After 2 years advising strangers about relationships and money, I still start with the same idea

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• I give advice about money and relationships in a weekly column — and I hear a lot from parents.
• I haven't experienced every problem my readers face, but I approach each question with empathy.
• Got a question about money and relationships? Write to For Love & Money using this Google form.

I've been advising strangers on the internet for over two years now on my weekly Business Insider column, For Love & Money. Some questions break my heart, others infuriate me, and others hit so close to home that I recognize, even as I respond, that my advice is as much for me as it is for the reader.

The questions I get are about money, and they highlight the ways that financial planning overlaps with the most important parts of life. As a mother of three children, the letters that often feel the most personally resonant are the ones seeking parenting advice.

Even though I haven't encountered all of the predicaments my readers bring to me yet, as a mom of young kids, I know I could face any one of them at some point. This understanding is also how I come by my advice. My answers always fall within the framework of the golden rule — treating others the way I want to be treated. Because knowing how to do the right thing is almost always an exercise in empathy.

Raising kids without entitlement

I got a question from a parent trying not to spoil their kids — their kids had a lot more financial privilege than the parent had growing up. It wasn't a stretch to empathize with this person; my story is quite similar. My husband and I are financially better off than my parents were, and because of this, my kids have more than I ever did at their ages.

I know firsthand that the parent was likely experiencing two feelings: a genuine concern that too much privilege can lead to spoiled children and a little bit of personal envy.

There's nothing that forces us to face our childhood wounds quite like raising children. For the first time, we are in our parents' shoes, understanding the pressures that led them to make the decisions that would define our lives.

Knowing this, I encouraged my reader to do something I strive to do with my children: Allow their childhood experience to inform how they raise their children without letting their scars interfere with that relationship. On a more concrete level, I also advised the reader to teach their kids gratitude at every turn, especially through the example they set.

Worrying about kids' financial choices

But not all of the parents who are writing me are still raising their kids like I am. This is why, in the case of a parent worried about their son's purchase of a $70,000 pickup truck, I drew my advice from my experience as a mother and as a daughter. I am all too familiar with how it feels to have parents lecturing me on my choices as a 30-plus-year-old woman. It's always annoying, especially when they're right.

As an adult daughter, my advice was obvious — parents need to stay out of their adult children's financial affairs — but, as a mother, I know just how difficult that can be.

I would like to think that I will quit feeling so deeply invested in my children's experience of the world as they get older, but I don't think it's likely. So I tempered my advice with this understanding.

Giving money to kids

And in the case of a reader who gave their son $16,000 and now feels pressured by their spouse to seek repayment, I had no experiences to compare it to. However, I realized I know how it feels to be caught between loved ones, pressured on both sides to appease one at the expense of the other.

When this happens, there never feels like a correct answer. So I decided to take the feelings out of it for the reader's sake and focus solely on the facts. This meant focusing on the original agreement. Was it a gift or a loan? By sticking to the original agreement, no one could blame the reader for following through on their commitment and expecting everyone else to do the same.

However, despite this being the practical solution, I recognized that the reader wouldn't have the luxury of removing their feelings from the situation and focusing only on the facts, so I wanted to let them know their feelings were valid. The pressure they felt to pick a side was unfair and not their fault. I also try to remember that good advice only goes so far; sometimes, you just need someone to understand.

No matter what, I try to start with empathy

Every week, I receive several messages from readers telling me they love or hate my advice. Recently, I received two messages on the same day in response to the same article. One reader began their letter, "Your advice is going to hurt more than it helps." The other reader felt differently, writing, "You were clearly born to do this work. Your advice is astounding." (I may have printed that one off to hang on my bedroom mirror as a daily affirmation.)

I wouldn't be writing an advice column if I thought my insight hurt more than it helped, and "astounding" may be a bit of an overstatement in the other direction. But I believe, to the core of who I am, that if we lead with empathy, wisdom is never far behind.

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Looking for advice on how your savings, debt, or another financial challenge is affecting your relationships? Write to For Love & Money using this Google form.

This article was originally published in March 2024.

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