A couple of years ago, while conducting genealogical research online, I stumbled across an extraordinary document. It was a called a “Declaration of Intention” from the Bureau of Immigration and Naturalization, and it was signed, in a wobbly hand, by my great-grandfather, Charles Eil. By signing the form on that day — October 4, 1909 — my grandfather, who was 26 at the time, was affirming that he was neither an anarchist nor a polygamist, and that it was his “intention in good faith to become a citizen of the United States of America and to permanently reside therein: SO HELP ME GOD.” He was also permanently renouncing “all allegiance and fidelity to any foreign prince, potentate, state, or sovereignty, and particularly to” — and the next part was rubber-stamped — “Nicholas II, Emperor of Russia.”

As historical documents go, it was a fascinating snapshot of the cultural anxieties of the times. But I was more interested in the personal information, like the fact that Charles was 5 feet, 6 inches tall and 151 pounds, with brown hair and brown eyes; that he was born in 1883 in “Jitomar, Russia” (what is now Zhytomyr, Ukraine); that he came to the United States via a ship from Rotterdam, Holland, and arrived in June 1907, and that, at the time of signing the document, he was living in New York City, about 4,600 miles from his birthplace. In the space listing his occupation was the word “carpenter.”

Image by Courtesy of Philip Eil Charles Eil’s Declaration of Intention

I had known very little about Charles, or any of my great-grandparents. And in an instant I could suddenly picture a living, breathing, brown-eyed young man who had made a remarkable trek from one continent to another, where his descendants, including me, still lived. It sparked a mix of excitement, pride, curiosity and wonder.

But there were other, less pleasant feelings, too. Because seeing my great-grandfather more clearly meant seeing my connection to him more clearly. Charles’s son, Harry, became a doctor, and his son, my father, is also a doctor, who eventually married my mother, a lawyer. Together they had three sons, of which I am the youngest, and we grew up in considerable comfort and affluence. I went to private school. I have no college debt.

But now I’m in my 30s and doing my best to assemble a normal life within two tenuous career tracks, as a freelance journalist and an adjunct college English instructor. And it’s clear that, like an untold number of American Jews my age, I’m almost certainly going to make less than my parents did. Thus, I will begin to chart a trajectory different from any of the generations that preceded me. Before me, for the better part of a century, the financial direction of my family in this country went in one direction: up. And now I am, however gradually and slowly, headed down.

Thanks to the wonders of the internet (and to months of subscription fees paid to Ancestry.com), I’ve since been able to find information about that entire generation of great-grandparents. Seven of the eight were Jewish immigrants from Eastern Europe. They came from Russia and, according to census documents I’ve found, arrived here between the years 1898 and 1909. This made them part of the enormous cohort of 2.5 million Jews who emigrated from Eastern Europe from the 1870s up until 1920. This, the historian Daniel Soyer told me, is how the story of America begins for the “overwhelming majority” of American Jews.

While I can’t speak to the exact reasons my grandparents had for leaving the old country, Soyer was one of a group of historians I turned to. And while, certainly, there was anti-Semitism, state-sanctioned discrimination and paroxysms of deadly violence in the old country, for most Jews, the decision to leave was financial. The late 1800s and early 1900s were times of massive economic change in Russia, and Jews were feeling squeezed. “What was going on in Eastern Europe is that a lot of Jews were downwardly mobile,” Soyer explained. In the process of losing economic niches in trades like tailoring, carpentry, shoemaking, clothing and food production, Eastern Europeans were feeling frustrated, he said: “Imagine, like a shoemaker making shoes in some little town and selling them to the peasants. And then all of a sudden there are these factory-made shoes coming from Germany by the railroad, and they’re cheaper and they’re better.”

“People weren’t able to support their families,” historian Annie Polland, executive director of the American Jewish Historical Society, told me. “And when you can’t support your families or are starting a family and can’t do it, you go somewhere else.”

The work that my great-grandparents found in this new country was also indicative of broader generational trends. Charles, a carpenter, went on to own at least one tenement building in the Bronx and appears to have become some kind of landlord. (One census document from after his death, in 1927, lists the profession of his widow, Sarah, as “rent collector.”) Another one of my great-grandfathers identifies as a butcher. According to later census records, he appears to have moved his way up to owning a dry goods store. Another worked in shirt manufacturing, which made him one of countless Jewish immigrants who found work in this booming industry. These three sets of great-grandparents all settled in and around New York City. The outlier was my great-grandfather, Abraham, who, for reasons I have yet to uncover, made his way to Ashland, Wisconsin; there he found work managing a movie theater. The woman he married — Claire, my great-grandmother — was the only one of my great-grandparents born in the United States. Her parents came a generation earlier and made their way to northern Wisconsin.

Image by Courtesy of Philip Eil 1940s Eil Family census records.

What followed from this generation of butchers, shirt manufacturers, carpenters and theater operators is a fairly classic Jewish tale of upward mobility. My grandfather, Harry, son of a carpenter, went to college and medical school and became a dermatologist with an office in the Bronx. And the woman he married, Lois, daughter of a movie theater operator, became a physician, too; she worked in New York City schools and then later for the state of New York combating Medicaid fraud. My grandfather served in the Navy, and after World War II, my grandparents left the Bronx and moved to a house in the suburbs, where they raised three kids, including my father. He became a physician, his sister became a lawyer and his brother became a financial adviser.

On the other side of my family, my grandfather Ralph, son of the garment worker, became a lawyer. And though he died at age 46 of cancer, my grandmother, Mae, sold dresses out of her home to the ladies in her town and raised three daughters. The youngest of the three, my mother, went on to become a lawyer.

