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Created: September 8, 2025
Modified: September 29, 2025

What Are the Biggest Regrets People Have in Retirement?

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It’s natural to carry regrets through any stage of life, and retirement is no exception. When you’re making major decisions about your finances, your family, and your legacy, things can go off course if you haven’t done the proper planning.

In this week’s Money Wisdom Question Series, Jake Doser, CFP®, CPWA® breaks down the most common financial regrets people have in retirement.

Regret #1: Not Considering How Long Retirement Will Last

We’re living longer than ever before, and that means your retirement could last 30 years or more. If you don’t plan for the possibility of a long retirement, you could risk outliving your savings and may have little or nothing left to pass on to your loved ones. Every retiree should prepare for this risk and ensure their income will last as long as they do, if not longer.

Regret #2: Underestimating the Impact of Inflation

Inflation can quietly erode your purchasing power over time, especially over a 20- to 30-year period. If your portfolio isn’t built to keep pace with rising costs, your lifestyle in retirement may become increasingly difficult to afford.

Without meaningful cost-of-living adjustments (COLAs) from your income sources, such as Social Security or pensions, the burden of inflation falls on your investments. That’s why it’s essential to design a portfolio that can grow and adapt not just today, but throughout your retirement years.

Regret #3: Being Too Extreme with Investments

Being too conservative or too aggressive with your investments can threaten your financial stability in retirement. Keeping all your money in ultra-safe assets may limit your growth potential and hinder your ability to outpace inflation. On the other hand, taking on too much risk can expose you to significant losses.

The key is a balanced investment strategy that aligns with your retirement goals, spending habits, and long-term financial needs. While your comfort level with risk matters, your approach should ultimately be guided by a personalized, well-structured retirement plan.

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Information presented here is considered current as of the created date. Over time, some information presented may become stale. We recommend you consult with your Financial Professional before making any changes based on information contained here.

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