My Journey Back to Writing

An on-again off-again love affair

“There is nothing to writing. All you do is sit down at a typewriter and bleed.”

– Ernest Hemingway

Like all adults, I look back on my youth with a mixture of nostalgia and regret, wishing I could go back and fix all the dumb things I did. One of these would be my effort towards my schoolwork. I wasn’t lazy — I was involved in student government, played varsity sports, made the morning announcements over the PA system, and was placed in the honors and accelerated classes — but I certainly didn’t try my hardest. I was the youngest of three and my parents thought they would be done after two, so I didn’t get the overbearing eye of being the first child like my brother or the first girl like my sister. I usually received the “Why can’t you be like the other two?” comment as a form of motivation for me and disappointment for them.

Of course, blaming my parents would be easy and, moreover, it would be incorrect. I was given every opportunity to succeed and thrive like my siblings and I pissed it away. I was often listless and depressed, bored and incapable of being happy. I was obsessed with my own self-awareness. I did work when I needed to and, in the middle of sophomore year, when it looked like I may not get into college (this was 1995, before colleges took anyone with a pulse and the ability to fill out a student loan application), I kicked it into high gear and achieved the grades I should have been getting my entire life. Some classes came difficult to me — I struggled mightily in geometry, but my best friend, who was brilliant, also struggled so I’m apt to blame the teacher and I still don’t get chemistry — but others came easily. History was a breeze, a subject that made sense to me and that I really enjoyed, and English was a piece of cake.

A decade later, my first business school class was in marketing and I couldn’t believe how easy it was. There were students in my class — professionals with good, high-paying jobs in the corporate sector — that were unable to grasp the simple aspects of the class and the field. I was stunned. Why wasn’t this so easy for everyone? I suppose that’s how geniuses like Stephen Hawking and Will Hunting feel with every subject, but for me I’ve only truly felt it twice: business school marketing and high school English.

English class was easy to me. Actually, that’s not true. I wasn’t enamored with iambic pentameter and couldn’t understand our teacher’s infatuation with The Canterbury Tales, but when it came to writing, it felt natural. If I didn’t receive exceptional grades on a writing assignment, it was usually because I was experimenting with new and unique styles and approaches. This is embraced by the literary community and certainly online, but most high school English teachers become annoyed by it. I’m not the most technically correct writer, but that’s often a product of style. I want to write the way I speak. I liked writing, but I never thought of it as a career.

Another regret.

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I was a tour guide in college (a damn good one) and I made sure I always did two things whenever I took a family around on a tour: get the student out of earshot of the parents and encourage him or her to ask me any questions that he or she were afraid to ask in front of mom and dad, and make parents realize that their child didn’t need to pick a major until about halfway through sophomore year. This was important to me, because I had been inundated since ninth grade with warnings that I had better pick a major — and a career — before I applied to college. When I realized this wasn’t true and changed my own major after 18 months, I wanted to be sure that others weren’t under the same unnecessary pressure as I. Plus, how many of us really know what we want to do with our lives when we’re in high school? To a high school student, 25 may as well be 75. I’m not sure if it would have changed anything for me, but I wanted to give those students coming behind me as much time as possible to decide.

Considering my personality and gregarious nature, I always thought I’d be famous (rare, I know) and I originally thought that would come in the form of being an anchor on SportsCenter. I decided to pursue communications and chose the schools to which I applied based on their comm. departments. After nearly two years of college, however, I realized that I hated communications and I hated the media field in general. I was naïve, but I never truly realized that to get to the ESPN desk you had to spend early morning and late night hours on holidays and in obscure places to get your foot in the door. Of course, I’m the type that always believes he could do something (like ace a test without studying for it), so I just figured it would all work out. I’d graduate and get a job easily. I’d be on camera after a week. I began to have my doubts when everyone was excited that a recent graduate actually made it on the air for the Bismarck station for which she worked. “See!,” one of the professors said, “if you’re lucky, that could be you.” That was lucky?

At the same time, I was thriving in my history classes and, more importantly, I was connecting with the professors. My school’s history department may have actually been stronger than its communications department, but history isn’t a subject that makes tuition skyrocket so it wasn’t really promoted. I loved history. It was reading and writing, what wasn’t to love? English was different. I understood grammar intuitively, but I didn’t want to study it and memorize what a gerund was. If I use it correctly, why do I need to define it? With history, I could read a book or article on a subject, often something I found interesting, and then write about it. I’ve always been in love with libraries and now I was expected, even encouraged, to get lost in the stacks, flipping through classic works and distilling them until creating my thesis on the legacy of John Adams or the assassination of JFK. The library was cozy and inviting. It was the opposite of the television station’s control room. I never felt comfortable working the switches or moving equipment. Conversely, I never felt uncomfortable sitting at a table with stacks of books and reading materials blocking me from the rest of the world.

