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.
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.
She cannot claim Social Security retirement benefits until age 67 and repeated disability-benefit denials have left her without another reliable income source.
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Prioritize income over equity
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 advised.
Instead, they urged her to generate modest but essential income through part-time remote work.
“You sound great on the phone,” said cohost Ken Coleman. 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, 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 advised Cherie to apply immediately for Supplemental Security Income (SSI), which averages about $718 monthly for all recipients (that number is slightly higher for someone aged 63, averaging $764). This will allow her to cover roughly two-thirds of her current expenses while bolstering her application for Social Security at age 67.
Read more: Want an extra $1,300,000 when you retire? Dave Ramsey says this 7-step plan ‘works every single time’ to kill debt, get rich in America — and that ‘anyone’ can do it
Increase income when retirement isn’t an option yet
Cherie’s predicament isn’t unique. Nearly half of Baby Boomers (49%) are working past age 70 and do not plan to retire. Their situation is driven as much by financial necessity (82%) as by a desire to stay active (78%).
Pew Research data backs this up, and notes it as a growing trend for those aged 65 and older. While, in 1987, only 11% of Americans in this age group were working, in 2023 that number was up to 19%.
Part of the reason is that many Americans do not have sufficient savings to retire (the latest number puts these at $1.26 million). By contrast, the Federal Reserve found the median retirement savings among Americans ages 65 to 74 is just $200,000 as of 2022, the last year for which data is available.
While the average retiree’s Social Security benefit hit a record $2,002 per month in May 2025, many cannot afford to wait or don’t qualify due to limited work history.
For seniors like Cherie, experts recommend treating job seeking as a strategic project:
Apply for SSI and appeal disability denials: Even partial SSI support about $700/month) can ease immediate cash flow.
Launch remote job searches tonight: Sites such as arise.com and flexjobs.com list customer service, data-entry and tutoring roles that require minimal qualification and offer flexible hours.
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.
Plan for Social Security at 67: You can delay full retirement age and raise benefits by up to 8 percent annually, which can make a long-term difference in your retirement situation.
Cherie owns her home outright and has no debt. “You got to happen to this problem,” says Coleman. Her 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 pragmatic plan, Cherie may transform her precarious situation into a sustainable next chapter.
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This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
