What does it take to build a thriving solo pet care business rooted in community? Olivia Hanson of Waggin Tails Winona shares her journey from a banking job to becoming a full-time pet sitter and dog walker. She discusses the power of word-of-mouth, the value of community collaborations, and the joy she finds in organizing monthly pack walks. Olivia also shares how boundaries and relationships with other sitters help protect her joy and prevent burnout. It’s a story about trusting your path and finding purpose in pet care.

Main Topics

• Transitioning from banking to pet care
• Community pack walks and how they started
• Collaboration with trainers, photographers, and shelters
• Client boundaries and protecting mental health
• Solo sitter support and peer mentorship

Main Takeaway: “Protecting my peace is my biggest thing—and that’s making me better at my job.”

As a solo pet sitter, it’s easy to feel like you have to say yes to every job, every time. But that can lead to burnout, overwhelm, and even losing the joy that got you into pet care in the first place. Olivia Hanson reminds us that setting boundaries isn’t selfish—it’s strategic. By focusing on quality over quantity and making space for rest and connection, she’s built a sustainable business she still loves. Protect your peace, and you protect your passion. 💛

About our guest:

Olivia Hanson is the owner of Waggin Tails Winona, a solo pet care business based in Winona, Minnesota. After earning a business and sales degree and working in banking, Olivia transitioned into pet sitting full-time with the mentorship of a fellow sitter. She now offers dog walking, yard cleanup, overnights, and drop-in visits—and organizes popular monthly community pack walks. Deeply invested in local partnerships, Olivia collaborates with trainers, photographers, and the Humane Society to bring people and pets together. Her business philosophy is rooted in connection, care, and protecting personal joy.

Links:

https://www.facebook.com/waggintailswinona/

https://www.instagram.com/waggintailswinona/

Check out our Starter Packs

See all of our discounts!

Check out ProTrainings Code: CPR-petsitterconfessional for 10% off

📞 Call us: (636) 364-8260

Follow us on: Instagram, Facebook, Twitter

Email us at: [email protected]

Full show notes and transcript

Disclaimer: The views and opinions expressed by our guests are their own and do not necessarily reflect those of Pet Sitter Confessional, its hosts, or sponsors. We interview individuals based on their experience and expertise within the pet care industry. Any statements made outside of this platform, or unrelated to the topic discussed, are solely the responsibility of the guest.

Sponsored by:

❤️ Our AMAZING Patreon Supporters

Time to Pet Visit: https://timetopet.com/confessional Code: 50% off first 3 months

Viists petsit.com/join and use code ‘confessional15’ at checkout to save $15 off your first year!