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The UnCollege Blog

Millennials, Parents and Hard Conversations


Editor's note: SkilledUp's Anna Cherry knows millennials. She is one. She deals with the same unique generational issues that millions of her fellow peers face. Anna recently took to the streets of New York City to interview people from the millennial generation. She found many differences in backgrounds and a lot of common themes.

If you speak with a sample of millennials about that question, the one that we’re asked all too frequently by our parents – “What are you doing with your life?” – the same anxieties surface. Money, fulfillment, placelessness.

Depending on which article you read on the Internet, you may find that millennials are ungrateful. Or brave. Or bumbling. Or narcissistic, or we love volunteering. We’re lazy, passionate workers with poor social skills on too many social networks. The apple of employers’ eyes and the bane of their existence.

We’re full of contradictions, apparently — some of which have been put into our mouths.

What are we really doing? Are we succeeding or failing? And what do our parents think of our progress?

We’re all unique, but the majority of us are hungry (hungry sometimes in many senses of the word), and chasing opportunities that we’re passionate about. But let’s not take my word for it. Why not collect millennials’ own words on the matter in our nation’s cultural capital – New York City?


Chris Griffith, 31

Woodbury, Connecticut

Chris Griffith responded gracefully to a stranger’s non sequiturs: “Hey, are you a millennial? Would you let me interview you?”

Chris was on the sidewalk near his apartment, about to head into his local cafe. By day, Chris works as a broker and owns a branch of a broker’s firm. That’s not what he imagined himself doing a decade ago. In college, he wanted to do “a whole bunch of different things,” he said. Criminal justice and European business, for example.

Chris is an only child and very close with his parents, he said, but that didn’t prevent some hard talks about money, living in New York, and going to Korea, where he stayed for six months.

“I was supposed to live there for a year and they thought I was crazy,” he said. “I was a young 23-year-old guy who was in love and came home to salvage a doomed relationship.” Looking back, Chris said, he wishes he would’ve stayed and continued his cultural experience. “But that’s the way things work!”

Asked if his parents are proud of what he's doing now, his answer was quick and definite:

“Yeah, they are.”

James Mentor, 26

Canarsie, Brooklyn, New York

James Mentor is hungry. He believes you have to be if you want to make it here.

He’s lived in Newark, Brooklyn, San Francisco, and Kyoto, Japan. Dubai and Chicago are on the table for future moves. “My mother never fought me on it; she wanted me to do it,” he said. “Part of that is just because she … understands that employment, the work environment, how, you know, people are getting hired, it’s different. Nowadays you kind of get in where you fit in and opportunities are springing not domestically but internationally,” he said. “The world is getting smaller. It’s a bunch of emerging markets that are going to sync with ours.”

Last year, soon after relocating from California, James snagged a sales job at ZocDoc. This year he’s moved on to being a financial analyst for Port Authority. Still, he said, “I’m nowhere near what I want to be doing, or what I will be doing in the next two years.”

Because, his mother knows that “I’m here today, gone tomorrow, she only requires one thing of me, and that’s daily communication,” he said. “...And that’s it, it’s the hardest conversation I ever had, every single day, every time I miss a 24-hour period of communication, I hear about it.”

He understands why. “Every morning you wake up and somebody is biting it for the wrong reasons,” he said. “You’ve got 12 innocent journalists that did not see the end of anything coming … We live in that world.”

But, he said, “At the end of the day, the way I see parenthood is, they have one job: to teach us how to survive in this world.” Their “hardest test,” he said, is “to eventually let us go.”

Max Kimble, 28

West Long Branch, New Jersey

Not far from Chris Griffith’s apartment and Columbia University is Lion’s Head Tavern, where Max Kimble has worked one day a week for almost the past five years. The bar is owned by his cousin’s husband and it comes up when you type “best college bars NYC” into Google’s search engine.

Bartending isn’t Max’s full-time gig. He’s co-founder of Metronome3, a marketing agency with a hospitality-and-restaurant-focused subsidiary agency called Simmer Group Simmer Group.

“I grew up very lucky — my parents are both entrepreneurs and they always kind of knew I was going to go in that direction,” Max said. Still, when he left his first professional job in his mid-20s “to do my own thing and just go for it,” he said, “it was kind of nerve-wracking for them.”

While his parents believed “eventually it would come around,” they worried about his pace in the meantime. The first couple of years “when I was working, you know, 70-plus hours a week and then bartending more than one night a week and just hustling and grinding,” he said, they wanted him to “slow down and take a second to enjoy it.”

Now they can see that the race wasn’t for nothing. “The light’s at the end of the tunnel,” he said. “Things are good.”

From left to right: Jessica Cokins, 24, from Amsterdam, Netherlands and Courtney O’Keefe, 24, from Holley, New York

While Max worked at his Lion's Head Tavern job on this night, Jessica Cokins and Courtney O’Keefe talked over drinks.

