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When small firm owners fail to secure a successful exit, it’s rarely a market issue. More often than not, they get in their own way long before the market ever enters the picture.
I’ve spent over fifteen years having conversations with lawyers considering retirement, and I’ve noticed a clear pattern. When those conversations don’t progress, it’s rarely because the attorney decided to work with someone else. It’s usually because the lawyer isn’t ready to confront the decisions in front of them. This post will explore some of the most common ways lawyers unintentionally undermine their own exit from practice.
1. You Overestimated How Long You Could Keep Practicing
After decades of sharp, high-level thinking, many lawyers assume they will recognize cognitive decline long before it affects their work. In reality, those changes often creep in unnoticed. You may still know the law and show up, but the margin for error narrows in ways that are easy to overlook.
Because of this, many lawyers continue carrying the same workload well past the point where it is sustainable. They assume they can continue to do what they have always done. That assumption carries real risk, since a sudden health issue or cognitive disruption can leave clients, staff, and family members scrambling.
Even without a crisis, a gradual decline can affect client service and office dynamics. Response times slow. Stress tolerance drops. Small mistakes become more frequent.
2. You’re Afraid of Life After Retirement
For most lawyers, the most unsettling part of retirement is not financial uncertainty. It is the question they quietly avoid: What comes next?
After decades of structure, deadlines, and professional identity, life beyond law can feel unsettling. Many lawyers push this discomfort aside and tell themselves they will think about it later. In the meantime, succession planning conversations are delayed, and decisions are postponed.
It is a natural human tendency to avoid change. And retirement is a BIG change. Until a lawyer is willing to look directly at that transition, succession planning will feel premature or unnecessary.
The way forward is not to force a decision, but to take baby steps. Start thinking about why you will get out of bed in the morning when you retire. You need a purpose. Plenty of great ideas to explore on the web. Then, start experimenting with some of them during the weekend.
Successful exits occur when the retiring lawyer treats succession planning as a process rather than a single event. Retirement comes with challenges, but avoidance does not make it easier. It becomes easier when the process is given shape, structure, and time.
3. You Fear Your Clients Won’t Be Taken Care Of
Many lawyers hesitate to move forward because they feel personally responsible for their clients’ well-being. After years as the trusted advisor, it can be hard to imagine anyone else serving them with the same care and judgment.
For some, you are not just a lawyer; you are the one who helps. Letting go of that role can feel like abandoning people who have relied on you, sometimes for decades.
But let’s face it: we’re all replaceable, including you. Lawyers often falsely assume their clients won’t get the same level of care from someone else. There are other capable lawyers out there who can serve them well. What clients need most is continuity and clarity, not indefinite dependence on one individual.
The harder truth is this: you cannot be in the helping role forever. When there is no plan in place, clients are left to deal with uncertainty about who is handling their matter and what happens next if something changes abruptly. Remember, preparing for a thoughtful transition is not a betrayal of your clients. It is the most responsible way to take care of them.
4. You Feel Guilty About Leaving Your Staff
The same sense of responsibility that keeps lawyers tied to their clients often extends to their staff as well. You may have built your team over decades and feel a strong sense of responsibility for their livelihoods. While loyalty to staff is commendable, it can also complicate succession planning.
Lawyers may delay decisions because they worry about how a sale or transition will affect long-time employees. They fear layoffs, cultural change, or disruption to people who have been deeply committed to the firm.
Ironically, avoiding the issue creates more risk for staff, not less. Lawyers who navigate this well recognize that protecting staff does not mean preserving the status quo indefinitely. It means planning early enough to consider continuity, communication, and leadership transition.
Guilt is understandable, but it does not protect anyone. Thoughtful preparation is what gives both staff and successors the best chance at stability and continuity.
5. Your Practice Is Too Closely Tied to Your Identity
For many lawyers, their practice is more than a business. It is their life’s work. It’s who they are.
This can be somewhat problematic when it comes time to approach succession planning. When stepping away from the firm feels like stepping away from who you are, the emotional challenge often gets postponed. Planning focuses on numbers, timelines, and documents, while the deeper question remains unaddressed: Who am I without this role?
The issue arises when you don’t allow your identity to evolve beyond a single role. Lawyers who navigate this well can separate who they are from how they practice before a transition occurs.
6. You Held Out for the Perfect Buyer Who Never Arrived
Many lawyers approach succession planning with a specific expectation in mind. They want a successor who shares their style, values, background, and practice philosophy. On paper, this feels prudent. In reality, it often becomes an obstacle.
A successor does not need to practice law exactly as you did to serve clients well or to run a stable firm. In fact, some differences are not only inevitable, but also healthy.
By holding out for perfection, many lawyers pass on capable buyers who could have ensured continuity and value. Be careful, because waiting indefinitely for the perfect buyer can leave you with no buyer at all.
What These Exit Mistakes Mean for Retiring Lawyers
The behaviors described above are common. What distinguishes an admirable exit from a poor one is addressing them early, rather than waiting for circumstances to dictate the outcome.
Succession planning works best when it’s approached as a process, not an urgent transaction. If you’d like to explore your situation in a thoughtful, low-pressure way, I invite you to contact me. Even a brief conversation can bring clarity about what’s realistic and what comes next.
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