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3 Lessons Dog Sitting Taught Me About Entrepreneurship

As I began the journey of entrepreneurship in 2015, I didn’t question if it was what I was supposed to be doing. But I did question if I would make enough each month to pay the bills. I was also worried about being lonely working from home alone. I found a solution to both worries … dog sitting. I could make money while trying to make money and have furry friends all day long!

I remember the night I decided we would be dog sitters. We were sitting on our couch watching tv, I told Aaron I created a Rover Dog Sitting profile. I told him not to worry, we might not get any requests. Little did either of us know, we were one of the only dog sitters on the Rover app in the area that weren’t college students and had acres of land around us. We quickly became the crazy dog-sitting people with more stories than I could share with you here. We also learned A LOT along the way. We don’t dog sit as much as we did when I first started my business. Thankfully, we don’t have to worry about paying the bills but it is nice to have some companions while I still work at home.

As I look back over the years of dog sitting, I am so thankful for what it taught me early in my business and career. I thought I would share 3 lessons that dog sitting taught me about entrepreneurship.

#1. Feed The Bird At Christmas

Don’t be above any task

We live in a college town and many students leave for Christmas break. For some reason, I thought it was in our suite of services to feed a bird in an apartment across town one Christmas. I learned many things from this experience. I quickly realized I needed to keep our services to dogs but more importantly, I could make it in business because I had been taught to serve others and do any task needed. As we grow in our businesses or careers, our responsibilities will change and we will need to say no or delegate to others. But my hope is that our attitude does not change from the young professional who is eager to hustle and serve. It is no longer the best use of my time to be driving across town to feed a bird for a few dollars, but I hope I will always have space and a heart to do the most simple task for someone else.

I think it is also important to remember that “feeding the bird” tasks or paying your dues or hustling doesn’t just happen in the first year of your business or career. It is something you continue to do year after year.

For my business owners or aspiring entrepreneurs - know that it's sometimes year two, three, four, that are the hardest because the glow of a new business has faded but the work has not. Resiliency and consistency are your marks of success.

For my friends who are comparing to others who appear to be successful - know that they had to sacrifice time, money, security, pride, etc. Instead of comparing or assuming, ask them about their story.

#2. 7 Dogs Is A Lot On New Year's Eve

Learn from your decisions

There was one New Year’s Eve that we ended up with 7 dogs in our house. I know - excessive. All of them got along and were good dogs that we had taken care of before. People ask how we knew they would get along. Three answers - intuition, hoping for the best, and we run a pretty structured puppy party! Every dog wore a festive hat and we took pictures for their owners.

I think there were a couple of other times that we had a lot of dogs at once. I guess it took me a couple of times to learn my lesson! I learned I couldn’t say yes to everyone at the same time. Communicating expectations and availability is important for any professional but especially for businesses that offer services because of the amount of output that is expected. Setting boundaries is not only healthy, it is mandatory for long term growth. If you serve many bosses or clients, they don’t necessarily know about the other projects or bosses you have. It is not their responsibility to know. It is our responsibility to let them know what we can do and when we can do it. I am speaking to myself when I say - control what you can control from the beginning so that you don’t feel out of control of your own life, career, or new years eve!

# 3. Put The Diaper On, Tie the Hair Bow, Send Pictures

Do More Than Is Expected. Don’t let someone else’s standards affect yours.

As I said before, we were one of the only adult couples without kids who had a yard in our area on the Rover app. I also worked from home which was very attractive to dog owners. We realized our customers were people who loved their dogs as their children and did not want their dog in a cage all day when they were gone. We realized we were offering a premium service. We could not compare ourselves to other dog boarding options.

Because of our willingness to go above and beyond, we quickly gained 50+ 5 Star reviews. There were dogs that got a different hair bow each day, some of the older dogs needed to wear diapers, and all the owners loved picture updates. This taught me that it doesn’t matter if you are dog sitting or creating a branding strategy for a client, my standard should not be affected or decided based on others or the competition.

I believe firmly that if you are going to do something, do it well. Do it to the best of your ability. Don’t do the bare minimum and expect excellence or success in return. We have been able to bless many dog owners and in return, they have blessed us.


My hope is that these stories and lessons encourage you as you continue in your career and business. Every journey is different on purpose. Don’t compare yours to others. Look at your own and find the lessons that you can share with others.

1 Comment

Billi Jean
Billi Jean
Nov 30, 2023

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