Although I work primarily with senior leaders who expect to remain in their roles for the foreseeable future, I've also worked with a number of clients over the course of a professional transition. In some cases their move was triggered by a business event, such as an acquisition, the expiration of a lockup period, or the accomplishment of a long-awaited milestone. In other cases they simply felt that it was time to move on, and that the business would be better served by new leadership.
None of these clients considered themselves retired, and almost all intended to start another company or seek a new leadership role after a period of time. Some worked with me continuously during this phase, while others would hold occasional coaching sessions that allowed me to keep up with their progress. To be clear, I'm not suggesting that there's only one approach to a transition, but I've observed the following themes among clients who feel that they made the most of the opportunity.
Have a Plan, Hold It Loosely
You may begin your transitional period with a simple desire to take a break. You want an empty calendar and nothing more. In a sense you're "on vacation," and the last thing you want to do is plan. But vacations are respites from our day-to-day lives with clearly defined end points. Open-ended transitional periods are day-to-day life, and although it's initially thrilling to have no onerous obligations, eventually an empty calendar starts to feel just empty.
So after a few weeks, maybe a few months, it becomes important to have a plan. This can take many different forms, but in general there's value in having a set of A) daily routines and B) long-term goals. "Daily" need not mean "every single day," but, rather, "on this particular day" or "more often than not." The emphasis is on routine: a reliably predictable set of activities that guide one's investment of time and attention.
Some of these routines involve experiences that are ends in themselves, such as a reflective walk or time with friends and family, and it's essential to allow sufficient time for such "atelic" activities, which "do not aim at a point of termination or exhaustion, a final state in which they have been achieved." [1] But it can be equally valuable to establish a set of goals to accomplish during the transitional period, and I've worked with clients who've traveled to far-flung destinations, conducted lengthy meditation retreats, and mastered skills from needlepoint to alpine climbing.
And yet these plans must be held loosely, lest they come to feel like onerous obligations themselves. Sometimes this means going with the flow on a given day, relaxing or even abandoning your routines in order to be open to spontaneity and serendipity. And sometimes this means letting go of a goal when it threatens to diminish the intrinsic sense of fulfillment that motivated the activity in the first place. [2]
If It's Not a Clear Yes, It's a No
In some cases transitions are well-publicized, while in others they occur quietly. But when leaders move on, eventually word gets out that they're no longer working and "available" in some way. Once this happens you'll typically receive a number of inquiries from people seeking your time and attention. Some such inquiries involve full-fledged job offers, but many more involve part-time opportunities of one sort or another: consulting projects, advisory roles, speaking gigs, podcast appearances, and the inevitable requests to "pick your brain."
In the initial "vacation" phase of a transitional period, it's easy to turn down these requests, because the appeal of an empty calendar outweighs anything a part-time opportunity can offer. But as the weeks turn into months, you may begin to feel somewhat uneasy when confronted with so much spaciousness. You're probably used to feeling busy and being productive, and once you're sufficiently rested an open-ended vacation will lose some of its savor. It's still pleasant, but you likely want more out of life than that, particularly if you're envisioning a long-term transition.
At this point some of these part-time opportunities begin to seem more appealing, and you now have to wrestle with the challenge of how to decide which ones to accept and which ones to turn down. This is one reason why having a plan is so important--even when held loosely it helps ensure that proximate choices are guided by an overarching intention. A framework that's immensely useful in this context comes from the work of my colleague Dan Oestreich:
If it's not a clear yes, it's a no. The phrase tests our clarity and commitment... [While considering a project] I dithered and the phrase came back to me. It was clear this project was not for me. The real question, of course, is what’s behind the dithering. And there, I believe, calling up the phrase can help us identify where our sensitivities really are. As in, what’s really going on here? Will I disappoint someone else? Will I create an awkward moment? Will I violate my self-image in some way? Will I show my true colors, the ones I have trouble admitting to myself? [3]
Dan highlights the reasons why saying "no" can be so difficult: Someone will be disappointed. There will be awkward moments. You like to think of yourself as generous and accessible, so you will violate that self-image. And in so doing you will reveal your true colors, your real priorities, which may well feel vulnerable or embarrassing. And yet when you overcome these difficulties and say "no" to everything that's not a "clear yes," you'll invariably be happier as a result.
