How to Win at Retirement (Or just be ready when you decide to post that permanent Out of Office Message!)

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As a former accountant and current financial planner for the past 20+ years, helping clients become “work optional” is one of the greatest joys of my job. On the other hand, having to tell someone that they really can’t afford to retire is arguably the worst, especially when they had not even considered that my “retirement” advice would be “keep working!”

About a year ago, I had answered the same questions about Medicare so many times, that I decided to to commit the answers to paper. Now, we regularly send it out clients as they approach their 65th birthday. (If you’d like to receive a copy, shoot us a note at and include your email address (if you’d like an electronic version) or your snail mail address if you’d prefer a hard copy. We’ve also posted it as a blog post!

This blog will be my attempt to help people know whether they’re prepared for retirement, what steps to take as they approach retirement and pitfalls to watch out for along the way. If any of my current clients are reading this, I’m sure you’ll find some of the stories and advice familiar. Thanks for reading. If you have a topic, that you’d like addressed, please feel free to email at the address above.

When you consider your retirement, spend some time thinking about how you will spend your days. What time will you get up? What will you do? If you regularly go to exercise class in the early morning hours, will you switch to one that starts later? Will that change your friend group? Do you want to golf 5 days a week or do you prefer to stick with 2-3 days? How does your spouse feel about you being around during the day? One thing that I can absolutely promise you – your spouse does NOT welcome your input in how to structure their day! Nor do they necessarily want you following them around offering suggestions on their activities. I actually had the wife of a very successful executive call me about two months into her husband’s retirement and tell me, “Stacey, you have to find a reason to send Joe back to work! He’s driving me crazy!” Obviously, Joe is not his real name, but you can see that he was used to managing a large organization and letting go of those duties was hard. His wife did not appreciate being the recipient of all his managerial skills.

I will say that most of my clients love retirement. A common refrain I hear is “I don’t know how I had the time to work. I stay so busy now!” That brings up my second bit of advice. Resist the urge to say yes to all the offers to join boards, serve on this committee, volunteer here and there. I’m not advising you to say no to everything, but to go slowly. Accept one or two key roles that you’re passionate about and see how they impact your schedule. After 6-12 months, your life will take on a new rhythm and you can decide then whether you really have the band or capacity to do more. The last thing you want to do is to get so busy volunteering that you lose the things you most looked forward to in retirement – the ability to have a leisurely cup of coffee, watch the birds out the window, take a walk, spend extra time with family, pick up the grandkids from school, take that cool trip just because…you get my point.

As you approach retirement, take a hard look at how much you’re spending each month. The quickest and usually most accurate way to do this is to look at how much money is flowing into your household each month from paychecks and other income. These are your inflows (take an average over 6 months or 12 months if you get an annual bonus). Then look at your checking account. Does it steadily increase? Are you sending money to investment accounts? If your checking account stays about the same and you’re not making investments, this tells me that you’re spending all of the income coming in. What will change in retirement? Will the mortgage be paid off? Are you planning to move to a new city in retirement? Are you looking to downsize? Is downsizing really possible in your area? For example, I’m in the Memphis area and many of our clients live in beautiful houses of 3600-6000 square feet and they readily acknowledge that they don’t need or want that much room. However, they like living near people with similar interests and they have certain expectations on how their kitchen and living areas should be outfitted. They also don’t want to give up a large master suite with plenty of closets all on the main floor. Unfortunately, these smaller but still upscale homes don’t much exist and when they do, their cost per square foot makes them similar in cost to their current home. Other areas of the country, Florida for example, have a greater abundance of homes designed for the retiree demographic.

Thanks for reading and check back for updates and send any ideas for topics as well!

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Our approach is to discover a client’s goals, determine the personal financial plan that is needed, and aid the client in reaching those goals. Our success is measured by how well our clients achieve their goals.
Hank has had a distinguished career in the financial services industry, including more than 40 years in the financial planning and securities fields. From 1985 to 2013, Hank provided fee-only financial planning services through his firm, Lifetime Planning, Inc. Hank merged his practice with Stacey’s in 2014. In addition, Hank is a member of both the local and the national chapters of the Financial Planning Association (FPA).
Hank received his bachelor’s degree in business administration from the University of Mississippi, where he also lettered in football. He received his initial securities training at Merrill Lynch. He was a financial planning consultant for the Memphis office of Ernst & Young and financial planner at Morgan Keegan & Company, Inc. from 1982 through 1984. In April 1984, Hank completed his CERTIFIED FINANCIAL PLANNER™ professional requirements with the College for Financial Planning in Denver, Colorado.
In addition to his financial planning practice, Hank has enjoyed serving on the boards of Presbyterian Day School, Second Presbyterian Church, University of Mississippi, and the Christian Community Foundation. Hank served as the chief financial officer of the Christian Community Foundation from its inception in October 1998 until October 2000. Hank enjoys reading, hunting, and attending baseball and college football games.
Clay serves Envision Financial Planning’s clients as the investment officer and portfolio manager. His duties include overseeing the firm’s investment process and money management strategies with a strong focus on “goals-based” investment planning.
As a firm, we believe in concentrating on things we can control such as:
Clay is a native Memphian and a graduate of the University of Mississippi. He began his career working for a regional broker/dealer specializing in fixed-income securities, and prior to joining Envision, Clay was an investment research analyst and portfolio manager for a private wealth management firm in Memphis. Clay currently holds his FINRA Series 66 securities registration and obtained his CERTIFIED FINANCIAL PLANNER™ designation in 2021.
In his free time, Clay enjoys playing golf, exercising, reading, and cooking with friends and family. He and his wife, Margot, have two boys named Callan and Wiley.