I have attempted to retire on two occasions, and both times I discovered the same thing: I was not ready to stop working at my craft. I could golf a couple of times a week, meet with a men’s group for breakfast on a weekly basis, enjoy time with my daughters and grandchildren when their schedules allowed, work out five days a week, participate in a once-monthly book club (and of course read in preparation), travel a few times a year, socialize with extended family and friends, surf the Internet on interesting topics, and manage my investments—but I still felt a need to be mentally challenged and, in a real sense, to “stay in the game.”
That realization has made me think more deeply about the many founders and business leaders I have worked with over the years. A large number of them are not resisting succession because their children and/or successors lack ability. Rather, the business itself remains a source of stimulation, identity, contribution and pleasure. Indeed, retirement can feel less like freedom and more like a loss of purpose, particularly if one’s mind has remained sharp and they are physically able.
Retirement is not just financial
We tend to talk about retirement as though it is mainly a financial event. In real terms, it is just as much a psychological and social transition. Research repeatedly shows that work is not just a paycheque; it is also a source of meaning, status, structure, relationships and identity. It has been well documented that forced withdrawal can even be unhealthy.
That matters, because business leaders do not experience themselves as “employees” who are leaving a job. They experience themselves as the builders, the problem-solvers, and the people others count on. When that role disappears, the question tends not to be, “Can I afford to stop?” It is, “Who am I without this?” It is a search for meaning.
Why founders struggle
Founders can have a particularly hard time letting go because the business is often inseparable from the sense of self. Succession is therefore not only a transfer of ownership or management; it is an emotional handoff of identity, control and meaning. That is one reason succession planning is so often delayed or incomplete, even when the next generation is capable.
In family enterprises, this can become especially complicated. The founder may genuinely believe in the successor and still feel reluctant to step away because the company continues to provide challenge and satisfaction. If the business is healthy, profitable and still evolving, stepping aside can feel unnecessary rather than noble. In that sense, the issue is not always ego; sometimes, it is simply that the work still feels alive.
What the research suggests
The research paints a fairly consistent picture. Retirement is characterized as a major identity shift, and leaving work can create a loss of structure, purpose and social connection. At the same time, while there are known well-being risks to retiring, the research also shows that retirement is not universally negative. Some people flourish when they leave full-time work, especially if they have new roles, interests and relationships waiting for them.
That is the key point: retirement works best when it is not framed as an ending, but as a transition into another meaningful chapter. For leaders who have spent decades solving problems, mentoring people and building institutions, a “plain” retirement may feel too thin. They often need a second identity—one that still allows for contribution, challenge and recognition, even if on a smaller scale.
What is the Judeo-Christian view on retirement
Most religious traditions do not treat older age as a time to become irrelevant. In the Christian sources I reviewed, the emphasis is less on stopping work and more on stewardship, purpose, and service in every season of life. The Bible is often interpreted as supporting continued usefulness, mentorship, generosity and faithful stewardship rather than withdrawal from meaningful activity.
From a Jewish perspective, retirement is not about becoming irrelevant. Judaism honours age, experience, and continued service, and it does not generally celebrate a life that turns passive simply because a person has reached a certain age. The Torah’s discussion suggests that some roles may change with age, but it does not imply that a person should stop contributing altogether. In fact, Jewish teaching often emphasizes that when one door closes, another form of service opens—through wisdom, mentoring, community and example. That is one reason the idea of “retirement” can sit uneasily in a Jewish worldview: life is still a calling, even after formal work has changed
These perspectives are helpful because it reframes retirement. Instead of seeing it as the moment when productive life ends, it becomes the season when work changes form. A person may no longer need to build the enterprise, but can still build people, wisdom, community, and legacy.
Advice and personal conclusion
When consulting to family businesses in transition, I most often recommend that the founder move into a senior advisor/ board member/executive chair role. First, the practical reason is that you don’t want all that knowledge and experience walking out the door prematurely. Secondly, the founder can help play the consigliere role when advice is sought, not only on strategic issues, but on the occasional operation matter as well. It can be a source of comfort to the next generation to know that they have a vehicle to seek advice until such time that they have decided that untethering is appropriate.
My own experience has taught me that retirement is not a one-size-fits-all finish line. For some, it is exactly the right next step. For others, especially those who are healthy, curious and still energized by challenge, retirement may need to be redesigned rather than simply accepted.
That is where I find myself: still working, perhaps not at the same level of intensity, but nonetheless enjoying it. I no longer think of that as failure to retire. I think of it as learning the truth about myself. I do not only want leisure; I want meaning, mental engagement and the feeling that I still have something to contribute.
Maybe that is why so many founders struggle with succession: not because they cannot leave, and not because the next generation cannot lead, but because the business remains a living source of purpose. For them, as for me, the deeper question is not whether to stop working. It is how to keep growing, contributing and feeling alive when the old role no longer defines the whole person.
Gerald Pulvermacher & Associates (GPA) is a North American consultancy focused on guiding family businesses and family offices in transitioning leadership responsibilities to the next generation of leaders. Founder Dr. Gerald Pulvermacher, Ph.D., C.Psych., began his career as a clinical psychologist in Ottawa. He expanded his training into Industrial & Business Psychology in 1980 and founded PSS Consulting along with a separate clinical psychology practice. PSS Consulting was acquired by Deloitte Consulting, and he moved to the USA to serve as Senior Partner and Global Practice Director for the Change Leadership, Learning, Executive Development Human Capital and Organization Performance lines of service. Upon leaving Deloitte Consulting he assumed the role of Canadian President, Oliver Wyman Delta, a firm focused on supporting organizations undergoing transformational change. He developed a strong interest in family business and, since 2007, has led Gerald Pulvermacher & Associates. He can be reached via gerald@gpulvermacherassociates.com. The firm’s website is located at: www.gpulvermacherassociates.com.
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