Catching Up with Rory Macleod ‘96

Rory Macleod has had an interesting ride since graduating from Shorecrest Preparatory School in 1996. He first went to Colgate University to study history and political science where he found his passion for writing, which led him to an internal communications career at various companies (including technology giant Apple Inc.).

While working for Apple, Rory started dreaming about riding a bicycle across the United States. One day in 2015, he decided to do just that. He quit his job, moved out of his San Francisco apartment, sold off his belongings, and in July of that year began riding his bicycle across America. He reached the Atlantic three months later, but his journey did not end there. He has since biked through 39 countries across Europe and North America, and two years after leaving home he is still at it. We had the chance to catch up with Rory during his day off from biking over the Alps.

Rory was a Lifer at Shorecrest, meaning he attended from kindergarten all the way through senior year. He remarked, “I remember there being an unusual number of Lifers in my class. There were sixteen of us.” When thinking about which teachers impacted his life the most, Rory immediately said, “Definitely Mr. Moore. He had a way of making you feel like you weren’t in high school, but that you were already in in college.” One of his other favorite teachers was Mr. Beaton, also a Colgate alumnus.

His favorite Shorecrest memories center around Homecoming Week and the powder puff football game. He remembers staying up late with his classmates to toilet paper the school and then “going to class the next day like a zombie.” Rory has fond memories of his time as a Charger and is very grateful for the Shorecrest community, who have been some of his biggest fans during his trip.

After graduating from Shorecrest in 1996, Rory wanted “to go as far north as possible,” so he decided to move to upstate New York and attend Colgate University. Although he went in thinking he would follow a law track, Rory’s history and political science degree led him to an enthusiasm for writing.

After leaving college, Rory moved to Boston where he spent a few years trying to crack into the writing world while managing a bar and tutoring children. This all changed when he got “the phone call that changed everything.” An acquaintance called out of the blue asking Rory if he would be interested in an internal communications job in San Francisco. While Rory knew nothing about communications, he knew that this position would allow him to work on his writing skills, so he moved to California and a few years later ended up working for Apple.

During his time at Apple, Rory worked as a senior copywriter in charge of employee engagement. But his great passion during his years in San Francisco was his annual bike trips. Through a travel company, Rory would spend a week biking through different countries which “planted the seed to ride across the States.” Rory soon began “to obsess over the idea. I read blogs and books, talked to people who had done similar trips, and researched everything I could about what it takes to ride across country.”

According to Rory, he was, “getting to a point in my life and career when I was tired and burnt out from daily life and all the negativity in the news. I mean, I had a pretty good life: I had a great job, a great apartment with views of the Golden Gate Bridge, and plenty of money in the bank. But I felt like there had to be more to life, and I also really wanted to rediscover my passion for America.” It was on a bike trip to Canada where everything clicked and he decided he needed to start planning his trip immediately. Although the decision was scary, Rory was determined that he “could not allow the fear to control him.” So he started to negotiate with his boss at Apple on whether or not he could take time off to bike across country.

“When my boss told me that they could not grant me the time off, I entered into a crisis moment. I was terrified to leave everything I had spent my life building up, but I knew that if I didn’t do the trip at that moment, then I never would.”

That decision turned out to be an unexpected blessing. “Once I made the decision to quit, I realized I was free to keep going.” Rory said. “There was no reason to stop at the Atlantic.” So after completing his initial goal of riding across America, Rory turned south and began to complete a circle around America. He stayed with friends, family, and strangers along the way, and even stopped by Shorecrest when he arrived at his mother’s house in Tampa over Christmas. Then in April 2016, exactly nine months and 14,500 miles after leaving home, he arrived back in San Francisco with a surprise for everyone waiting for him on the beach. Instead of calling the trip an interruption and heading back to work, Rory told them he was taking his bike and heading to Europe, and exactly one month later he touched down in Dublin. His entire trip as of July 11, 2017, has totaled more than 30,000 miles over 39 countries in two years.

One of his main focuses of this trip has been raising money for World Bicycle Relief, which “mobilizes people through The Power of Bicycles.” According to Rory, “a lot of their effort focuses on helping girls get to school, since they often have to walk a long distance and have too many responsibilities at home, causing many of them to drop out. The bikes help them stay in school and still have enough time to complete their chores.”

Rory’s original goal was to raise $14,700 for 100 bikes, but he has since doubled that goal. As of July 2017, he has raised $30,453 for 207 bikes. Rory is taking his philanthropy one step further by actually going to Zambia in October to deliver bikes to a group of schoolchildren. And if that wasn’t already enough, Rory will then “hop on one of those bikes and ride it to Cape Town to raise awareness of the work.” Rory estimates his Africa ride will take about two months and 2,500 miles. “It’s going to be hard because I won’t have any of my normal gear with me,“ he said. “There’s also a lot of obvious challenges with riding through Africa, such as malaria, political unrest, and dirt roads. But the challenges I will face pale in comparison to the ones people there face every day.”

After his side trip to Africa, Rory hopes to continue his trip and head to Asia. As far as his end goal, Rory says, “I just hope to go as far as I can and see as much as possible. I recognize I might not get this opportunity again and so I don’t want to stop until I’m truly ready.”

Rory's advice for someone who wants to pursue their dream is: “Just do it. Don’t think about whether or not it’s crazy because then you’ll never do it. Just pick a date and go for it. Everything else will fall into place. At the beginning of my trip I was scared of everything. I didn’t know where I‘d be staying each night. I worried about everything from dogs to bears, lightning, bad drivers, you name it. But mostly I worried about whether I was making the right decision. But now I know: it was the best decision of my life.”

A big thank you to Rory for speaking with us! If you would like to follow Rory’s journey or donate to the World Bicycle Relief on his behalf then check out his fundraising page.