Retirees’ Anti-Bucket List: 10 Experiences You Don’t Want

Your retirement bucket list is no doubt packed with fun stuff, so let’s discuss how to help ensure you don’t get blindsided by things that could be prevented.

An older man sits on a park bench alone, facing away from the camera.
(Image credit: Getty Images)

About 10,000 people retire each day with dreams of the future and a bucket list full of items to check off. Unfortunately, many retirees may encounter hardships that, had there been proper preparation, could have been avoided. No one can predict your future health conditions, financial markets, tax rates and so forth. But, with a well-structured comprehensive plan, you can move into a better-prepared position for the emotional, physical and financial fluctuations that retirement may bring.

With over a decade of experience in retirement planning, I wanted to share my retirement anti-bucket list, featuring 10 common blind spots that you probably do not want to experience as a retiree. These potential problems can significantly disrupt a well-intended retirement and its associated financial plan. I hope that you do not encounter any of the following issues during your retirement. If you do, I hope that you are prepared accordingly. Let’s begin.

1. Working longer than necessary

One of the most common retirement misconceptions is the belief that one must work until a specific age or accumulate a certain amount of savings, say, $1 million, to retire. Much of this is rooted in oversimplified financial planning and generic assumptions.

Subscribe to Kiplinger’s Personal Finance

Be a smarter, better informed investor.

Save up to 74%

Sign up for Kiplinger’s Free E-Newsletters

Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.

Profit and prosper with the best of expert advice - straight to your e-mail.

Sign up

If you create a comprehensive financial plan that considers your individual financial situation and personal lifestyle preferences, then you may discover that you can retire sooner than anticipated. Others might find that they can transition from full-time work to a more enjoyable part-time gig while maintaining their financial stability and desired lifestyle.

Time is a precious resource, and how you spend it matters. I strongly recommend individuals age 55 or older to work with a retirement professional who can help them run their numbers and create a comprehensive retirement plan while providing guidance on how to navigate the complexities of retirement and beyond.

2. Coping with loneliness

Many individuals underestimate the void that retirement can create in their lives. Watercooler conversations, team meetings and other workplace interactions may have played a more significant role than they realized.

For single retirees, loneliness in retirement can accelerate mental and physical decline, affecting the individual’s overall well-being. It's crucial to stay engaged in social activities by participating in community groups, volunteering or reconnecting with old friends to build a fulfilling retirement where you’re surrounded by a supportive network.

Regardless of your relationship status, different forms of loneliness can affect you. Your significant other may not be able to provide all that you need, and that’s OK. Ensure you surround yourself with many different individuals with different backgrounds who can help fulfill your emotional, physical, spiritual and intellectual needs.

3. Battling depression due to lack of purpose

Maintaining a sense of purpose is vital for happiness in retirement. Whether you pursue hobbies, start a new business venture or devote your time to a meaningful cause, having a sense of purpose will keep you motivated, positive and eager to embrace each day's opportunities. Make sure you have a reason to get out of bed in the morning.

4. Dealing with a just-in-case retirement

The fear of running out of money often leads to a “just-in-case” retirement strategy, which can create unnecessary budget constraints and concerns. Building a retirement plan that gives you the confidence to enjoy your early retirement years while you’re still energetic and healthy should be the goal.

For some, that could mean having extra funds for additional travel during the first few years of retirement while you are still healthy. For others, it could mean spending more time with family.

5. Tightening budgets based on market mayhem

Markets have historical patterns that may not always be favorable, such as crashes occurring every seven to eight years or flat market cycles lasting 10 years or so, that seem to show up every 20 years or so. Drawing income from an account that has already lost money can accentuate the loss, making it harder to sustain financial stability in retirement. This is referred to as sequence of returns risk.

Many retirees tighten their budgets when markets decline, or they use annuitized income streams to navigate challenging times. I personally don’t recommend either strategy. Instead, I personally use something called a Principal Guaranteed Reservoir™, which helps a portfolio maintain growth potential, protection and liquidity while dynamically providing income throughout retirement.

Regardless, it is important to have a plan and a series of strategies that allow you to keep income coming in without accentuating losses when markets go down.

Health care costs must be anticipated in retirement planning. It can be a tricky situation if one spouse's health leads to financial difficulties for the other. Self-insuring is a wonderful option for those who can afford it and have time to plan accordingly. Using asset-based long-term care insurance can be a good alternative to help lessen the potential blow to the overall estate for those who may have less or not as much time to prepare.

7. Fumbling relationships and legacies

Inadequate estate planning can leave a legacy of resentment and ruined relationships. If you intend to leave assets like vacation properties, ensure that your heirs can afford their maintenance. If you have family heirlooms, make sure they are noted in your estate documents. Clarify your wishes and intentions to help avoid ambiguity and ease the transition when you pass.

8. Focusing too much on the 0% tax bracket

While the idea of the 0% tax bracket may sound appealing, the cost of getting there is often higher than expected. Many people could potentially have more retirement income to enjoy and/or pass more assets to their beneficiaries if they understood the delicate balance of tax planning based on your effective tax rate.

9. Supporting capable children

Just like they say on airplanes, “If your oxygen mask is deployed, put your mask on first before assisting others.” Your assets are there to support you and your desired quality of life first. Prioritize your own financial well-being before offering extensive support to your children.

10. Managing high-interest debt

Retaining low-interest debt in retirement is acceptable if it aligns with your overall financial portfolio. Based on your individual situation and preferences, you may keep some low-interest debt, while others who are more focused on cash flow may pay it off. It just depends on what you want and what you are comfortable with.

High-interest debt, particularly when it exceeds your investment earnings, should be addressed promptly to help secure your financial stability during retirement.

In conclusion

Time is your most precious asset; don't spend it in a state of fear. Retirement should offer some of the best years of your life. Take the time to craft a comprehensive retirement plan, potentially with the assistance of an experienced retirement professional, to tackle these challenges head on.

Related Content


This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

Mike Decker, NSSA®
Author, Wealth Planner and Money Manager, Kedrec LLC

Mike Decker is the author of the book How to Retire on Time, creator of the Functional Wealth Protocol, and the founder of Kedrec, a Registered Investment Advisory firm located in Kansas that specializes in comprehensive wealth planning and management at a flat fee. He specializes in creating retirement plans designed to last longer than you™, without annuitized income streams or stock/bond portfolios. In addition to helping people achieve their financial goals, Decker continues to act as a national coach to other financial advisers and frequently contributes to nationally recognized publications.