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Most retiring lawyers assume the most challenging part of selling their firm will be finding the right buyer or negotiating the best deal. In truth, it is the emotional side of the transition that surprises them the most.
Especially for Baby Boomers, retirement stirs far more emotion than lawyers expect. This is not simply stepping away from a job. It is stepping away from a role that has shaped your identity, routines, and sense of purpose for decades.
An exit raises questions about your legacy, your contribution, and what comes next. These are human concerns, not financial ones.
In this post, we will explore the emotional landscape of selling your law practice: the positive feelings that may emerge, the challenging ones to watch for, and practical strategies to navigate both. The goal is to help you move through this transition with clarity, steadiness, and confidence.
A Note on Lawyers & Emotions
If you're like me, you probably consider yourself strong-minded, rational, and not someone who spends their afternoons journaling while burning incense. As lawyers, we're trained to detach, stay logical, and help clients move forward even when they are emotional.
Yet emotions exist. And occasionally, they even dare to show up in lawyers! Selling your law practice is a major life transition, and transitions come with consequences, whether you consider yourself "emotional" or not.
Positive Emotions To Expect (And How They Can Go Sideways)
Excitement
After decades of deadlines, billable hours, and constant responsibility, the idea of stepping into a new chapter can feel liberating. You might look forward to free time, travel, hobbies, grandchildren, or a completely different daily rhythm. You may even feel a renewed sense of curiosity about what life outside the practice could look like.
What to watch for: Too much excitement can lead to rushed or poorly considered decisions. A healthy level of enthusiasm is okay, but impulsivity can undermine your transition.
Pride and Accomplishment
Retirement often brings a well-earned moment to reflect. You built something from scratch, served clients for decades, and created stability for your family and employees. You may feel a mix of pride, gratitude, and accomplishment as you reflect on your loyal clients, long-standing staff, and the reputation you worked so hard to build.
What to watch for: Too much pride might cause you to overestimate how smoothly the transition will go. You may assume your successor will run things exactly as you did, or you may step back too slowly because it is difficult to watch someone else take the reins.
Relief
For some, relief is the biggest emotion of all. The weight of constant responsibility begins to lift. Stress that felt normal for years starts to loosen its grip. There can be a profound physical and mental exhale.
What to watch for: Relief can lull you into checking out too early. This can include letting revenue slide, avoiding hard conversations, or mentally leaving the practice before the transition is secure.
Negative Emotions Retiring Lawyers Should Watch Out For
Next, let's look at the emotions most lawyers prefer not to discuss. Most of us did not learn much about emotional intelligence in law school, and I am pretty sure it was not covered on the bar exam. That said, it's helpful to recognize which emotions may arise and how to manage them so they don't subtly influence your decisions, or worse, sabotage them altogether.
Identity Loss and Loss of Purpose
For many retiring lawyers, the deepest emotional challenge is the sudden question of identity. After forty years of thinking like a lawyer, scheduling your life around deadlines, and being the person clients rely on, stepping away can feel disorienting. It is common to wonder, "Who am I now?"
This shift often shows up long before the sale itself. Many lawyers quietly resist moving forward because, underneath the spreadsheets and succession plans, there is a more uncomfortable truth: you don't know who you are without being a lawyer.
What to watch out for: Identity loss can turn into hopelessness or prolonged avoidance. This can look like obstructing the sale, postponing retirement planning, or staying deeply involved in firm matters long after your successor is ready to lead.
Sadness and Grief
Grief may show up when you least expect it. You are not only leaving a job, but also a professional home and a community. For many lawyers, the practice has been a source of purpose, pride, challenge, and identity. It makes perfect sense that letting it go brings an emotional response.
But think about it– grief only appears around things we value. Sadness is evidence that your work, your clients, and your colleagues meant something. It might be an uncomfortable emotion, but it's also a sign that this chapter was meaningful.
What to watch out for: Sadness can deepen into depression or persistent low mood. This can look like withdrawing from family and friends, losing interest in daily routines, or feeling increasingly weighed down by the transition.
Anxiety
Anxiety thrives on uncertainty, and retirement has more uncertainty than a politician answering a yes-or-no question. You may worry about money, clients, your spouse, or other family members. Instead of treating these thoughts as red flags, see them as normal retirement jitters that can be addressed one step at a time.
What to watch out for: Anxiety can loop into paralysis, endless second-guessing, or repeated delays while you wait for perfect clarity. It can also show up as irritability or impatience, especially when the transition feels slow or unfamiliar.
Management Strategies: How Lawyers Can Work With These Emotions
Below are some strategies to help manage emotions.
Verbalize It
A good first step is simply acknowledging what you are experiencing. Name what you feel. Saying something like "I am anxious and excited" is far more helpful than insisting you are fine.
Create a Simple Emotional Check-In
A simple weekly self-check can keep emotions from building unnoticed. Ask yourself:
- What is on my mind this week?
- What is causing stress?
- What needs attention?
Comparing this with the previous week helps you identify patterns and stay level-headed, rather than letting short-term reactions influence long-term decisions.
Bring in the Right Support
Support can take many forms:
- A professional advisor who understands law firm sales and can offer practical guidance.
- A therapist, coach, or peer group for help with grief, anxiety, and identity questions.
- A spouse or trusted friend who can offer perspective about life after practice.
Build a Vision for Life After Practice
One of the best ways to steady yourself is to picture what comes next. Start envisioning what your first year after closing might look like. Consider:
- How you want to spend your mornings
- How much contact do you want with the firm, if any
- Activities that bring meaning: mentoring, teaching, volunteering, travel, hobbies
The more precise you are about the life you are moving toward, the less frightening it becomes to let go of the role you are leaving behind.
Take Care of Your Body and Brain
Emotional steadiness is easier when your physical foundation is solid. Simple habits make a meaningful difference:
- Regular movement, even if it is just walking or stretching
- Consistent sleep routines
- Healthy, steady eating schedule
- Social engagement with people who energize you
- Limited use of alcohol or other substances, especially during periods of uncertainty
Support for the Emotional and Practical Sides of Lawyer Retirement
Exiting the legal industry is both a financial step and an emotional one. It is essential to be prepared for both aspects of the transition. This is also where professional guidance makes a difference. Many advisors focus solely on valuations, deal terms, and logistics. Roy Ginsburg takes a more comprehensive approach.
With decades of experience and a background in lawyer coaching and consulting, he supports lawyers through both the practical mechanics of succession planning and the emotional realities that accompany retirement.
If you are considering retirement, or recognize some of these emotions in your own experience, it may be time to explore your options. You don't have to do this alone. With the right help, selling your practice can shift from a source of stress to a confident transition into the next chapter of your life. If you are ready to explore what your transition could look like, contact Roy to discuss your options.
