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."
Tyler can rattle off a quick opinion on almost any issue in the news. He thinks we should rework education and job training entirely, move away from using coal for energy and give women complete, unbiased medical information if they have an unexpected pregnancy. He's fine with paying taxes but wants the money spent wisely on libraries, fire departments and schools. He does not like public money to be funneled to boondoggles, like, he thinks, Boston's Big Dig. After all that time and money, he doesn't understand why it still needs fixing, or why he sits in traffic for hours to visit his girlfriend at her apartment near Fenway Park.
None of those issues are likely to decide his vote. He would back a candidate he disagreed with if he thought the person could make people work together, he says. Tyler thinks all elected leaders -- not just the president -- should cooperate to help the country grow. He might not like some of their decisions, but he respects the process.
"Being a voter, you just want to see progress, and there really hasn't been for how many years now?" Tyler says. "If you have a strong argument supporting your opinion that's different than mine, I'm more than willing to have that conversation with you. I want to talk, I want to understand why you think that way. It could change my mind ... but I won't know unless I have that conversation."
He thinks his vote will be decided by watching Romney and Obama debate. It's the ultimate test of whether they're listening to each other, he says. During primary season, Tyler was sold on Huntsman after watching him in a Lincoln-Douglas-style debate with Newt Gingrich. The former House speaker seemed like a loose cannon, he says, but Huntsman seemed like a smart guy who wanted to connect.
Tyler does not like to feel played. He does not want to be appeased. He doesn't want candidates to say what they think voters want to hear.
He doesn't want candidates to tailor their policies to him, his family, his situation, his state.
Of course he doesn't want his friends or family or anyone else to struggle or be at a disadvantage, he says, but he doesn't think that'll happen if politicians will stop being stubborn and start working together.
"It might be naïve, but it's sort of what my vision is," Tyler says.
"Typical millennial," Kyle says.
Millennials are the generation born between 1981 and 2000, the first to come of age since the turn of the century, the Pew Research Center says. The oldest have just crested 30; the youngest are in middle school. The majority are white, although it's the smallest majority of any generation as the Hispanic and African-American populations grow. Millennials text, Facebook, tweet, YouTube. They trust the wisdom of their parents, teachers and government, but fewer attach themselves to religion. Politically, they are more progressive. Those who are old enough to vote often do.
Kyle, the middle brother, is a millennial. So is the youngest, Dylan. They, too, are undecided voters. Dylan was a few days shy of 18 this summer when it first occurred to him he'd be able to vote this November.
Because of their ages, they'll be lumped in with Tyler, but he is the stereotype: The one who moved to his parents' house after college. The one who got his oldest buddies together to smack a tennis ball around a Little League field in a weekly game they call "tennis baseball." The one who wants to do something bigger, more world-changing than the track already laid for him. The one who turned his back on a 40-hour-a-week job, then conjured up three creative endeavors to fill his time and bank account. The one who says he'd keep working even if he won the lottery -- he wants to work for something more meaningful than money anyway.
"All the work that I do now, I believe wholeheartedly that what we're doing is right," Tyler says. "It will pay off in the end, whether it is the paycheck or knowing that we're able to help 'X' amount of people."
Eventually, he thinks any of his jobs could morph into full-time work, that they will help him buy a home, get married, support a family -- everything he always wanted to do, and thinks he still probably will.
There are deadlines approaching. Tyler will be 26 by the middle of next year and booted off his parents' health insurance. Gail and Don would be OK with him still living at home, but he knows they won't tolerate him going without medical coverage. His expenses are low -- car insurance, gas, eating out, his portion of the family's cell phone plan -- but health care could add up.