Tyler was up for an athletic trainer job while he was still in college, but it evaporated. By the time he graduated, he didn't have another one lined up -- nor had he passed the exam to become a certified professional. He thought the four-hour, typed test was "a joke and a half," an absurd way to measure a hands-on profession. He failed on his first try.
His parents were happy he wanted to move into the little apartment above their garage; it meant he'd be around more during his youngest brother's last years of high school. But they worried he was too willing to stay up late, sleep in, snack on leftovers, hang out poolside and spend his savings on overseas trips. They wanted him to at least attempt to find a job in the field he'd studied.
"He was floundering," Gail York says. "He'd be watching TV or playing a video game or something like that. He wanted to travel. You want them to do those things, but ... you want them to recognize that's not real.
"Someone bought the chicken. Someone is paying for the propane for the pool. It's not really a free ride."
He failed a second time but was already making other plans. In college, he'd started planning and promoting charity benefits around Manchester, and that work was starting to draw clients and a little income.
After re-reading textbooks front-to-back, he passed the exam on his third try. His parents were relieved, but he was nonplussed. Athletic training had become more a profession of paperwork than passion. Passing the test was not a satisfying win.
"I almost felt, like, defeated," Tyler says. "That was really strange for me."
It seemed like everyone else was marching through life's milestones: His friends and brothers were settling into marketing or engineering careers, jobs that absorbed them 10 or 12 hours a day. They were buying houses, finishing advanced degrees and having babies. Wedding invitations were showing up in the mail. Occasionally, there were funerals for people he knew, or their parents.
He played the game as best he could. In fall 2010, he landed a one-year gig as an athletic trainer and teacher at a boarding school an hour away, and he commuted there and back from his parents' house. He liked the students but realized he wasn't aching for that type of job. He watched a documentary online, "Lemonade," about career climbers who'd been laid off in the recession and used the time to rediscover their passion through art, yoga, parenting, coffee roasting, running a small business -- even changing genders.
Tyler went on long drives or stared at his bedroom ceiling: Was he too young for a second career?
When the boarding school asked him back, he thought fondly of the kids and the classes, of maybe getting to use the athletic training education his parents' planning had paid for. He was tempted by a reliable income and benefits, by getting his own place and starting a life away from home. It seemed like a job he could grow into and enjoy for a long time to come.
He turned it down.
"I don't necessarily need to have a full-time job," he says now. "It's part of that system. You work hard to get good grades, get a job. Your life is almost planned from when you're born."
Instead, he pieced together part-time work producing videos and managing interns for his brother's marketing firm; guiding the speaking and writing career of a friend, an African refugee; and managing a music- and brand-marketing site his brothers helped launch, 1 band 1 brand. He works from home, from the marketing agency office, and from a shared workspace for tech startups in Manchester.
In each role, he feels like he's learning something new, like an apprentice with flexible hours. He's meeting all kinds of new people and generating new ideas. He likes being able to grab a bagel from his parents' fridge between Skype meetings, and to talk business with his brothers over birthday cupcakes.
As the party for his nieces winds down, the little girls turn their attention to one of Uncle Tyler's presents: Silly String. His sisters-in-law hate the stuff, but he brings it to every birthday anyway. Tyler chases his nieces around the yard, lines of goo trailing behind them, wrapping their ankles and streaking their hair.
Here's a choice made: He's willing to work hard, to take risks, to learn more. But he never wants to miss a Silly String battle because he was too busy talking about a job.
One morning this summer, Tyler hangs out in his brother Kyle's office at Dyn Inc., a tech company in downtown Manchester. A whiteboard covered in notes and calculations fills most of one wall. Above the board, a sign reads "Welcome to New Hampshire -- Live free or die." Kyle is the company's chief revenue officer. He's married, and their first child, a boy, is due in a few weeks. They recently bought a home in Bedford, close to Don and Gail's.
Kyle travels a lot, spends hours on e-mail and Twitter every day, and the company is taking off. Dyn employs about 160 people and operates from a 30,000-square-foot space in one of Manchester's old mills; it's filled with desks and conference rooms -- and a rock-climbing wall, a stage where bands sometimes play, a comfortable room for breast-feeding moms, and, behind that, a hangout space with a well-stocked bar. The median age is 34.
Between Kyle's meetings, the brothers debate who would make a better president: Matt Damon or George Clooney?
It's a joke, although the brothers agree the actors seem like passionate guys who care about the world and know how to command a room.
"What is the role of the president?" asks Adam Coughlin, a childhood friend of the Yorks who works with Kyle. "The CEO of the country? The ambassador of the country?"
"First and foremost," Tyler says, "he's the leader of the country. He's in the position to lead."
"What's leadership?" Kyle asks.
"It's people flocking and encouraged around what you're doing," Tyler says. "Motivation. You inspire."