“I think we made it.”

The sight of the colossal “press play” sign outside the YouTube facility in the Los Angeles neighborhood of Playa Vista stirs up feelings of finality.

After traveling more than 3,000 miles in an exhausted rental car, here – at a 41,000-square-foot former helicopter hangar near the sapphire shores of the Pacific – we have come to the end of the trail and the end of the country. It’s no coincidence that we finish the odyssey at a site that screams “Millennial.”

We check in at the main lobby, tapping our names onto the touch-screen kiosks. A brief tour reveals a 47-seat screening room just beyond the reception area, a production control room that looks like a mini NASA command center, an equipment catalog that would impress Steven Spielberg, and three fully equipped main studios where most of the magic happens.

Photo by Paula Rogo

Welcome to YouTube Space LA – a state-of-the-art production studio open to established users of YouTube who want to produce video content for their online channels.

“When we are here, we bump into so many people, and be like, ‘Hey, we’re shooting something. Wanna just ... pop in?’ ” says Shira Lazar, describing the spirit of collaboration that infuses the venue. An online host and entrepreneur – first through YouTube, and then her own start-up – Ms. Lazar often shoots and produces video for her channel here, the flagship digital studio for one of the most influential technology companies of our era.

At 33, she’s on the edge of the 18-to-34 Millennial age group and at the forefront of the digital revolution that has come to define Millennial culture today. In her we see the foremost characteristics of this space and this generation: openness, boundless energy, and a cheerful disregard for coloring within the lines. Her career trajectory also reflects both the disillusionment and dreams of the dozens of Millennials we’ve met over the past 13 days.

We had hit Interstate 90 west out of Boston with a plan to investigate a series of sprawling questions: How do members of our generation – the ones known as Millennials – define themselves? Which traditions do they still hold sacred? Which do they eschew and why? Above all, what future do they envision for the nation?

What we found is that conventional milestones – securing a college degree, starting a family, owning a home – remain important to Millennials. But their youthful optimism is tempered with the practicality of a generation that has come of age confronting terrorism, economic recession, and the relentless advance of technology. They understand that the established ways of doing things are not always the best, and that working hard and following the rules do not guarantee success.

So they look for other paths to get where they’re going.

Beneath it all run two currents of idealism: one that views independence and self-determination as the pinnacles of success, and a second that believes that success should be shared – with both fellow Americans and the world.

“If you had to sum up Millennials in just one behavior,” says Morley Winograd, an author and speaker who has co-written three books on the generation, “it’s wanting to change the world for the better – together.”

It’s a noble sentiment. But is it really achievable?

Photo by Paula Rogo

Our search for answers begins at a 150-year-old academic institution on the eastern end of the continent. There we meet Mark Reiland, a graduate student and lecturer at the department of environmental conservation at the University of Massachusetts Amherst.

Mr. Reiland is manning a forestry booth at the campus center, educating people in the care and cultivation of trees. An arborist who grew up clearing fallen timber off roads in North Carolina’s “hurricane alley,” Reiland doesn’t quite fit the image of the tech-

savvy Millennial. But he’s no less part of this generation when it comes to his views on ambition and achievement.

“I live out in the woods ... where I want to live. I work in a field I care about and gives me purpose,” he says. “It’s less ‘This is what I want,’ and more, ‘This is what I want to do to get where I want to be.’ ”

We would hear that position restated in other ways by other people in cities and towns along the way. We would also meet young people with more orthodox visions for the future.

Take Liam Byrne, a communications major whom we find sitting alone at a table across from the campus center coffee bar. If his goals are anything to go by, then – contrary to popular opinion – this generation has not yet given up on the old notion of raising a family behind a white picket fence.

Success “is about having a house and kids ... about work ethic and working hard,” Mr. Byrne says. Despite his formidable student debt and the slow decline of his industry of choice, he remains optimistic about his chances of securing that version of prosperity. “If my parents can do it, and their parents can do it,” he says, “so can I.”

