Is There a “Right Time” for Retirement? —Insights from a Recovering Retiree

The news this week that Amazon CEO Jeff Bezos is stepping down to pursue other passions may have come as a surprise to many. An incredibly accomplished executive at the top of his game: Why leave now? In reality, it shouldn’t be surprising. Whether it will make the news or not, every professional comes to a point in their career when it’s time to start contemplating their next season—and transitioning from a life of productivity to a life of purpose.

I am now 36 months out from retirement as the Head of Wealth Management at Merrill Lynch, and I’ve learned that it’s never too early to start thinking about life after your primary career. When I announced I was leaving Merrill, I was told I was “too young” to retire and “making a giant mistake.” But in reality, I had no intention of retiring at all. I was ready for what’s next.

One of my best “first decisions” in retirement was to engage MyNextSeason to support my transition. I was paired with an advisor and support team to help me evaluate my priorities and work in partnership with my wife to make a plan that created new connections and fulfillment. It was exactly what I needed to help me navigate this dramatic life change, because no matter how much self-esteem you have, or how confident, balanced, or successful you are, self-doubt creeps in.

Rather than making knee-jerk choices, I was encouraged to pause and be thoughtful about my next steps. I enjoyed the discernment process so much that I then joined MyNextSeason as an advisor to use what I’ve learned to provide empathy and perspective to others. 

I now consider myself a “recovering retiree,” because the journey of transition can be more emotionally challenging—and take longer—than you might expect. I thought I had everything mapped out when I walked out the door of Merrill, but some of those things did not happen in the timeframe I wanted. That turned out to be a blessing, because I learned how important patience is in achieving the goals you really care about.

Along with being an Advisor at MyNextSeason, I’m also a board member for the V Foundation (Victory Over Cancer), a Trustee at Florida State University, and member of the FINRA Investor Education Foundation. I am supporting missions about which I am deeply passionate. Yet, even though I feel very fulfilled, and sleep more soundly at night, I am inspired to know there’s always something new out there that I can explore while keeping the promises I made to myself when I went through the transition process. No matter what I do, I won’t jeopardize my “untouchable” priorities: time with family, exercise, and reading.

As you think about your transition, listen to those who know you best, and to those who have “been there and done that”—retiring from a main-stage career. Don’t let anyone tell you what you should or shouldn’t do—or make you second-guess your timing.

Your next season may not be obvious on your last day of work, but trust me that there is more—so much more. While transitions are never easy, with the right support, you will discover what’s next while celebrating and embracing the many accomplishments that have prepared you for this journey.