Retirement Retirement Planning

9 Things Successful Retirees Do That Struggling Retirees Don’t

A few key things can make or break your retirement.

elderly businesswoman with a laptop
Updated May 15, 2025
Fact checked

Retirement should be a time to enjoy your freedom, not worry about money. While "success" looks different for everyone, most people hope for a stress-free retirement where finances aren't a daily concern.

When it comes to that kind of success, small choices can make a huge impact, and things like planning a bit more carefully or spending smarter can make a big difference. Take a look at the nine choices successful retirees have made that have allowed them to live more comfortably in their golden years.

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They create a flexible spending plan

Successful retirees often adjust their spending based on market conditions and personal needs. According to a 2024 T. Rowe Price study, 70% of retirees classify themselves as "savers" who prefer to adjust their spending to maintain their balance in retirement, as opposed to "spenders" who draw down their balance to maintain spending.

Successful retirees often remain flexible in what they're willing to spend, rather than spending no matter the amount of money in their bank account, thereby preserving their resources.

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They maximize retirement account contributions

Contributing the maximum allowable amounts to retirement accounts, including catch-up contributions for those over 50, can lead to a lot of extra retirement savings. The IRS allows additional contributions to 401(k)s and IRAs for individuals aged 50 and above, providing an extra opportunity to add a bit more to your current savings.

Successful retirees take advantage of this additional earning potential. If you missed out on some savings earlier in your career, now is a good time to catch up.

They develop a comprehensive healthcare plan

Healthcare expenses can be a huge burden in retirement, as healthcare costs tend to rise as we age. Planning for these healthcare costs should be a big part of your retirement plan, whether this involves funding an HSA or considering supplemental insurance on top of Medicare.

Successful retirees assume that their healthcare costs will increase in retirement, and they plan accordingly so they can avoid spending more than they had budgeted for.

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They utilize government retirement planning tools

The government provides tons of different retirement planning tools that retirees can use online for free. These can help you predict certain costs or determine how much you might receive from Social Security. There are even interactive worksheets to help you set savings goals and determine how much you need to save.

Successful retirees use all of the resources available to them when it comes time to plan, especially those free ones, keeping more money in the bank for other activities.

They diversify retirement income sources

Successful retirees often diversify their income streams beyond Social Security so they aren't only relying on one income stream for the duration of their retirement.

A strong financial foundation is made out of many sources, including pensions, annuities, and personal savings. Social Security can absolutely play a role, but not as the only source of income. Otherwise, that foundation may be less stable than you think.

They stay updated on retirement plan options

Retirement planning is always changing. What worked when you first started planning may not be the best option now, especially when it comes to government options.

The IRS provides detailed information on different retirement plan options, including 401(k)s, IRAs, and pension plans, allowing you to stay updated. Successful retirees try to stay informed throughout their retirement so that they can continue to make choices that align with their financial goals and risk tolerance.

They regularly review and adjust retirement plans

Successful retirees understand that retirement planning doesn't end upon retiring. They periodically review their retirement plans to adjust for changes in expenses, healthcare needs, and market conditions.

Your situation and the tax code can change at the drop of a hat, and you may need to adjust your retirement plan appropriately. Otherwise, you may find yourself entering retirement with a plan that no longer works for you.

They understand the tax implications of retirement income

Retirees often have multiple income sources, each with different tax implications. Successful retirees educate themselves on how Social Security benefits, pensions, and withdrawals from retirement accounts are taxed.

The tax code can be pretty complicated, so some retirees may need to work with a tax professional to fully understand their options. Figuring out tax-efficient withdrawal strategies is a big part of retirement planning.

They plan for long-term care needs

According to the Center for Retirement Research at Boston College, the majority of retirees will require long-term care at some point, with around 20% having significant needs. Long-term care can be a significant expense in retirement. Successful retirees proactively plan for potential long-term care needs by exploring insurance options and setting aside funds.

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Bottom line

A financially comfortable retirement often hinges on proactive planning and informed decision-making. Successful retirees typically plan ahead for all potential expenses, including long-term care, and stay informed on how taxes and new laws may impact their retirement.

It's never too late to become a "successful" retiree, but you may need to start working on your retirement plan today to make it happen. Not sure where to begin? Consider hiring a financial advisor to help you on your way.

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