Across the hall at the university cafeteria, Guy Jean Baptiste isn’t so sure. Originally from the Caribbean island nation of Martinique, Mr. Baptiste – “Junior” to friends and family – says the future is less promising for immigrants like him: “People from foreign countries think of America as the land of the free where all is possible. But when you come to this country, you realize that ... it’s not entirely what you expect.”

“I feel the pressure to be successful,” adds the pre-med major. “[My family] kind of relies on me.... I’m the first child so I have to lead the way. [But] college is debt, to be honest. And there is no way that you will be guaranteed a job when you graduate.”

Photo by Paula Rogo

The anxiety Baptiste feels is perhaps understandable. His generation is growing up at a time when disruption is a byword and once-seemingly absolute values are up for debate. It is the age of Donald Trump and Bernie Sanders; the era of “Black Lives Matter” and social wars over public bathrooms.

It is a time when Cuba and pot are becoming increasingly accessible, but a steady job and a comfortable retirement aren’t. Marriage is now a choice open to all. Education can be gotten, sans classroom, by peering at a tiny screen. And any moment can be captured in a tweet, snap, or ’gram.

For some, this permissiveness and change is welcome news – a sign of progress and evolution in the United States. For many others, it’s a flashpoint: 53 percent of Americans say the nation’s culture and way of life has mostly changed for the worse since the 1950s, according to the 2015 American Values Survey. Forty-nine percent believe America’s best days are behind it.

Part of that insecurity stems from how other generations of Americans view Millennials. In 2013, Time magazine labeled them “The Me Me Me Generation.” Since then, articles and op-eds have often pontificated on that stereotype and added others: Not only are members of this generation self-obsessed, but they are lazy, feel entitled, and are unwilling or unable to settle down.

Most of the Millennials we spoke with agree, to a point. But they suggest that these labels are often flung indiscriminately – and may miss the mark altogether.

Understanding the generation is important. This is, after all, the age group most likely to make the biggest impact in the next chapter of the American narrative: In April, the Pew Research Center pronounced Millennials the largest generation in American history, their numbers hitting 75.4 million in 2016.

Photo by Paula Rogo

In upstate New York, we take a detour off I-90 after a sign for the International Boxing Hall of Fame catches our weary eyes.

The site consists of two unassuming structures on a patch of concrete just off the highway, in a town called Canastota. One is the hall itself. We spend half an hour there, wandering through three rooms of boxing history that comes to life in the displays of gloves, belts, posters, and cast-iron fists of famous fighters.

In the second building we meet Zack Babcock, who works behind the counter and assists visitors who come to see the world’s most famous boxing ring. The ring came to Canastota in 2007 after 80 years in Madison Square Garden. It was the site of some of the biggest bouts in history – including the “Fight of the Century” between Muhammad Ali and Joe Frazier in March 1971.

But proximity to glory has little effect on Mr. Babcock. Unlike many of the young people we encounter in other parts of the country, he harbors no dreams of escape, has no desire to leave the town where he grew up and his family and friends live.

“I love it here,” Babcock says, looking at the signed posters, mugs, shirts, and other souvenirs around us. “I always imagined my kids coming here. I just want to live a happy life.”

• • •

We push on toward Chicago, but veer off in Gary, Ind., to catch a glimpse of the town’s main claim to fame: Michael Jackson’s childhood home.

The city hits us like a bad wind. Dilapidated buildings, boarded-up windows, and littered lots dominate the landscape.

We knew this was coming: Gary has suffered the fate of other Rust Belt towns since the automotive industry’s decline in the late 1970s. The Great Recession further marred the city. Gary’s average median household income today is $27,500 – about half that of the nation’s. Crime remains stubborn.

On a Saturday afternoon, the city is near-deserted, even though it’s sunny. The basketball courts we drive by are empty, and church after silent church stands watch over the hollowed community.

We turn onto Jackson Street – named after the president, not the pop star – and park across from the house where Jackson and his siblings were raised. A black iron fence, peppered with messages from visiting pilgrims (“Michael Jackson, maker of dreams,” says one), surrounds the small property.

We run into Anna Punjwani and Nawroz Pirani, who are in town, as we are, to see the humble home that brought forth a legend. She studies biological sciences at the University of Minnesota; he works in corporate finance in Chicago. They are both of Pakistani heritage and their responses to questions about Millennials carry the sense of motion inherent in the immigrant experience.

