constantly being in messy situations and dealing with her signature awkwardness… my girl was confident!

Issa may have been broke, but the fits were not. I don’t know how she did it, but whatever was done was worth it. Because Issa’s fits were always nice. She always looked good no matter the bracket. She took pride in her appearance, even while barely making anything at her nonprofit job.

And working at a nonprofit isn’t necessarily a bad thing. The issue was that she had NO passion for it. And when you’re not passionate about your work, there’s no room to grow or flourish. On top of that, while she’s navigating this uninspiring job, she’s also carrying the emotional and financial burden of her boyfriend, who’s been stuck in a career fog for, what, 4 years?

Now, if your work life is a mess and your relationship is shaky, it only makes sense to lean on your friends, right? But Issa’s circle wasn’t just any friend group. They were a crew of high-achieving Black women. Molly was killing it at a big law firm. Kelly, A well paid accountant. Tiffany, A bougie event planner. These were quality women who didn’t hold their tongues. They spoke their minds, told l issa she’s cheap, got on her about her finances, and commented on her relationship. And sure, it was all jokes, but what they say… there’s truth to every joke.

I don’t think their words were ever meant to be malicious, but still, imagine going through the lowest of lows in your life and constantly taking those blows from your friends. It takes a serious level of confidence not to internalize that. To allow your friends be fully themselves without getting intimidated or resentful of their success. Still supporting them on with a pure heart, while you are experiencing (arguably) the worst part of your life… THAT’S confidence.

Outside of friendship, when Issa couldn’t afford her rent anymore? She humbled herself and moved in with her ex-situationship, Daniel. Yet even in that situation, she still had the confidence to speak up when something didn’t sit right with her. Most people would’ve either felt entitled and tried to control the space. Having no respect, or since they’re being helped, would’ve stayed quiet out of guilt for crashing at their place. But Issa. She balanced humility with self-respect.

Then there was the whole Condola and Lawrence situation. When Issa found out her ex was dating Condola; a woman she was working closely with. It was awkward at first. Understandably so. But after a while, Issa didn’t care. She loved working with Condola. She admired Condola. She wanted the best for both of them. Turns out, Condola and Lawrence were the ones who weren’t confident in their relationship. That’s why it didn’t work.

Issa, on the other hand, had already made peace. She wasn’t stuck in the past or threatened by their future.

Being supportive and happy for others comes easy when you’re where you want to be in life. But can you still do that when you’re broke, lost, and trying to figure things out? That’s what made Issa’s confidence so powerful. It wasn’t loud or flashy. It was quiet, grounded, and real. Even in the midst of chaos, she knew who she was.