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What It's About
A retiring teacher organizes DIY adventures in Canada.
Words of Wisdom
Jennifer recommends being persistent with your marketing. Post every day, comment and share, and have real dialogue with others over social media. And be willing to change up things up. Jennifer always listens to her customers and uses their feedback to improve her business.
Fun Fact
The name Ottawa is derived from the Algonquin word adawe, which means “to trade”. The word refers to the indigenous peoples who used the river there to trade, hunt, fish, and camp.
Notes from Chris
Episode 1942
Jennifer Sloan wasn’t meant for retirement. A former schoolteacher, she’d only been retired for a week when her husband convinced her to turn her love of planning into a thriving side hustle. You see, Jennifer had always loved planning vacations but found the most memorable trips were the ones that left her surprised and full of awe. You know, the little side trips where you discover the most amazing restaurant that only locals know about, or the perfect hidden park nestled behind the shopping district—the one you never would have found if you hadn’t taken that wrong turn. Therefore, her new business, Unexpected Journeys, takes people on surprise one-day adventures around Ottawa, Ontario. But here’s the twist! Customers choose from several options listed on Jennifer’s website and she mails them a package with all the details. Each itinerary comes wrapped in vellum with a wax seal, similar to a wedding invitation. Inside, there are five notes. Customers open each note one by one along the way with each stop leading to the next destination. Right now, the business is a one-woman show. Jennifer personally visits each spot along each journey she creates to make sure it is special enough to be included. She also does all the planning, research, mailing and social media herself. All her hard work has paid off…Faces Magazine recently awarded her Best Tour Company in Ottawa. Startup costs were about $5,000, with the biggest chunk being a new laptop to replace the one she returned to her school board when she retired. She also bought a high-end printer and paper supplies to create her packages and hired a designer to make her business look its best. Sales started off slowly but picked up and she made over $35,000 in her first year. The best part is when someone emails her to say they had an incredible time and discovered places they never knew existed.MENTIONED IN THIS EPISODE:
- Learn more about Jennifer and check out her trips at her website,, UnexpectedJourneys.com.
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- Bucket List Becomes Swashbuckling Adventure Tour Company: A small-town Oregonian grows a travel blog into a multiple six-figure business.
- Busy Marketing Professional Fills Niche with Biking Wine Tours: A marketing executive sees an opportunity to fulfill a niche tourism need in an up-and-coming wine region.
Quote of the Day
"Venture out, learn what makes you uncomfortable and repeat. What I learned about myself in 15 years I could never have learned just from reading books or hearing others tell their stories."
—Eva Rosales #SideHustleSchool