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Graduation day. As I sat in my cap and gown, making jokes to friends and barely listening to the speaker, I kept repeating one phrase over and over again: “I don’t know.” I kept saying this because people kept asking me what I was going to do next. Did I have a plan? Did I have an idea? I just kept saying, “I don’t know.” I knew that I was going to spend the summer — and maybe longer — living in Portland, Oregon with my older brother, but I had no idea what I was going to do out there and had no clue what would happen if and when I came back. I wasn’t prepared to start a career. Internships? None. Graduate school? Eventually, but not yet. Job postings? I hadn’t looked at a single one. I knew I wanted to be a history professor — what better way to be involved in history while also being able to spend my years on a college campus? — but I had no idea how to get there. I had been so intent on enjoying every last second of my collegiate life that I hadn’t given a thought to the next 60 years. I imagine this mentality is why so many retired athletes go broke.

I was home for a few weeks before going to Portland and that period of time was a disaster. For my parents, college was never even an option, and though they now see the reality of the job market and the glut of college graduates, at the time they thought a degree was a guaranteed path to a career. After all, that’s the way it had been in the ‘70s and ‘80s. So while I spent the month of May lying around the house reading, doing housework, and moping because the best days of my life were now behind me, they thought I was lazy. My father suggested I apply for a job at McDonald’s. When I told him that I hadn’t gone to college to work in fast food, he shot back, “So you went to college to sit around here and do nothing?” Touché, sir.

Portland wasn’t much better — I had zero money, zero contacts, and zero motivation, a deadly combination — but I began studying for the GRE. I’d been wallowing in self-pity long enough. I had decided that I would go home, take the test, apply to grad school for a master’s degree in history, and start the process of becoming a professor. I decided that I would go to school part-time so as not to incur more debt. A plan was slowing taking shape, but I still had no prospects for the full-time part of my schedule. I went back to the delivery truck job that I had worked the previous few summers and prayed that I wouldn’t become a lifer there. I threw my resume on Monster and Careerbuilder and figured something would happen.

Something did. Sort of.

In early October, I received a call from a staffing recruiter for a temp agency. She asked me to come in to their office so that they could talk to me, test my typing skills, and make sure that I was appropriate to represent them on some thankless temp assignment. I threw on my suit, went in, did my thing, and came out with a promise that I’d probably have something in a few days. I did.

The following Monday, my father and I drove the twenty-plus minutes to the train station — he behind the wheel, me riding shotgun — then hopped on the train for the hour ride into the city. My assignment was at a well-known, international fundraising organization and its Philadelphia office was literally across the street from my dad’s. Pretty remarkable. We would commute together and occasionally have lunch, but I was still under his roof, and thus still his responsibility, so it was hard for him to not fret about my future. Now that I have my own home and my own family and I see him about once a month, I miss this time together and wish I had handled myself — and our relationship — differently. Just another regret.

I was promoted within a week (“head temp” wasn’t the title, but that will suffice for the purposes of this story) and I quickly felt like I fit in with the office perfectly. I stayed there through the holidays, but the assignment expired at the end of January. I had to move on to another, far worse assignment in the exurbs, before being rescued because someone at the fundraising organization was retiring. (This was early 2003 and she had never turned on her computer. I think she had an affair with Don Draper at her previous job.)

Now I had a regular, full-time gig with benefits and I would be starting graduate school in the fall. Though it was later than expected and I had taken a circuitous route to get there, I had arrived. The spring and early summer are the lean times in the office and there were entire weeks where I had nothing to do, but was told to try to look busy. With nothing to do and nothing to read — compared to today, the internet of 2003 is like black-and-white TV compared to an LCD — I began to write. I didn’t have a specific motivation or reason. I had time, quasi-privacy, a computer with Microsoft Word, and a need to do something with myself, so I wrote.

I didn’t think I had anything imaginative to write, so I decided to write nonfiction. Like all twenty-somethings, I thought my life was fascinating and unique and had to be documented for the annals of history, so I wrote a collection of essays detailing stories that had happened to me. They were no different from anyone else’s stories of partying in a major American city and most of them could have doubled as Entourage fan fiction (“One night, while we were hanging out at a bar trying to talk to girls…”). Though the stories were honest, my emotions were not. I wasn’t being honest and the writing suffered greatly.

At the time, though, I didn’t know that. I, of course, thought I had a masterpiece on my hands. Never mind that there was not only someone else doing the same thing, but doing it far better and far more successful than me, I was going to get published. Who needs a job with benefits when your book sells a billion copies? I found the names of literary agents and their addresses and spent my own money sending out copies of my manuscript to them. I knew it was a shot in the dark, but I held faint hope that someone with vision would see what I was up to, snatch me up, and get me a book deal.

Instead, I received nasty rejection letters. For people charged with preserving and promoting the written word, I was stunned by how vicious these letters were. Apparently, I’m not alone. The nicest of them were the standard rejection of “This isn’t for us. Good luck!,” but others were far more personal, telling me to “stop wasting [their] time,” “keep my head out of the clouds,” and “quit writing.” The experience scarred me. Just like my failed music career, I realized that I would not be a professional writer and I vowed not to send another manuscript to some old, bitter agent that hated my entire generation.

