An Education
Growing up I hated school. Learning wasn’t necessarily the problem; I’m sure I liked it as much as the next kid. My issue was sitting still for what felt like endless stretches in a scratchy Catholic school uniform. Like a cartoon when the bell rang, I’d leave a cloud of smoke in my wake, racing to the park or back home to shoot hoops, play stickball, or run one-on-ones with my older brother—I got “Mossed,” a lot.
Neither of my parents went to college. As a consequence, success for them meant that my brother and I would. Ideally, and in traditional blue-collar household fashion, one of us would become a doctor (Chris) and the other a lawyer (me). My parents believed simply that “education is a great equalizer.”
One typical weekday afternoon, while I was neglecting my homework and playing in the street, a beat-up Saturn sedan parked in front of my house. It really shouldn’t have been a surprise that for the remainder of my adolescence I would now have an hour tutoring session per week, and that my dad would take on a third job to pay for it.
Roger Perkins pulled up blaring Jimmy Buffet’s “Margaritaville.” This might be a confabulation, but with his flowy white hair bordering a mullet, cross earing dangling from one ear, and go-to Hawaiian shirts, if he wasn’t officially a Parrot Head, he was an honorary member. It’s difficult to describe his methods: a soft-spoken rhythmic voice, a magical ability to read and write upside down, a partially missing ring finger shrouded in mystery.
Whatever his tactics, it didn’t take long for Mr. Perkins to Miyagi me into a disciplined student, who could not only tackle reading comprehension exercises on end, but actually enjoy it. For me, the appreciation for my studies and the stillness it required was the ultimate gift. As my mother likes to remind me, “You were never a talented student like your brother, you had to work really hard.” Like all great teachers, Mr. Perkin’s impact reached far and wide. When he passed there were countless teary-eyed teens like me who would deeply miss his weekly presence in their lives.
It’s only now that I recognize the commonalities between him and my favorite college professor, Barry O’Connell. They not only share strikingly similar appearances, but identical demeanors and philosophies. In discussing career prospects post-graduation, BOC suggested I hop a train behind the Social dorms at Amherst College to the Pacific Northwest to volunteer as a forest fire lookout. Like a total cliché, who had the structure of being a student-athlete behind him and recently read On the Road in his class, I took the suggestion to embark on an adventure, cumulating in wooded seclusion with novels as my only companion, literally.
In hindsight, it’s likely he was only emphasizing his point: the world is your oyster. I couldn’t reconcile the positioning of the future as some boundless opportunity. Didn’t that mean this was the beginning, and wasn’t I reaching the finish line? My transformation from the boy who couldn’t finish a one-page book report on a half-heartedly skimmed Matt Christopher book to an honors graduate of a top Liberal Arts institution was nearly complete. My diploma would hang in my parent’s home as validation of their job well done. Mr. Perkins would look down proud.
In reality, graduation was the starting line, and I didn’t just stumble out of the blocks, I missed the starting pistol completely. The appeal of escaping to the West Coast stemmed not from a romantic desire to join the counterculture movement of a past generation, but the real need to run away from the problems of my present. I lived in constant dread that every conversation would inevitably transition to after graduation plans. Eventually, my plan became to study for the LSAT and go to law school.
Did this happen because: (a) the arbitrary assignment of future lawyer in my youth, (b) the well-trodden path for alums other than Finance or Medicine, (c) the need to grasp for something familiar like school when you’re utterly lost, or (d) all the above? Yes, it was “D,” but partial credit for “C.”
Law school went from hopeful dream to nightmare faster than the opening verse of the Meek Mill track. Hundred-person classes, the Socratic method, timed issue-spotting exams, betrayed everything I had come to love about academia. The picturesque New England campus replaced by an indistinguishable office building in Downtown Brooklyn. Once again hating school, I found respite in play—depending on the season I joined adult soccer, basketball, and flag football leagues. I also coached youth football and ran an offseason tutoring and training program, as if living vicariously would allow me to siphon joy like a Dementor.
Despite the overwhelming generosity and mentorship of my best friend’s mom, who fabricated a 2L summer internship program at her firm for me, I continued to regress. Years of muscle memory poured out of me like sweat underneath my ill-fitting polyester suit squeezed in an overcrowded July subway. While clicking through corporate emails looking for evidence of fraudulent gift card usage, I’d anxiously have one eye on the clock waiting for the earliest moment I could respectably dash for the elevator.
Needless to say, entering my final year of law school I needed to find a job. While I ran in place for the past four years, my peers signed lucrative offer letters to prestigious law firms, entered residency programs, and joined private equity shops. Like old Kanye, I questioned whether “I was havin’ a nervous breakdown / Like ‘Man these rappers that much better than me?’”
Determined not to let history repeat itself, I submitted job applications to any entry level role that tenuously related to the law. Mutually assured desperation resulted in a role at a legal startup developing a proprietary algorithm to match a network of vetted attorneys to SMBs. During my interview, one of the cofounders hovered awkwardly over me because there wasn’t a third chair anywhere in the office. As it turned out, this gig provided many foundational lessons. Now, I mostly view the experience as a missed opportunity to write an HBO sitcom about my experience. Back-to-back sales Directors were fired: one for spending more time getting swole at the Silicon Alley CrossFit; and the other for exclusively working on his hoverboard enterprise.
After a couple years at the startup, I finally made my cross-country trip. Not for solitude, but because, stealing Will Hunting’s line stealing Sean Maguire’s line, “I had to go see about a girl.” Through her friend, I landed a job at, as Anna Wiener describes in her memoir Uncanny Valley, “the social network everyone hates.” Despite bearing so much ill will, working for this company provided outsized social capital. For the first time in my career, a term that only loosely applies to my arc, when people found out where I worked their demeanors changed, for the better. Instantly, assumptions were made about enduring a rigorous hiring process and being carefully chosen from countless candidates. I, by extension of my employer, must be successful. No one knew I snuck in a back door.
Stepping through that door sent me careening down a rabbit hole. Work became building and launching products that turn lawyers into cats with augmented reality filters, bring cannabis to your door with a tap, and fuel binging together. These seemingly random initiatives, in aggregate, have given way to something new: an opportunity to make it easier to connect with teachers. In other words, helping others find their Mr. Perkins. Looking back, I’m starting to think, “It is written.”
Thankfully, this honed my skills making the transition from QB to lockdown DB seamless. Sean Legister, Andre Gary, Will and Andrew Reed never caught a ball on me in practice in my three years in the secondary. Check the tape or ask Billy McBride.
As someone who grew up with incredible privilege, this often-cited Horace Mann quote continued to carry some weight; however, as Anthony Jack’s The Privileged Poor demonstrates education alone cannot be an equalizer.
When he wasn’t tutoring me and other hyperactive kids in the pre-ADHD diagnosis days, Mr. Perkins would migrate south to Sanibel Island, Florida where he would stroll the beach collecting conch shells and shark teeth. Nothing’s cooler than when you are in fourth grade and your tutor gives you a bunch of shark teeth.
In my defense, “The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or a saw a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars.”
#freebritney
Cue the Drizzy “Right Above It” outro.