Your first next season

Executives in transition — carefully stepping from their primary career into an eagerly anticipated retirement — may find themselves in a mindset much like high school seniors who are deciding which college to attend. They may feel there is a “right choice” with far-reaching implications that will control their future happiness/fulfillment. And they may feel a near-paralyzing pressure to “choose correctly.”

As part of this experience, executives may struggle with the question “What should I do?” (and imagine that “for the rest of my life” is whispered next).

Remember in high school, when friends asked at every turn, “Where are you going to college?” “What will you major in?” “What do you want to do for the rest of your life?” It can feel like that same drill again when an executive is transitioning.

Associates seem to abandon conventions of politeness and privacy, and share their “expert” opinions on what you should do. It’s a perfect storm, and it can overwhelm many executives in transition.

You have choices; don’t jump too quickly

Thankfully, here is the reality: your transition is to your first next season—not to your only next season. Your decision, really, is: Where to start? Which thing to do first? And rarely are there binding consequences for your initial choice.

It’s a fact that most executives need a detox period after decades of a hard-charging, demanding, productivity-oriented lifestyle in service to an employer.

The detox priorities are new, and these include sleep, spending (overdue) time with family/friends and focusing on personal health and wellness. Many executives feel spent and need to recharge their batteries before summoning the energy to contemplate the next move.

Executives are accustomed to being decisive and having a plan, with a ready answer to questions about what’s next. Thus, a common mistake is to say yes prematurely to the first board offer, the first work opportunity or the first chance to join/be part of something. Some executives jump at the first-available, convincing themselves (incorrectly) that it may be the one and only opportunity, or that they must have a fully baked plan on day one.

Take your time

The change from corporate executive life to the next phase is a real paradigm shift, from a scarcity mentality (no time for anything) to an abundance mentality (suddenly, time to do things). The typical executive career is filled with a sense of scarcity, but post-transition this flips, and the executive re-enters a world where “what to do” and “how to spend your time” are limited only by imagination and physical stamina.

At My Next Season, we stress the importance of pausing — taking time to reflect on what you like and dislike, what brings you joy and what you want your legacy to be. This will all help to identify your longer-term aspirational objectives.

During your career, you have amassed many gifts, talents, experiences and dreams, so now you have the luxury of being thoughtful in how to spend your retirement, and all the others to follow.

Again, your first next season is not your final one. A bountiful world of options and opportunities is spread before you. So give yourself permission to take your time as you dream, explore, network and contemplate future possibilities. You have many next seasons to live into!


Leslie W. Braksick, Ph.D., is the co-founder and senior partner of My Next Season, a company whose purpose is to help executives transition from careers oriented around productivity to lives anchored in purpose.