Outside the Box: When a family member is struggling financially, here’s how to help without offending

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If you’re fortunate enough to be financially secure right now, find out if your loved ones need financial help. I know that sounds daunting and easy to get wrong and inadvertently offend, but there is a way to do this gently and effectively.

Most of us are never taught how to manage our own money, much less how to help others. The idea of “helping” is usually associated with charity or an annual donation. But what if your sister just lost her job? What if your parents are late on their mortgage payment? And what if you can help?

These conversations terrify us because they surface our hidden emotions around money: scarcity, guilt, anxiety and judgment.

If you try to help someone with money, will they think you’re presumptuous or condescending? How will it affect your dynamics going forward? One reader sent me a message about her struggling parents. “I want to help them,” she wrote, “but they’ve always taken care of me. We don’t have the dynamic of me helping them.”

My suggestion: If you have the ability to help a loved one with money, forget about your discomfort, have the difficult conversation, and write a check. In ordinary times, a gesture like that might be appreciated. In times like this, it can be the difference between life or death.

Here are three ways you can push past the awkward conversations and help loved ones who may be hurting right now:

• Seek out an opportunity to talk

Open the conversation with this: “I just saw the unemployment numbers. How are you feeling about the economy?” Start with yourself — “I’m hearing more and more people getting laid off” — and tell them how you feel. If you’re nervous, share your vulnerability.

The responses are revealing. Some people will openly tell you if they’re worried. For others, you’ll have to read between the lines when they say, “I’m sure everything will be fine” (Because If It’s Not, I’m Not Sure What I Would Do). If they have children, ask how the kids are doing. Most parents will gladly take help for their children before they would acknowledge help for themselves.

• Make the offer

If a loved one needs help, say this: “I’ve been fortunate when others helped me. I’d like to help you.” Tell them you’ll be sending them something and you want them to use it. Don’t get into specifics — just let them know to look out for it.

When you send a check or a gift card, attach a note that says, “I want you to have this.” They can choose to use it or not — you’re never forcing them to accept it. But you’re letting them know you want to help.

Interestingly, of all the readers I’ve spoken to, it’s clear that the fear of “awkwardness” comes from the sender, not the recipient. People in need are thrilled to get help. It’s the senders — the ones fortunate enough to be able to help — who overcomplicate it. Stop overthinking it and write the check.

• Get creative

One of my readers came up with a great way to support one of his family members without it being awkward for any of them. He offered a 70-year loan with no interest — essentially a gift that he knew would never be repaid. It was a beautiful gesture that allowed the recipient to accept help as a loan — but they both knew it was a gift.

Another reader knew her sister would never accept help directly. She offered to help with her nieces’ school fees, a much easier offer to accept.

Before you have these conversations, be sure you’re in a place to help. Just like oxygen masks on an airplane, make sure you’re secure before helping anyone else. Here are some factors you should consider before offering help:

• Is your job or your partner’s job potentially at risk?

• Do you have a one-year emergency fund?

• Do you have any debt?

If you’ve played defense effectively, and have the right financial security in place, you’ve earned the right to play offense. One of the best ways you can do that is to help someone else in need. This is a key part of a Rich Life.

Ramit Sethi is the founder of iwillteachyoutoberich.com, where he writes on money, business, careers, and psychology.