The offers and details on this page may have updated or changed since the time of publication. See our article on Business Insider for current information.

• For Love & Money is a column from Business Insider answering your relationship and money questions.
• This week, a reader wants a portion of their inheritance now, rather than after their parents die.
• Our columnist says it's OK to ask, but that it's important to be self-aware and approach thoughtfully.

Dear For Love & Money,

I am lucky enough to come from a family with a lot of generational wealth. My great-grandparents passed down a large fortune to their kids, who passed it down to my parents when they died.

Before their deaths, my grandparents also used a large part of it to make their children's and grandchildren's lives better. They gave my parents enough to pay off most of their house, paid for my college, bought me my first car, and did the same for my sister and cousins.

Now, my parents have their share of the family inheritance. My sister and I fully expected our parents to follow our grandparents' example and give us some money up front — not the whole inheritance, but enough to help us pay off some debt and make our lives a little easier.

My parents have shown no signs of giving us a penny right now. I am sure they intend to leave it to us when they die, but until then, it doesn't seem to have even occurred to them to bless their children and grandchildren the way their parents did.

My niece will begin college next year, and my sister has dropped several hints. My wife says I need to just come out and ask them for some of the money because we could use the cash, but the idea of doing that makes me really uncomfortable. What do I do?

Sincerely,

Possibly Presumptuous

Dear Possibly,

If you are presumptuous — and perhaps you are — you have every reason to be. A large inheritance, it seems, is a family tradition (you lucky thing). Traditions are typified by the rituals that accompany them. In your family, this has looked like the bulk of the cash going to the next generation as a traditional inheritance, with a tidy sum set aside to ease the way for all direct descendants in the form of an early inheritance.

As such, it makes sense that you would have those expectations. However, no family tradition happens automatically, and each new generation must determine which parts of the legacy to leave and which to keep. In your case, this decision belongs to your parents.

I agree with your wife that asking directly is your only option for an advance inheritance payment. After all, your sister has already tried the heavy hinting method, and while you refer to it as "generational wealth" and "family inheritance," the money is your parents'.

Before you talk to them, however, I suggest you examine your motives first. There are two different types of entitlement: justified and absurd. Justified entitlement looks like someone driving to pick up their paycheck after working all week. Absurd entitlement looks like an adult racking up a credit card on a luxury vacation and then expecting their parents to pay it because they raised them to enjoy that lifestyle.

Based on your letter, I would guess your entitlement is justified — or at the very least, understandable. There is nothing wrong with having expectations because your family has always done something a specific way. However, the justified entitlement begins veering into the realm of the absurd if you feel resentment toward your family for not giving you something that isn't yours.

Self-awareness in this regard is crucial for personal growth. When I called you lucky at the beginning of this letter, I meant it. I, like most people, don't have an inheritance to look forward to, to help pay off my mortgage or send my kids to college. You hit the generational wealth lottery just by being born into the right family, as did your parents. I don't say this as a jealous sneer, but as a reminder.

You don't need to bow your head in shame for lucking out, but you must remember this money is a gift. Nobody likes the kid screaming at the tree on December 22nd because they want to open their presents early.

Not being that person is really a matter of tone. If your parents sense you're upset with them for even having to ask, they will be understandably hurt, which will only break down your dynamic. If you come to them with gratitude, humility, and curiosity, they might remember when they were in your shoes.

I mention curiosity because your parents may have hopes and expectations for this inheritance of their own. I can only imagine they had years to plan what they would do with it when it was finally their turn. Ask them about it. Show them your intention isn't to leapfrog over their moment holding the generational wealth, but to honor it.

Not only does this eliminate any ideas of absurd entitlement they may see around your request, but it might also help them see an early inheritance to you and your sister as a kind of collaboration — and the money as a family business. For now, they are co-CEOs and get to call the shots, but you, your sister, and your children are the future and worth the investment.

That said, I wouldn't shy away from reminding your dad that his parents did the same for him. I wouldn't make this reminder heavy-handed or accusatory. Instead, it should be a gentle way to introduce your request. Start by saying something like, "Hey, Dad. Remember how Grandma and Grandpa gave you part of your inheritance even while they were still living? I was thinking…"

You'll want to prepare a well-thought-out financial plan. Research investment options, savings accounts, and trusts, and determine how to maximize the financial gift you're requesting. Then, pitch this plan to your parents.

Whether your parents are holding onto the inheritance tightly because they still see you and your sister as fiscally irresponsible teenagers, because they have personal retirement concerns or priorities, or because they just didn't think you needed the money in the moment, presenting them with a plan is a great way to inspire their confidence and show them that giving you the money is not a risky indulgence, but a sound choice.

