Most attorneys I work with don't fear retirement itself. They fear not being ready for it.

Last year, I went out to dinner with some friends. One of them announced to the group that after working for a large telecommunications company for more than 25 years, he was being offered an early retirement package with very attractive incentives.

He further shared that he had already planned to retire within the next year. So, the offer was not going to change his planned retirement date in any significant manner. Despite this, he seemed paralyzed about whether to take the deal. He feared he was not as ready to retire as he had thought.

I spend my days working with attorneys who face similar crossroads, so I leaned in. I probed deeper, asking him questions in three key areas that I believe determine whether someone is truly ready to retire.

#1 Status: How Closely is Your Identity Tied to Your Work?

I asked him, "Is your identity tied very closely to being an upper-level manager at your well-known, prestigious company?"

He said no without hesitation. He had a modest ego and would have no trouble introducing himself as a retired executive. What others thought of his relevance in corporate America did not keep him up at night.

For many attorneys, this question lands differently. For them, a legal career is not just what they do; it’s who they are. Letting go of that identity can be difficult.

#2 Engagement: How Much Do You Still Enjoy the Work?

I then asked, "On a scale of 1 to 10, how much enthusiasm and passion do you have for your job right now?"

His answer was somewhere around a 5. Not much fire in the belly, but enough to function.

For attorneys, this number matters. There is a meaningful difference between someone who is still energized by the work and someone who is simply going through the motions. If the fire in your belly is low, retirement starts to make more sense.

#3 Vision: Do You Have a Clear Picture of What Comes Next?

Finally, I asked, "What do you think you will do when you are no longer working?"

He lit up. “Woodworking,” he said. A longtime hobby he had never had time for. He had tackled serious projects in the past and was eager to go deeper.

That answer told me a great deal. Retirement without direction is one of the strongest predictors of dissatisfaction.

For many attorneys, stepping away from a structured, fast-paced practice can leave a void if it’s not replaced with something meaningful. Having something to move toward, not just something to move away from, can make a significant difference.

Where Do You Stand on These Three Areas?

My friend’s answers across all three areas clearly pointed in one direction, and I told him so: "You will do just fine in retirement." The decision, in his case, was clear.

But not every conversation ends that way. In my work with attorneys, I hear very different answers to the same three questions. See if any of these sound familiar:

• On status: “I have spent over thirty years building a reputation in this field. I am not ready to walk away from that."
• On engagement: "I still love the work. I get a high when the deal closes, and I see the smile on my client's face. I am not ready to give that up."
• On vision: "Practicing law is the only thing I know. I don’t have any real hobbies. I suppose I’ll figure that out once I have the time."

If any of those responses sound familiar, it’s not a reason to panic or make a decision. It’s simply something to pay attention to, and perhaps explore further.

A Smarter Approach to Lawyer Retirement

Retirement is not something you figure out the day after you stop working. It is something you should prepare for while you are still running your law practice.

As an attorney and consultant who has worked with hundreds of lawyers navigating this transition, I have seen firsthand what separates those who thrive in retirement from those who struggle. The choices you make now determine which category you’ll be in. If you would like help thinking through your next steps, I would be glad to talk. Please call me at 612-524-5837 or connect online.

As for my friend, last I checked, he was elbow-deep in a woodworking project. Not a bad way to spend a Tuesday.