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This Season, Issa's Insecurity Is About So Much More than Self-Esteem

On Sunday's episode of "Insecure," we see the financial side of Issa's problems—and it's painfully relatable.
Photos courtesy of HBO

Less money, more problems.

Or at least that’s the case for Issa, who’s just trying to find a way to stay afloat. In what might be Insecure’s most relatable episode yet, we learn that Issa’s money troubles are not going away anytime soon. Though the last two seasons have hinted at Issa’s financial problems, we’ve never gotten as explicitly into the nitty-gritty as last night’s episode. Insecure shines because of its relatability. Few shows dominate Twitter trending topics or fuel fiery debates between the sexes quite like Insecure. It is because the show feels so honest and real that it succeeds. But this season, the show enters more uncomfortable terrain with its characters and the problems stemming from insecurity. Here, vulnerability is not just a question of self-esteem; it also applies to the emotional insecurities we feel when facing others or, more troubling, the financial insecurities that continue to plague a generation of Black millennial women like Issa. It is an honest look of dismantling one’s pride and overactive ego—useless defenses built up from one’s insecurity.


We know that besides Lawrence’s unemployment checks, Issa likely financed her and her ex-boyfriend’s entire lives in the two years before their season one breakup. The couple didn’t live in a fancy neighborhood of Los Angeles (even though Issa was still eventually priced out of her home by gentrification), and after receiving a demotion at work last season and losing her car, Issa’s finances certainly haven’t gotten any better.

But in Sunday’s episode, these issues come to a head as Issa grapples with trying to find an apartment in a highly competitive market. Time and time again, she is rejected for not meeting the right credentials. Unlike past situations, like when Lawrence broke up with Issa and Issa began a dating rotation, there doesn’t appear to be a quick "fix" for Issa. She can’t just run to Molly for advice after cheating on a partner or hop on Tinder for a self-esteem boost. No, Issa is essentially "on her own," left to make a real game plan about her future that won’t just neatly resolve itself in a few days.

But unlike the Issa of season one, who waffled over a breakup with Lawrence, season three Issa is ready to take (some) action. She is a slow mover, but she still moves. Unlike Lawrence, who finally got his life together and snapped out of a depressive un/underemployed funk within a matter of weeks, Issa has only taken small steps to improve her life, like getting a side gig as a Lyft driver. But Issa’s most profound step toward self-improvement just might be her new willingness to relinquish her ego and reach out for help. Not all of us can jump into lucrative fields of work to snap out of a personal or financial bind—some of us must humble ourselves to those closest to us just to make it through the day.

When do we allow ourselves to be vulnerable? When do we let go of the fear of failure and instead lean into the possibilities of personal progress, however small they may be? For Issa, that time came swiftly. No longer comfortable with her boundaryless living situation with Daniel and frustrated with demoralizing working conditions, Issa turns to her friend Kelly. Always one of the frankest sources of humor on the show, Kelly is also perhaps one of the first people to honestly keep it real with Issa. Kelly is privy to some of Issa’s most personal (and sensitive) details, from her financial bank statements to her credit score (which hovers stressfully in the low 400s). This is not the kind of information one typically shares over brunch—and yet, this kind of vulnerability is precisely the sort of thing that many of us need to survive our twenties and thirties.

Though most television characters have prominent and successful careers which leave discussions of finances off the table, we’ve seen over three seasons that Issa is not like most television characters. As the episode progresses, Issa quickly learns she is not the only insecure one, as Daniel’s vulnerability is on full display when he grapples with feeling inadequate in his career. Although she is in an awkward place financially, Issa still exhibits moments of agency, like when she finally squares up to talk to her boss about their company's numerous problems. Knocked down nine times, but Issa gets up ten.

In the end, there’s no quick and easy solution for her financial troubles. Unlike Carrie Bradshaw, who received a fat check from one of her best friends when she needed help keeping her apartment, Issa’s friends are here instead to offer her concrete advice and real-world solutions. Issa’s decision to be vulnerable with her friends and open up about her problems results in steps to better her life, not an end-all-be-all solution—which is deeply familiar and true to life. Getting older doesn’t always mean we’ve mastered growing up.