Preparing for the Personal Side of Retirement

Preparing for the Personal Side of Retirement

Retirement isn’t what it used to be—and that could be great news! Thanks to advances in health and technology, individuals are living longer lives and, therefore, enjoying longer retirement periods. Sounds great, right? Who is going to argue against more time to travel, pursue new hobbies, or visit with family and friends?

In theory, a longer retirement period sounds like a win—and it can be. Unfortunately, many individuals will spend more time mapping out an itinerary for their upcoming vacation than they do thinking about how they will spend their time after they leave their careers. Once the honeymoon phase of retirement wears off, they quickly grow bored and find themselves struggling with social, personal, and emotional issues they didn’t foresee.

There are many considerations to be made on the path towards retirement, especially in the final years leading up to it. Because retirement is as much a lifestyle decision as it is a financial decision, you’ll want to make sure you prepare for both.

Replacing Workplace Benefits

Generally when we hear “workplace benefits,” we think of health insurance and access to 401K retirement accounts. But, there are qualitative benefits we receive from the workplace we tend not to think about, as well. As you put together your retirement vision, go through the following list of benefits and explore how you might replace these factors in your post-career life.


For individuals who spent decades deeply tied to their work, the transition to retirement can lead to a feeling of a lost identity. What will define you in retirement? Who do you aspire to be? Some individuals may find that they prefer to stay in their careers longer, or transition gradually, since their career is such a big part of who they are.

A Sense of Purpose

What will you do that you feel gives your life purpose? This could be a spiritual pursuit, volunteering to support a cause you are passionate about, helping to raise your grandchildren, or pursuing a dream you never had time to. What brings you a sense of purpose now? And what from that will you carry into your new life?

If you’re not sure where to start, begin by asking around. Question other retirees you know about their experiences. Their input might just help you find your niche or turn you on to an idea you never considered.


As humans, we are social creatures by nature. How will you replace social interactions from the workplace in retirement? Where will you find a sense of community and belonging? Keep in mind, many of your friends and colleagues may not be retiring at the same time you are. You may need to venture out into other circles of retirees to find more consistent camaraderie and interaction.

Physical and Cognitive Challenge

Research continues to support the fact that remaining physically active and cognitively challenged helps to lower the risk of life-threatening illnesses like stroke or heart failure and also combats depression. Playing tennis, going to the gym, or doing laps in the pool are great for stimulating the body, but they also help to provide a sense of accomplishment and progression, as well. Many individuals will use these activities as anchors in their day and schedule non-recurring activities around them.


Routine is one of the most overlooked aspects of personal retirement planning because so many individuals are looking forward to the sovereignty and freedom that retirement offers. Building a new routine feels counterintuitive. However, studies have found that retirees with planned activities tend to be happier than those who don’t.

Of course, too much predictability can be boring and potentially more stressful. After all, options and spontaneity can be the spice of life. But sticking to some sort of schedule can help you remain productive, active, social, and personally fulfilled when getting used to this new chapter of your life.

Exploring the Possibilities

Retirement is an exciting time, and planning for the personal side of this experience should be fun. The possibilities for how you will spend your time are virtually endless. Plus, you may be surprised to see how your retirement vision affects your financial plan. You may find you need less, or should save more, depending on the outcome of this self-exploratory exercise.


At Uncommon Cents investing, we specialize in helping pre-retirees not only plan for the financial side of the retirement, but the personal one, as well. We know that there is more to success, and to life, than having your fiscal ducks in a row. Whether you already know how you will spend your retirement years or are just starting to think about it, we can help. Schedule a call with us today to learn more or subscribe to our newsletter for monthly tips and helpful planning resources. In the meantime, we think you might like reading our eBook, Uncommon Retirement Realities of Today: 8 Key Insights You Won’t Want to Miss Before Your Big Transition. Simply click the link above to download your free copy.


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More About the Author: Sheena Hanson

Sheena is a highly regarded financial expert known for her clear explanations and practical advice on complex financial matters. She earned her CERTIFIED FINANCIAL PLANNER™️ designation in 2010 and holds a Bachelor of Science degree in Finance from the University of Wisconsin LaCrosse.