Passion For Change – How A Dog-Walking Side Hustle Became A Successful Full-Time Business

Have you ever day-dreamed about starting your own business doing something you love, but didn’t have the confidence to give it a try?  Well meet Holly, who started her dog-walking service as a side-hustle and is now running it as a successful full-time business that has replaced her previous income – her story might just give you the inspiration you need to take that first step

This is the first in a series I’m calling Passion For Change.  I’ll be speaking to people who have chosen to take control of their lives by making a significant change in their lives – I hope you enjoy it.

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"Success" written in sand on beach

The Dog Lady

If you live in my neighborhood and you find a dog, lose a dog, or have a question about a dog, you’re probably going to contact Holly.  Holly has grown a reputation over the last four years as the go-to-person for all things canine (and feline, and whatever the appropriate word is for chickens, as I know she’s taken care of those too.)Smiling lady with dog

I love seeing the success she’s having and know she’s a busy lady, so I felt really lucky that she agreed to make some time in her schedule to talk to me about how she got to where she is today: a successful owner of a dog-walking and pet-sitting service.


Why Did You Start Your Own Business?


I began by asking Holly about where she was in life at the point that she decided to start her business ‘On Pointe Pet Sitting Services‘.  It was 2014 and she was working two jobs: one in a pizza restaurant in town, and the other in the bar of the local clubhouse – and she wasn’t happy.  “I woke up every day filled with dread that I had to go, and honestly that feeling even started the night before – it would be so busy and customers would be so rude, I just dreaded it” she explained.

Knowing that she needed to make a change, Holly asked herself what it was that she really loved in life.

It turns out that ‘dogs’ was the answer. TwoDogsAsleepOnBed

She began to explore the possibility of opening a doggy daycare facility, but after some initial research into properties, she quickly realized it would be cost-prohibitive for her at that time.  So she decided to try the next best thing: dog-walking.

Holly had no experience of running a business or advertising, but that didn’t hold her back.  “I didn’t even have a computer, so I made flyers by hand, photo-copied them and started putting them up.  Every day they would get taken down and every day I would go and hang more.  I got 250 business cards made and ordered magnets for the side of my car advertising the business with the catchphrase ‘Big or Small I Love Them All'”.

(Funny aside, that tagline attracted a few of the perverts in the area and she got some unsavory telephone calls asking if she really did love them all…. she’s since changed her car logos.)

“Every time I was out and saw someone walking a dog, I would go up to them and hand them a business card.  Sometimes I wondered about my approach – if I was doing it wrong – some people made me feel like I was intruding on their life.  But it worked – some of the least receptive people turned out to be my best customers.”

Initially, Holly kept working at the restaurant in town while she could see if her business idea was going to work, and in just 6 months she found she was making more money taking care of animals.  Holly described the day she resigned: “I felt the biggest sense of freedom,  I’ll never forget it.  I let out a big sigh – I’d had so much anxiety and then the feeling of dread was gone”.

However it was then that reality set in: that her income would be completely dependent on her business, so she continued on with her flyers and soon the phone inquiries were picking up and it began to snowball from there.


How Do You Stay Organized?


In Holly’s words “I don’t do computers”.  Like some of us, Holly likes to write things down and cross things out.  “I bought a big desktop calendar that I’d use for tracking each job.  I figured out that I could fit in all the things I needed to do for my family around the jobs.  I learned I had to be honest with my clients if I was having a really busy day and people would be fine with that – I give each owner a 2-hour window when I’ll be there and let them know they’re still my priority.”

Sheet Of Paper WIthTo Do List And Pen“I live by a hand-written list, I write everything in pencil and I like crossing things off.  I list everything I want to accomplish for the day, the list helps me tremendously – it’s mostly psychological.”

I asked Holly about the administrative and financial side of what she does, and it has been fairly straightforward: “When I first started I spoke to a business accountant and got some advice – they told me to keep a ledger and track all my mileage and money earned, so I did that and I keep track of everything in a book.”


Have You Developed Any Tricks To Manage Your Time?


