You Are Setting Yourself up for Retirement Disaster If You Do These 3 Things

  A lot of people look forward to being able to retire. But it takes a lot of planning to pull off a successful transition into those post-working years. And the moves you make ahead of retirement may dictate whether…

Published February 11, 2026, 7:15am ET · 3 min read

This post may contain links from our sponsors and affiliates, and Flywheel Publishing may receive compensation for actions taken through them.

A senior man with gray hair and a beard, wearing a light-colored collared shirt, sits at a desk, looking down intently at a white document he holds with both hands. His left hand, holding a pen, rests on his chin in a pensive gesture. A silver laptop is visible to his left, and a blurred background shows white shelves with books and potted plants.
An individual carefully reviews documents, a common scene when navigating complex financial decisions like 401(k) rollovers, which can have significant tax implications. © JU.STOCKER / Shutterstock.com

 

A lot of people look forward to being able to retire. But it takes a lot of planning to pull off a successful transition into those post-working years. And the moves you make ahead of retirement may dictate whether your senior years are filled with struggles or not. With that in mind, you may be headed for a terrible retirement if you do these three things.

1. Expecting to Get Most of Your Income From Social Security

It’s pretty common for retirees to fall back on Social Security once they stop working. But if your game plan is to get most of your senior income from Social Security, you may end up with a serious financial shortfall on your hands.

If you earn an average salary, you can expect Social Security to take the place of about 40% of it. And that doesn’t even account for potential Social Security cuts.

Most retirees can’t get by on just 40% of their former income, though. Even if you’re willing to lead a frugal lifestyle, you may end up needing more like 70% to 80% of your former paycheck to cover all of your costs.

Rather than plan to get most of your retirement income from Social Security, set yourself up with additional income streams. That could be a combination of withdrawals from savings, investments, and even part-time work.

2. Investing Your Savings Too Conservatively

The more money you’re able to accumulate ahead of retirement, the more you should be able to withdraw each year from your IRA or 401(k). But if you invest your savings in conservative assets during your working years, your IRA or 401(k) may not generate very strong returns, leading to less money for you later on.

It’s appropriate to invest somewhat conservatively when retirement is right around the corner, or when you’re already retired and are dipping into your savings consistently for income. But when retirement is many years away, it pays to go heavy on stocks for the strong returns they’re known to produce.

If you don’t like the idea of having to pick stocks for your portfolio individually, you could instead load up on broad market ETFs. The key, however, is to generate decent enough returns to let your savings grow while you’re still working.

3. Assuming You Won’t Have to Spend Any Money on Healthcare Once You Enroll in Medicare

Many people wait until age 65 to retire so they can enroll in Medicare. But if you expect to not have to spend any money on healthcare expenses as a Medicare enrollee, you could end up in a tight spot financially.

Not only are there premiums associated with Medicare, but there are additional costs you might face that include deductibles, coinsurance, and copays. There are also a number of services that Medicare actually does not cover at all, like dental cleaning and eye exams.

It’s important to understand what Medicare costs and covers ahead of retirement so you know how much to save for healthcare. Better yet, if you have access to a health savings account during your working years, it pays to fund that account and reserve the money for retirement.

At that point, your health-related needs may be more substantial. And having funds to cover medical bills could take some of the pressure off of your savings and Social Security checks.

Contact [email protected] for any questions or corrections.

Maurie Backman

Maurie Backman has more than a decade of experience writing about financial topics, including retirement, investing, Social Security, and real estate. Her work has appeared on sites that include The Motley Fool, USA Today, U.S. News & World Report, and Kiplinger.

Prior to becoming a full-time financial writer, Maurie worked in the financial industry trading distressed debt. She then changed course and spent a few years designing electronic toys. After a stint in content marketing and UX, she shifted back into writing and has since covered everything from the housing market to estate planning to Medicare.

When she's not busy writing, Maurie can be found hiking, walking her dogs, driving her kids to their various sports practices and games, and curling up with a good book. She cooks on occasion and bakes way too often.

All articles →