How to Win in Retirement

Alan Spector

Alan Spector

Each of us deserves to enjoy a winning retirement, but how should we go about figuring out how to increase the odds that, in fact, we will win?

For the past decade, I’ve had the opportunity to research, write, speak, and blog about retirement life planning, focusing on the non-financial aspects.  My focus has been on helping Baby Boomers and beyond.  But there is a segment of our society that also retires but does so in their 20s, 30s, and sometimes 40s; and even sometimes in their teens.

They are the elite athletes, the professionals, Olympians, and collegiate players, and guess what—we can learn something about how to create a successful retirement from them.  Who better understands how to approach winning than an elite athlete?

In my recently-published book, After the Cheering Stops: A Retirement Game Plan for Elite Athletes and Baby Boomer Career Professionals Seeking a New Future, I’ve used an athletic construct to introduce the concepts of retirement life planning to elite athletes.  And, as it turns out, the construct works for Baby Boomers as well.

There are five steps athletes take to prepare to win.  One of those is to understand the conditions in which they will be playing.  Is the turf, track, or ice fast or slow?  Which way is the wind blowing and how strong?  Where are the steep hills and tight cures on the course?  As Boomers, we need to anticipate and understand what the retirement conditions will be like.  What might the challenges be?  What are the opportunities?

Another aspect of winning is building the right team.  Whether an athlete is playing in a team or individual sport, he or she needs a capable and dedicated support team.  There are teammates, coaches, medical and training staff to help on the field—there are family, friends, agents, and financial advisors to help off the field.  As Boomers, we’ll benefit from the right team, among them being our financial support, advisor, estate planner, accountant, our well-being support, medical professionals, workout buddies, and our life teammates, family and friends.

Athletes and athletic teams identify their strengths and weaknesses as a basis for building their game plan—take advantage of the strengths and plan to account for the weak areas until they are improved.  Boomers can similarly approach retirement.  That’s why in both of my books about retirement, I start the planning process with a personal assessment.  The result can be a winning game plan.

Another important part of planning is making sure everyone on the team is following to the same game plan.  In sports, this requires locker-room meetings, discussions during timeouts, visits to the pitching mound.  For Boomer retirements, this requires the “crucial conversations.”  Our retirement will affect others, and others will affect our retirement—developing our game plan with those closest to us will help us win.

The next step toward winning is practicing.  Perhaps no one knows more about the value of practice than elite athletes—some say it takes a minimum of 10,000 hours of practice to perform at that level.  They practice individual skills, and they practice the game plan.  Boomers who are still working have the opportunity to “practice retirement,” bringing aspects of their retirement game plan into their lives early.  Doing so helps confirm the plan is right and enables us to enjoy our retirement dreams early.

The final aspect of the sports construct as it relates to retirement recognizes that a game plan must be adjusted as in-game circumstances change.  So too do life circumstances change, some positive and some not, such that a retiree must be ready to change the retirement life game plan to adjust to new conditions.

Understand the retirement playing conditions, build your team, develop your game plan and have the crucial conversations, practice retirement, and make adjustments as life circumstances change—a winning approach even After the Cheering Stops.


Alan Spector is the author of two books on retirement, Your Retirement Quest, coauthored with Keith Lawrence, and After the Cheering Stops.  Alan conducts retirement life-planning workshops around the country and blogs about retirement.  In his own retirement, Alan has been a founding partner of three businesses, the author of six books (, and deeply involved with social service organizations, community initiatives to reduce violence, and education programming.  He is a management consultant, baseball player, nonprofit Board member, community volunteer, frequent traveler, and most importantly, the active and proud grandfather of four.  Alan lives in St. Louis with his wife, Ann. 



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