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The death of a lawyer: A journey from law school to retirement

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Douglas Halpert

Douglas Halpert.

On some mornings, fog shrouds the Ohio River, settling into the river valley like loosely applied caulk. Twenty-three years ago, while on my way to work, my car weaved through the thick, shape-shifting strands as I navigated Kellogg Avenue, which follows the contours of the river toward downtown Cincinnati.

It was then that I noticed a cluster of turkey vultures astride a deer on the right side of the road. They clung tenaciously to its carcass as their impossibly large, pitch-black wings flapped in the wind. As my car approached, one of the birds tore off a piece of venison and consumed it as it lifted off.

What was once a deer was now part of the vulture. With stunning speed, the buzzard attained considerable height and glided above the roadway. It seemed to escort me on my way to the office before circling back toward its cohort.

Perhaps it was my bone-tired weariness—it can afflict even young attorneys in their late 30s when juggling a role as a partner at a large regional corporate law firm with a growing family—but my thought was that it was unfortunate that the deer had not met its end at a time and place of its choosing. I reckoned that it would be more desirable to select the setting for my professional demise.

My dream upon attending the University of Chicago had been to become a novelist, screenwriter and poet—not a lawyer. Like many lawyers, I had bent to the suggestion of family and friends that the legal profession fit my skills. That was their polite way of expressing that I lacked the abilities necessary to be a doctor, engineer or anything else of practical use.

Accordingly, out of a desire to avoid math classes, support my future wife through medical school and find an occupation where I could help others, I wound up at Fordham Law School in the mid-1980s. It was a time when the iconic Socratic teaching method displayed by Professor Kingsfield in the film, The Paper Chase, was still in vogue.

As I neared graduation, in the wake of the economic devastation that followed the 1987 Black Monday stock market crash, the law school career center advised me to pursue a career in estate law—just as the protagonist in the film, The Graduate, was informed that the future was in “plastics.”

After graduating and getting engaged, I found myself on a Greyhound bus headed to Buffalo, New York, to join the law firm Cohen Swados, where I quickly learned that I did not want to be an estate lawyer. Fortunately, an opportunity almost immediately arose to be the firm’s sole immigration lawyer. I had found my professional passion. However, I only had the knowledge gleaned from one general course in immigration law, so I needed to figure out what to do in the pre-internet age.

The only available resources to figure out how to ply my trade at the time were the AILA Monthly Mailing publication of the American Immigration Lawyers Association, and the SUNY Buffalo Law School’s law library. I can still feel my nearly frostbitten feet as I trekked across snowbanks from the distant visitor parking lot, to pry open the heavy steel side door of the law school. At night, I foraged for immigration law books in its collection.

I successfully learned the trade and flourished in Buffalo and then was knighted partner at Frost & Jacobs in Cincinnati in 1998 after migrating with my wife to relatively warmer climes. But these successes did not inspire me to want to spend my entire life practicing law.

It was not that I was dreadfully or even moderately unhappy being a lawyer. After all, I had indeed found something I was equipped to do and was able to earn a living. I was helping hundreds of people from all around the world each year. Some clients were in dire circumstances and a successful conclusion to their immigration case made an unfathomable difference in their life.

I also cultivated a work persona of my own creation to motivate myself: an immigration lawyer who relentlessly pursued approvals for my clients despite significant obstacles—with a bravado akin to that exhibited by Liam Neeson’s character, Bryan Mills, in the movie Taken. In a post-9/11 world, immigrants have often been vilified in the public arena, even though they have made many of the greatest contributions to our country.

While some immigrants have made historic contributions, such as Albert Einstein or Google co-founder Sergey Brin, many more make modest but equally noble contributions. U.S. Citizenship and Immigration Services’ challenge and denial rates have markedly risen over the decades. This is due primarily to shifting attitudes toward immigrants, driven by fear that spawned a regulatory and administrative “culture of no.” Shepherding cases through the regulatory maze is not a profession for the meek.

But no matter their specialty, most lawyers I encountered were unhappy: gloomily sitting at their desks; griping about the pressure of producing at their law firm; miserable at the constant demands of their clients; and weary from being browbeaten by their spouses about their long hours.

The common theme is that unlike many professions, where one effectively has a shift and punches a clock, lawyers in private practice have no natural boundaries to their work hours. The result is an unbalanced life, and lawyers sacrifice their creative dreams of earlier years, such as designing stained glass or writing novels.

And so as I traversed the decades, I saw lawyers burn out and leave the profession; lawyers with seemingly solid marriages get divorced; and lawyers have incapacitating strokes either just before or after retirement. I even knew of lawyers who literally died at their desks. It conjured up the words of the famous filmmaker, Jean Cocteau: “Every day in the mirror I watch death at work.”

In 2011, my then-8-year-old daughter asked me, “How much time do we have left?” on a random Sunday morning while playing the Chutes and Ladders board game, given that it was the only day of the week that I would spend significant time with her. Her comment served as accelerant for my instinct that I needed to exit the legal career merry-go-round.

So, I plotted an elaborate escape. First, I shed the intractable golden shackles of BigLaw partner expectations and migrated from Dinsmore & Shohl to Hammond Law Group, a boutique immigration firm that had a ready-made work-life balance. Then I renegotiated my contract to reduce my hours and cede control over many corporate and other clients to younger lawyers.

I abandoned the delusional fallacy I share with an abundance of other lawyers that, in Bryan Mills-speak, only my particular set of skills gained over a long period of time would suffice to properly serve my clients.

The death of my mother and her incredibly brave words in her final hour, “Let’s get this show on the road!” was yet another impetus to push my plans further ahead. I changed my job to focus more on marketing and associate development, before becoming part-time, and ultimately advising my partners that Nov. 8, 2021, will be the date of my retirement. “Retirement” may be an inaccurate word, as I will be entering a full-time profession as an aspiring author.

As I write these words at dusk, a cloud of starlings is circling the 32nd floor of the Carew Tower, the 1930s-era art deco masterpiece in which I work. Many colleagues think that their sudden appearance in recent weeks is happenstance and find their screaming fly-bys to be terrifying—like a scene from Hitchcock’s classic movie The Birds.

But I recognize them as the ghosts of lawyers past as they fly by: bankruptcy, matrimonial, corporate. There goes labor and probate. I know that they have come for me.


Douglas Halpert is senior counsel at Hammond Neal Moore and a 33-year veteran in the field of immigration law. He was appointed by Mayor John Cranley as co-chair of the Education and Talent Retention Committee of Cincinnati’s Immigration Task Force, was a co-recipient of the 1998 Volunteer Lawyer of the Year Award in Cincinnati, and has been included in Best Lawyers in America for over a quarter century.


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