You Earned the Ph.D., Now Write the Dissertation
You undoubtedly learned a great deal in your previous role, and yet much of that knowledge has remained tacit and implicit, stored in your head, because you were too busy to write it down. One of the most valuable uses of time in a transitional period is documenting that knowledge and making it explicit, which I think of as "writing the dissertation after earning the Ph.D."
If you're a founder, this will undoubtedly take the form of a manual for structuring and scaling a company more effectively, drawing upon what went well--and what didn't--in your prior venture. But there are a number of topics that you may find worthy of reflection, no matter what your particular role or industry:
- How to be a better leader, particularly under adversity.
- How to build a stronger culture with more productive norms.
- How to interview, hire, level, and fire people more effectively.
- How to have better working relationships, particularly across differences in style.
- How to resolve conflicts and handle difficult conversations.
- How to invest in self-care and establish necessary boundaries.
A key in this effort is finding the format and process that work best for you. By calling it a "dissertation," I don't intend to suggest that it should in any way resemble a dry, academic undertaking. It has to feel alive. You may prefer a stand-alone written document, a tool such as Roam or Evernote, or even PowerPoint. You may want to publish your efforts (or an edited version) on a personal site or via social media, you may want to share it only with close friends, or you may want to maintain strict privacy. And you may want to engage former colleagues and other thought partners in active dialogue, or you may prefer the solitude of your own thoughts.
It's easy to not make the most of a transitional period simply by not following the guidelines above. The lack of a plan allows time to pass unproductively, while a rigid, inflexible plan leads to frustration. An inability to say "no" allows other people to set your priorities, leading to overwhelm and a lack of focus. Failing to document lessons learned makes it more likely you'll make unnecessary mistakes in your next venture or leadership role.
But an even easier way to mismanage a transition is to rush through it and take another full-time position too soon, against your better judgment, or for the wrong reasons, e.g. "the money's too good." Such mistakes are usually attempts to quell anxiety, and it's preferable to simply acknowledge that anxiety is an inevitable feature of what William Bridges called "fallow time," referring to the period between crops when land is left uncultivated: "First there is an ending, then a beginning, and important empty or fallow time in between. That is the order of things in nature." [4] Bridges encourages us not to shrink from this aspect of experience, but to embrace it:
One of the difficulties of being in transition in the modern world is that we have lost our appreciation for this gap in the continuity of existence. For us, "emptiness" represents only the absence of something. So when what's missing is something as important as relatedness and purpose and reality, we try to find ways of replacing those missing elements as quickly as possible...
You should not feel defensive about this apparently unproductive time-out during your transition points, for the neutral zone is meant to be a moratorium from the conventional activity of your everyday existence. [5]
There is undoubtedly something unique to be learned during this transition, something that can only be learned in a fallow time, a neutral zone between endeavors. I hope the guidelines above help you make the most of yours.
This is a companion piece to the following:
Footnotes
[1] Midlife: A Philosophical Guide, pages 133-134 (Kieran Setiya, 2017. This volume expands considerably on the topics Setiya explores in his 2014 paper, "The Midlife Crisis.")
[2] Babies, Bathwater and Goal-Setting
[3] If It's Not a Clear Yes, It's a No (Dan Oestreich, 2020)
- I've been inspired by this passage of Dan's before: The Final Third (On Mortality, Values and Spending Time)
[4] Transitions: Making Sense of Life's Changes, page 17 (William Bridges, 2004, Revised 25th Anniversary Edition)
- I highly recommend Bridges' work for anyone going through a transition. For a further discussion, see William Bridges on Transitions.
[5] Ibid, pages 133-135.
Photo by Richard Walker.
