The Conversation That Never Happened
One morning, I came into the office and began sorting through the mail that had accumulated since the previous day. In the stack was an envelope from one of our staff members, a psychotherapist in the business Sheila and I had built. I opened it expecting something routine, but instead found a resignation letter.
At the time, Sheila and I were running one of the larger independent outpatient behavioral health businesses in the Southwest. What had begun as a small clinical practice had grown into a broader organization that included therapists, therapy groups, and corporate training programs. Like most health care organizations, the work required balancing excellent clinical care with the practical demands of running a business. Eventually, the company would be purchased by a national health care organization, but at that moment, it was still very much the enterprise we had built ourselves.
The therapist, whom I’ll call Anne, had been with us for about two years. She was talented, but early in her career when she joined. Like many clinicians starting out, she needed guidance not only with clinical work but with the practical side of developing a professional practice.
Sheila helped Anne refine her clinical skills, while I worked with her on the business aspects of the profession: how to market herself, build a caseload, and develop the confidence that comes from watching your calendar slowly fill with appointments.
The most important investment, however, was something less visible. At the time, access to managed care networks was limited, and getting a therapist credentialed often required calling in relationships built over many years. Those requests were not made casually. Once you used that kind of professional capital, there was no guarantee you would be able to do it again for the next person who joined the organization.
I used one of those relationships to help Anne gain access to the network, which allowed her to begin building a full caseload much more quickly than she otherwise could have.
When I read the letter, my reaction wasn’t anger. It was a surprise, largely because we had never talked about it. Transitions happen in every career. People grow, new opportunities appear, and sometimes the next step is to move on. I have always believed that people should pursue what is right for them.
What caught me off guard was not the decision itself but the absence of any conversation beforehand. There had been no signal that she was thinking about leaving, no discussion about what might be changing in her life or her career.
Over the years, I have thought about that moment more often than I expected. Much of my professional life has involved helping leaders think through communication, relationships, and difficult conversations. Yet here was someone trained in a profession built on communication who seemed unable to sit down and say, “I think it may be time for me to move on.”
The experience made me wonder whether the challenge in moments like this is not communication but courage. It takes a certain amount of courage to have an honest conversation about a transition that may disappoint someone who has helped you along the way.
The longer I have been in my career, the more I have come to see something else as well. When you help people grow, you are also helping them develop the independence to eventually leave. The very things you invest in them, the skills, the opportunities, and the encouragement, eventually become the tools they use to build their own path. That realization does not make the moment any less surprising when it arrives, but it does put it in perspective.
Looking back now, the letter in my mailbox feels less like a resignation and more like one of those quiet turning points that appear in a career. Nothing dramatic happened that day. There was no confrontation or argument, just an envelope and a few carefully written sentences.
Yet the moment stayed with me because it revealed something about how transitions actually unfold in professional life. Often, they arrive quietly, without much warning, leaving everyone involved to adjust to a new reality.
It also reminded me that careers, and our lives for that matter, rarely unfold exactly the way we expect. Over time, I have learned that the best we can do is remain present, adaptable, and open to the surprises that come from colleagues, friends, and even family.
And sooner or later, those moments leave us facing the same question.
What comes next?
Most careers have moments like this. A quiet turning point, a conversation that never happened, or a decision that changes the direction of the road ahead.
Have you ever experienced one?
These reflections are part of my ongoing exploration of What’s Next. The current series, Career Turning Points, explores the moments in our lives and careers that cause us to pause, rethink, and consider the path forward.
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