Your letter describes a lineage of security — not only the financial kind, but the kind that only happens when each generation looks after the next. While your parents may be playing with the timeline a bit, you mentioned having little doubt that they will leave the money to you and your sister when they die. This tells me your family looks out for one another. No matter how this conversation goes, take comfort in that security. That's the kind of wealth that can't be spent in a single generation, and you've got it. You lucky thing!

Rooting for you,

For Love & Money

An earlier version of this article was originally published in September 2024.

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 as-told-to essay is based on a conversation with Jeff Kinney, the 55-year-old author of the "Diary of a Wimpy Kid" series, who lives in Plainville, Massachusetts. It has been edited for length and clarity.

When I wrote "Diary of a Wimpy Kid," I worked on it for eight or nine years without thinking I was writing a book for kids.

I thought I was writing a book for grown-ups that would feel like "The Wonder Years" or "A Christmas Story" — looking back on childhood through the lens of an adult.

The first thing that surprised me was that my publisher said I'd actually written a children's series; it caused a lot of cognitive dissonance.

But what also surprised me was that kids understood the irony in the books. They understand that Greg is an unreliable narrator; they seem to get the joke.

After writing the series, and after raising two kids of my own — ages 21 and 23 — I've learned a few things about kids. Here's my best advice about getting kids to read, screen time, and more — plus a few things I'd go back and change if I could.

1. To get kids to read, feed their interests

I recently heard author Jack Gantos say that after dinner, he and his family would get out their books and read. I think that's really cool and also very old-fashioned, in a way. I wish we'd done it when raising our kids.

With reading, I think the most important thing you can do is feed your kids' interests, whether they're interested in Pokémon cards or sharks or tornadoes. Get them books or magazines that speak to their interests, rather than trying to give them books that we read as kids or books that are too high-minded for their age level.

A lot of authors who write for kids start with some sort of a lesson, and there's a time and place for that. But kids read for the same reason that adults read: to be entertained. If we start from a position of trying to teach kids a lesson, they'll sniff that out and turn away from it.

It's really important to encourage kids down a path that gets them reaching for the next book. I want them to feel a feeling of success in having finished a book because that's an important act of completion. But mostly, I'd like them to keep reading, whatever form that might take.

2. Listen to them

In everyday parenting, sitting at dinner with our kids and hearing about their day without judgment is a really good foundation. Just about everything that kids today are going through, we've been through in some form. The most powerful thing that we can say to kids is "I understand," or "I've been there myself," and share stories, making sure that they feel seen and heard.

As parents, we should make ourselves vulnerable to our kids by telling them about the struggles that we went through.

If we do that without moralizing and without judgment, I think it draws us closer to our kids and turns us into a resource for them.

3. Envision your future relationship

I've always thought about my relationship with my kids by imagining, How do I want our relationship to look when my kids are adults? I've tried to anticipate that and treat my kids that way the whole time.

I think it's working out because my kids will call me and want to go see the Patriots or the Celtics with me. I think that's partially because I've always had this version of our relationship in mind.

4. Don't get too wrapped up in kids' sports

As parents, we live and die by our kids' successes in sports. I certainly got too caught up in it and couldn't really anticipate that there would be a life beyond sports for my kids.

If I were to go back in time, I probably would change my approach on that. We like to see our kids succeed, and of course, sports is a big stage where there's a lot wrapped up in their success, including social issues and self-esteem.

When our kids are thriving, we feel really good for them, and when they're failing, it's tough for them and us. I can understand why that happens with parents, but I can also see that it's good to take a step back.

5. Help them understand that social media manipulates

Social media bullying is something that we never had to face growing up, and it's really unfortunate and damaging.

Screen time has changed things — you see studies finding that kids are dating a lot less, and there's a loneliness epidemic.

As parents, we can help kids by educating them and helping them understand that social media companies are incentivized to make you spend more time on your screens. The more that my kids, who grew up immersed in the social media world, began to understand that, the more they wanted to move away from it.

They get out there in the world — touch grass, play sports, and pick up basketball. My son will put lockouts on his social media.

It's important for us to think for ourselves before we turn to AI

As AI becomes a part of schoolwork and daily life, my concern is that AI makes a lot of things very easy.

At times, I look for solutions through AI that I could conjure up myself, so I worry about how that rewires the brain when you feel like there's always an agent that can solve your problem for you. It could reduce your own capacity for problem-solving.

It's really important for kids to be able to think for themselves before turning to the tool.

To counteract that, getting out in the world and interacting with one another is really important. Put kids into social situations; for example, my son has been working as a bookseller this past year, where he's had to interact with lots of different types of people and solve problems.

A lot of kids or young people in this generation are more isolated. They spend a lot more time in their rooms on their phones, and so I think that getting them out there interacting with other human beings is going to give them a competitive advantage.