I inherited the family business from my older brother, Neil. He steered it well during his two-year tenure, packing sixty-two papers in one or two large cotton Ann Arbor News bags draped over his shoulders, then hurling them at front doors from his three-speed Red Robin bicycle.

When I was a fifth-grader, Neil took a job as a busboy at a Big Boy restaurant and passed the route on to me. From day one, I made it my own. Somewhere I got the idea to use a metal folding utility cart to carry the papers; possibly from visits to Grandma Bess in Brighton Beach, where in the early 1970s, every Pearl, Dick, and Fannie pushed and pulled such carts to carry groceries or laundry.

I never understood why I was the only kid in Ann Arbor to hit on the idea. The papers fit neatly in the cart, I didn’t have to carry a heavy load on my shoulders, and even the bulky Sunday papers could be hauled in one trip. I did have to make numerous repairs to the cart over the years, however, with jerry-rigged wires and clumps of duct tape. My old cart should be in a paper route museum somewhere with a placard: “Carried over 65,000 papers.”

I should mention that my oldest brother, Peter, did have the route for two weeks before Neil. It was an afternoon route, except for Sunday morning. Peter, up late one Saturday night, made a game-time decision to deliver the papers when they first arrived in front of our home, at 1 a.m. While Peter did live to see another day, those days did not include working as an Ann Arbor News carrier. The argument that ensued between Peter and my parents brought about his abrupt resignation.

My mother often contrasted Neil and me as delivery boys, with increasing detail over the years: “When Neil delivered the papers he would time himself, racing on his bicycle, trying to break his twenty-seven-minute record. And when you delivered, you’d have a friend with you, you’d stop off somewhere along the way, and maybe you’d come back two hours later. You always had a story to tell.” She would then comment how little had changed in her sons’ styles over the decades.

The paper route was my first extended foray into independent life, away from the shelter of home and school, away from the supervision of parents and teachers. For an hour or two, I would enter another world, a world of my own making. I was laying down the tracks for my independent connection to the outside world: a world of relationships with customers and friends; a world of interactions, transactions, and distractions; a world of choices, mistakes, reparations, and growth that would help set the course for who and what I would become.

For me, delivering papers was a social enterprise. When I did the math (three cents times sixty-two papers), I figured I made about $2 per day. So, I’d pay a friend somewhere between sixty cents and a dollar to join me. Sometimes I’d bring Starbursts or Spree along to keep the hired help happy.

Doug, Allen, and David (not his real name) were my most frequent partners. Their assistance wouldn’t speed things up; I wouldn’t take one side of the street and my friend the other. We would walk together, deliver papers, eat candy, and talk.

Those were the good delivery days anyway. There were just as many where conversations and paper delivery became complicated. With David the conversation would often go deep, although perhaps not with a great deal of accuracy.

Once, when abortion was in the news, he informed me that the procedure involved a woman being “scraped.” When I asked him how it was done, he said, “with a coin.” I accepted his explanation. We were on Norway Rd. at the time, near the home of my pediatrician Dr. Saunders. If I could do it over again, I would turn around and go right up the hill to his home for a consultation. It would have saved me a few years of misinformation.

If David and I went serious, Doug and I brought out the delinquent in each other. The Murphys’ house on Washtenaw was high up off the street, with a pear tree and several other tall trees in their front yard. Hidden behind a fortress of trees, Doug and I felt like lords in a castle. Watching the busy street below, we decided to pick pears and hurl them at the moving cars.

As we prepared to throw the last of the fruit, an angry man walked up the path and found us beneath the pear tree, holding the proverbial smoking gun. One of us had hit his car. He didn’t lose control, he didn’t call the police or ask for our parents’ phone numbers, but he did describe his shock and fear when the pear hit. And then he left.

Silent and stunned, Doug and I headed up the hill to deliver the remaining papers, absorbing on our own what had just happened. Life was real on the grounds outside of our castle.

Fortunately, Doug and I had faith in a being far greater and more powerful than us. At the final stop on the route was an Irish setter puppy chained to a post in the front yard, a puppy so beautiful he must have been touched by God. Doug and I named this puppy Guru Maharaja Gershtbaum. When we arrived, Gershtbaum would jump up on us, lick us, twist, and twirl about. He was our spiritual reward at the end of our long pilgrimage. We’d get down on our knees, arms stretched out in front of us, genuflect, and chant:

“Guru Maharaja Gershtbaum, oh mighty, Guru Maharaja Gershtbaum. Our savior, Guru Maharaja Gershtbaum, oh mighty, Guru Maharaja Gershtbaum.”

The route was done. No place we had to be. We could pray to and play with our Far Eastern Jewish canine savior to our hearts’ content.

