1. On Laziness (and Quitting a Job)

“Every business is trying to target Millennials, but who are Millennials? Now we are finding out that they are living with their parents. They don’t have the initiative to go out and find a little apartment and grow a tomato plant on the terrace.” — Martha Stewart (b. August 3, 1941)

Heaven is a place called your college graduation. I remember being enthroned on a foldable metal chair as I basked in endless praise from family, friends, and faculty members. My only concern was the fact that I had to quietly bake in hangover sweat as I donned a black cap and gown in the middle of May. While cameras and selfies captured every angle, I adjusted my decorated cap to make sure its Nicki Minaj lyrics were visible. It read, “Shout-out to my haters.”

It only takes a few years for a twenty-something to look back and envy the naivety they had on their graduation day. The lackadaisical attitude combined with a blissful ignorance as to what laid ahead. For Millennials, that would include a sluggish post-recession economy. One that was still learning to crawl out of a double-digit unemployment rate. That kind of economic climate lit a fire under the ass of every graduating member of Generation Y.

Disappointment was never an option for me. My Baby Boomer parents were college-graduates who built long and established careers at their respective companies for more than 25 years. Their success provided me with benchmarks for my own career path. That’s why I expected my college diploma to lead to employment — and it did. After all, rewards were reserved for those who worked hard. However, this reward paved the way for a disappointment that my parents could hardly fathom. Quitting my job after only four months.

There were a few red flags — starting with the interview. I handed over my resume, which I made my college roommates proofread at least fifteen times. I delivered impeccably rehearsed answers for every question I received. I performed this dog-and-pony show to perfection for every round of interviews. There was one minor setback. I didn’t exactly know what I was interviewing for. I knew that I applied for a job that could get my foot in the door of advertising. But, I couldn’t tell you what an Assistant Media Buyer and Planner actually was.

There was a solution for my ignorance: Google. One search gave me all of the information I needed. I discovered that Media Planners chose where advertisements should run and Media Buyers negotiated the price of the ad space. They determined whether a brand should put their money toward an expensive, show-stopping Super Bowl commercial or an affordable, reoccurring banner on an online newspaper. The job that I was interviewing for was a combination of these two roles.

Not only was I applying for a job that I knew little about, but I was also suppressing an initial career pursuit. I wanted to become a copywriter. One of those “creative types” in the advertising world who came up with the concept of the ad and wrote it. (Think: Peggy Olson from Mad Men, or as an IRL reference, Dan Wieden — the lucky guy who penned Nike’s multi-million-dollar “Just Do It” slogan.) However, in spite having a love for writing, I had zero professional experience as a writer. I didn’t even have the educational background. My parents would’ve chewed glass sooner than drop $125,000 on an English degree. That’s why I did something practical with their money. I majored in Business Administration (also known as the modern-day “undecided”).

Putting my ambitions on hold came naturally. The post-recession economy left little room for idealism. The job market was still tough, and every interview was to be treated as a godsend. Plus, a broke college graduate living at home was in no position to bargain. The last thing I wanted to do was look like an unemployed failure who was complacent and lazy. Especially on social media where all of my fellow graduates seemed to already have their dream careers. That’s why I interviewed my ass off for a position that I didn’t care about.

After three successful interviews, the final round was with the company’s founder. Kamran had the gravitas that every tall, burly, and bearded man in New York City seems to possess. His thick black eyebrows allowed him to pull off a clean-shaven head. Highlights from his elevator speech included an extensive background in media, a passion for what he does, and the fact that he’s a bacon-eating Muslim. He had an enviable level of charisma that you could hate him for if he wasn’t so impossible to dislike. I wanted to work for him. I wanted to be successful like him. I accepted the position as soon as he offered.

After one month, I became fully immersed in my new post-graduate career. I experienced the occupation in ways that no search engine could ever prepare me for. There was ad planning and buying as anticipated, but there were also late nights, tight deadlines, and Microsoft Excel. Not the kind of Excel that you throw onto your resume to make yourself seem more appealing to employers. The kind of Excel that makes you cry because you fucked up one equation and now your entire report is filled with question marks rather than numbers.

I knew better than to complain. My parents taught me to push myself and tackle challenges head-on, so I did. I took step-by-step notes on every Excel equation that I needed in my reports. I spoke up and bugged supervisors regarding any questions I had. I made a checklist on the subway every morning before I went into work. And with every attempt, I still managed to fall on my face. Incomplete reports, botched projects, and increasing side-eye from co-workers who couldn’t understand why I didn’t just get it. Their annoyance was especially obvious when one colleague accidentally IM’d me her shit-talking. “Why would Kristen even think she could do that?” she unknowingly messaged me. It was just the kind of woman-to-woman support that I needed.

