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In this episode, I sat down with Eric and Kali Roberge of Beyond Your Hammock and the Money for Life podcast to talk about one of the hardest parts of family finance: how to help your kids financially without losing sight of your own goals. We covered retirement versus college savings, 529 plans, custodial accounts, Trump Accounts, allowance systems, and how grandparents can help without making family money conversations more complicated.
What I liked about this conversation is that we never treated any of this like a math problem with one right answer. Raising kids around money is messier than that. You are balancing your own future, your child’s future, and family dynamics that are not always easy to navigate.
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Kids learn more from what we do than what we say
Kali made an important point early on: teaching kids about money can be harder than managing your own financial life.
Your own financial plan may have a fairly clear set of steps. Teaching kids is different. They are watching how you spend, how you save, how you talk about money, and how you react to it. That means the lesson is not just what you tell them. It is what they absorb from the way you live.
That is why Kali emphasized self-awareness over perfection. Parents are not going to get this right all the time. The goal is not to create a perfect script for every money lesson. The goal is to be intentional, pay attention to what your child is picking up, and keep adjusting as they grow.
Save for your kids without sacrificing your own retirement
When I asked Eric how he helps parents think about saving for their kids, he kept coming back to flexibility.
Most parents do not know what college will cost. They also do not know what path their child will take. One kid may go to a four-year private school. Another may choose a public university, community college, trade school, or something else entirely. That uncertainty makes it hard to build a precise college funding target.
Eric’s answer was simple: first, save money. If the money is there and invested, you have options. If it is not there, there is not much to optimize later.
That fits with a point I often make to parents: your kids can borrow for college, but you cannot borrow for retirement. Helping your child matters, but not at the cost of blowing up your own long-term security. In practice, that usually means saving for your child in a way that leaves room to adjust later rather than trying to perfectly fund an unknowable number today.
529s, custodial accounts, and Trump Accounts each come with trade-offs
We spent a lot of time walking through the different accounts families might use, and the main takeaway was that each one solves a different problem.
On 529 plans, none of us were arguing against them. I still think they are the default starting point for a lot of families, especially if you get a meaningful state tax deduction and you are already doing a good job saving for retirement. Kali and Eric agreed they can be useful, but they do not like treating a 529 as the only answer. The value of the account depends on how certain you are that the money will be used for education and how much flexibility you want to keep.
Eric also raised a point that matters more than many people realize: the college strategy is not just about where you save now. It is also about where the money comes from when tuition bills actually show up. Your tax bracket at that point matters. The accounts you can draw from matter. The broader plan matters.
We also talked about custodial accounts and why the trade-off there is often control. Eric was pretty clear that he does not love the idea of turning over an account to a child at age 18 and hoping the money gets used well. For many families, keeping assets in a parent-owned taxable account may offer more flexibility and more control than an UGMA or UTMA.
Then we touched on Trump Accounts. Kali’s view was pretty pragmatic. If a child is eligible for the government seed money, it may make sense to open the account and take the free money. Beyond that, though, she had real concerns. The accounts will be administered through the Treasury rather than a traditional custodian, the investment options are limited to U.S. companies, and the long-term rules still feel politically uncertain. So while they may have a place, they do not look like the obvious first choice for most families.
Allowance works best when kids can actually handle money and make choices
One of the most practical parts of the conversation was hearing what money lessons look like with a four-year-old.
Kali talked about involving her daughter in small ways. When she tracks household spending in a spreadsheet, she sometimes lets her help enter the numbers. She is also trying to use more cash so her daughter can see money physically changing hands instead of only seeing a card get tapped.
They also give her an allowance, but not because she completed chores. The chores are part of being in the family. The allowance is there so she has money to hold, sort, and decide what to do with. She uses a give-save-spend setup, which gives her a simple way to start making trade-offs.
That part really resonated with me because one of the biggest benefits of allowance is what happens at the store. When your child asks for something and you can say, you are welcome to buy it with your own money, the whole conversation changes. Sometimes they still want it. Sometimes they decide it is not worth it. Either way, they are learning.
I also shared that we used a similar save-share-spend system with our boys, and it worked differently with each child. That is worth remembering. A system that clicks with one kid may not work the same way with another. Money personality matters. So does consistency from the parents.
Parenthood can make you less theoretical and more realistic about money
This part of the conversation felt especially honest.
Kali said that before having a child, she was much more focused on the technically correct answer. Parenthood changed that. Life felt less linear, less controllable, and less responsive to perfect planning. Instead of trying to optimize every detail, she has become more comfortable doing her best and letting go of the rest.
Eric described a different tension: the relationship between work, income, ambition, and time with family. He knows that the more he works, the more money he can make and the more flexibility that money can create. But he also wonders what that teaches his daughter. Is she seeing work ethic, or is she seeing that work crowds out family life? He was honest that he does not always know where the right line is.
I can relate to both of those perspectives. Parenting changes the way you think about control, spending, work, and what it even means to use money well. It also changes the kind of pressure parents feel. There is pressure to provide experiences, pressure to make memories, pressure to keep up, and pressure to make the “right” choices in a world where money is increasingly digital and spending is easier than ever.
Grandparents can help most through communication and shared experiences
We closed by talking about grandparents, which is where generosity and family complexity often meet.
Eric said he generally prefers the idea of giving while living. If grandparents have the means, helping create experiences now can be more meaningful than simply passing along more money later. Family trips, outings, and shared memories may leave a bigger mark than another contribution to an account.
Kali came at it from the communication side. In her view, grandparents and parents often make assumptions about what the other side wants without ever talking about it. The best first step is simply to have the conversation. Ask what would be helpful. Ask what the goals are. Ask how support would be most useful.
She also pointed out that even when a family is not ready for a full money conversation, a 529 can still be useful because it gives grandparents a clear place to direct gifts. It is a clean, practical way to help.
Eric’s advice for parents was to be willing to go first, especially if you come from a family that never talked openly about money. A practical question can be the easiest opener. If grandparents already have a 529 for the grandkids, for example, parents can explain that they are trying to plan responsibly and do not want to overfund their own account without understanding what is already there.
And if those conversations are not possible, Kali’s advice was to focus on what you can control and let go of the rest. Not every family dynamic can be optimized. Not every financial choice is worth creating resentment over. Sometimes the best decision for the family is not the mathematically perfect one.
Resources:
- Download: Common Savings Accounts For Children
- Download: Can I Make A 529-To-Roth Transfer?
- Greenlight: The banking app designed for kids and teens.
- Making Money Simple
The Long Term Investor audio is edited by the team at The Podcast Consultant
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