For thousands of Microsoft Elites, there is no actual edge to the leading edge—no line between safety and free climbing. As Shantyr said, it’s all around them.
Does this way of living follow them outside of the digital realm? When they log out of their work computers, are Elite members all jumping off mountains in wingsuits or kayaking over waterfalls? Yes and no.
Tehrani, as a kid, had such a knack for technology that her parents would put her on the phone with software support if something broke. She’s more digitally adventurous than most, but in real life she is one of the most risk-averse people she knows. She can’t even do roller coasters.
“I went on one in high school and it was awful,” she said. “I didn’t want the reputation of being the backpack holder, so I got on. I hated it, but I did it.”
Instead, she prefers hanging out with her dogs, reading, playing Candy Crush, and doing those escape room games with her boyfriend. They’re all the rage in Dallas.
“My boyfriend teases me that I have ‘analysis paralysis.’ Everything I do is calculated in terms of pros and cons,” she said. “Maybe that’s why I love trying new software. Even if my computer is bricked, there’s always a way to fix it, and I get to figure that out. And when I do, it’s incredibly rewarding. I guess there’s a small group of us who think things like that are fun, and not a hassle.”
Heffney said the spirit of exploration definitely transcends both his personal and professional life. A whitewater rafter, astronomy enthusiast, and avid hiker, it’s not unusual for him to wake up well before sunrise to head to the mountains before work.
“I always try the most difficult trail on the mountain first, because if I can do that, it means the others will be easier,” he said. “It’s all about trying things and experiencing and evaluating. You’ve got to take those chances in the things that you do so you can be the Indiana Jones of software, but also of life.”
And Shantyr. Even before he earned two Elite leather jackets, one of his favorite things is getting lost, on purpose, in an unknown city. Last year he had a 20-hour layover in Chicago, and decided to wander the city. He found the second-tallest building in the city (“that was fine”) and then recalled something he’d heard about deep-dish pizza.
“I started wandering around trying to find some, and I actually found the one where it was invented,” he said. “I was on the subway, in a rush to catch my plane, and realized I still hadn’t seen the Willis Tower, the tallest building in Chicago. So, I got off the subway and ran like hell to have a peek. I went to the top. It almost caused me to not catch my flight, but it was worth it.”
Life, as well as dogfooding, is a journey—not a destination.
“You take your left turn, and your right turn, and what do you see? What new things can you learn? I like that in the digital world as well,” Shantyr said.
Sometimes those turns take Shantyr and others like him into rough seas, or dangerously close to dragons. And when they do, these explorers tip their hats and sail on past.
“I like to explore by fate,” Shantyr said, “not just by guide.”