“I don’t think I would have been able to go to school, get a job, be able to afford certain things if I was still living in Karachi,” says Mr. Pirani, who moved to the US with his family when he was 14. In America, he says, people have not just the freedom to make their own decisions but also the opportunities they need to succeed.

And that’s as true for this generation as any other, Pirani says. “People [just] have to ... go out there and make something out of [themselves]. If I, an immigrant, was able to accomplish things, not knowing English very well when I first got here – then people who are born here? Come on.”

We wonder how true his words could be in a place like Gary, where it seems talents at the level of a Michael Jackson are key to making it up and out.

Photo by Paula Rogo

In both Chicago and then St. Louis, we face a grim reality: Day-to-day struggles cast long shadows on bright futures.

“It always feels like everything is in flux for this generation,” says Michael Calmese. We find him lingering after Sunday service at Quinn Chapel African Methodist Episcopal Church, a historic black parish along South Wabash Avenue on the South Side of Chicago, a city that has been rocked by gun violence.

“Let’s say you get a job,” he says. “Somehow, some way, they cut back on your hours. Or the cost of living goes up. Somehow ... something happens to make things worse.”

What’s more, he says, Millennial stereotypes overlap with racial bias around young black men like him. People think we are “violent, ignorant, uneducated, just don’t have nothing going for [ourselves],” Mr. Calmese adds.

We hear his words echoed in the St. Louis suburb of Ferguson, Mo. While everything here seems normal, vestiges remain of the violence that took place following the fatal shooting of Michael Brown, a young black man, in the summer of 2014 – if you know where to look. Mark Robinson, a resident for seven years, agrees to show us around. As we drive down West Florissant Avenue, he starts pointing. That used to be a business, he says, and there used to be a store there.

He feels as if he is trapped by geography. “You can eventually be what you wanna be, go where you wanna go, do what you wanna do,” he says. But “if I’m not in the right place, the right neighborhood, I can’t follow my dream.”

Yet the outlooks of both Calmese and Mr. Robinson waver between harsh and hopeful. Calmese says he plans to have a small business going in five years “to provide for myself and my family.” Robinson envisions opening a vintage car repair shop with his dad someday, though his big dream is to join the Marines.

“They’re heroes – protectors,” he says. “They’re the people everybody should want to be.”

• • •

Hannah Estes and Austin Zarbuck hold a more jaded view of their Millennial compatriots. Sharing our table at the Horizon Cafe – a brunch spot in a trendy neighborhood on Chicago’s North Side – Ms. Estes says too many of her peers come off as feeling entitled.

“I think Millennials ... are not thinking that this is what I have to do to get [to my goal]. They are thinking, ‘This will happen for me,’ ” she says.

Mr. Zarbuck goes even further. “I don’t think most Millennials care” about their futures at all, he says. “They are not thinking, ‘Let me start a job to reach the next economic rung.’ It is all about spending my money on all these experiential things and not saving much.”

What bothers Estes the most, however, is what she perceives as a lack of effort. “I see a lot of Millennials my age and they are just on Facebook all day and on their phones. I see people taking bathroom selfies and I think, ‘Come on! Do something for

yourself,’ ” she says. “My end goal is to be respected – not just be another Millennial at work with their phone attached to their face.”

Chelsea Smith would agree with that. We find her a day later, at a music venue in St. Louis.

In her pink leather jacket and tan booties, Ms. Smith exudes the kind of youthful self-assurance so often interpreted as Millennial arrogance. Yet she rejects the idea that all Millennials aren’t hard workers. She says she has toiled for everything she has accomplished at the interior design firm where she works.

“People are dealt with what they’re dealt with, and they either make the right choice to do something with their lives or dwell on it constantly and never move on,” she says. “And that has everything to do with who you are.”

Photo by Paula Rogo

The last of the High Plains gives way when we hit Denver, sitting at the eastern edge of the Rocky Mountains. A song by Millennial pop star Drake booms from the radio: “Man, what a time to be alive.”