Image by Courtesy of Philip Eil Mae and Ralph Geffen

While my parents are distinct personalities who could be the subject of another essay, they also represent classic Jewish-American Baby Boomer types: a doctor and a lawyer. As for me, I have had a life of near-infinite choice. I was born in 1985, into a country of unfathomable wealth, riding the crest of financial success accrued and wisely invested by preceding generations. I was never lacking for food or rent or summer camps or books or sports equipment or family vacations.

After high school, I was able to go to whatever college I wanted, choose whatever profession I wanted and, later, live where I wanted. I was encouraged to follow my bliss, and I found mine, in journalism and nonfiction writing. I chose those fields out of pure love and passion. And my work brings me ecstatic meaning and purpose. I am, in terms of spiritual and intellectual fulfillment, an overwhelming success.

But my paychecks are sporadic and underwhelming. I have no job security. I have no employer-provided health insurance. I have little ability to plan the future beyond my next teaching and writing gigs. And when I found Charles Eil’s Declaration of Intention, I experienced a spike of a familiar, icy feeling that the rise of the family — the pride-inducing, All-American, deeply Jewish tale of education and hard work and upward mobility — stops with me.

I want to be clear that this is not a complaint. The feelings of discomfort I feel are negligible compared to those of hunger, or scarcity, or debt, or discrimination, or lack of opportunity that define the American experience for so many people in this country. And the fact that I even have a forum to express my mixed feelings publicly is an indication of the many privileges I have.

I also don’t want to overstate the drama of my situation. Because of the way that the financial red carpet has been rolled out for me — and, I suspect, for many American Jews my age — my concerns about being downwardly mobile are, at this point, academic. My lights will not be shut off anytime soon.

But I am a reporter who sees stories in the world — and, sometimes, in the mirror. And, as I dug into my family’s story, and thought about the broader trends, I had a sense I am not the only one with mixed emotions about my place in my family trajectory: pride and gratitude, but also shame and sadness and unease.

There is a practical element to this, in the large and small ways that I have realized will not afford the lifestyle in which I was raised. And there are emotional and psychological implications, too. What does it mean to raise children who will have fewer opportunities than you had? What does it mean to see America as a place of all-too-tangible limitations rather than limitless possibility? What does it mean to be born after the American Dream — in its financial form, at least — has already been achieved in your family? What does it mean to depart from the upward financial trajectory from which American Jews, collectively, and families, individually, derive so much pride?

It seems to me that navigating this complex terrain will be one of the projects of my generation of American Jews.

I do not claim to have found an answer to these questions, to have created that language. But I do have some thoughts.

One is that, while I will fall so far short of my parents’ income, there are other ways in which I have indeed exceeded and continued an upward ascent, for different metrics. I believe I am more fulfilled by my work than previous generations, including my parents. My work is joyous and challenging and ever-changing and public and interactive, and it feels like a perfect representation of who I am and what I care about. This is an amazing, rare thing. Meanwhile, my brother, who previously worked at the State Department and is now a consultant in the world of finance and sustainable development and constantly flying to one far-off country or another, has undoubtedly seen more of the world than previous generations, even those that moved to the United States from Russia and served in World War II.

Though I’m inclined to feel an underlying sadness and shame about my downward mobility, there are also ways in which it can actually be a beautiful thing. I was recently speaking with an old friend, with whom I went to Hebrew school, who also chose to pursue a career in journalism. And as we talked, he said something striking: “I think a lot of what Jews have done throughout history has been out of necessity.” We had to live in certain places. We had to work in certain sectors of employment. Now, he said, “I think there’s a certain sense of ‘Well, we’re free now. So let’s use that freedom.’” In that light, the pure freedom to choose a profession — any profession — isn’t a betrayal of my ancestor’s aspirations, it’s the purest realization of it. Our careers, my friend Max said, can be like “the same way that you sit back extra far in your chair on Passover, at the Seder.” He added, “Let’s lean into that freedom a little bit.”

And then there is the fact that my family’s ascent — and thousands of others — took place during the American Century. And we are not in that century anymore.

“The playing field was totally different when your great-grandparents arrived,” historian Rebecca Kobrin told me. “And they knew how to play the game to hit a home run. And now the playing field is totally different. And I think what occupation you choose is not going to be able to make you hit a home run.” My lack of income and career stability — my overall downward mobility — is not entirely my fault.

And, of course, there is a whole conversation to be had about the Jewish element of all this — the idea that, even as our economic horizons may have narrowed, never has a generation been freer to interpret Jewishness and Judaism in a way that feels authentic and meaningful. Meetup groups. Artwork. Activism. Choosing from many varieties of synagogues and services.

And then there’s also the simple, and yet easily forgettable, fact that my great-grandparents lived their lives in the present tense. It’s easy to look back and feel as though they knew the jobs they would hold, the kids they would have, the moves they would make and the illnesses that would strike them down. But, as Polland reminded me, “I think that one thing that’s really important for young people especially to think about is thinking about their parents, their grandparents, their great-grandparents, their great-great-grandparents as young people who did not know what would happen to them next.”

I take solace in the fact that when my great-grandparents thought of the future, they couldn’t necessarily see me, digging through online archives, squinting, trying to understand them better, and wondering what they would think of me and my choices. Their inability to see the future, and whatever joys and pain it holds, was exactly equal to mine.

This article was supported in part by the generosity of the 21st Century ILGWU Heritage Fund.