What This Scene In The Season 5 Premiere Of Issa Rae’s Insecure Can Teach Founders And


In yesterday’s Season 5 premiere of HBO‘s hit show Insecure, we saw creator Issa Rae’s character Issa Dee and her friends returning to Stanford University (Issa’s real-life alma mater) for their 10-year reunion.  

While the others drive from LA, Issa is flown out to campus after being asked to speak on a panel of alumni entrepreneurs. Not only have they paid for her travel, but they have also given her perks like a handler. These are “big things” happening for her finally, and she even wonders if she deserves it. “This is super official…am I official enough?” she asks her best friends, who are excited for her.

Having just experienced success in her venture called BLOCC, she seems to be on her way after so many years of career uncertainty coupled with a constant urge to serve her community and be recognized for her strengths. The panel invitation is another clear validation that she’s making her mark, and even more notable is that it is amidst her other former classmates.

When we get to the panel event, the moderator asks her fellow panelists about their entrepreneurial success. After the first panelist’s response, Issa notices how well he is playing up the audience, notably ending his story with a line from Notorious BIG: “I went from negative to positive…” inviting applause and admiration from the attendees.  

Anybody that watches Insecure regularly has come to love Issa Dee for her real-time processing of these kinds of moments. After her fellow panelist’s answer, her focus has completely shifted from what she is proud of about BLOCC to wondering how she needs to get the same kind of applause from the audience. Who among us hasn’t experienced this kind of insecurity when around peers we think are more successful than us, at one time or another?

So as Issa plods through her response to the moderator’s next question, she recognizes the audience doesn’t respond with anything but silence.  

What does she do next? She, half-jokingly, half desperately decides to one-up her peer’s reference to Biggie with Tupac’s “To Live and Die in LA.” And for those of us 90’s fans who are in on the joke, she whispers to herself the famous line from Snoop Dogg at the 1995 Source Awards….” Y’all ain’t got love for Pac? Well, let it be known then….”

We can now see Issa Dee feels like she doesn’t belong on this panel of confident, steady, even smug entrepreneurs about how much they have achieved as founders. 

When asked when each knew they were on the right path in their careers, the answers vary from when one raised their first round of investment to when another knew they could quit their “tutoring job” and be okay.

But when it is Issa’s turn to respond, she is at an internal crossroads. She doesn’t feel as secure in her work yet, but should she just act like it?  

Should she come up with something that plays up to what she thinks the audience wants, which is another “look at me and how successful I am” story?  

Instead, she decides to speak from her truth and say that she doesn’t think she actually is on her right path, and there’s no way to be sure you’ve made the right decision. She lets her inner voice out and says:

“Maybe I’ll wake up tomorrow and realize that I’ve wasted all my time, and that’s time I can’t really get back.”

Did the audience suddenly applaud her honesty and make her feel like she was courageous for her honesty? No.  

And so Issa left the event feeling perhaps exposed, a bit of a failure relative to her expectations, and even more insecure. While her friend, Molly, found her “being real” inspiring, Issa felt like she kept it “too real.”

As an executive coach to startup founders, CEOs, and corporate leaders in the Fortune 500, I see this sentiment of “lost time” come up often among my clients. It’s not just a statement on the potential of a business succeeding or failing in the market or with investors.  

It’s an existential concern and affects the life and well-being of anyone who has decided to commit to a venture that may or may not pan out and which offers financial and reputational rewards that may never come or take years to receive.  

Yet because we live in a hyperconnected, socially transparent world where everyone shares their best stories of success, it’s easy to believe everyone around you has it all figured out.  

The comparison is often more acute when we look at our alumni communities because we share a common experience and elite networks, be it Stanford for Issa a decade ago or Wharton, Georgetown, and Columbia for me, up to 30 years ago.  

Founders start their companies for varying reasons: they’ve come upon a solution to a significant problem; they love the idea of working for themselves or not for a big, established company; the financial potential is appealing; they’re yearning to lead and create instead of being stuck in middle management; they can’t find a job that suits them, or no one else is hiring them, and the list goes on.  

But the one thing I’ve observed that they all have in common is that they want to succeed according to external factors (how others see and value them and their company) and experience personal fulfillment (how they feel inside). 

And from a coaching perspective, I tell my clients that the one thing that will get in your way eventually is believing you have to be like Issa’s fellow panelists and find validation in saying what you think everyone needs to hear.  

Sure, when pitching investors, you want to have a big, optimistic vision and tell a compelling story. But not one that has more style than substance and ignores the realism, data, and honesty about what can go wrong.  

And of course, when you’re the CEO, you need to be confident and come across as having it all together so that your employees and board can believe in your resilience and stamina to lead. But you will develop more mutual trust when you admit you’re feeling shaky and uncertain and confidently ask for help rather than hide your shortcomings.  

They will partner with you to solve critical issues that may make or break your company when you decide to be vulnerable and competent. And you will be able to be of much better service to your company and all your stakeholders when you choose to inspire through a higher level of self-awareness the way Issa did, rather than let the stories of your peers sway you to act out of accordance with your truth.  

The best thing that Issa did in that moment of sharing her vulnerability, which even her fellow panelists took note of, was that she chose the one road they didn’t: she shared the realism of entrepreneurship, even the dark side of it. And as any successful entrepreneur knows, when everyone zigs, you zag.  

For founders, the world around you may not always respond to your efforts the way you wish. But the answer isn’t in trying to appear perfect like you believe your peers to be. It’s in being self-aware and having the courage to stand alone, even in sharing your weaknesses. With that fearlessness to take the road less traveled, you will become the true success story that inspires others.

Nihar Chhaya is an executive coach to founders, CEOs and the C-suite and leaders at global companies, including American Airlines, 3M, Cigna, Coca-Cola, Draft Kings, Lockheed Martin, Raytheon Technologies and more. You can access his tip sheet on delivering tension-free feedback to your team and receive his monthly newsletter. 


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