We meet Lillie Cartwright and Alexis Crews at the former’s home one evening. They launch into the experience of young, black women who feel pressure to achieve.

“I think that the whole notion that hard work will get you where you want to be is false,” says Ms. Cartwright. She’s a marketing associate for a local start-up. She had focused entirely on academics through high school, then went to Princeton University on a scholarship in economics. Her lifelong goal was to become an investment banker.

At her first internship, she realized she hated the field. Now Cartwright is torn: Does she work her way to the salary and lifestyle she has long sought even though it makes her miserable? Or does she work in a place that makes her feel happy but doesn’t quite meet her material expectations?

“Right now I have the freedom, but I need a lot more money,” she says. “I’m making enough so that my parents are quiet and I don’t bother them for anything, but there are so many things that [I want to be able to do].”

“I think that’s what drives this Millennial start-up culture,” Cartwright adds. “We love money, but we love freedom. And it’s like, how do you find that [balance]?”

Ms. Crews is familiar with the struggle. She works as the outreach coordinator for a US senator from Colorado. Her dream is to found a nonprofit to help women in developing countries who have been sexually assaulted. Most of her friends, however, have high-stress, high-

paying jobs either back East, in finance, or out West, in tech.

“They’re actually never happy,” Crews says. “They’re always searching for something else because they hate the toxic life and the amount of work they have to put in.”

Photo by Paula Rogo

We meet our first Millennial mother in Las Vegas. Mia Paguio agrees to have brunch with us at a restaurant on the Strip. Ms. Paguio moved here from the Philippines five years ago to marry her then-boyfriend and start a family. She is something of a Millennial anomaly: Members of her generation are starting families later and later. For a long time after her son was born, in fact, Paguio was hesitant to admit that she was a stay-at-home mom at all.

“Cause that’s what people say: ‘Oh, you’re just a stay-at-home mom.’ Just,” she scoffs. “Now I’m like, Just? Does my day end? No, it doesn’t. I don’t have sick days, you know. I don’t take time off. And I don’t want to.”

As her son got older, Paguio began wondering if she could do more with her time and energy while her husband – a member of the professional dance crew Jabbawockeez – was off rehearsing and performing. She decided to pursue her interest in fitness, bringing her little boy with her to classes until she acquired certification as a kettlebell trainer. That was in late 2015.

Today, Paguio not only teaches private lessons; she also competes in kettlebell tournaments nationwide. And she still gets to spend as much time as she wants raising her child, who’s now 2 years old.

Her own experience, she says, has led her to believe that, thanks to technology and other conveniences, this generation has unprecedented power to seize control of life.

“My parents had their 9-to-5’s. They put us in day care because that’s what they had to do,” Paguio says. “But my schedule is mine, and I get to fill it up how I want to. So, I am privileged. Absolutely.”

Suddenly, we’re in California. It’s no wonder they call this place the Golden State: Sunlight spills from the sky, gilding the palm trees and Priuses lining the freeways.

We swing onto I-405 and edge closer to the coast feeling like we’ve learned a few things. One is the optimism of Millennials like Paguio. Another is the conviction among many that they can reinvent themselves.

Shira Lazar, the internet host at the YouTube Space in Playa Vista, epitomizes this Millennial mind-set.

“I’d get these huge, high-profile jobs working for shows and networks,” she says of her early career, “and then a new exec team would come in and I’d get fired.”

Those were the years after she graduated from Boston’s Emerson College in 2004 and moved out West in an effort to find steady work in hosting and production. “I’d get hired and fired and hired and fired. It was never-ending,” Lazar says. “[So] I thought ... well, why don’t I create my own party?”

At the time, viral videos were just beginning to take off, and no one was yet featuring the people who filmed them. Lazar decided to be the first. Today, she’s five years into founding, producing, and hosting the interactive online show “What’s Trending.”

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But she is far from done.

“My mind’s constantly figuring out new ways to build and create and grow,” she says. The dream is “being able to do what you love doing, right? And support yourself. And help others with that. So in some ways, I’ve accomplished a lot. But I feel like there’s so much more to do.”