Now that I was working, I felt rich. I kept my money in a black metal box at home. Occasionally, I’d get old coins from customers: silver dimes, silver nickels, and wheat-stalk pennies, that I’d put in my dark-blue Lincoln coin books. They had much more value to my “collector” mind than they did for real. I would have been better off, I’ve been told, putting my wheat-stalk pennies in the bank, so they could collect interest, rather than treasuring them at home.

The Ann Arbor News had their carriers collect from the customers directly. The cost was $3.20 for two months and $4 for every third month. I’d bring the News its portion each month, and the rest was mine.

While I was rich, I could have been richer. I didn’t collect regularly, especially as the balance grew. If I had an issue collecting, I’d avoid it. Two customers owed for over a year: Ms. Moe and Youth for Understanding.

Ms. Moe lived in a beautiful brick home with a slate roof at the top of Norway. Neil told me to deliver her paper under the green garage door, left open a foot or so just for this reason. She was the widow of the original owner of Moe’s Sports Shop, where I bought my first pair of Adidas Gym sneakers and so much more. Adidas Gym were the most basic of all Adidas, but they were “cool” and I’d coveted a pair for awhile. I felt an instant kinship with Ms. Moe because of this connection, though I never saw her the entire first year I delivered her paper. In fact, the only time I recall seeing her was when I rang her bell, trying to collect.

A very old, thin lady came to the big oak front door. She had wiry silver hair that looked like a short lampshade, the sides sticking out at a wide angle. I nervously followed her in to a large oak desk in a stately parlor. The house was dimly lit and filled with old wooden furniture. I watched silently as she sat down at a long desk, took out a ledger, and tried to write a check. It was only when she finally said her pen didn’t work that I dared to tell her that she’d been using the wrong end. I don’t remember what happened next, but I left without the forty-plus dollars I was owed.

Youth for Understanding, an international student exchange organization, operated out of a mansion on Washtenaw, directly across from the Murphys and their pear tree. They didn’t pay me for the better part of three years, but it wasn’t their fault. I’d enter and be so intimidated by a sea of desks, busy people, and a long hallway that I’d turn around and walk out. I brought them the paper every day, but never figured out how to get paid for it. I don’t think I ever asked.

Ms. Botom (pronounced Bo-tum) lived at the bottom of the hill on Norway, just down the hill from Mrs. Moe. She was a small elderly woman, a widow, and incredibly nice to me. She was always well dressed, perfectly put together, and smiling. For the holidays, she would give me a card with several half-dollars carefully and artfully taped and arranged. And she’d write something very sweet, letting me know that she thought I was a nice and dependable paper boy.

I had a crush, of sorts, on Ms. Botom and found a way to act on it. Somehow I even knew back then that if you liked somebody but they’re not right for you for some reason, you try to fix them up with a close friend or relative. I tried to set her up with my great-uncle Ben, whose second wife had recently left him.

I suggested to my mother we introduce him to Ms. Botom, so that she could become part of our family. My mother declined to take on the role of a shadchanit (matchmaker in Yiddish), but she still loves to tell the story.

When it was time to retire my utility cart, Mr. Wirth, the head of the circulation department, came to our home to thank my parents for raising children who served the Ann Arbor community so well. He also inquired whether there was a younger Chethik in the house. There was, but my much younger sister, Ducky, wasn’t yet ready.

Though Neil and I both served, our tracks were very different, and not just because his were left by bicycle tracks and mine by an old-lady utility cart. Neil took the shortest distance from point A to point B to point C. I stopped and started, zigged and zagged, and followed the sun and the moon rather than the clock, taking time out to throw pears at moving cars and stopping to pray to a beautiful Irish setter puppy. I once stopped in my tracks for thirty minutes or so at the O’Neals’, the first house on my route, to help Andrew celebrate his fourth birthday with his pre-kindergarten buddies. I put on a blindfold, played Pin the Tail on the Donkey, ate some chocolate cake and ice cream, and delivered sixty-one more papers … late.

Forty-five years later, as a child therapist, I think back to my years delivering the News as a time of building connections: with my friends who traveled by my side, with my customers who joined me during my business of growing up, with Guru Maharaja Gershtbaum and the other animals that showed up along the way. Delivering papers was more play than pay, more fantasy than fiduciary.

Today, I build castles and create stories with kids. I take care of business but see the present moment as more important than the endpoint. I attend to my goals, but I enjoy the tangents along the way. After all, it is the detours that often enliven us, making the rote a riot, and the route full of chances to play, stumble, learn, and grow.

Leigh Chethik is a child psychologist in private practice in Chicago. In May, he and his father, U-M emeritus professor of psychiatry Morton Chethik, published Cartoon Boy and other Stories about their play therapy work with kids.