
Almost from the moment my middle son Ben could speak, he began asking for a pet. As much as my husband and I love animals, with full-time jobs and two other children, we weren’t interested in taking on any additional responsibilities.
I grew up with a spirited Siberian husky who possessed the energy and endurance of a cross-country team and was asked not to return to training school. So, despite Ben’s repeated pleas for a pet, we turned him down again and again. Undeterred, he befriended every dog on our block.
When he turned 9, he began asking if he could start a pet-sitting business. Initially, that seemed like a major undertaking, but when I was laid off in 2014, I found myself with more free time and fewer reasons not to support our son’s entrepreneurial spirit.
Ben called his business “Ruff With Me.” I had to tell him that with a name like that, we wouldn’t be advertising on the internet. Instead, he and his older brother made flyers and raced around the neighborhood, dropping them into mailboxes. I limited his business footprint to within walking distance of our suburban home.

He started getting clients
Before long, he had a few clients — a shih tzu, a black lab, and two cats. Because Ben was young when he started, my husband or I accompanied him on these gigs, ensuring he followed all the instructions, locked the houses, and went the extra mile by bringing in packages and mail and pulling up garbage cans and recycling bins from the curb.
He would text families with updates and photos so they could see their pets were doing well. We jokingly referred to this as the “Ruff With Me difference.”
Through word of mouth, his business grew, and as he got older and we became more confident in his abilities, he started doing all of the work by himself.
During his 2016 spring break, Ben found himself particularly busy caring for about five different pets in our neighborhood. After about a week of waking up before 8 a.m. to walk dogs and feed cats, he realized that perhaps pet-sitting was far easier than managing daily care indefinitely.
He learned a lot from this endeavor
It wasn’t always treats and belly rubs. One morning, we arrived to walk a dog and found that she’d gotten into a bouquet of flowers left on a low table. We alerted her family, researched the flowers to ensure none were toxic, and stayed with her for the rest of the day. Luckily, she was fine.
Seeing how Ben had risen to the challenges he faced while pet-sitting gave us greater confidence in his abilities. Eventually, when a friend who knew of his love for animals told me an 8-year-old cat needed a home, we adopted him, and he brought us years of joy. When he passed, we adopted two more cats.
Ben’s 20 and in college now, and a few of his clients have crossed the rainbow bridge, but he’s still in touch with several families. Over the past decade or so, he estimates he earned around $8,000. Early on, he opened a bank account and saved most of the money he earned, but he did spend some on outings with friends and golf gear.
Though he has a summer job lined up this year, Ben says he’ll never fully retire from pet-sitting.
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