A leap into the unknown in late career


One day about 14 years ago, I was having lunch with a friend who asked me what I was thinking of doing next. At the time, I was a content senior partner at the New York law firm where I had spent a good deal of my career, but I was moving toward mandatory retirement from the firm. When I described my written plan about the kinds of jobs and activities I wanted to pursue, he mentioned that there were a number of law schools in the New York area that were engaged in searches for a new dean and suggested that I talk to them. Higher education was nowhere on my plan and my first response was “why in the world should I do that!”


Higher education was not in my plan because I didn’t think of myself as an “education person.” I thought of myself as a “corporate lawyer and financial markets person” because that had been the focus of my professional life – at my firm, in government and in the corporate sector. I thought of myself that way in spite of the fact that a high percentage of the nonprofit activities I was then engaged in were about higher and K-12 education. In retrospect, I was astonished that this deep interest did not find its way into my plan. Happily, I had the good sense to ignore my initial reaction and take my friend’s advice. That was the origin of a whole new venture in higher education academic leadership: 3 years as a Dean of Pace Law School and 10 years as President of Pace University.

Was I blind and narrow-minded in thinking about my future? That’s certainly one way to look at it. But looking at it another way, we can begin to gain more insight: Why does that thinking happen? And also, when does that thinking happen? The answers to both questions lie in the context in which they are being asked – they are all about the nature of life and career transitions in late career.


We all go through many transitions in life – in our careers, marriage, children, the loss of loved ones - but the transition that begins when you stop doing what you have been doing for most of your life and you face the question of what to do next and how to get there, that transition is very special.


These transitional moments are sometimes involuntary – they occur because of retirement or a reduction in force, the sale of your company, dissatisfaction with where you are in life or your career, a realization that you want to do something wholly different, a desire to become a teacher or to move into the nonprofit sector, or to move from the nonprofit sector to the private sector. In both cases, you are often confronted with the need to leap into the unknown.


The unknowns are legion: what you would like to do, what you think someone would hire you to do, what you would be successful doing, whether you would like it, how your family would feel about the change, and on and on. Some of these are pretty scary questions.


In these moments, we are often blind to the breadth of our interests and the transferability of the skills and experience. My proximity to my professional life restricted my ability to project the skills, understanding and knowledge I had acquired in years of varied experience on a wholly new canvas. I was behind walls of my own construction.


How to step outside those walls when a transition demands it? With respect to the practical questions – how to explore the possibilities, be prepared for the inevitable rejections, and have the confidence to take on a radically new set of challenges – see the article that I wrote for Financial Executive Magazine in 2015 entitled “What, Me Retire?”


More interesting is what is probably going on in your mind (and your gut) when you contemplate this leap into the unknown:

  1. A whole new set of perceived uncertainties about whether you feel qualified for something very new.

  2. The risk that you will have some failures as you test your skill base in a very different set of circumstances.

  3. The financial and emotional impact of your decision on you and your family.

  4. More generally, fear of the unknown.

These questions arise from our sense of self-worth: our internal attitudes regarding failure, money or level of authority, and external pressures like the attitudes of our families. Dealing with these issues is frequently complicated by assumptions about ourselves that were created in our “former” life. A transition is inherently a journey to a new place, but we all start that journey as, in a way, prisoners of our assumptions about who we really are.


These self-created walls limit the potential we see for ourselves. In my transition from “corporate lawyer/financial services,” I unknowingly viewed myself in a well-defined context with which I was comfortable. In fact, there were a whole range of new possibilities that I had not even thought about. I threw my hat in the ring at two law schools searching for new deans and at a state university searching for a president of a new graduate school in international finance. I considered becoming a judge and explored other possibilities – all as the result of a chance lunch which opened my eyes to what was possible.


It is not, of course, wise to rely on having a chance lunch to open your eyes at this critical moment in one’s life. Through coaching, I can help you understand the constraints that are holding you back as you consider new alternatives and the range of possibilities that are open to you. I have written and spoken about mid- and late-career transitions for 20 years or more. I initiated programs at Pace Law School and later at the broader university for professionals – lawyers, accountants, marketing professionals, television producers and many others – who were facing major life transitions. And my own career has been a series of transitions to new jobs that presented very steep learning curves.


These transitions can present extraordinary opportunities for new growth, new learning, new people and new kinds of challenges. Depending on your financial circumstances, it is a time when you can seek an inflection point in your career in service to the excitement and satisfaction involved rather in service to promotion and compensation. In any case, deliberately seeking coaching, transition becomes a proactive step to shape a professional future with intent rather than default.


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