Dog days

Author: William Kearney ’08

We are a restless generation. We do not have the patience to let our existential crises simmer until middle age. At 25 I found myself, like many others, a winner of the Millennial Trifecta —college graduate, unemployed, living at home. I realized it was a full-blown quarter-life crisis when I no longer felt compelled to wear pants when I took my puppy for a walk. He couldn’t hold it, and I couldn’t take it. Each night I hoped that somewhere between the end of the block and back I would find the answer to what I should do with my life.

The dilemma was not new. After college I moved into my brother’s apartment in Washington, D.C., and quickly landed a job with a global public relations firm. I took the job because it satisfied my only criteria: It was offered to me. Unlike most of my friends, I did not have a job offer before graduation so I was desperate to find something. Anything, really. Since the job cleared that high standard of excellence, I figured I was well on my way to success and personal fulfillment.

Illustration by Jeffrey Fisher

Two years later I came to the unsettling realization that I chose my job not because it felt right but because it looked right. I finally faced the questions I had quietly tiptoed around each day. Why, I asked myself, am I not fulfilled? What do I want to do with my life? Why does my brother’s sizable dog insist on sleeping with me in a twin bed when his master luxuriates in a queen bed just a few feet away?

In pursuit of answers, I traded my PR firm in D.C. for a small start-up in New York City. I hoped a fast-paced job at a growing company would help make up for lost time. I did not want to fall further behind my peers professionally, and a start-up seemed like the perfect place to catch up. In my haste, I fell victim to the same mistake I’d already made. Yet again, I elected to define myself by where I worked instead of by who I was. Except, who was I?

That question and the questions that brought me to New York remained unanswered, but my company gave me plenty of free time to reflect. A year after my arrival, the entire staff was fired because the venture was hemorrhaging money. The company lacked purpose, and so did I.

Thus began my quarter-life crisis. I watched friends tack letters like M.A., J.D. and M.D. after their names and upload Facebook albums of weddings and babies. Human babies! Meanwhile, I felt like I could barely take care of myself. Maybe to prove that was not the case, I got the puppy I always wanted. I named him Mr. Eko, after my favorite character from the TV show Lost.

I spent the better part of a year freelancing and scraped together just enough money to keep my tyrant of a landlord (love you, Mom!) from tossing me to the curb. Eko, too, did some scraping and freelancing, but it happened to be on the legs of our landlord’s favorite couch. During that time, I loudly and publicly blamed my puppy for my lack of opportunities — I could not go to graduate school or find another job because I had to take care of Eko.

I do not know if anyone else believed my proclamations, but I certainly did not. Eko was not my captor, he was my liberator. He gave me time to think about my future. He was my unwitting co-conspirator. After our late night walks I would hold Eko against my chest and whisper, “What are we going to do?” as if he might have the answer.

Eko did me one better. Turns out, he was the answer. While scanning a job board I saw a post that read, “ is looking for a freelance writer/pet lover to travel the country with their dog, explore the best pet-friendly destinations and write about them.” I immediately convinced myself the post was a prank. I figured it was my sister’s retribution for April Fool’s Day when I posted her phone number to Craigslist under the title “FREE PUPPIES!!!” How was I supposed to know half the island of Manhattan would call her?

I did not know what was, I did not know what the details of the gig were, but I immediately knew I had to go for it. Not only would an adventure with Eko be fun, but a road trip would also give me more time to think about what I should do with my life. Terrified the opportunity might be fake and more terrified it might be real, I submitted my application.

I made the first cut and submitted the requested writing sample. I made the second cut and scheduled a final round video interview. They asked that Eko participate as well. When I sat Eko down next to me and answered the call, there was still a part of me that believed my sister would be laughing uncontrollably on the other end, reveling in her glorious payback. Thankfully, that was not the case.

I felt I did an admirable job determining which questions were directed at which interviewee. “What is your vision for the blog?” was for me. “How did you get so cute!?” was not. Three days later, based largely on Eko’s good looks, we were offered the gig. Yes — I am sticking with “we” — if your dog gets you a job it is only right you give him some pronoun credit. My co-conspirator was now my co-worker. Two weeks after that I picked up a red rental SUV, which my dad christened “Clifford” after the Big Red Dog, and we hit the road.

Once the journey was underway I noticed a slight problem: I alone was responsible for charting our course and choosing what to write about, and I had no idea what to do. My existential question of purpose had become a functional question. Sure the blog had a general directive, but I elected not to ask my contacts at Petcentric any follow-up questions. I worried my inquiries would prompt someone in accounting to ask, “Why are we giving this guy money to play with his dog?” so I kept quiet.

Our trip was a year-long, cross-country, cross-species adventure that included everything from marching in a Mardi Gras parade to surfing together in the Pacific. I never quite figured out what we should do on our journey, but I think people enjoyed reading about it for that very reason. At some point I stopped looking for answers and started looking for opportunities. Those were plentiful. One day we hiked a mountain, the next day we dressed up as the Blues Brothers and went to a costume party at a bar.

We traveled alone, but Eko saw to it that we were never without friends. From children to business executives to a bride on the way to her wedding, countless people felt compelled to stroke Eko’s soft coat, sigh and share a piece of themselves.

“I really needed that,” said one. “I miss my family,” said some. “Thank you,” said all. I started to suspect that in the space between those words hid the truth: No one is ever completely sure they are where they should be, doing what they should do.

I thought about that suspicion as I drove. Thoughts of careers, degrees and family stretched into a tangled future. Feelings of regret and envy reached out from a recent past. But was it past? I lived in a rental car with my dog. I loved the adventure, but what about afterward? Did I regret my choices? Would I regret my choices?

Fifteen thousand miles and one year later, those questions remain. I learned that no amount of road and no amount of time can put any distance between me and myself. I am 27 years old, and my livelihood is contingent upon the whims of my dog. This is not the answer I was looking for, but it is the opportunity I have found.

The rest is up to me. And Eko, of course.

William Kearney’s essay was one of four second-place winners in this magazine’s 2013 Young Alumni Essay Contest. The author and Eko live in Chicago; check out their adventures at and contact him at