As parents, we want to protect our kids.

We want to protect them from pain, embarrassment, financial stress and the mistakes we made.

But what if that instinct is quietly holding them back?

That’s the challenge Lee Benson put in front of me during our conversation. Lee is the author of Value Creation Family and founder of Dinner Table, a global community of more than 50,000 families focused on helping parents raise value-driven, self-reliant kids.

His message is simple but uncomfortable.

Stop removing struggle. Start preparing your kids to create value.

As a dad of two kids, ages 14 and 11, this one hit me. Because I’ve caught myself doing exactly what Lee warns about.

Why parents overprotect

When I asked Lee why parents resist letting their kids struggle, his answer was immediate. Most parents don’t want their kids to struggle the way they did.

Lee grew up in a low-income household with significant instability. He was kicked out during his senior year of high school and started adulthood in debt because credit cards were opened in his name. He began life financially in the hole.

And yet he says he wouldn’t change it.

Those struggles shaped him. They forced him to think differently. They pushed him toward financial self-reliance and eventually toward building multiple companies with significant exits. Today, he focuses on helping families intentionally develop their kids through what he calls “healthy struggle.”

His definition stuck with me. Struggle is any effort to improve a life condition, develop a character trait, build a capability, or modify a limiting belief.

That’s not trauma. That’s growth.

The danger of protecting too much

Lee pointed out something we’re all seeing more of today. Kids legally become adults at 18, but many don’t feel fully self-reliant until their late 20s or even 30s.

Why?

Because we removed too much friction.

I’ve had moments at home where I’ve tried to eliminate inconvenience for my kids because it was easier for me. It’s faster if I just do it. It’s smoother if I handle it. It avoids complaints if I solve it myself.

But what if that convenience is costing them capability?

Lee calls this the transition from entitlement to self-reliance. And it’s one of the biggest struggles facing families today.

A simple system that changes everything

If you’re wondering where to start, Lee does not recommend a massive overhaul. He suggests beginning with one powerful habit: a monthly family meeting.

Sit down together and talk about three things:

1. Family goals
2. Everyone’s job for the family
3. What it means to be a leader in your household

This isn’t a lecture. It’s a collaboration.

Lee believes every family member, including kids, should have a job for the family. Parents list theirs too. This models responsibility instead of hierarchy.

When kids understand they are contributors, not passengers, something shifts. Lee said every child he’s worked with lights up when asked if they can be a leader in the family. Every one of them says yes.

That framing matters.

Running the household as a training ground

One of the most practical ideas Lee shared was this: running the household is the best laboratory for teaching financial self-reliance.

In one example, a 16-year-old manages the entire family budget. Every line item has a “family sponsor,” including younger siblings. If the family beats the budget, the kids decide how to use the savings. One year, they funded a trip to Yellowstone together.

Imagine the lessons in that.

Budgeting.
Delayed gratification.
Teamwork.
Tradeoffs.
Opportunity cost.
Leadership.

As a dad, I had to pause here. We do chores and responsibilities in our home. My kids earn money. They manage spending. But could we involve them more deeply in the financial operations of our household?

Probably.

If you’re looking for tools to help kids manage money responsibly, there are great options available today. Platforms like Crew give kids hands-on experience with banking, saving, and budgeting in a real-world way. For younger kids, even starting with structured debit access can build confidence. We’ve written about some strong options in this guide to the best child bank accounts.

The key is not just giving them money. It’s giving them responsibility.

Earning versus entitlement

Lee separates family contribution from paid work.

Every child has a job for the family. That is not paid. That is contribution.

Then there are “gigs” where they can earn money beyond their family responsibilities. These should reflect real-world expectations. Overpaying for simple tasks may feel generous, but it distorts future expectations.

This resonated with me.

I’ve made the mistake of occasionally speeding things up by throwing money at a task. It felt efficient. But Lee’s point is that earning money should mirror real-world value creation, not convenience for the parent.

Kids who learn to earn, protect, budget, and spend wisely build confidence. They feel capable. They feel prepared.

And most importantly, they feel self-reliant.

The emotional side of financial education

What I appreciated most about Lee Benson’s philosophy is that it isn’t just about money.

It’s about emotional energy and connection.

Family dinners. Intentional conversations. Showing up consistently. Playing the long game.

Lee reminded me that kids don’t need a perfect speech. They need repetition, presence and patience.

Sometimes I forget my kids are 14 and 11. I speak to them like they’re adults and then get frustrated when they don’t respond like adults. Lee’s reminder was simple. Play the long game. Give them time. Keep showing up.

That’s leadership too.

One small step you can take this month

If you’re reading this and thinking, I may be overprotecting my kids, don’t panic.

Start small.

Schedule a family meeting this month. Ask your kids:

• What are our family goals?
• What’s your job for the family?
• What does it mean to be a leader here?

You might be surprised by their answers.

Lee Benson’s new book, Value Creation Family, dives much deeper into this philosophy and offers practical frameworks for raising kids who are emotionally strong, financially capable, and prepared to create value in the world around them.

Protecting our kids feels loving.

Preparing them is even more loving.

And if we want financially confident, value-creating adults, we have to let them struggle a little today so they can thrive tomorrow.

What are some healthy struggles you provide to your child?

Please let us know in the comments below.