Retirement Readiness Questions that Have Little to do with Money

For many, retirement feels like a double-edged sword. On one hand, it can be what we’ve worked toward for so many years — a well-deserved break for a lifetime of hard work. On the other hand, there are so many unknowns and financial risks on the road ahead, it can be difficult to think about leaving the workforce and the steady paycheck it provided.

While being financially prepared for retirement may be crucial, there are several other aspects that can help ensure you retire to the fullest. To those nearing retirement, here are five retirement readiness questions to consider that have little to do with money:

1. Where will you live?

While most retirees plan on staying in their current homes, that is by no means the only option. You could move to another state, whether to live closer to family, find a more tax-friendly location or even a different climate. You could also downsize to a smaller, more low- maintenance home, townhome or condo.

If you’re planning on changing cities, consider visiting your planned destination during all four seasons to make sure you can stand any swings in climate before taking the plunge.

It’s also a good idea to review any relevant tax laws of the state you live in, as well as where you may want to move. For example, Mississippi doesn’t tax Social Securityand other qualified sources of retirement income, including 401k distributions and pensions.

2. How will you fill your days?

In retirement, every day can feel like a Saturday. This may seem very appealing when we’re punching a clock every week. But in retirement, we’ve found that without a plan, many retirees may fill their days with household chores. Household chores may be a necessity, but they definitely won’t make retirement feel like the reward it was meant to be.

Are there hobbies or passions you’d like to pursue? Did you play an instrument in high school or college that you always said you’d like to pick up again?

Are there causes or organizations where you’d like to volunteer your time a few days (or a few hours) a week? There are many nonprofit organizations that would love to use some of the skills you used in your work life such as project planning, scheduling or accounting. The great news is, in addition to filling a need, you can be in control in determining how much of your time you’d like to donate.

3. What kind of lifestyle are you envisioning?

When you think about retirement, do you see yourself slowing down the pace you’re currently living, or increasing your activity level? For instance, while you are working, you may only have time for the gym two or three days a week.

When you are not working, will you go every day, or will you trade in your gym shoes for a new bike and trail ride? Retirees can benefit from giving serious thought to how they’ll adjust their lifestyles when their calendars are wide open.

4. How will you stay social after leaving the workplace?

One of the things we lose upon retiring is the daily social interaction we had with co-workers. Loneliness in retirementhas been linked to cognitive decline. But fortunately, maintaining a social circlecan help retirees feel happier and healthier.

Staying connected can be as simple as a weekly coffee date with a friend or a joining a book club. Volunteering, serving in some capacity at your church, reconnecting with family, neighbors, all of these are ways to help bring interaction back into our daily lives.

5. How’s your health?

Many people nearing retirement may be concerned with their financial health, and understandably so. However, medical health should also remain a priority. 

Whether it’s a change in diet or adding a little more physical activity to your weekly routine, any steps you can take now to improve your health and well-being in retirement can help save you costly medical bills and treatments down the road.

Most of us have some medical, dental or hearing issues that we have been putting off for a variety of reasons. Those nearing retirement should consider addressing these issues while you still have private health insurance, as some treatments may not be covered under Medicare.

Retirement is an exciting change, and we’ve found that retirees who weigh their financial and lifestyle factors before making the switch help set themselves up for success. Heyday’s retirement income planner app can help you identify the expenses and income so you can address any financial gaps before transitioning into retirement.


1“10 Most Tax-Friendly States for Retirees,” 2017.

2”Loneliness is a Mind Killer – Study Shows Link to Rapid Cognitive Decline in Older Adults,”

3”Friends Can Boost Health, Well-Being Among Older Adults,”         

Materials offered by Heyday Retirement, including articles, ebooks, and workshops are designed to provide general information on the subjects covered. They are not intended to provide specific financial, legal or tax advice. Heyday markets insurance products and its representatives do not give investment, legal or tax advice. You are encouraged to consult your tax advisor, attorney, or investment advisor.

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Cindy Collins

Written by Cindy Collins

Forbes Contributor & Retirement Financial Professional

Cindy Collins is a Heyday Retirement contributor with over 30 years of experience in personal financial services.

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