Ask a Retirement Coach: When Should I Retire?

When should I retire is a question that is often asked by many people. Retirement Coach Gary Foster shares his perspective and some things to be considered.

Gary Foster

6 min read.

Dear Retirement Coach;

At 61 I’m stuck on the horns of a dilemma. I am REALLY struggling with the decision of when to retire.

We have enough money to be comfortable. My husband and I between us have made three trips to the cancer club. Thankfully we’re both fine right now, but I’m very conscious that the clock is ticking.

I have no lack of other interests (I’ve self-published two books and am working on three more, have successfully sold jewelry I designed and made and have taken up collage as another creative outlet, manage three rental properties I own, am President of the homeowners association where I own the rentals, plus serve on the board of a local nonprofit) outside my full-time job.

I stuff a lot into my non work hours, but I’d like to call my time my own. It would be nice to book a trip without having to think about whether I have enough leave time or not.

Going back to the office after the pandemic is going to be an adjustment. It’s not my dream, but I enjoy and find satisfaction in my work managing a 250-person federal contact. I know every employee’s name and get a lot of positive reinforcement on my leadership style and a lot of satisfaction out of solving problems for my employees and helping them achieve great things.

The salary is more than I ever expected to earn, and almost anyone would say I’d be nuts to give it up. We also get our health insurance through my job.

But I’m dogged by the idea that this isn’t my highest purpose. I realize this sounds like a “problem” a lot of people would love to have. I know no one can decide this for me. What I am looking for is advice on HOW to make the best decision I can.

Thanks for any help you can offer!

Ann

Ann, I agree that, on the surface, this would seem to be a "problem" most people would like to have:

Adequate savings – check!
Good health – check!
Lots of interests, no boredom – check!
Doing what you love – check!
Health insurance covered – check!
A good, well-paying job – check!
Service to others – check!

What's not to like?

So let me start my response with a question:

What if you eliminated the word "retire"?

To allow the idea of a traditional retirement to take up residence in your mind is a ball-and-chain that is likely stealing your mental energy and bandwidth that may not be necessary to do.

Consider this:

We didn't do it anywhere on the planet 150 years ago.
Few of the world-changers that we revere ever retire – and they typically live longer.
Traditional, off-the-cliff, labor-to-leisure retirement has been shown to accelerate physical and mental decline and to shorten longevity

Thus, my response to your struggle with when to retire is a simple – DON'T.

You are in new territory with no roadmap.

We're living longer than previous generations with a potential longevity bonus of 20-40 years beyond the normal retirement age. But we lack the guideposts we've had for all the other phases of our lives.

At 61, you are asking the right questions at the right time.

This awareness and uneasiness is providing the seed for you to develop a roadmap that can lead you to a great period in your life of having both meaning and fulfillment.

Without knowing a great deal more about you and your specific situation beyond what you've shared, it’s risky for me to state a specific plan for you to personally take. Nonetheless, with what I have and your confirmation that your financial situation is in good shape, let me suggest five steps for you to consider:

1. Determine your true drivers.

Now would be a good time for serious reflection to figure out what will help narrow your focus and give you the most satisfaction in this "third age" of life. Drivers are what make you tick and give you deep satisfaction because they go deep inside you.

If you could use some help in doing this, I would suggest that you read the book Don't Retire, REWIRE!. In the book, the authors share their extensive research of the top 30 drivers that retirees and pre-retirees most commonly told them were the reasons why they worked.

I suggest undertaking the process the book offers to isolate your own top five drivers.

Core drivers don’t change over time but the choices we make to fulfill them do.

2. Prioritize and narrow your focus to what is most important to you based on this reflection and these personal assessments.

With your drivers identified, it's time to begin to define a sense of purpose for this third phase.

The happiest and healthiest in this phase operate with a strong sense of purpose. Those that don't tend to drift into and through their retirement years with boredom, feelings of irrelevance, social isolation, and declining health.

3. Commit to deep couples conversations, now!

You mention your spouse but not his situation.

Is he retired? Due to retire? What are his thoughts about your retirement and your thoughts about his? Are you anywhere close to being on the same page about retirement? If you both retired, would the dates coincide or be staggered?

There is significant danger and a potful of surprises that can result from not having deep conversations about this well ahead of projected retirement dates.

Start now to get on the same page about things such as timing, location, family relationships, how you plan to spend time together, social life, travel.

4. Protect your health.

In light of what you've already been through, this is a bit like preaching to the choir but it's important that health remain a priority with focus on the four main pillars of good health: exercise, healthy diet, high social engagement and continuous learning.

5. Develop a written plan

Put the plan on paper, keep it flexible to allow for inevitable surprises and contingencies, and revisit the plan and adjust as necessary every quarter or six-months.

And move toward a lifestyle built around a combination of labor, leisure, and learning – balanced in a way that honors your strengths, skills, experiences, and creative nature but removes the frustration of not having total control of your time.

Some might even call it semi-retirement for the lifetime!

That has been my personal choice.

Thanks for taking the time to ask your question. I hope you found this helpful. Those of us in the retirement coaching community are pulling for you!

Gary

Do you have any questions about the non financial aspects of retirement that you would like a Retirement Coach to answer? Send them to [email protected].

About the Author

Gary Foster is a former executive healthcare recruiter, over-70 “portfolio-career” guy, and audacious ager dedicated to helping folks in the over-50 crowd adopt a new, healthier, and more purposeful perspective on the second half of life. With national certifications as a retirement coach, résumé writer, and online presence expert plus over 18 years of career coaching and recruiting experience, he coaches, speaks, and writes publicly on the issues of mid-life career transitions, planning for purposeful retirement, and achieving better health and greater longevity. You can reach Gary through his website: Make Aging Work.