Cohosts Jade Warshaw and Ken Coleman listen to a caller's predicament.

The Ramsey Show

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Cherie, a 63-year-old San Bernardino, California resident, has been surviving on dwindling savings since 2007. Now she’s down to her last few thousand. Concerned, she called in to The Ramsey Show for some advice.

With multiple disabilities that prevent consistent work, Cherie lives in a fully paid-off home held in a trust. She has no 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 said on her recent call to The Ramsey Show.

She cannot claim Social Security retirement benefits until age 67, and repeated denials of her disability benefits have left her without another reliable income source.

Cherie asked if she should borrow against her trust-held home, or sell it, 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 — income is an issue for you, so you don’t want to do anything that will add debt to your life,” co-host Jade Warshaw said.

Instead, they urged her to generate modest but essential income through part-time remote work.

“You sound great on the phone,” said co-host Ken Coleman. The hosts recommended customer service roles that require only a headset and about four hours of work per day.

They also advised Cherie to apply immediately for Supplemental Security Income (SSI), which averages about $718 per month for all recipients. In her case, Cherie could probably receive a slightly higher sum, averaging $764. This would help her cover roughly two-thirds of her current expenses while bolstering her application for Social Security at age 67.

She could also find ways to cut back on expenses, like by shopping around for better rates on fixed monthly costs. For instance, 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 for her home insurance.

Similarly, OfficialCarInsurance.com can help you switch to a more affordable auto insurance option 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. Depending on factors like the make and model of your car, you can find rates as low as $29 per month.

Read more: Rich, young Americans are ditching the stormy stock market — here are the alternative assets they’re banking on instead

Cherie’s predicament isn’t unique. Nearly half of Baby Boomers (49%) are working past age 70 and do not yet 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. In 1987, only 11% of Americans in this age group were working, but that number had shot up to 19% by 2023.

Part of this is because many Americans don’t have sufficient savings to retire (the latest estimates put this number at around $1.26 million). By contrast, the Federal Reserve found that the median retirement savings among Americans aged 65 to 74 was 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. That’s why it’s so important to make sure your cash is being put to work in the background.

One easy way to get started is with an automated investment advisor. These services typically help you invest in low-cost index funds without having to work with an advisor or pick funds directly.

With Wealthfront Automated Investing, you can start investing in the stock market with as little as $1.

Depending on your risk profile, Wealthfront will create a customized portfolio with low-cost index funds, combining up to 17 global asset classes. Wealthfront automatically rebalances your portfolio, diversifies your deposits and can help reduce your tax liability by tax-loss harvesting.

Even better, up to $500,000 of your deposits with Wealthfront Invest are protected by the Securities Investor Protection Corporation. This means that, in the event of a brokerage failure, your cash and securities are protected.

New accounts can get a $50 deposit bonus and fund it with $500 or more.

For seasoned investors with portfolios of $50K or more, you might consider diversifying your nest egg through a flat-fee self-directed retirement account.

A self-directed retirement account is a tax-advantaged individual retirement account (IRA) that lets investors allocate funds to a significantly broader range of alternative assets than typical IRAs offered by banks or brokerage firms.

With IRA Financial, you can work directly with experienced retirement specialists. If you prefer making your investments online, their platform and mobile app make it easy to manage your account. They also have an in-house tax team to ensure your investments stay fully compliant with IRS rules.

With over $5 billion in retirement assets under custody, guaranteed IRA audit protection, 25,000+ clients nationwide and a 97% client retention rate, IRA Financial can help you grow your retirement fund with alternative assets.

Simply answer a few questions — including the kinds of assets you would like to invest in and how much you’d like to start with —  to prequalify for an account in just 90 seconds.

Beyond ensuring her savings and investments are running smoothly, experts recommend that seniors like Cherie treat 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 issues.

Search for remote jobs: Look for remote positions in roles like customer service, data-entry tutoring roles, ideally with minimal qualifications and 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% annually, which can make a long-term difference in your retirement situation.

Find other ways to earn money in the meantime: With cash back apps like Upside, you can get a little bit back every time you shop. Simply download the app, and you can earn an average of 8% cash back on groceries and dining. You can also earn up to 25 cents per gallon back on gas, plus a bonus 25 cents off per gallon with code MONEYWISE25 on your first transaction when you sign up.

Cherie owns her home outright and has no debt. Co-host Coleman said her next step 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 could 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.