Nov 22, 2025
For 10 years, Roger has sent $700 a month to an estranged sister he’s only seen three times in 30 years. He told The Ramsey Show hosts his sister, now 75, lives in Nevada with an ill husband.
Now the money pot he used to support her is almost gone and he doesn’t know how to cut her off.
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“Everybody told me I was going to be in this spot,” Roger told co-hosts John Delony and Jade Warshaw (1). “I'm not sure I can sustain her lifestyle."
“You can’t,” Delony said bluntly.
Roger retired four years ago and his wife is retiring next year. His sister has never worked and his brother-in-law can’t work due to illness.
Delony and Warshaw told Roger he needs to come clean with his sister and cut her off for good, with a two- to three-month runway to figure out her finances.
The problem is, Roger is wracked with guilt. The last time he broached the topic with his sister, she said: “Well, I guess I’m going to have to sleep in my car.”
But Delony and Warshaw noted that most of Roger’s guilt is self-inflicted, and told him he’s not doing her any real favors by enabling her.
“Why are you taking yourself on a guilt trip that she didn’t invite you on?” Delony asked.
Ramsey hosts advise cutting off support for everyone's sake
Roger agreed that most of the guilt he’s feeling comes from his sense of obligation to family.
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This prompted Warshaw to delve into his motivation, asking whether Roger felt he was making up for something that happened to his sister in the past — and whether he really wanted to change.
"The bigger work is for you to figure out why you're having a hard time letting this go," Warshaw said.
They said if Roger doesn’t cut off his sister, he must work her support payments into his monthly budget without jeopardizing his own nest egg or compromising his own family’s future.
He added that he’d looked into social support alternatives to help his sister, and Jade said there were plenty, but that it wasn’t Roger’s job to find them.
Supporting a family member — whether a sibling or an adult child — based on emotion can jeopardize your own security and your relationship with others.
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It’s not just Roger’s golden years at risk. His wife might want a more comfortable retirement. If Roger keeps sending his sister money, that could limit the cash he and wife need to fulfill their shared retirement dreams and strain his marital relationship.
As the Credit Counselling Society points out, offering unlimited financial support can make it easy for your family to continue bad habits and stunt their personal and financial growth, leaving them worse off if you run out of money or pass away (2).
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Setting boundaries when family support has gone too far
The key is to take care of your own financial needs first.
If you have room in your budget after covering your essentials, you can help a loved one as long as you’re not enabling their bad decisions and you won't end up resenting them.
As Delony told Roger: “You can’t enable somebody and complain they’re [a failure to launch]. If you keep funding her, keep doing it with a glad heart and stop grumbling about it.”
Here are a few things to consider to ensure your generosity doesn't go too far:
- Establish a set budget with a very strict limit on monthly family support.
- Be very clear on how much you can afford to help out and for how long.
- Set ground rules for what your support can be used for, especially if your loved one struggles with overspending or addiction. You could even do things like paying their rent directly instead of giving them cash.
- Encourage your loved one to take control of their own finances.
- Consider family therapy if your loved one is codependent and if you are enabling them.
- Give them advance notice when you plan to cut off support and encourage them to take advantage of social services available to them.
By taking these steps, you can make sure that your help is a short-term bridge to success rather than a financial handicap.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
The Ramsey Show (1); Credit Counselling Society (2)
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Christy Bieber has 15 years of experience as a personal finance and legal writer. She has written for many publications including Forbes, Kilplinger, CNN, WSJ, Credit Karma, Insurify and more.
