The Top 10 Money Mistakes Women Make In Their 50s & 60s

As a financial advisor, I’ve had the privilege of walking alongside many women in their 50s and 60s—some recently divorced or widowed, others preparing for retirement or navigating a major life transition.

These are decades filled with potential and personal growth, but also some serious financial turning points. And unfortunately, I’ve also seen some common money mistakes that can quietly chip away at long-term security—often by women who are incredibly smart, capable, and successful in every other area of their lives.

The good news? Most of these mistakes are preventable with a little clarity and guidance.

Here are the top 10 mistakes I tend to see women make, plus very real and practical ways to avoid them.

1. Taking Social Security Without Considering the Survivor Benefit

Many women claim Social Security as early as possible (age 62), thinking they’ll “get more over time.” But I’ve seen this backfire—especially for widows or women married to high earners. If your spouse passes away first, your survivor benefit may be based on what they were receiving—and if you claimed early, that amount is permanently reduced.

Avoid this by:
Working with a financial advisor to run survivor benefit scenarios. For example, I had a client delay her own benefit until age 70 because her husband’s was significantly higher. When he passed at 75, she stepped into his full benefit amount—$1,200/month more than what she would’ve received had she claimed early. That’s over $14,000/year, for life.

2. Forgetting to Update Beneficiaries After Divorce or Death

You’d be shocked at how many people’s accounts still list an ex-husband—or deceased parent—as the beneficiary, even months after that life event (such as death or divorce) has taken place. You have to remember that beneficiary designations override your will, and if they’re outdated, your money could legally go to the wrong person.

Avoid this by:
Scheduling a “beneficiary checkup” every couple years—or anytime there’s a major life change. Quite frankly, your financial advisor should do this for you, but it’s smart for you to keep it on your own radar as well.

3. Underestimating How Long Retirement Lasts (and Costs)

Women tend to live longer, which can lead to us often underestimating how long our money needs to last. Retirement isn’t 10 or 15 years anymore. For many women, it can be closer to 30+ years, especially if you retire at 62 and live to 90+.

Avoid this by:
Stress-testing your retirement plan with different life expectancy and market return assumptions. I like to show clients how long their assets last in a “worst-case” scenario (long life, high inflation, modest returns) so we can plan conservatively and build flexibility into the plan.

4. Leaving a Pension as a Lump Sum—Without Realizing the Tax Hit

If you're offered a lump-sum payout on a pension or old employer plan, you might be tempted to take it. But if you don’t roll it properly into an IRA, the entire amount could be taxed as income—and possibly push you into the highest bracket for that year.

Avoid this by:
Working with a CFP® or tax advisor before initiating any rollovers. I had a client who almost requested her entire pension payout be deposited directly into her bank account—not realizing it would’ve resulted in over $100,000 in taxes. We caught it in time and properly rolled it into her IRA instead.

5. Not Factoring in the Cost of Long-Term Care—or Assuming Medicare Covers It

Medicare doesn’t pay for most long-term care needs like in-home help or assisted living. I’ve seen women spend down hundreds of thousands caring for a spouse or aging parent, with no plan for themselves.

Avoid this by:
Exploring long-term care insurance while you’re still insurable. I often recommend hybrid policies (life + LTC) or strategies like carving out a portion of assets for care planning. Even setting aside $75,000–$100,000 now in a dedicated “care bucket” can make a huge difference down the road both for yourself and your family who may end up stepping up to try to care for you out of their own pockets.

6. Missing the Medicare Enrollment Window—and Getting Hit With Lifetime Penalties

If you don’t enroll in Medicare Part B on time, you could be penalized for the rest of your life. Literally. And it’s not a flat fee—the longer you wait, the higher the penalty. Many women who transition out of group health coverage don’t realize this.

Avoid this by:
Knowing your enrollment timeline: If you're not actively working (or covered by a spouse’s plan) at age 65, you must enroll in Part B within 7 months of your 65th birthday. Please don’t forget!

7. Co-Signing Loans or Taking on Debt for Adult Children

It’s natural to want to help your kids—but I’ve seen women jeopardize their own financial stability by co-signing on a home loan, car loan, or private student loans. If your child misses payments, please keep in mind that you are the one who’s responsible.

Avoid this by:
Offering alternative support. For example, you could offer free rent for six months instead of co-signing a mortgage—giving your child time to save more and build credit. My general advice would be to look after your own balance sheet first; there are other ways to be supportive and generous.

8. Holding All Assets Jointly Without Understanding the Implications

Joint accounts can seem simple, but they can cause big problems in estate planning or asset protection. For example, joint ownership with an adult child could expose your assets if they’re sued or go through a divorce.

Avoid this by:
Being strategic about titling. Instead of joint ownership, consider Transfer-on-Death (TOD) designations or naming children as beneficiaries. A client of mine recently moved her brokerage account into her own name and added TOD instructions for each child—giving her more control without complicating her estate.

9. Believing “No Debt” = Financial Security

Many women take pride in being debt-free—and that’s not a bad thing. But I’ve seen clients drain investment accounts to pay off low-interest mortgages or avoid using a 0% interest credit card for a necessary home repair, simply out of principle.

Avoid this by:
Running the numbers before making any major financial decision. For example, imagine you’re deciding whether to pay off a remaining $250,000 mortgage with a 2.75% interest rate. Instead of using that cash to eliminate the debt, you could invest it in a diversified portfolio with long-term growth potential. If that investment earns an average return of even 6–7% annually, the net benefit over time could far outweigh the interest you’d save on the mortgage. The key is understanding when debt can be used strategically—not all debt is necessarily bad.

10. Thinking It’s Too Late to Start Over or Catch Up

I’ve had women walk into my office in their late 50s or 60s and say, “I’m embarrassed. I should have done this years ago.” But it’s never too late to get serious about your finances.

Avoid this by:
Letting go of the idea that it’s “too late” to take control of your finances. You don’t need to have it all figured out overnight—but taking one intentional step today can set real progress in motion. That might mean scheduling a financial review, consolidating old accounts, or simply starting automatic monthly savings. The most important move is the next one.

Final Thoughts

Financial clarity in your 50s and 60s isn’t just about retirement. It’s about feeling independent and confident… and knowing that your money is aligned with your life, your values, and the things that matter most.

And if you’ve made one or more of these mistakes? Don’t beat yourself up. The goal isn’t perfection—it’s progress.

If you’re ready to get your plan in motion, I’m here to help. Feel free to schedule a complimentary financial consultation with me today: https://calendly.com/winstone-wealth-partners/financial-consultation-with-lauren-smith