Knowing how successful Holly’s business is, and the fact that she runs the household (it’s her, her husband, 2 sons, 2 dogs, a cat, plus any pets that she might be boarding), I asked Holly if she’s developed any new habits or tricks to manage her time and stay on top of everything.

“Not being on Facebook has made a whole lot of difference.  I have to not allow myself to do that – my time is very precious. I was looking at my phone way too much, reading Facebook, talking with friends and reading the news.”

Although she doesn’t care for computers and has reduced how much unproductive time she spends on her phone,  she does use it to help her stay on top of things.  “I use Siri a lot, and if I’m in a position where I can’t write something down, I text myself and then every night I look through all my texts and write it down then.  I text myself more than anyone else…”

What Is The Hardest Thing About Running Your Own Business?


Blue sky with sun rays


Having a pet-sitting service sounds like a fun job, so I was interested to know if there were any downsides to Holly’s new career.

“The hardest part is scheduling time with my family as it’s a 7 days a week, 365 days a year business.  Last year I took 14 days off total.  If I want to do something with my family, I have to schedule things out way in advance, and it can be hard to find reliable help when I need time off.”

“But I have no regrets.  Every day I wake up in full control of my life.”


“Some days are harder than others, for example if it’s bitterly cold or raining I still have to get up and do my job.  On those days I may dread going, but my attitude completely changes when that dog comes round the corner and I kiss it and hug it.  I talk to every single one of them – I talk to all of them and kiss all of them”.

Lady Pressing Noses WIth Dog

How Have You Changed?


I asked Holly if she’s changed at all or learned anything new about herself since starting her pet-sitting service.  “I’m changed as a person” she replied.  “I’m not as concerned about my appearance anymore.  Before I always had to look my best, my tips were based on my appearance and having a certain kind of personality.  Now I can just be myself.”

“It’s also made me realize that the most simple things are the very very best things, and money cannot buy peace of mind.  I’m never going to be a millionaire, and that’s OK.  I often say ‘Some people are so poor, all they have is money’.  My life is so good.  This business has made me realize that simple things are the luxuries in life – it’s made me look around and look at nature.  I love being connected to nature now.  I used to dread spring but now I love it.  I never noticed birds before but now I hear how their song changes by the season.”

“I have learned to really take in the time with each dog when I’m out walking.  I look at nature, I look at houses.  I learned that if I take a really deep breath I smell things I wouldn’t smell before.  You have to breathe in really deeply.  When the cement is hot in summer for example, it has a really specific smell when the rain hits it.”


What Advice Would You Share?

Finally I asked Holly if she had any advice for anyone who has something they’re passionate about and are considering starting their own business.

“Just DO IT.  Your passion will be enough to get it done.  It’s true, when you do something you love, you never really feel like you’re working”.

Close-up of brown dog

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Comments (10)

This is one of the best success stories! Holly is of one of most loving, caring and beautiful persons I know! So proud to call you my friend sweet Holly! ❤ Teri Bogard

I agree with you – she’s a very special lady!

My dogs are 2 of the lucky ones that get to call Holly “theirs”. What a wonderful story about a woman who deserves recognition for all she does to makes our lives so much easier. We LOVE Holly!

She really does love them all!

Kathy Groseclose

Holly has been a dear friend for many years, she has a heart of gold. She has been my inspiration to start my own pet sitting/walking business where I live ♥️

I love that Kathy! I hope your business is going well 🙂

I think my dog Hoosier was one of the first dogs Holly watched. Even before she started her business. He loved her so much as she did him. Holly was the first person I called when Hoosier passed away at the age of fifteen years. She also watched our cat Cece. We don’t go as much anymore but I will always recommend Holly. She’s a beautiful Christian Lady.

She really is someone special – thank you for sharing Jeannie!

Holly is an authentic and caring woman, and people know they can trust her with their fur babies. Such a great
story for your blog, Catherine! I am very thankful to be able to call both of these ladies my friends.

Likewise Liane, I’m thankful to know you and call you a friend 🙂

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