How to Find Contentment Amid Career Ambitions

I hate to lose. Some people are pretty competitive, and most Americans would say they hate losing. Hate is an incredibly strong word though; perhaps we simply don’t love to be seen as “not winning”?

My older brother routinely taught me that not winning was, in fact, an abject failure. When we were growing up, board games were supposed to be a constructive, non-physical outlet for two rambunctious boys who were otherwise deep into a wide range of sports. My parents dutifully supplied Stratego, Risk, Checkers and Chess and many others about which we were less interested. These games felt like a test of both military intellect and creatively timed domination––at just the precise moment. Often the games became too creative: my bomb pieces would move around the Stratego board (known in “the biz” as cheating) and sometimes my brother would change the rules mid-game or timely remember the actual chess moves when they worked in his favor. I never successfully changed the rules because he jealously guarded the rule book for each game. In the end, the only move to affect the decisive blow was surrender, the earlier the better since I was the only one who would play board games with him.

Having It All

Nobody likes being swindled and, on the other side of the spectrum, some lawyers invariably cannot get enough. I’m not suggesting that lawyers are ripping off their clients, though Alex Murdaugh graphically proved that corruption in law has generations of shelf life. Instead, I’m suggesting that great lawyers doing top-shelf work to help excellent clients achieve their organizational and financial goals is profitable––and how much is enough?

The answer to this question is deeply personal, makes everyone squirm and depends heavily on whether each lawyer has set specific practice goals. At what point is the philosophical greater good no longer served by working to satisfy bills for the third house or the kid’s second master’s degree? Are you really willing to complain to your firm administrator that the parking garage is too small to safely park your iridescent Tesla Cybertruck? Indeed, America is rife with conspicuous wealth and flush with credit card debt: the definitive appetite to buy what we cannot afford right now. According to the Motley Fool, the average credit card debt balance reached $6,501 per cardholder in the third quarter of 2023, a record high and up 10 percent from 2022.

Just a Little Bit More

When John D. Rockefeller was asked “How much is enough?” he famously answered “[j]ust a little bit more.” It’s a profound statement echoed by the Rolling Stones in their biggest hit “(I Can’t Get No) Satisfaction” about the insatiable human desire for more. No offense to the Baby Boomer generation but they have done little to model contentment for follow-on generations. Robert J. Shapiro, the former Under Secretary of Commerce for Economic Affairs, stated that between 2024 and 2030 “well over half of [people reaching retirement age during these years] will find it challenging to meet their needs . . . let alone maintain their current standard of living.” And so, retirement ages persistently grow older.

It’s time to take a hard look at ourselves. We’ve all seen partners work until they had nothing left and died––most of the time not at their desks, as some have threatened. Does a successful career require the gravestone epithet “I should have worked harder”? (Hat tip to Jack Donaghy from the show 30 Rock.)

Universal Panacea 

Perhaps the right first step in answering these questions is to take stock. As with many questions worth answering, one size fits one: there is no silver bullet. Many better authors have written deeply truthful books on practicing gratitude, not comparing ourselves to others, and related concepts, so investigate Brené Brown, Greg McKeown and others. For more practical purposes related to your law practice:

1. Reconnect with your financial planner on what you really need to retire. For those of us who already know (but don’t love) the answer, this reconnection is a good way reinforce what you understand and listen with new ears. It could change your opinion.
2. Next, qualify your best clients and your favorite work. Ideally those two are not mutually exclusive components but, even if they are, how much longer do you want to practice law assuming that great clients and rewarding matters exist? Be honest with yourself.
3. Now, compare the verdict from your wealth planner with your professional inventory and measure, in terms of length of time, whether they match up. If your retirement horizon doesn’t match to your practice goals, you have some serious thinking to do.
4. Reconnect with your mentors. No, there aren’t many people still breathing who are too senior to have mentor relationships. Request brutally honest feedback and then accept it gratefully: the right mentors are ones you trust with big questions and don’t consistently tell you what you want to hear. 

Giving It All Away

Typically, in the workplace when we receive encouragement to give it all away, the concept is put forward by a superior who wants more from you. To be sure, effective law firm leaders have made a career out of exhorting their team to more and better. However, what about the leaders who push for more and better to overtly stockpile more power, status or money? Those are goals that everyone else on the team simply find uncompelling.

Many law practices of any size suffer from a lack of trust brought on by muddy transparency, if not years of the shell game where the goal posts constantly change. It’s difficult for busy lawyers to quantify what is more offensive, the invitation to participate in the shell game or how frequently the rules change.

When you have that sneaking suspicion, whether by partner vote, firm acquisition or combining with a group that has a “different” compensation structure, your time to ask the hard questions may already be late. Bottom line: even if the firm operates in true good faith, what will it take to force a lawyer’s surrender to their nonwork life? When is enough, enough?