As I was approaching 40, working too hard in marketing jobs, driving because I had to, I felt that sense of freedom slipping. I needed something just for me, a way to quiet the noise of events and demands, but I also wanted a challenge. So I biked from Vancouver, British Columbia, to Tijuana, Mexico, 35 days with just my thoughts as company. No music, no distractions—only the hum of the road. The next year, I rode from Miami to New York City, through plantations and swamps in the Deep South. As a person of color alone in that landscape, I couldn’t escape the layers of history around me. Freedom took on a different kind of weight; it was hanging in the air, stitched into the roads I traveled.