Should you speak up when you see bad money decisions?

On any given Sunday after church services, fellow parishioners seek me out to ask personal-finance questions. I will, when I have time, try to help on the spot.

But I’ve always found it frustrating that strangers often see the value of my financial wisdom more than the people closest to me.

So, what’s a financially astute person to do when watching co-workers, friends or relatives make monumentally bad money decisions? Such a quandary was the subject of a question I received from a reader during a recent online chat.

“What advice do you have for someone with a longtime friend (mid-40s) who doesn’t have the best finances and lacks reserves? I don’t want to ‘finance shame’ this person, but how do you address these issues and start a meaningful and well-intended dialogue with someone about getting them headed in the right direction?”

As much as you care, you can’t make grown folks do right. And often your advice — no matter how well-intentioned — can seem smug.

In my younger years, I was the self-righteous, butt-in friend and relative who tried to steer people to better decisions. I’m a natural-born penny-pincher, so it just seemed crazy to me that folks would go on vacation without having an emergency fund. Or I would question why someone was buying a new car when they could repair the one they had.

I would — without success — discourage people from buying homes that I knew would stretch them to their financial breaking point.

After I had children, my social circle increased to include a wide network of other parents. I was dismayed at how many overindulged their children. When I’d ask if they had established a college fund, they would admit that they were saving very little or nothing at all. Yet many of these same parents complained that their children were being deprived of need-based financial aid for college because they made too much money. Their resentment was ridiculous to me when they had the means to save — at least something.

And don’t get me started on the ill-advised decisions to send their children to colleges they couldn’t afford without decades of student loan debt. Too many times to count, I lost this battle to bring them to their senses.

I became increasingly exasperated that the people who know I meant well just wouldn’t act on my advice. Their financial struggles weighed heavy on my heart, as if I had failed them. I write about personal finance for a living, so no one in my sphere of influence should be financially reckless, right?

However, with age comes the wisdom that I cannot always be my brother’s — or substitute any close relationship — keeper. Sometimes people have to fall flat financially before they get up and make better choices.

Or maybe they are living paycheck to paycheck, and all your advice does little to address the core issue, which is that they need more income.

So when should you butt in when your friends, family and colleagues lack good financial judgment? Here’s when.

After being asked. You have an increased chance that your advice will be taken if your opinion has been solicited. Once the door is open, provide guidance. But don’t be a bully about it.

You suspect a scam. Step in immediately if you think someone is about to be scammed. This becomes your business. This is definitely the time that if you see something, you should say something.

Any fallout may affect your finances. Let’s say your mother is a bad money manager and you know that if she doesn’t become a better financial steward, you’ll have to rescue her when she retires. And you will, because she’s your mother.

It’s OK to step in with advice if it’s likely that it will cost you more to help down the road. Share your concerns. Be candid about your fear of not having enough money to bail someone out if that’s the case. Also, communicate clearly what you’ll be able to afford should your family member or friend fail to change. Then don’t cave if you know the person didn’t take your advice. You don’t want to facilitate irresponsible behavior. If you do, you become an impediment to their growth.

If you’re the financial guru in your social network, make it known you’re willing to help, and do so without being judgmental. However, if folks exercise their free will to mess things up after you’ve given them good advice, don’t blame yourself for their fall.

— Washington Post Writers Group