The Second Prong of Retirement

Kathy Fortin

June 22, 2018

The other day, at the end of a meeting with a lawyer, he thanked us for helping him craft a plan for internal succession for his small law office.  He is nearing seventy and came to us for assistance in devising a succession plan that would transition his practice to a younger lawyer.  As the succession planning is coming together and his professional life coming together, he shared with us his other concern.  He has no idea what he will do when he is no longer in active practice.  This statement expresses the second prong of contemplating retirement – the personal side.  His revealing admission has stayed with me, as it has relevance for other lawyers contemplating retirement.

At my stage of mid-life, I am surrounded by family members, friends and many lawyers, and our clients in the consulting business, who are contemplating retirement or are already engaged in this phase of life.  Reflecting on how they have adjusted to the transition, I realize there are a few distinct camps into which they fall.

Camp 1

“I love it” is one of the common reactions.  These retirees explain that they get to do what they want, when they want, and each day is full, with their pursuit of many interests. Spending time with grandkids, traveling with their spouse, gardening or playing tennis fill the void that was once occupied by exhausting work. One year into retirement, they say, “I feel busier and more satisfied with my life than I imagined.”

Camp 2

“It has taken me took me two years to decide, but I am beginning to like it.” This is the evolving retiree. They may still be missing their work life. Most do adjust; it takes longer than the Camp 1 type.  One lawyer I know was mournful in the year leading up to his retirement and was convinced he would have a hard time. He was wrong and is enjoying it, although it took him time. He realizes that the anticipation, like other things in life, was worse than the event itself.

Camp 3

This group is apprehensive and fearful. They freely admit, “I don’t know what I’ll do when I retire. I don’t golf…” like the client who recently got me to thinking about the personal challenges of retiring.  Some I know find their new way by volunteering to serve on boards, developing a second career in the legal field or related to it. They decided to continue working in a second-career capacity at a reduced level and learned to embrace the free time, of which there had always been very little.


Getting to know our clients, I understand how difficult it is for them to contemplate changes that will lead them from a career that involves running their own law firm to letting go. Lawyers who have been entrepreneurs in their own practice, building it, managing and controlling every decision, day in and day out, amidst incredible client demands, are special people. Fast forward forty or so years. How do they relinquish control and discontinue doing what, most admit, they have loved? How do they retire? The answer will be different for everyone. I have seen other clients (like the one who left me pondering) take the leap, in the face of their insecurity. The following are some of my observations:

  • The “leap” does not happen all at once. It is a process that begins with taking small steps, which eventually leads to a plan, even if a rough outline of ideas.
  • The fear is real and many others understand it. Talking about it and realizing you are not alone helps shape your perspective.
  • Take it gradually. Wind down over time. Continue working in an “Of Counsel” role which can allow you more flexibility to branch out your interests, while still feeling engaged in the law. Staying with the law firm to mentor younger lawyers is a huge asset to the firm. And, you can terminate your commitment, if ever you decide to take the full leap.


For many of us, our work life or career, is integral to who we are. The challenge of retiring is not limited to lawyers. It applies to everyone. We are proud of ourselves—our accomplishments, recognitions, reputation and so on. Letting go of a productive, satisfying part of our lives can be hard.  How “you” will do it remains to be seen. Remind yourself that you have many options and that contemplating your next steps can be very exciting.