What It's Really Like to be a Dog Walker with Two Side Hustles

In our 9–5 series, we ask inspiring #bosses what a day on the job entails. This week, Lauren Reid, owner of City Paws dog walking service—and part-time server and flight attendant—gives us a glimpse into her grind

Dog walker

Lauren Reid and her dog squad (Photo: courtesy Lauren Reid)

Age: 32

Education: Bachelor of arts in anthropology with a minor in geography from McMaster University

Length of time at current gigs: Six years as a dog walker and owner of City Paws; three years as a server; seven months as a corporate flight attendant.

Instagram: @tocitypaws

How did you start dog walking? 
I traveled after university for about four years and during my last trip at the end of 2009, the remainder of my friends who had been lingering in my hometown of Mississauga moved to Toronto. I was in Buenos Aires, Argentina at the time and dog walking is really big there. You see people everywhere walking [multiple] dogs and I was like ‘I should do that. That would be really fun and I think I’d be good at it.’ When I got back from that trip and had no friends left in Mississauga, I was like ‘OK, it’s now or never, I’m going to move to Toronto and try and start a dog walking business.’

Did you always want to work with animals? 
I remember wanting to be a vet when I was young but as I got older, I couldn’t bear to see animals in pain. So I figured out a way to work with them in a positive way.

How did you get the business off the ground?
My start up costs were a couple hundred dollars. I had to build a website and get some business cards printed and I just started there. I compare it to being a hairdresser with little experience in terms of gaining clientele. It was a hard start for the first 14 months or so. I was barely making ends meet and then all of a sudden, once I could build it up to having more than one or two dogs on a walk, people would ask me for my card and from there it got bigger really fast. I was at the point where I was about to throw in the towel and then very quickly that changed into me having to hire somebody to help me.

How many employees do you have now?
I’ve had up to six employees but at the moment, I’ve got three really good people working for me that handle things when I’m on the road but I oversee everything—scheduling, payroll, meeting new clients and taking in referrals.

What was a typical day like when you were walking dogs yourself all day? 
When I was only walking dogs, I would be up and out of the house at 9:30 a.m., in my car, with my coffee, my lunch packed, and doing three or four walks with six dogs each all day, every day. Those were definitely really busy, stressful days, so I’m at the point where this is the way I like to do it—to oversee the business.

Do you still do a lot of actual dog walking yourself? 
I don’t have a walk of my own anymore but I end up walking dogs on average once a week, especially in the summer as my employees want to take days off and go on holidays.

Have you ever gotten attached to any of the dogs that you walked?
All of them. Even the ones that are terrible, I still love so much.

What’s your dog walking clientele like?
It’s a total mix. I would say the majority is people who are in the spot where they weren’t having kids and they got a dog. They got the dog first and now three years later, they’ve had a kid and they decide to keep the walks for convenience. Then they see how happy the dog is or, if the dog has behavioural issues, how the group walks are helping. Often my clients are also people who have a short work contract where they’re going to be really busy for a few months and in the end, they stay on because they see the difference in how happy the dog is.

What’s something that would surprise people about being a dog walker?
That it’s hard work. It’s a lot of fun being around the dogs and they’re really good for you emotionally and make you feel really happy and that’s why most people are drawn to the job. But on top of that, being with dogs all day is extremely trying on your patience, especially when you’re doing it in the city where things like parking and random people on the streets are serious obstacles. Summer and winter are also absolute polar opposites in terms of quality of life while working. The summer is so much fun and even the beginning of winter is still fun when you first get snow but then by the time you get to March, you’re like, ‘I feel dead inside.’ [laughs]. But then May through October, you have the most amazing job in the world.

Dog walking

“By the time you get to March, you’re like, ‘I feel dead inside.'” (Photo: Courtesy Lauren Reid)

What is the best part of being a dog walker?
Being with the dogs and seeing how happy they are. Being in a pack is really empowering for them, because that’s how dogs are meant to be. We domesticate them, they live in our homes and we give them lots of love, but in the pack is where they really thrive. And you can see that, so it’s a serious pick-me-up.