Jessica, “an expat kid,” was born in Minnesota and grew up in the Netherlands. After college she moved to NYC to attend Columbia University. With one semester down and two to go, “I had to tell my parents that I didn’t want to go to grad school because I hated it,” she said.

It wasn’t sunk costs they were worried about. “They just thought that I shouldn’t give up what I’d already started,” she said. They advised her to “embrace living in New York,” cut school to part-time, then “get a job and figure out what I wanted to do.”

Jessica currently works a part-time job and continues to study human rights at Columbia.

Courtney is also in grad school, studying media management and media studies at The New School. She’s from Holley, New York, “where nobody goes to college.”

It’s not surprising then, that “the most difficult thing to explain to my mother was the fact that I was going to college,” she said. They “couldn’t afford it … my family was essentially not going to have anything to do with me going to school.”

So, she said, she’s paying for it by herself.

Chris Sinclair, 29

Wyandanch, Long Island, New York

Chris Sinclair had just come from the School of General Studies at Columbia University, where he’s majoring in political science with a concentration in business management. His ambitions are great: go to law school and reform the legal system.

His hard talk, he said, involved finances, which is “prevalent among the [General Studies] community … when you talk to your parents, especially when you’re not on the traditional path and you’re having to find a way to pay for your education, and they’re not necessarily willing or able, or both, to support you financially or otherwise,” he said.

“I had a conversation with my mom about helping me get a student loan without having to co-sign, and she wouldn’t so much as give me a pay stub,” Chris said. “Her alternative was to tell me to transfer to Stony Brook. Meanwhile, I’m in an Ivy League school, so why would I leave?”

Ignacio Moreno Basañez, 23

Viña del Mar, Chile

Ignacio Moreno Basañez is from Viña del Mar, Chile, a town part of the Valparaíso metropolitan area a couple of hours away from Santiago.

He was enjoying the fifth day of his New York visit. “I like it a lot,” he said. “It’s like, a lot of people, movement, the buildings, the statue ... infinite things to do.” He was staying with his brother at the hostel leading their group — travelers from Argentina, the Netherlands, Germany, and France.

Ignacio learned some English in school and improved his language skills two years ago working at a shipyard in California. He was doing a three-month internship with a welding company. Since finishing his engineering studies in December, he has been on the job search and going to interviews. Despite loving recent work with a solar energy company, he said, he’s still unsure which direction he’ll take.

One issue is whether Ignacio will stay near his hometown. It’s difficult because in his country, he said, people generally go to college near home. “We don’t leave,” he said. “I live in Valparaíso and the best opportunities are in Santiago, so it’s possible that I’m going to Santiago, but I think that my parents ... for them it’s hard.” But, he said, “it’s my decision and my parents ... they know that.”

Andrew Gonzalez, 29

Westwood, New Jersey

On a Thursday night at a Harlem Public’s bar, Andrew Gonzalez considered a chocolate egg cream stout. “What is a chocolate egg cream even supposed to taste like?” he asked.

Andrew didn’t have many tough conversations with his parents, he said, because they “have a lot of trust in me.” Except maybe once, he said, in high school when his mom caught him smoking weed. “She was like, ‘You’re smoking weed and you’re not going to do anything!’” he said. “I was like, ‘Calm down, I’m going to turn out just fine.’”

Andrew is the antithesis of “not going to do anything.” He has five jobs: substitute teaching at private schools across Manhattan, tutoring at a math center in the Upper West Side, tutoring a private student, teaching at a small private school with classes as small as one student, and doing Saturday test prep for a supplemental education program called Summer on the Hill.

“I have really cool jobs, I love my jobs,” Andrew said. The only problem is money. “It pays like a part-time salary... So, if you think of what teachers get paid, I get a part of that,” he said.

Tutoring can be lucrative. “I need more students!” he said. “If you know any 13-year-olds...”

Ginger Cline, 26

New Haven, Connecticut

For three years, Ginger Cline lived in Madrid, Spain. Now she’s living in her hometown while working as a coffee shop barista, studying for the LSAT, and trying to save money for law school.

On a Friday night visiting New York, she ate dinner in an Irish pub. She’s “definitively back in the U.S.,” she said, because “my father really encouraged me not to go back to Europe.”

“I was thinking about trying to spend a few more years there, but my parents kind of talked some sense into me,” she said. They made her realize that, “the way to go, since I have wanted to be a lawyer for a long time, is just to get that done, to go to law school, and since I‘ll want to be practicing here in the U.S., it makes more sense for me to be here than it does for me to be teaching English in Europe, as I had been.”

She’d considered spending time in Thailand, South America, or India. But her parents made her see something: “If I wanted to realize my longer-term goals, then I was going to have to make some harder choices right now.”