10 Important Takeaways About Success from Issa Rae’s ‘Insecure’

Insecure is a goldmine for success tips…if you’re paying attention. HBO’s Insecure is an Emmy-nominated show and one of the platform’s hottest shows. Written and directed by Issa Rae and Larry Wilmore, the show gives us a peek into the lives of four successful African-American Millennial women living in Los Angeles, California.

We watch Issa Dee, Molly Carter, Kelly Prenny, and Tiffany DuBois as they come of age in their late 20s and early 30s. While the show is full of laughs and entertainment, it’s also full of lessons about life that, at some point or another, we’ve all learned (or will have to learn). They’re just the facts of life.

Here are 10 things we can learn about success from Insecure.

1. Follow Your Passions

When the show first opens, Issa is presenting to a middle school class, discussing the after-school program she works for called We Got Y’all (which is a little racist, but the owner seems to mean well). While she’s up there, the kids are asking some hilariously inappropriate questions, but it’s clear that Issa isn’t enjoying what she’s doing. Especially after that first scene is over and we get to see her at her office and in other field assignments, we can tell that this isn’t really what’s in Issa’s heart. She doesn’t want to be doing this.

And I think that’s a great lesson in life. Always work towards doing what you love. You might have to do what you don’t like for a while, but as long as you’re headed in the direction of doing what you love, you’ll be a lot more successful.

2. It Can Take Some Time to Figure Out What You Want

Everyone would love it if we all just had it figured out and knew exactly what we wanted to do and be in life. But that’s not how life works. Life is a journey. And it takes you through different experiences to prepare you for what’s coming — for what you really want. Issa has to learn this. In later seasons, it’s revealed that Issa was going to go to law school with Molly but took a different path. It seems the path she’s taken isn’t one she’s happy with either, though.

So, she finds herself struggling to figure out what she really wants out of life while dragging her feet at her job. It’s not until she moves out on her own that she truly discovers who she is and what she wants to do with her life and her career.

3. Maybe Being Alone Isn’t All That Bad

We’ve been conditioned to believe that we should find a soulmate, settle down, get married, and start a family. We’ve also been led to believe that being alone is terrible, horrible, no-good, and very bad. But the fact is, being alone can push you to figure out who you are, what you like, and what you really want out of life.

That’s definitely the case for Issa. After she moves out on her own, she discovers that she still wants to do something positive for the community — just not as part of We Got Y’all. So, her being alone might’ve been painful, but sometimes it’s what you need to grow and change into the person you need to become to get the things you want.

It led her to success with The BLOCC, and later to working with NBW, that company that funds her projects and collaborations, allowing her to bring her ideas to fruition. 

4. Friendships Can Get Rocky, But They Can Be Repaired

As you grow and change, so do your friends. And sometimes that can seem like things are falling apart. But sometimes, all you need to do is talk things out, take things slow, and just support each other.

That’s clearly what Issa and Molly did in the later seasons of Insecure when their friendship began to get a little shaky. It’s not clear how it all started, but both women got a little too sensitive about each others’ jokes on one occasion after another. After a while, it wore on their relationship and they eventually needed some space from each other, which is completely okay.

Sometimes you need some space to reevaluate whether you want to remain friends. (Molly didn’t want to at first, but later changed her mind.) So if we give our friends a little bit of space when they need it, it could end up being the best thing for your friendship in the end. 

5. Sometimes You Have to Start Back at Square One

When Lawrence gets back on his grind and starts looking for a job again, he works with a headhunter that tells him he may have to settle for an entry-level job just for the moment. But Lawrence doesn’t want to get caught in the minimum wage trap and see his dreams shrivel up like a raisin in the sun. He doesn’t want to start back at square one.

But eventually, he caves and starts working at Best Buy until he can get the job of his dreams or until Woot Woot! (his app) takes off. Eventually, he ends up taking a job and being part of a team (something he didn’t even realize he wanted). That goes to show that sometimes life takes you back to square one for a reason. Trust the process and let life be your guide. 

6. Your Friends and Co-Workers Won’t Always Support You

I think this is clear when Lawrence presents his ideas to his new bosses who seemingly like the idea — or at least, they pretend they do. They then proceed to compliment his sneakers. The fuckery!

And then later, when he tries to stick up for his idea, his co-worker Aparna isn’t the most supportive, either. (But, then again, she knew what she was talking about, so…). And let’s not forget how Lawrence’s own friend (and girlfriend) didn’t exactly see the viability of his idea. We’re not sure if it was because of that horrible name (Aparna jokingly asks if any owls were harmed in the making of the app) or if they just didn’t think it was a viable idea.

Bottom line? You won’t always get support in the beginning, so be prepared for that or just keep your ideas to yourself until you’re finally on your way up. 

7. With Success Comes Great…Headaches

When Issa decides to follow her heart and throw the block party, she realizes what a huge undertaking it is almost immediately. From the mountain of paperwork she has to fill out to the vendors repeatedly and blatantly telling her no, they won’t participate (or donate) food for the block party, she feels defeated and wants to give up (and does for a while).

It seems like an uphill battle from the start. And it is. And things only get worse when her own best friend, Molly, doesn’t want to help her secure a music guest by using her semi-new boyfriend’s work connections (because she’s afraid that she’ll jeopardize the relationship…huh?). 

When the block party actually starts, Issa worries that no one will show up (or that only white people will) when it’s a festival meant for her community. There are tons of things to worry about when you’re trying to do something great. Nobody ever said being successful was gonna be easy. But it’s usually worth it in the end.

8. No Matter How Successful You Become, You’ll Still Have to Deal with BS

This is clear when Molly’s faced with a dilemma at work when one of her superiors (a white woman) asks her to talk to the other black girl at work for being too loud. She doesn’t say it in those terms, but we know what that means.

Instead of getting mad or acting out, Molly handles this situation in probably the best possible way she could. Instead of telling her superior that she’s not comfortable doing that, she tells them she doesn’t think it would bear as much weight coming from her as it would coming from someone in her superior’s position, which is really smart, actually. Go, Molly! Dealing with headaches is a part of life. You need to learn to deal with difficult people and situations. Working on your emotional intelligence will help you navigate the rocky waters of life with much more ease.

9. All Good Things Take Time

For a lucky few, success comes quickly and easily. But for most of us, it takes time. And that’s certainly the case for Issa Dee because she doesn’t even know what she wants to do. Success takes time to come for her, but she eventually does achieve it. If you can understand that instant gratification does nothing for your growth or success, you’ll be much more willing to wait.

So don’t rush it. Relax and enjoy the ride. As long as you’re actively working towards your goals and consistently reevaluating the methods you’re using to reach those goals (knowing when something isn’t working and when to change focus), you’ll get there one day. 

10. You Gotta Have Faith

Even if you can’t necessarily see the fruits of your labor yet, you’ve got to have faith that all of the hard work you’re putting in will one day pay off. That’s a hard truth for Issa to accept, especially when her friends are all so successful already. Molly’s a successful lawyer, Kelly’s a successful accountant, and Tiffany’s a…well, I’m not exactly sure what Tiffany does other than stand there and look pretty (oh, and pop out a baby two years too early).

It’s hard for Issa to watch her friends not only know what they want but be successful at those things. But she has faith deep down that what she wants will eventually be hers. And you should, too. Always have faith that you deserve what you desire.