Are You Ready? A Pre-retirement Checklist for ‘50-something’ Baby Boomers

Updated on March 5, 2024

By Donna M. Bennett

For 50-something Baby Boomers, if they think about retirement at all, it’s likely about sleeping late, time to themselves, and having enough money; which may be as clear as it gets.  At this age, it’s typical to feel vague and unclear about those approaching years.

Why the vagueness? Boomers’ retirement will have no resemblance to their parents’ or grandparents’ retirement.  They will live longer, healthier lives, with a lot more options.  In fact, the word ‘retirement’ no longer fits!

Boomers want lives filled with purpose and meaning.  They may continue to work in the same career, take a part-time job, or start a new project or business to satisfy their need to feel useful, and purposeful.  Boomers will not accept a ‘one-size-fits-all’ post-career life.  They are breaking the mold, with no rules or script to follow. 

For Boomers then, ending one phase of life, and approaching a new and unknown one, may feel like age 25 again with a sense of excitement, and a bit of fear about what’s next.  If so, taking proactive, intentional steps can allow a greater sense of control, and less uncertainty about those post-career years.

How to plan then for age 65+, feeling (emotionally) like 25?  Here’s a checklist of 5 questions (and suggestions) for 50-something Boomers to consider:

What values are most important to you? Core values are the foundation from which we make our choices and decisions.  Identify your 5 most important values, and hold yourself accountable to them.

Do you want to use skills that currently fulfill you, and/or learn new skills? Whether you decide to (or need to) keep working, or to work and volunteer, or  to solely use your skills as a volunteer, identify the skills you want to use most and/or want to learn more about (like social media).  Doing what you love will make the experience a win-win for all.

Do you want to resume old hobbies, or try something new?  You may want to increase the time you spend on a hobby, and/or turn a hobby into a new skill (like creative writing).

What are the personal and social anchors that give your life meaning (family, friends, church/synagogue, climate, culture, community involvement, entertainment, location, health care, etc.)  If you plan to move your residence, consider what you may lose and/or gain in the process.

What financial resources will you need to live a meaningful life?  Once you decide how you want to live your post-career life, the answer will be up to you and your financial advisor.

Following the checklist is one way to pre-plan, and may divert some of the emotional surprises that often arise during the ‘honeymoon’ phase of retirement.

Here are a few (paraphrased) comments from retirees who wish they had been more emotionally prepared, and hope to help others before they jump head-first, and unknowing, into retirement:

“Losing the status I had received in my work group was difficult. It actually took a couple of years to get over the fact that, in retirement, no one cared what I had accomplished. I found that building my woodworking skills, and taking woodworking classes replaced my technology skills.  Now I am getting back into technology, but in a different and new way.”

“Moving to a new state after retirement, I missed having my circle of guy friends that I could call upon to help or advise me on something, even something as simple as moving a piece of heavy furniture or ideas on a car repair.  It took awhile to recreate those kinds of friendships. “

“Joining organizations, and being on various boards and committees was a way to get involved. Yet, going from no outside commitments during my work life to all this activity began to feel like a burden.  I had to find a good balance for how I wanted to spend my time.”

Retirement is coming, and by focusing on a realistic set of expectations and early planning, 50-something Boomers can save precious time.  Planning a course for how to use their skills, where they want to live, what they want to learn, and incorporating core values into their activities, can make this time of life an exciting, fulfilling new endeavor.

Donna M. Bennett, M.A. is a Licensed Psychologist, and author of “Is 65 the new 25?…reclaiming your life;  becoming who you were meant to be”.  She is co-founder of and instructor for Encore Transitions: Preparing for Post-Career Life in the College of Continuing Education, University of Minnesota., 3300 Edinborough Way, #550, Edina, MN 55435.


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