Mar 2, 2025
Cheryl Waters, now 74 years old, never imagined she’d have enough money to retire — let alone do so comfortably. But as she packed her bags for a wedding anniversary trip to Puerto Rico, she took a moment to reflect on just how far she’d come.
“I never thought that I would be able to retire,” Waters told The Washington Post. “If anyone had told me I was going to live like this, I would not have believed it.”
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For much of her life, retirement felt out of reach. As a former public school teacher, Waters found herself in her 50s with almost nothing saved after a divorce. And she likely wasn't alone in that struggle.
A recent study by Fidelity Investments found that fewer baby boomer women invest (70%) compared to Gen Z (77%) and millennial women (74%).
But by 70, Waters had managed to turn things around, retiring with a stable nest egg that allowed her to live on her own terms.
Never too late to start planning
A 2024 AARP report found that 20% of adults aged 50 and over have no retirement savings. Waters was in the same boat — until she made a decisive shift in her financial strategy. Determined to take control of her future, Waters sought guidance from a financial planner recommended by a colleague.
She approached the meetings with intent, pressing for actionable advice on which stocks to sell to eliminate her consumer debt. But the most valuable insight she received had little to do with cutting losses.
Her planner made it clear: to secure a comfortable retirement, she didn’t just need to manage her money — she needed to grow her income. So she took on several tutoring jobs over the years to supplement her full-time income and applied for an interest-only mortgage, which gave her the cash flow to diversify her investments.
It’s not uncommon for Americans to look for additional income streams. According to NBO’s 2024 Financial Wellness Survey, 53% of Americans report having at least one passive income stream. The survey highlights that economic uncertainty — driven by inflation and the rising cost of living — is a major factor pushing people to have multiple sources of income.
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Leveraging Social Security
When Waters turned 66 and a half, she made the decision to begin collecting her Social Security benefits, but continued working and funding her retirement accounts.
Retirees who start collecting Social Security at 62 receive up to a 30% reduction in benefits for the rest of their lives. By waiting a few extra years, Waters ensured she had passed her full retirement age so she could receive the full amount she was entitled to. Though, if she delayed even further past that age, she could have gotten an 8% benefit increase each year until she reached 70.
But by collecting at a reasonable age, she was able to use her Social Security payments as an opportunity to continue building wealth. With the extra cash, she even started a 529 education savings plan to provide future support for her grandchildren. Waters was ultimately able to make up for the years she let her employer-based retirement account sit passively.
By taking a thoughtful approach to retirement planning, she demonstrated that working a little longer and making strategic financial moves – even later in life – can significantly strengthen financial security in later years.
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Victoria Vesovski is a Toronto-based Staff Reporter at Moneywise, where she covers the intersection of personal finance, lifestyle and trending news. She holds an Honours Bachelor of Arts from the University of Toronto, a postgraduate certificate in Publishing from Toronto Metropolitan University and a Master’s degree in American Journalism from New York University’s Arthur L. Carter Journalism Institute. Her work has been featured in publications including Apple News, Yahoo Finance, MSN Money, Her Campus Media and The Click.
