My father spent his entire 37-year career working for a major oil company, and retired at 62 with a “golden handshake” that provided well for him and Mom until he died at age 87. Because he never truly loved his job, his last quarter century became the most enjoyable years of his life. He filled them with travel, acting in amateur theater, exercise, puttering around his property in the country, watching PBS, supporting his Lions Club and county museum, and keeping up with family and friends. His retirement let him do what he wanted to do, without stress. He died a reasonably happy person.

It dawned on me recently that my legal career has now been going on for over 47 years, a full decade longer than my dad’s business career. Because I still enjoy my work, I have no plans to retire anytime soon, but when a person enters the seventh decade of life, the R-word pops up in conversations more often with each passing year.

This question has now moved to the front of my mind: What are the most pertinent considerations in deciding when to walk away from the workplace?

An obvious starting point: When the brain and body inevitably slow down and lessen one’s ability to perform a challenging job at a high level, it’s definitely time to retire. My legal mentor, my uncle Charles Boston, told me he quit trying cases at age 68 because he could see that his skills in the courtroom had started to slip, and he believed his clients deserved only his best.

I’ve spent the last several weeks in heavy preparation for a jury trial. Preparing to try a lawsuit that involves several witnesses, thousands of document pages and complicated facts that must somehow be presented in simple terms to a jury requires intense focus. With a steady stream of legal landmines to navigate around, pre-suit filing deadlines and an awareness that because the nonstop work generates large legal bills, the client darn sure expects his lawyer to achieve victory, the experience makes for long days and sleepless nights.

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Enduring this frenzied experience at age 72 gives me an opportunity to reflect on the road that lies ahead. Here are my conclusions, aided (not surprisingly, given my avocation) by lessons from presidential history.

Arena awareness

To use the word made famous in a speech by Theodore Roosevelt, for most of us, the workplace is one’s primary “arena.” According to TR, the person in the arena has a face “marred by dust and sweat and blood” and is one “who, at the best, knows, in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly.”

Roosevelt spoke those words at the Sorbonne in Paris a year after leaving the White House at age 51; after which he proceeded to burn himself out in the nine years that followed with over-the-top zealous conduct that led to his meeting his maker at age 60.

Conclusion: Yes, it’s exhilarating to slay dragons in the arena, but it’s important to have the self-awareness to know when one no longer has the power to do it.

Energy awareness

Another key factor in deciding whether to remain or leave one’s longtime workplace is to take an accurate measurement of the fire in one’s belly. To succeed in taking on major challenges is simply not possible when operating on an energy tank that’s well below full.

George Washington knew he was out of gas at the end of his second presidential term, so he refused to consider a third term, went home to Mount Vernon and died there at peace with himself two and a half years after delivering his farewell address.

Contrast Washington and the positive recognition he received for leaving the arena while he still had horsepower with Joe Biden, whose tank emptied during his White House years, yet he stayed on the job in that depleted state, greatly harming his legacy.

Conclusion: Staying in the workplace without ample energy and passion for the job is a recipe for disaster.

New arena possibilities

As one rounds third base and heads for home in the game of life, it’s smart to consider engaging in new arenas that provide a better fit for the remaining tools in one’s shrinking tool kit.

A good example of successfully executing this maneuver has taken place over the last 17 years as George W. Bush left the political arena when his presidency ended, read Winston Churchill’s book Painting as a Pastime, and proceeded to shift his focus to painting portraits and landscapes that have been well received and produced a great deal of personal satisfaction for him.

Conclusion: Be open to the possibility that there are other arenas beyond one’s current workplace, and they may well provide a better path for flourishing in the years ahead.

Weighing these retirement considerations while entering a new year, and fortunate to work at a great firm with a nurturing culture for productive attorneys of all ages, I end this piece knowing that the key to choosing the best time to retire is tied to having accurate self-awareness of one’s remaining horsepower and energy level, and having an inner circle of trusted work colleagues willing to give honest feedback when they see any sign of slippage. I know that as of now my horsepower and energy are still firing on all cylinders — and may that continue for a few more years as I continue to enjoy my litigation practice.

When the time comes for me to retire, however, I hope to have the courage to change horses and ride forward to a new destination at a different pace, recognizing that the distance between where one stands today and the location of the ever-sinking sunset shortens every single day.