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Business and Commercial Law

A Time to Reap . . . A Dozen Sure-Fire Signs That You're Ready to Retire

By James C. Freund

I recently retired at the age of 62, as a partner at a major law firm. I enjoyed a long and successful career practicing law and still retain strong affirmative feelings toward my firm, but I finally decided I’d had enough of lawyering. This decision wasn’t made suddenly—it was the product of much reflection over an extended period. I retired because I observed–and ultimately, heeded–a number of signs that collectively signaled me that it was the right step to take.

I’m steering clear of the issue of finances here. If your resources are skimpy and you’re dependent on legal fees or other compensation for your daily bread, you probably shouldn’t be thinking about giving up your main source of income.


Sign No. 1. On weekday mornings, you stay in the shower a few minutes longer than usual. You linger at the breakfast table over coffee and the daily newspaper. Instead of arriving at the office at 9 or 9:30 a.m., as you once did, it’s now more often in the 10-to-10:30 range.

When this happens your body is telling you something–what it told me was that the zest I used to feel about tackling the day’s challenges wasn’t there anymore and, moreover, seemed unlikely to return.


Sign No. 2. After an hour of hard negotiating with the other side, you settle the major issue between the parties. Although a number of less significant questions remain unresolved, you excuse yourself from the meeting, leaving your younger colleague to handle the rest. When later that week your colleague brings you the draft agreement, rather than read it through, you ask him or her to point out the sections that resolve the disputed issues, and you scan only those portions.

One of the most important qualities for any lawyer to possess is intensity. I had it in spades for a long time, and then in recent years it waned. My brain was alright, but without intensity, I had become less of a lawyer than I once was.


Sign No. 3. You daydream about what you would like your practice to be. My fantasy was helping clients on strategy and judgment calls, and letting my younger colleagues implement the advice.

But lawyering isn’t like that. Clients want you to deal with their problems. And when you’re no longer willing to get down in the trenches, you’ve got a real problem.


Sign No. 4. You’re telling your client how to handle something—explaining why the course you recommend is preferable, although it’s not the precise path he wants to follow. But the client is resisting your repeated advice. Suddenly, you find yourself blowing up at him. Yes, I blew up on occasion; and even when I controlled myself, I probably treated a few clients with less respect than they deserved. In retrospect, I think I finally became a little tired of pursuing other people’s agendas—which is the very essence of what we, as lawyers, are supposed to be doing.


Sign No. 5. At a cocktail party, you’re introduced to a CEO, two presidents, and three general counsel of Fortune 500 companies. You spend the bulk of the next hour discussing (1) with the caterer, recipes for Tuscan pasta, and (2) with the pianist, whether Richard Rodgers did his best work with Lorenz, Hart, or Oscar Hammerstein.

New business is the lifeblood of a lawyer’s practice. Although hustling legal business was never my favorite pastime, I did my share over the years. Lately, however, even though I fully understood you have to "ask for the order," I found it harder to make the effort.


Sign No. 6. The business page carries an item about a new initiative being taken by a company you used to represent. Hopeful that you may be able to land some of the legal work, you place a call to your former contact at the company. You’re put through to someone who stops humming the theme from "The Lion King" long enough to inform you, in a voice reeking of adolescence, that your contact "uh, like, retired a while back—know what I’m saying?" having been replaced by guess who?—the young man on the phone, who turns out to be good friends with your most junior partner.

Even when you get the urge to solicit business it’s not so easy anymore. I suspect that most of us, are embarrassed to admit that we’ve noticed this kind of thing happening; but I’m willing to wager I wasn’t the only fogy around.


Sign No. 7. You have always prided yourself on being a mentor to younger lawyers. Gradually, however, you realize that the young associates you mentored have all matured into accomplished lawyers, doing their own deals and uncomfortable with you looking over their shoulders. Meanwhile, the younger lawyers who need the mentoring still seek it—but from that first group who were once your protégés! They wouldn’t think of bothering you. . .

Well, this may overstate the case somewhat—and it’s another kick in the shins that’s not easy to acknowledge—but my observation is that as you age there’s less opportunity to perform the kind of mentoring role you found so rewarding in earlier days. But then, as your coaching hours decline, another worthwhile aspect of legal practice is diminished.


Sign No. 8. You have a healthy ego, taking pleasure in the plaudits you receive from others for your achievements. Recently, however, you notice that the bulk of the kudos coming your way relate to past accomplishments.

I consider increasing frequency of rebuffs to the ego as central to the retirement decision. No matter what interests you intend to pursue in retirement, this much is clear: You’re voluntarily giving up the one thing you’re best at and best known for. If the ego gratifications of continuing in practice are undiluted, this is hard to do. When the bag is mixed, you’re more likely to stand down.


Sign No. 9. You hear a currently faddish phrase whispering in your ear as you undertake each new assignment: "Been there, done that."

Those of you with mountains yet to climb in your practice have a good reason for sticking around. But if you’re like I was—having done what you set out to do, and now simply repeating yourself with no particular heights to conquer—then the reason drops away. Alternatively, the mountain may still be there, but the time has come to acknowledge that if it hasn’t happened by now, the climb is unlikely to occur.


Sign No. 10. Your interests outside of the law—particularly those that hold out the promise of self-improvement—begin exerting a powerful pull, and you long to give them fuller vent than they’ve enjoyed up to now.

This is what happened to me, in terms of writing, teaching, music, and photography. If, however, you lack other strong interests, then retiring early can be dangerous.


Sign No. 11. When you open up the morning paper, you begin with a quick perusal of the obituaries. Even when you are enjoying good health (as I am, knock wood), intimations of mortality can start to creep in once you pass sixty. A sense of the days dwindling down can weigh heavily on your decision to call it quits if there are things outside of the law that you want to undertake or accomplish.


Sign No. 12. You fantasize about elder hostels and get your AARP card laminated. . . . That’s it, you’re ready!

James C. Freund recently retired as a partner of Skadden, Arps, Slate, Meagher & Flom LLP, in New York City, and is now of counsel to the firm.

This article is an abridged and edited version of one that originally appeared on page 13 in Business Law Today, Nov./Dec. 1997 (7:2).

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