To some, Milo Dentry is considered a nomad—the only four walls he calls home alternate between a Nylon tent and a Toyota Tacoma. He rises with the sun, but his days change with the seasons: in the summer, Dentry spends his time renting bikes in Yosemite National Park, whereas winter ushers in an era of ski related jobs, including lift operations. I met him by chance at a slam poetry night in Denver three years ago where he told me that he would be on the road again the following day, heading North to Big Sky, Montana. When I asked why he chose this lifestyle, he said, “I wouldn’t want to do anything else.”
Dentry is among the nearly 40 percent of high school graduates not enrolled in college in 2023, according to the U.S. Bureau of Labor Statistics. “I didn’t really know what I wanted to do with my career when I graduated high school,” he says, citing that he “didn’t see a need to go to college.” His decision to live an alternative lifestyle, in which he renovated his truck to accommodate as his portable home, comes with positives and negatives, he says. “I certainly wish that I could settle down sometimes and have my own place and my own homebase, but moving around means I get to see the world and meet lots of people.”
Of the 18 million 16 to 24 year olds not enrolled in school, Dentry meets a myriad of Gen Z’ers with alternate lifestyles like himself—many of his nomadic peers feel disillusioned after experiencing American high schools’ ever-changing curriculum and lowering engagement. But when asked whether he would have gone to college in retrospect, Dentry says it’s more complicated than that. While “college life seems pretty nice sometimes,” he says, he is comfortable in his assertion to “ditch the four-year university program in exchange for doing the things I love.” Climbing, skiing, and biking are all easily accessible for Dentry whilst working outdoors.
Still, alternative lifestyles come with downsides. “Moving around a lot is tricky sometimes,” Dentry says, explaining that “it’s hard to make friends and date when I am constantly between states.” While recent surveys reveal 56% of adults see a four-year university degree as unprofitable, Dentry still encourages those considering “breaking from the norm,” to “try something new. Especially if you’re not sure what you want to do in life. If you don’t want to go to school yet, and you don’t want to build up debt, it’s okay to do your own thing.”
But for now, Dentry is on the road again, headed back to Yosemite until the Colorado Rocky Mountains beckon him back for the winter.
Photo of Milo Dentry.
