It is the beginning of a new season in my life and, by all accounts, it feels much like fall.
The daylight hours are getting shorter and the air is crisp on most mornings. The leaves are past peak and descend haphazardly now on autumn’s breath. There are signs all around me of significant change and preparation for the coming winter. Some are way too close to home.
My brothers and father no longer walk with me. My wife openly talks about her planned retirement and what might be next for her. Our two daughters, who live a block from each other in Manhattan, are at the start of their adult journeys and all that comes with that. For our daughters it will be a vastly different season than mine but one no less important or influential in their lives.
At the other end of the generational spectrum, my mother and my father-in-law require something more and different from our family. And as much as we plan for such realities, our family barely weathers those moments when we make it up on the fly. Through it all there is laughter and tears, anger and sadness as we bear witness to our aging parents and their independent spirits, wisdom, defiance, and decline. I too am still learning from our parents on those days when I can remain open. The sad fact is that I am not always available to them.
The daily tides of my new season are now influenced by the gravitational forces of caring for young adults and aging parents. Think springtime tides with major ebbs and flows. Each tide in turn fuels my desire for personal reflection about what the future may hold for all of us. A few things are clearly evident right now. Winter is not that far away. And time—that most precious commodity–is taking on a whole new meaning for me.
Timing is everything in life, in love, and even in leadership. It is inextricably linked to the seasons in the natural world as well as major events and chapters in our lives. Think about love and loss. Weddings and funerals. Birthdays and anniversaries. Family gatherings and reunions. Graduations and ceremonies. Job promotions and resignations. All have the power to create new seasons in our lives.
As you might imagine, my new season is dramatically reshaping my professional journey. For the first time in 35 years, I am working for myself and operating a boutique consulting firm which helps organizations harness the power of authenticity and humility to achieve greater impact in community. This is far afield from last fall when I left Whitman-Walker after nearly 16 years of service. I am grateful for what that family by choice taught me about the importance of unconditional love, authenticity, and empathy in service of others. And I will cherish a few special friendships the rest of my days. Yet that life-affirming season at Whitman-Walker is over. It is time to learn more and embrace new cultures and experiences with the precious time I have left on this planet.
I am often asked why I chose to leave Whitman-Walker. The question usually comes from business executives and nonprofit leaders who are considering leaving their current roles yet hold that thought close. Professionally, these leaders seek a confidant who recently completed their own discernment process and, in some circumstances, implemented a successful transition plan. Personally, they crave safe and confidential space to explore their own feelings (anxieties, doubts and fears), learn from others’ decision-making processes (the good, the bad and the ugly of self-reflection), and begin to lay the emotional foundation (the need for making time and space) for saying goodbye to an organization (read people) that they deeply care about. In these candid conversations, no detail or feeling is too small because the emotional stakes are so high.
My response to this question still takes many leaders by surprise. It is far more nuanced and cannot easily be delivered as an elevator speech. And at first glance, it appears light on substance and heavy on emotional processing. But that is by design. Knowing if, when and how to leave a CEO role is a deeply personal decision that warrants gravitas, humility, time, and space to really do the discernment process justice. It is one of those rare moments in life where the journey matters more than the destination. And in my own experience, there is simply no way to short-cut or short-circuit this process. To do so is to risk too much–for the leader and the organization.
What ultimately worked for me—a 18-month discernment process centered on authenticity, humility, and vision for my future—may not be everyone’s cup of tea. Yet there are common threads in any formal process that warrant consideration. The need for a significant investment of time and the creation of much-needed physical distance and emotional space to reflect on one’s needs. A healthy dose of discipline and determination to protect such time and space from daily incursions. A personal commitment to humility and self-awareness about one’s own character, ambition and drive, and health and well-being. An honest assessment and keen understanding about the organization’s strategic direction for the future. These considerations inevitably give rise to this penultimate question:
Can I effectively lead this organization in its efforts to achieve specific strategic goals given my vision and passion, my identity and voice, my leadership philosophy and skills, and my own personal needs?
For me, the answer was self-evident. It is time for a new season.
I hope you find this post helpful wherever you are on your leadership journey. As always, I welcome your comments, experiences, and perspectives in the spirit of mutual sharing and learning.