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Cherie, a 63-year-old San Bernardino, California resident, has been surviving on dwindling savings since 2007. And she’s down to her last few thousand. Concerned, she called into The Ramsey Show for some advice (1).
With multiple disabilities that prevent consistent work, she lives in a fully paid-off home held in a trust. She carries zero debt and spends roughly $1,000 a month on essentials, living diligently within her budget, paying only utilities, insurance and food — supplemented by food stamps.
“I’ve burned through nearly all my savings, and I’m down to $4,000,” she confessed on her recent call to The Ramsey Show.
Cherie can’t claim Social Security retirement benefits until age 67, and repeated disability-benefit denials have left her without another reliable income source. Here’s what happened next.
Cherie asked if she should borrow against or sell her trust-held home to gain more money.
“Don’t borrow against it because that’s now putting the one thing that you have that’s safe and secure at risk because income is an issue for you, so you don’t want to do anything that will add debt to your life,” cohost Jade Warshaw said.
Instead, they urged her to try generating a modest but essential income through part-time remote work.
“You sound great on the phone,” cohost Ken Coleman added. The hosts recommended customer service roles that require only a headset and about four hours of work per day.
Warshaw mentioned her own experience working flexible hours on platforms such as arise.com (2), which allow workers to choose short shifts without competition. This is ideal for someone who hasn’t held a traditional job in years but needs flexibility due to health challenges.
They also told Cherie to apply immediately for Supplemental Security Income (SSI), which averages about $718 monthly (3) for all recipients (that number is slightly higher for someone aged 63, averaging $764). This should allow her to cover roughly two-thirds of her current expenses while bolstering her Social Security application at age 67.
Cherie could also search for ways to cut back on expenses, such as by shopping around for better rates on fixed monthly costs. For instance, with OfficialCarInsurance.com you can find a more affordable auto insurance plan rate within minutes.
After answering a few questions about yourself, your vehicle and driving history, you can compare quotes from trusted brands like Progressive, Allstate, and GEICO in just minutes. Depending on factors like the make and model of your car, you can find rates as low as $29 per month.
But car insurance isn’t the only monthly recurring cost cutting into your bottom line. Home insurance, even on a paid-off home, can put you in the red if left unchecked. To counter this, you could work with OfficialHomeInsurance.com. It takes just two minutes to comb through over 200 insurers for free to find the best home insurance deal in your area. The process can even be done entirely online.
OfficialHomeInsurance.com users can save an average of $482 per year. For Cherie, that would amount to about an extra $40 per month in savings, provided she can find a similarly low rate.
Read more: Warren Buffett used 8 solid, repeatable money rules to turn $9,800 into a $150B fortune. Start using them today to get rich (and stay rich)’
Cherie’s predicament isn’t unique. Nearly half of Baby Boomers (49%) are working past age 70 and do not plan to retire (4). Their situation is driven as much by financial necessity (82%) as by a desire to stay active (78%).
The Bureau of Labor Statistics reports that participation in the workforce for those over 65 has been trending upwards since 1985, with 23.4% of men and 16.2% of women working full- or part-time hours in 2024 (5).
Part of the reason is that many Americans do not have sufficient savings to retire. According to the Schroders 2025 US Retirement Survey, Americans believe they’ll need $1.28 million to retire comfortably (6), but data from Empower shows that the median retirement savings balance for those in their 60s in the U.S. is just $544,439 (7).
While the average retiree’s Social Security benefit is $1,925 per month as of November 2025 (3), many cannot afford to wait to collect benefits, or don’t qualify due to limited work history. That’s why it’s so important to save as much as you can, even when your means are limited.
You may feel like it’s almost impossible to find extra funds in your monthly budget to invest, but you can get started with pennies — literally — when you sign up for Acorns.
Acorns is an automated investing and saving platform that rounds up the price of each of your purchases to the nearest dollar and deposits the difference into a smart investment portfolio. Here’s how it works: Say you buy a sugar cookie for $5.55. Before you’re done dusting off the crumbs, Acorns has rounded up your treat and invested the 45-cent difference.
The platform also allows you to set up automatic monthly contributions to maximize your savings and, for a limited time, if you sign up with a minimum of $5 per month, you can get a $20 sign-up bonus.
For those nearing retirement who need a more aggressive plan to grow their savings, a fiduciary financial advisor could help you find out how to build a better nest egg for your retirement while optimizing your Social Security strategy.
Advisor.com connects you with vetted financial advisors who are ethically and legally required to act in your best financial interests at all times.
How it works is simple — just answer a few quick questions about yourself and your finances. From here, the platform will match you with up to three experienced financial professionals to help you develop a plan to achieve your homeownership or retirement goals.
You can view the advisors’ profiles, read past client reviews and schedule an initial consultation for free with no obligation to hire. From there, you can discuss your advisor’s fees and billing schedule to determine what’s right for you and your budget.
For seniors like Cherie, experts recommend treating job seeking as a strategic project:
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Apply for SSI and appeal disability denials: Even partial SSI support (about $700/month) can ease immediate cash flow.
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Launch remote job searches now: Sites such as arise.com and flexjobs.com list customer service, data-entry and other roles that require minimal qualification and offer flexible hours.
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Track and adapt: Keep a simple spreadsheet of applications, follow up weekly and tweak your pitch to emphasize reliability and interpersonal skills over technical credentials.
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Plan for Social Security at 67: You can delay full retirement age and raise benefits by up to 8% annually, which can make a long-term difference in your retirement situation.
Cherie owns her home outright and has no debt. These are both net positives that can give her more agency than many to start managing this issue. “You’ve got to happen to this problem,” Coleman said. Cherie’s next step, he says, is to increase her income until she qualifies for more retirement benefits.
“ Sum it all together and say, ‘I’m not going to be a victim here. I’m going to take control.’ And you can, but you have to go after it,” Coleman said.
With that plan, Cherie could transform her precarious situation into a more sustainable next chapter.
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
@RamseyShow (1); Arise (2); Social Security Administration (3); TransAmerica Institute (4); Bureau of Labor Statistics (5); Schroders (6); Empower (7)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.