It’s interesting that you got turned onto dog walking through traveling and you’re now also a flight attendant. How did you get into that line of work? 
I did the dog walking for about three years but I was getting a little bit lonely by myself all day, so I got a job working at the Ritz-Carlton hotel serving in the lounge; I wanted to be part of a team again. From there, I met a girl who is a corporate flight attendant and we hit it off and with my experience of working for a well-known luxury brand like Ritz-Carlton, I was kind of a shoe-in.

Is being a corporate flight attendant different from being a commercial flight attendant? 
When people charter private jets, they need a flight attendant on board, so I go along with them. The biggest perk of this job is that I stay wherever the passengers stay for however long their trip is. They pay for my hotel, food, taxis and cell phone, and I get paid by the day to be there. Some trips, it feels like you’re being paid to be a tourist. I get them there on the flight and then I have my free time until they want to come home.

Do you work directly for an airline? 
No, I’m an independent contractor and work for myself.  A flight attendant staffing company essentially works as my broker and puts me on flights working for several different corporate flying companies in the GTA.

So you basically have three jobs. What’s a typical day like?
No two days are the same but I would say generally, I’m overseeing things for City Paws. I’m double-checking the schedule and waiting for any cancellations or add-ons, so I sit by my phone in the morning until noon. Then I’ll go to the gym or grab lunch or if I have a couple of neighborhood dogs that I’m walking, I’ll load my Labradoodle Billy up in the car. She comes everywhere with me! We might walk dogs, we might go to the park, or I might take her to the beach—I try and get her to water every day—and then if I’m working at the hotel, I’ll go there in the evening and Billy sleeps all night. 

How do you juggle your three jobs?
I have to stay organized, especially because the flying is on call. I could get called to go on a flight tomorrow and I am walking dogs tomorrow, so I would have to make sure that gets covered. I have a lot of help, amazing employees who communicate really well with each other and iMessage is amazing for when I’m away and traveling—WiFi has changed my life completely!

What’s the biggest difference between your “day job” as a dog walker and your side gigs in luxury service?
It’s like working in opposite worlds. All these people that I’m serving expensive wine and champagne to have no idea that during the day, I have one of the dirtiest jobs possible. I roll out of bed and sometimes go work with dogs in my pajamas whereas when I’m serving or flying, I’m put together, dressed in a suit or something, with my hair and makeup fully done.

What’s the most exciting place you’ve been as a private flight attendant?
Buenos Aires, Argentina, and São Paulo, Brazil, for sure. So far, I’ve done a lot of trips in North America. We go to places like Vancouver, Florida and New York a lot and every few months something really cool comes up.

Do you give yourself days off? How do you unwind outside of work? 
During the week, if I don’t have a flight, I probably only work about 20 hours. I’ll work maybe two nights at the hotel and then I’ll take my dog to the beach or hang out at Trinity Bellwoods park. I live in Little Italy and love my neighborhood and doing anything outdoors with my dog.

I find I’m able to take a personal vacation every two to three months which is pretty nice, so in the winter, I try to make as much time for travel as I possibly can and in the summer, I try to spend as much time outside with my dog as I can.

Do you ever dream of having a single full-time job? 
Absolutely, for the stability and benefits. Starting this business has put me behind in terms of saving, especially for retirement, but for me, the freedom and autonomy of the job and my hours far outweighs that of a regular job. Also, something very important to me is that all three of my jobs require me to be active and on my feet, which benefits my health in the long run.  If I miss the gym here and there, it really doesn’t matter.  Maybe I won’t need the benefits as I get older [laughs].

What career advice would you give to someone considering a different career than a typical 9-5?
I would say give it a try, start small and manage your expectations. I had nothing to lose with starting the dog walking and if you can minimize your expenses and start something small and see how you fare as an entrepreneur before you sink everything into a business that has a high probability of failure, give it a try. For me, in the grand scheme, it was two or three hundred dollars and a year of my life. And I was literally on the cusp of giving up and then it just picked up, so hang out for that moment where it’s [tough]. It’s always going to be a slow start so manage your expectations.

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