I wanted to come into the office guns blazing with my diploma in one hand and my report cards in the other. I wanted to tell them that I successfully completed several internships. I wanted to prove to them that I was a perfectly capable human being. But, none of it mattered. Nothing could change the fact that I was failing at my job. And while the intention was to simply get my foot in the door of advertising, my end goal of becoming a copywriter could not feel farther away. I knew that aspiring writers should anticipate challenges in their career, but Excel is rarely one of them.

My misery was undeniable after the third straight week of crying during my morning commute. I found myself working late on yet another report that I felt completely apathetic toward. The office’s open floor plan made it painfully evident that I was the last person standing. I looked around only to find Excel on my screen and a half-eaten burger at my desk. The company celebrated every Friday by ordering burgers for everyone. I cried into my burger earlier in that day.

As I pushed through reports and burger tears, I saw someone out of the corner of my eye. Living proof that I wasn’t as alone as I thought. It was Kamran getting ready to call it a night. He smiled and waved goodbye as he headed out of the office with a carefree swagger. As he did, I searched his confident demeanor for guidance. Anything that could point me in the right direction — the one that he so clearly mastered.

“Hey, can I ask you something?” I hesitated before I sought his advice, but it was too late. He heard the anxiety in my voice and saw the half-eaten burger on my desk. His lighthearted smile transformed into an empathetic frown as he looked at me and nodded.

I asked him, “How do you know when to quit?”

My desperation gave him pause as he thought of an appropriate response. How is the founder of a company expected to answer that question? I was taken aback when his reply was both genuine and simple. But knowing him, I shouldn’t have been surprised.

“You quit when it’s not fun anymore,” he told me.

In high school, I thought it would be fun to run at a track meet. Sign-ups were easy, and the coach was laidback. On the day of the event, I gave up five minutes into the run. During that time, I realized that I never ran a mile in my life. I sat down and panted in a tree-covered area to hide my exhaustion from the cheering crowd. Then, I saw runners heading toward me. It was an all-boys track team. To prevent further embarrassment, I nonchalantly did some stretches as I pretended to be a jogger taking a quick break. Then, I looked down and noticed my huge bib number blowing my cover. The jig was up, and I didn’t look like a quitter. I just looked lazy.

I had about as much business being an Assistant Media Buyer and Planner as I did being a high school track runner. In both cases, I chose to fake it until I made it rather than accept defeat. For realms that I had zero real interest in, no less. Why? Because I thought I could be good at everything. Millennials were taught that true success was overall excellence — to be what college admissions called “well-rounded.” However, we don’t realize that attempting to succeed at all of the things means that you’re bound to fail at some of the things. It took four months in a mismatched career for me to understand that. When I did, things stopped being fun. So, I took Kamran’s advice and handed in my two weeks’ notice.

To my surprise, my parents were more than accepting of my decision to quit. When I broke the news to them, they empathized and shared personal challenges that they endured in the early stages of their own careers. The same careers of more than 25 years that I idolized to be long-lasting and unwavering. It was the first time I heard of such obstacles. And, I suppose that’s to be expected. People never talk about failures and pitfalls when they discuss their career. Everyone carries on with the guise of infallibility regardless of what generation they belong to.

On my last day, Kamran and the rest of my co-workers waved me off with a farewell gift. It was a Moleskine notebook that would mark the beginning of my writing career. As soon as I left, I used that notebook to write mock ads as I began building my portfolio. Then, I enrolled into the School of Visual Arts and paid for a copywriting class. After a few months, I officially restarted my career as a copywriting intern at a small advertising agency. Landing that gig was — in the words of my Nicki Minaj graduation cap — the biggest shout-out to my haters.

There’s a common misconception that quitters are lazy. I hear it a lot when people explain why Millennials can’t stick with a career or talk about the unemployed or find out that I quit my first job. The assumption is that I didn’t try hard enough, and therefore, I lacked initiative. That kind of rationale is convenient, simple, and in some ways, partly true. I was lazy — but not when it came to my newfound job in media. I was lazy when it came to pursuing my initial ambitions. I lacked the initiative to go after what I wanted. I gave up without even trying.

While quitting may be an admission of failure, quitting does not make you a failure. I’m now five years into my copywriting career, and I’ve had the pleasure of meeting a variety of fascinating quitters along the way. An art director who quit her job to become an entrepreneur. An account executive who left advertising to become an arborist. A fellow copywriter turned playwright. I smile for every big leap and transformation I witness. Because in my experience, quitting isn’t where your story ends. It’s usually where it begins.

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