I never stopped writing, though.

I dropped out of the master’s program after six weeks. For as much as I had loved history in undergrad, I hated it as a grad student. In my sixth class, I had a sudden epiphany. This was not for me. I enjoyed my day job far more than my night class, so why should I keep going? What was the point?

I suspect my parents were a bit disappointed, but I had a full-time job and I was making plans to move out of the house and let them finally get their retirement on. They still felt I had fallen far short of my potential, but they no longer feared that I’d be living with them well into my forties. A friend of mine bought a house and I moved in. I arranged my room with meticulous care and set up my computer so that I could look out the window while sitting at my desk. It was my first writing space. I loved it.

In the two years I lived in that house, I wrote whenever I wasn’t doing work or hanging out. I wrote five manuscripts, a collection of short stories, and long-winded reviews of books, films, and albums on Amazon and other sites. I wrote every chance I got on any topic and still the words just spilled out of me. I couldn’t contain them, I could only hope to organize them.

Toward the end of 2005, my friendship with my roommate/landlord was on its last legs (if you want to end a friendship, live with that person after college) and I was shopping for a house of my own. I found one, moved out, and became focused on my home and my future. I had met a girl and we were starting to get serious. The job that had so excited me two years earlier was becoming stale and monotonous. It was time to live like an adult rather than trying to keep living like a college student with a little extra money. It was time to grow up.

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New Year’s Day, 2011. I took stock of my life. Over the previous five years, I had asked a girl to move in with me, changed jobs, been accepted to business school, asked the girl to marry me, graduated from business school, changed jobs again, gone to Montreal for my bachelor party, and gotten married. I had done a pretty good job of growing up. My former roommate hated me and I didn’t see my friends as often as I had, but there were more important things on which to focus my time and attention. I began wondering what was next.

Aside from two very short guest posts and other minor contributions to the website for the hip-hop magazine XXL, I hadn’t written a thing since buying my house. My future wife really enjoyed my writing and urged me to return to it, provided that it didn’t conflict with my career in finance or our plans for the future. I dismissed these thoughts almost immediately and, like my days of playing varsity basketball, made my peace with moving on.

Then, during the first week of January, I received an email from the founder and editor-in-chief of a fledgling Baltimore-based sports and pop culture website that I had been reading for some time. He offered me the opportunity to write a weekly column about the NBA, my favorite sport, and anything else I wanted to address on the site. He couldn’t pay me, he said, but he would give me almost total control over the content. In his mind, he was offering me a roster spot that he had been unable to fill. In my mind, he was offering me a road back to the world of writing.

I attacked the opportunity with zeal and although my first few months were far from spectacular — I was rusty and hesitant — I slowly began to find my rhythm and my voice. Most of all, I found the joy. I remembered why I had loved writing and why I had done it for no one but myself. Now that I had an audience, I was going to make the most of the opportunity.

I watched and studied the NBA as I never had before, spending hours crafting my column and thinking of topics to address. I tried to write as well as those that I read religiously on Deadspin, Yahoo!, ESPN, and, eventually, Grantland. Then, I began to get the itch to write about other things, not just sports, but life and my experiences. I didn’t think of it as catharsis. I thought of it as something that a person may want to read and, if they liked it, maybe they would read my other stuff.

For the next eighteen months, that column helped me slay a lot of my inner demons and come to terms with my life, both in the past and the present. In addition to the NBA, I wrote about going to therapy, the founding fathers, Jay-Z, depression, food, 50 Cent, regret, craft beer, Macklemore, my prom date sleeping with my friend, Wu-Tang Clan, becoming a father, becoming a godfather, 2Pac, racism, Superman, the Beastie Boys, ESPN, IKEA, Chuck Klosterman, being bullied, cooking, Tina Fey, and the death of my best friend, among many, many other things. I wrote guest posts for other blogs and began the process of writing books, the latest of which, The Notorious B.O.O.K.: Sports, Rhymes & Life, is a collection of the greatest of these essays. I wrote things I had never admitted out loud before and gave an outlet to the voice in my head that wouldn’t leave me alone.

Most of all, it gave me the courage to keep writing. Whether anyone is reading or not, I’m going to keep writing. I’ve had books sell and I’ve had books not sell, but I’m going to keep writing. I have a demanding job, a long commute, and take pride in being a very involved father in all aspects, but I’m going to keep writing. Family and career commitments forced me to relinquish my regular column, but I’m going to keep writing. Recently, when I didn’t have my laptop with me as I ate dinner alone at a hotel bar, I began writing longhand. No matter what happens, I’m going to keep writing. Stephen King has said, “Writing is not life, but I think that sometimes it can be a way back to life,” and I could not agree more. Just as I’m going to keep living, I’m going to keep writing.