Unexpected Journeys: A Unique Adventure Crafted by Jennifer Sloan

Jennifer Sloan, a passionate and enterprising businesswoman, is the proud owner of Unexpected Journeys, a company that offers self-guided, surprise road trips designed to explore Ottawa and the surrounding areas. These day-long journeys, which arrive at your door in beautifully wrapped packages, take you on a series of unexpected outdoor destinations, with five different locations carefully chosen to inspire awe and create lasting memories. Each trip begins from a location within an hour of downtown Ottawa, and as you journey through the day, you will uncover secret spots and local gems you never knew existed.

The charm of Unexpected Journeys lies in its mystery. Travelers don’t know the destinations until the journey begins, with five sealed notes leading them to each location. Along the way, participants can discover optional bonus activities, local restaurants, and charming shops, all designed to enrich the experience. Jennifer’s goal is to encourage people to stay outside, explore nature, and support local Canadian businesses that fit the theme of the journey. She believes that the best gift you can give someone is time spent together, and her carefully crafted itineraries aim to help people connect with one another and the beauty of their surroundings.

The concept for Unexpected Journeys has its roots in Jennifer’s love for adventure and her desire to help others find inspiration in their own backyards, particularly during the pandemic when people were limited in their travel options. As Jennifer explains, “I wanted others to feel that same sense of wonder we had experienced on our own journeys.” By guiding travelers off the beaten path to destinations less traveled, Jennifer encourages exploration and the discovery of moments that might otherwise be overlooked.

The name Unexpected Journeys holds a personal significance for Jennifer. She recalls retiring early during the COVID-19 pandemic after a 28-year career in teaching. While she never planned to start her own business, the company’s name reflects both the surprise and delight found within each road trip and Jennifer’s own unexpected path in life.

“I retired early and had no intention of opening a business, but I’ve always been someone who loved planning our own adventures,” she says. “The most memorable experiences were the ones that left us surprised and in awe. I wanted to share that with others.”

Though Jennifer always imagined starting a business someday, she initially thought it would involve greeting cards. However, after retiring from teaching, she found that creating these self-guided journeys combined everything she loved—planning, writing, guiding, and having a positive impact on others. The shift from teaching to entrepreneurship was a natural one. It became her perfect retirement passion project.

“I had the time to dedicate to something I really loved,” Jennifer shares. “And this has been so much more fulfilling than I ever expected.”

Starting a business during the height of the COVID-19 pandemic was no small feat. Jennifer launched Unexpected Journeys in December 2020, and like many entrepreneurs, she was figuring it out as she went along. She conducted extensive research, worked with a web designer to bring her vision to life, and learned how to leverage social media platforms like Instagram and Facebook for business purposes.

“It was a huge learning curve,” Jennifer reflects. “There were so many things I didn’t expect, but there have also been exciting milestones along the way.”

Those milestones include winning the Ottawa Faces Awards for Best Tour and Best Experience and being featured in major publications like Narcity Ottawa and Faces Magazine. She’s also sent over 4,000 groups on Unexpected Journeys in just under four years—an accomplishment she is immensely proud of.

Jennifer has learned many lessons since starting her business, and she’s open about the challenges. One key takeaway? Your product doesn’t need to be perfect when you launch—it can evolve over time.

“I’ve made many changes based on customer feedback, and I’m so grateful for it,” she notes. Another lesson? Managing time is crucial, especially when running a business solo. Jennifer spends countless hours on everything from creating new journeys and conducting site visits to packaging orders and maintaining social media accounts.

“I’m constantly multitasking, but I love it. It’s part of the process,” she says.

While growing her business, Jennifer has also made giving back a central part of Unexpected Journeys. To date, she has donated over $3,000 to Tree Canada, and she has supported several local and national charities, including the Ottawa Special Olympics, CHEO, the Terry Fox Foundation, and Ronald McDonald House.

Jennifer is also a proud supporter of local Canadian businesses, ensuring that the products used in her packages and the locations featured on her journeys all celebrate Canadian craftsmanship and culture.

As she continues to grow her business, Jennifer is focused on refining her marketing efforts. While her business relies heavily on word-of-mouth referrals, she is exploring creative ways to spread the word about Unexpected Journeys and reach even more adventure-seekers.

Reflecting on the journey so far, Jennifer says, “It has been exciting, rewarding, and full of surprises. I’m so grateful that people have trusted me with their memories, and I look forward to sharing even more unexpected adventures in the future.”

Unexpected Journeys offers a unique way to experience the beauty of Ontario and Quebec, and Jennifer Sloan is proud to lead the way with her passion for adventure, local businesses, and the joy of discovery. Each journey is a chance to explore the unexpected, both in the world around you and in life itself.