What Molly’s Therapy Session On ‘Insecure’ Taught Me About Myself

Issa Rae’s Insecure provides unlimited fodder for Twitter’s never-ending battle of the sexes. While the incessant arguing occasionally feels like the modern day version of the Crusades, a series of religious wars between 1092 and 1291, there are other parts of the show worthy of dialogue that extends past the relived trauma of failed relationships.

On Season 2’s second episode, “Hella Questions,” Molly’s therapy session hit on something I suspect people who live ambitious lives have dealt with. The problem of “should.”

Molly, Issa’s best friend, is the only black woman at her law firm. Last week, she discovered although she was “killing it at work” she’s paid less than her white male counterparts. Her therapy session was a chance for her to unpack the dissonance between her salary in relation to the sacrifices she’s made for her job.

Molly listed a number of actions and activities she’s participated in. She breathed a sigh of resignation midway through her rant and stated her environment is an “all-boys club.” She told her therapist she’d eventually figure out how to navigate it and if she works harder “everything should be fine.” The therapist paused Molly’s rant and the following exchange occurs.

Therapist: You say that a lot. “Should.” You frame a lot of things in your life with “should.” Have you noticed that?

Molly: *dismissively* No.

Therapist: Two weeks ago you said “things should be easier for me as a successful black woman.” And another time you said “things should’ve fallen into place by now.” Is there a certain way you think your life should go?

Molly: I mean, I do have specific life goals. And I think that, if you work hard it sho…..ought to yield certain results.

Therapist: There’s a medical term called “magical thinking.” When we believe what we want can influence the external world as opposed to accepting things how they are.

Her therapist summarized her situation and ended their session with a question. “If your ‘shoulds’ didn’t come to fruition, would you be open to your life looking a different way?”

I think I owe Molly’s therapist some money.

It was at that moment I realized most disappointments in my adult life came directly from the idea I “should have been there by now.” I should have a high paying job. I should be a husband and father. I should be able to walk down the street to the dealership and walk off the lot with a brand new car.

Unfortunately, the goals I’ve set for myself are, for the moment, unattainable. I’ve had a number of false starts, self-inflicted mistakes, and some good old-fashioned bad luck. At various points, my aspirations, and lack of success, became such a burden I frequently daydreamed about a life free from it all.

In the past, there’s been a number of times I’ve stopped living, wanting, or having an inclination to do anything other than exist. I’d fantasize about quitting life and simply returning to a more meager existence in the spare room at my mother’s house. A choice my mother would more than welcome with open arms and a warm plate of oxtails.

Part of the difficulty for me, was examining where these desires came from. I’ve done a fair amount of legwork to actualize these dreams because I was brainwashed with the idea if you do things the way you’re supposed to do them, you’ll be rewarded. What I wasn’t taught, however, is what I should do with myself if none of them come to pass.

I don’t know what a life without a wife and children look like. I don’t think about how my life would change if I never found a rewarding, and high-paying, career. I’ve yet to consider my reality if I never got the chance to do the things I want to do in the exact way I’ve envisioned them.

Delayed gratification is a fact of life. Each time I was denied the chance to move forward with my dreams I figured some higher power deemed my sacrifices unworthy. Shit happens, so my upbringing taught me to think about two things when life doesn’t go as planned: either I wasn’t ready to receive the blessings I was so desperately working toward or I was being protected from whatever it was I desired.

I’ve been down on myself. I’ve cursed myself. I’ve compared myself to others and become irate at what I was judging to be a lack of progress. I played the “shoulda-coulda-woulda” game, which is essentially a self-pity party where I told myself I’d have all of the things I wanted if I would’ve made better decisions.

But what would happen if I just accepted life for what it is? How much better would my mental health be if I let go of everything that should’ve happened and take stock of everything that already did?

Seems like I “should” try accepting life as it is and not what I thought it’d be.