In 2009, the New Yorker featured Eric Drooker’s drawing “The Iron Worker & The Stranger” on its cover. The image depicts a WPA-style lone beam-rat straddling an I-beam on an incomplete building rising so high above the rest of Manhattan that the island’s jutting skyscrapers look more like the ridges of a wind-blown sea. The iron worker looks more bronze sculpture than man, not caught in the hurried pace of construction, but lost in a moment, gazing up at a yellow butterfly that somehow has found its way to the top of the metropolis on the trade-winds of New York City.

My cubicle is near a window overlooking those same lower Manhattan canyons. Twenty-eight stories up: The highest I’ve ever been in a building in my life. I keep Drooker’s cover in a frame in the corner of my window. Had my ancestors lived in New York, it’s possible they would have ascended this high, if not higher, on the Manhattan skyline—but they would have done it in Levis and steel-toed boots, not Florsheims and a suit.

I’m waiting on our corporate travel agent to let me know whether he’s going to have my passport finalized by the end of the day. At the last minute, the passport office sent me a letter requesting additional documentation to prove that I am who I say I am. With less than a week before my flight to Abu Dhabi, I won’t have many options if he can’t straighten this out. Still, I stare at that painting in my window, and my passport seems like that butterfly: It’s probably within grasp, but it could, at any moment, drift out of view, leaving me with nothing to do but get back to work.

The notion of upward mobility is something slippery, something I don’t understand. Yet it’s also something tangible. Things change as you ascend. You start removing words from your vocabulary and incorporating new ones. You walk differently. When you go to the airport, you no longer have to listen to what the TSA agent is saying at the security gate. You’ve been there. You’ve done that.

The things you need to carry in your wallet start to change. I realized this just yesterday while rifling through my own wallet. My union card, my student ID, a health insurance card under my mother’s plan: When I took my new job, I took them out. Now they’re in a box somewhere, no longer necessary extensions of my identity, but tokens of my past lives.

Things change as you ascend. You start removing words from your vocabulary. You walk differently.

What’s replaced them? My building access card, my own health-insurance card, a dozen receipts that I need to itemize and submit for reimbursement, and 600 U.A.E. dirhams for the trip I may or may not be taking on Saturday.

But these changes are all superficial. I still make less money than either of my parents. I still struggle to cover my bills and pursue my artistic ambitions. I still have to call my mother when things are hard and I don’t know what to do. So what part of me is upwardly mobile? To where am I ascending?

I have a friend who, like me, was raised by a single mother. But his upbringing, until he moved to Ventura, Calif., and transferred to my high school, was more metropolitan than mine. And while my mother only had a high school education (and my father, even less than that), our families struggled to raise their children in very different ways. My mother worked two jobs to make enough money to pay the rent; his mother struggled as she tried to raise two kids while attending graduate school and starting out as a professor. My friend tries to explain to people that while he knows what it’s like to belong to a lower economic class, he’s never known what it’s like to belong to a lower social class.

This is not to discount his struggles, or his mother’s successes. And my mother’s success was measured in the fact that she raised five children on her own. But a professor of mine once illustrated the difference between the worlds in which mine and my friend’s mother struggled when he told our class, “As a student of the liberal arts, a lot of what you’re learning is just stuff for you to say at cocktail parties.”

When he said that, a lot of people in the classroom scoffed. But then, a lot of those people had grown up in homes where their parents hosted cocktail parties, parties to which the children might have been invited, asked to wear little suits or polo shirts or dresses to match their mothers’, and recited poems in front of the group. In college, a lot of these students were performing dry runs as young socialites in their dorm rooms with boxed wine and joints, talking about obscure pop music, professorial scandals, and Jacques Derrida.

No one in my family knows who Derrida is. When my mom or dad had company over, they would drink Coronas and pre-mixed margaritas and ask me to take out the guitar and sing “Cocaine Blues” and “Friends in Low Places.”

I still struggle to cover my bills and pursue my artistic ambitions. I still have to call my mother when things are hard and I don’t know what to do. What part of me is upwardly mobile?

I sincerely believe that both of these types of upbringing have value, though I wouldn’t trade mine for any other. But it leaves me in a strange place on this path of upward mobility. Every time I call home, the gap has increased between my sisters’ experiences and my own. We read different news, watch different television shows, not because of intelligence but circumstance. We have come to know the world in a different way.

My younger sister called me last weekend, after she heard about my trip, and said, “Bubba, I heard you’re moving to Africa.” After I told her where Abu Dhabi was, she explained to me that a relative had told her that I was moving to Africa and would be taking a job as a reporter in Palestine. I told her that I wished my life were that exciting.

And that story is not a dig on my sister. At 22, she spends her time dealing with the complications that come with raising two daughters who have no father around to speak of. It makes no difference to her where Abu Dhabi is. The exact geographical coordinates of the Palestinian territories don’t matter. But what does matter to her is where I am. And I get to be this portal to the world for my family and friends back home. I get to send them pictures from the places I’ve been, and to tell them stories from places outside Ventura. And I think what matters most to me is that my nieces and nephews (I have something around 10 of them), can see me as one person in the family who did something a little different, and see in me another model for life, in addition to the hard-working, blue-collar examples they have back home.

What I don’t tell them is that I often feel as distant from the people here in New York as I do from them. The friend I mentioned earlier came to New York to visit me for a weekend. We went for a walk on the promenade in Brooklyn Heights, where you can look out on the Manhattan skyline. It was night, and the buildings were lit up in that miraculous way that almost makes up for the fact that you can’t see a single goddamn star any more. We both thought it was beautiful, but when I asked my friend which building was his favorite, he said, “It’s just a bunch of corporate phalluses to me.”

I couldn’t figure out why his comment bothered me. The next day we went to Indian food for lunch. I ordered chicken tikka masala. He laughed.

“That’s pretty much what every white businessman orders at an Indian restaurant.”

Yeah, fuck you too, dude.

When we said goodbye, I hid how angry I was. I tried to figure out why his barbs had bothered me. But then something clicked. Yeah, white businessmen order chicken tikka masala. But so do people from working-class families who rarely go out to eat at Indian restaurants (I didn’t know what naan was until I was 20). And when we both looked at the skyline, he was thinking about the people who lived and worked in those multi-million-dollar condos and offices, while I was thinking about the people who built them. I imagined the past and present men who risked their lives every day to feed their families. The Irish and the Italian and the Mohawks and the Puerto Ricans and the man on the New Yorker cover: everyone who climbed, day after day, higher and higher, to create the skyline that now dwarfs the image of Lazarus’s “New Colossus.”

That poem was written when the tired, poor, huddled masses came to America by boat, and they looked up at the Statue of Liberty as an ideal: grandiose in its scale but human in its depiction. Now the vast majority of immigrants from overseas fly into the United States with passports that they often had to go through immense hurdles to get. As I wait for mine, I can walk to one end of my office and look out at One World Trade Center, and on the other side I can see the ferry that shuttles people from Manhattan to Staten Island. It floats past the Statue of Liberty, a green toy, distant and beneath me.

The travel agent comes through the door and hands me my passport. I call my mother to let her know that I’ll be making the trip. I try to hide that I’m choked up.