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Retirement: 5 questions you never knew you would need to answer

Updated: Mar 6, 2022

By: Leah C. Schulte, CFP®, MA, LPC

The 60s and 70s are back! And I don’t just mean tie dye t-shirts and jumpsuits. The so-called “senior” demographic is hotter, healthier, and more energetic than ever before. My 64-year-old father is definitely more fun than I am and, I hate to admit it, but he’s probably in better physical shape, too. If he chose to retire from his career, he could enjoy another 30+ years of work-free, child-free life. After all, he spent the last 30+ years building his net egg, paying into Social Security and Medicare, and getting his kids off of his couches. What more is there to worry about?

Actually… quite a few, (surprisingly obvious), things. To set himself up for success, he might consider answering some questions to help plan for the next phase in his life.

1. What will I do all day?

Answer this once. Now, think about it. And then answer it again, but this time be realistic. The truth? It is so easy to get lost in too much unscheduled time! The first thing you might want to do upon retirement is…well….NOTHING. And that’s great, at first, but have a timeline. For how long will you do nothing? When you’re done doing nothing, how will you occupy your days? Try to make room for daily, nonnegotiable regiments. For example, taking a morning walk at 7:30 a.m. everyday or having the guys over for poker on Thursdays at 6. Write some ideas down in a log!

2. Who will cut my grass, drive me to the airport, get storage from high shelves, and grocery shop?

The fact of the matter is, eventually our bodies don’t move well enough to get up on ladders or the roof. And although this question seems obvious, (um…call a maintenance service?), if you’re accustomed to doing this type of activity yourself, it helps to plan ahead. Which maintenance service? How much will it cost? Do you have a specific point of contact? Write down names, numbers, and method of requests in your log. Learn about new technology that is designed to make life easier and understand how to use it (i.e. LawnLove, Uber, chore services like Spruce, Amazon Prime Now, Rover). Write down instructions in your log so you don’t forget.

3. What will I do for lunch?

Without coworkers and business colleagues, lunch schedules suddenly become unplanned. Research restaurants you have always wanted to try, recipes you love, and names/numbers of people you’d enjoy meeting for lunch. Write down these plans in your log.

4. How can I give back to my community?

Maybe this is a question I selfishly want the older community to ask themselves. There is so much wisdom and power in that community to harness.

More importantly, once careers end, retirees find themselves with a surprising thirst for purpose, which came so easily, before.

Of course we usually work to make money, first and foremost, but that feeling of usefulness and growth that we gain from our careers also helped drive us out of bed and into the office. In retirement, purpose is yours to find again. Will you care for grandbabies? If no grandbabies, does anyone in the neighborhood need a sitter? Tutor? Which schools in the area could benefit from your expertise as a guest speaker? Where else can you volunteer or take up a part-time, meaningful job? I already have an idea for myself someday. For example, I always thought it would be fun to work at a flower shop during retirement. Adrian Durban, if you are hiring in 2050, let me know. What about you? Write down ideas in your log.

5. What will I learn?

Somehow taking the pressure off of school makes it… dare I say it… FUN! Have you ever thought of learning a new language? Instrument? Dance? What about revisiting calculus? Biology? History? Check out online and in-person courses for seniors. For example, the online database of courses, Coursera. In-person classes can be a fun way to meet new people who have similar interests, as well. Write down courses you might be interested in, where you can take them, and when.

The financial team at Brass Tax Wealth Management are available to take appointments and would be honored to help you with this life transition as it pertains to your mental health and your finances. Call 513-791-4575 or message us at for more information. 

I hope these questions serve as prompts for thinking more in depth about what life could look like during retirement. Retirement is a celebration of hard work past, yes, but it is also a time to reinvent yourself and embrace the next decades of your life with a healthy body and a healthy mind.

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