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Retirement · The Second Career · M10

Elite Law Firms Have a Problem: Their Partners Won’t Retire. So They Hired People to Ask Them What They’d Do on Day One.

The richest professionals in America cannot figure out how to stop working, and their employers are paying consultants to help. The question those consultants ask first is the one every retirement plan skips.

By Sean Anees Saifi · Capital Wealth · Published Saturday, September 19, 2026 · Source: The Wall Street Journal, September 19–20, 2026 weekend edition, whose market figures are the Friday, September 18 close
Key Points
55+
age of roughly a third of U.S. lawyers
59
the age two of the profiled partners retired
40
retreats a year run by one retirement consultancy
28 days
Norway to South Africa, a world record, in retirement
A silver-haired executive in a dark suit works alone at a broad desk in a corner office with a city view, a colleague at a second desk beyond.
“It’s in the DNA of lawyers to work,” said one who retired at 59 anyway. He tracked his time in six-minute increments for 25 years and now refuses to quantify it.
In one line: The people best paid to plan for other people cannot plan their own exit, and the fix their firms bought is a question, not a number: what would you do on the first day?

David Shapiro spent three decades at Latham & Watkins handling high-stakes real-estate, financing and merger deals, tracking his time in six-minute increments. When a consultant asked what he would do if he could be guaranteed success, he confessed a dream of producing on Broadway. He retired at 55, started investing in small plays in Chicago, and within a few years co-produced “Hadestown,” which won a Tony. People still ask what he does all day. He says he is glad to no longer quantify it.

Shapiro is in the Journal this weekend because his profession has a bottleneck. About a third of American lawyers are 55 or older and 14% of those are over 65. Cradle-to-grave partnership means senior partners in their 80s still hold the biggest clients and the juiciest cases, which starves the next generation and feeds an unprecedented poaching spree. When six lawyers left Wachtell for Gibson Dunn recently, one reason cited was a sense that the firm wasn’t clearing the way for new leadership — a characterization Wachtell disputes.

What the firms are doing about it

Paying for help. Latham, Morgan Lewis and Debevoise have hired consultants; Latham adds financial incentives at 55 and counseling through Zelinka Parsons, a husband-and-wife firm in Tucson that runs 40 retreats a year and is now taking calls from Mayer Brown. “There is a talent war out there,” said David Parsons. “It’s easier to recruit them away where they can lead a practice.”

The consultants’ method is the interesting part, because it is not financial. They ask how many healthy years a lawyer has left and what he plans to do with them, two years at a time. John Balsdon, a corporate lawyer who worked 80-hour weeks for 25 years, “initially balked” and could not answer “How would you spend your first day of retirement?” He loved travel and photography. He retired in December 2024 at 59, runs a business shooting aerial photography from helicopters in remote places, showed his work at St. Paul’s Cathedral, and this year drove from Nordkapp, Norway, to Cape Agulhas, South Africa, in 28 days, a world record by four hours. Sven Völcker, a top litigator, thought he would start an arbitration practice; after counseling he took a course at the New York Film Academy and wrote a romantic comedy set where an underground DJ scene meets the legal world.

Elizabeth Zelinka Parsons, who founded the firm after leaving Milbank to raise her children: “I felt like someone with a superpower and didn’t know where to put it.” Lisa Smith of Fairfax Associates: “Sometimes people wait until it’s too late.”

Our read

This desk builds retirement plans for a living, and the failure mode in this story is the one we see most: a plan that is a spreadsheet with no Tuesday in it. The arithmetic of a Latham partner’s retirement was never the problem. The problem was the first day, and nobody had asked. The teachers and public employees we sit with have pensions instead of partnership shares and the same blank where the day should be.

Notice what the consultants’ question does to the money. A helicopter business, a Broadway production company and a screenwriting course have different cash-flow shapes, different start dates and different failure costs, and none of them appears in a plan that assumes retirement means stopping. The pension-maximization decision, the Social Security timing, the withdrawal order — every one of those is downstream of the answer to “what would you do on day one,” and a plan built before the answer is a plan for someone else.

What It Means For Your Portfolio

Hold — write the first day before the withdrawal rate

The people best paid to plan cannot plan their own exit. The fix their firms bought is a question: what would you do on the first day? Every dollar in the plan is downstream of it.

General planning principles, not advice for anyone in particular. Before the withdrawal rate, the Social Security date and the pension election, write down the first Tuesday, two years at a time. A second career, a business or a volunteer role changes the cash-flow shape of a plan more than any market assumption does.

For a pension-eligible teacher or public employee the mechanics are the pension-maximization choice and the timing of Social Security; both are decisions that get made once. Make them after the day-one question, not before it.

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