Fans of Kenny Rogers, and even those who have never heard of him, may recognize this phrase from his best-selling song, The Gambler. Knowing when to hold them and when to fold them is more than just a snappy catchphrase. It’s knowing when to move on. In poker, do you keep betting, hoping to win the pot, or do you get out of the hand and hope the next one is better?

For those approaching the end of their legal career, the phrase means, do you keep plugging away working, or is it time to fold them and start playing an entirely new game called retirement? So how do you know? Here are some questions to ask yourself on when you should retire.

Can you afford to retire?

Or, as some others say, “Have you reached your number?” Talk about a moving target. One financial columnist for my local paper said it best. He wrote, “Those with half a million will respond on a survey that they’ll feel secure with $1 million. Those with $1 million believe they need $2 million. People with $5 million don’t think that’s enough.”

Further, this calculation is so hard for many because one’s health and the associated costs of failing health are so unpredictable. Don’t expect to be able to arrive at some magic number because there is none.

How is your physical and mental health?

For some, if bad enough, this factor alone will decide when to retire. Consider this maxim for the more fortunate ones: “Listen to your body.” It doesn’t lie. Don’t ignore what it is telling you. And I’m not just talking about aches and pains, but also your mental acuity.

What about your family?

It’s not just your health you need to consider, but also your spouse’s and, if alive, your parents. You may need the time and money to care for any of them. On the flip side, there may be new grandchildren to spoil. You wouldn’t be the first attorney to regret not spending enough time with their own children as they were building their career and hope to make up for it with their grandchildren. Better late than never!

Do you still have the “fire in the belly?”

Yes, I know some days are stressful, but that comes with the territory of being a lawyer. But on most days, do you look forward to work? Still enjoy helping your clients? Being intellectually challenged? Closing a major deal? Winning a big case? Interacting with coworkers and colleagues?

Do you still have the stamina?

This factor is especially important for those who frequently go to court, even if you have the “fire in the belly.” You would hardly be the first lawyer to admit that “litigation is a young person’s game.” It can be mentally and physically exhausting. Pushing the envelope to reach the finish line of a contested matter is not fair to you or your clients.

Do you have any unfulfilled hopes or dreams?

When you look back at your career, do you wish the work had been more meaningful and satisfying? Retirement gives you the time to explore something completely new that may give you the fulfillment that practicing law failed to provide. Possibilities such as teaching, mentoring, or volunteering just scratch the surface of the opportunities you could pursue that many retirees find rewarding.

Are you envious of friends and family members who are retired?

Does the grass look greener? It usually does, so I wouldn’t put too much emphasis on this factor. Nonetheless, it is something to think about. Ask retired colleagues if they miss working; sometimes the best way to predict how you will feel about a situation is to ask someone else who is already in it. Whatever the answer you receive, it will offer you insight.

Do you have a plan for your retirement?

Finally, when retiring from the legal profession, you need to ensure that you are retiring to something. What are you going to do with all of that free time? Checking out new movies and restaurants will make you feel as old as you are if that’s all that’s on your radar screen. Talk to those who have already retired, and do some Google searches to get started.

Do What Feels Right

At the end of the day, there’s no algorithm for this decision. Not even Chat GPT can help. The decision about when you should retire is always a “guesstimate.” Everyone will rank these factors differently. Additionally, many of the best predictions could be easily disrupted with little advance notice. Nevertheless, it remains important to at least think about your answers to these questions—and then simply do your best to determine a time that feels right to “fold them” and ride off into the sunset.

Feel free to reach out to me to discuss this further. You can reach me at 612-524-5837, or contact me online.