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Let Them Make the $100 Mistake

Let Them Make the $100 Mistake

September 16, 2026

We all want our kids to become financially responsible adults.

So we teach them to save.

We tell them not to spend too much.

We explain how credit cards work.

We warn them about debt.

We try to help them avoid the mistakes we made.

But I have started to wonder if, in our attempt to protect our kids from financial mistakes, we sometimes protect them from the very experiences that could teach them the most.

The Credit Card Bill

Recently, my 16 year old son came upstairs and asked my wife a question.

“Mom, why is my credit card bill so high?”

There is some backstory here.

When our kids turn 16, my wife and I add them as authorized users to a credit card we rarely use.

The card essentially becomes theirs.

They use it for their purchases, we receive the bill, and then they pay us back.

Our goal is to give them some experience managing money and using credit while the stakes are still relatively small.

So when my son asked why his bill was so high, my wife could have simply told him.

She didn’t.

Instead, she asked him a question.

“Did you look at the charges line by line?”

He hadn’t.

He just knew the bill seemed much longer than usual.

So he went back and looked.

A few minutes later, we heard:

“Uh oh. I went to Darcy’s way too much.”

Darcy’s is a local coffee shop he loves.

Then came the part that made us smile.

“Lesson learned. I need to pay way more attention to what’s coming in and how much I’m spending.”

There was no lecture.

No budgeting lesson from Mom and Dad.

No spreadsheet.

He experienced the consequence of his decisions and came to the conclusion himself.

Knowing Is Different From Experiencing

My son already knew money was finite.

He knew you shouldn’t spend more than you make.

He knew that buying something today means having less money available for something else tomorrow.

But knowing something intellectually and experiencing it are very different.

That credit card bill made the lesson real.

And I think that distinction matters.

As parents, we can tell our kids how money works over and over again.

But eventually they need the opportunity to experience financial decisions for themselves.

Which has led me to a new philosophy:

I would rather my kids make the $100 mistakes today than the $10,000 mistakes later.

Too many trips to a coffee shop are not going to destroy my son financially.

But discovering that his spending added up faster than he realized taught him something.

And he learned it while the stakes were small.

What Are We Actually Trying to Accomplish?

I think this is where parenting can get difficult.

What is our goal?

Is it to make sure our kids never make a bad financial decision?

Or is it to raise adults who know how to make financial decisions without us?

Those are two very different goals.

If we make every decision for our kids until they are 18, 22, or even 25, we may have successfully protected them.

But have we prepared them?

Someday my wife and I are not going to be there to hand our son the bill and ask:

“What do you notice?”

The goal is for him to eventually ask himself that question.

To notice.

To evaluate.

To understand the consequences.

And then to adjust.

That is financial responsibility.

Not perfection.

The Numbers Get Bigger

There is another reason I think this lesson matters.

The decisions do not stop when we become adults.

The stakes simply get bigger.

Instead of spending too much at the coffee shop, we start making decisions about homes, careers, college, investments, stock compensation, businesses, retirement, taxes, and the lifestyle we want to live.

A series of relatively small decisions can quietly become a very big financial decision.

That is why one of the most important questions we can continue asking ourselves is:

What do you notice?

Look at your cash flow.

Look at where your money is going.

Look at the decisions you have made over the last year.

Look at what you say matters most to you.

Then compare those things.

Do they line up?

Financial Planning Should Not Require Perfection

This is also one of the reasons I believe financial planning should be about more than accumulating the biggest pile of money possible.

Life is not that predictable.

Priorities change.

Careers change.

Families change.

Markets change.

What you want from life can change.

So the goal cannot be to create a perfect plan based on the assumption that everything happens exactly as expected.

The goal should be to develop enough clarity around what you want that you can make better decisions today and recognize when you need to adjust.

That is what my son did.

He saw the bill.

He looked at the decisions that created it.

He recognized the problem.

And he adjusted his thinking.

The numbers may have been small, but the process is one he can use for the rest of his life.

Let the Stakes Be Small

As parents, there will always be an instinct to protect our kids.

And sometimes we absolutely should.

But there may also be moments when the better decision is to let the stakes stay small and allow the lesson to happen.

Let them buy too much coffee.

Let them look at the bill.

Let them experience the consequence.

Then instead of immediately giving them the answer, ask:

What do you notice?

Because the goal is not to raise kids who never make financial mistakes.

The goal is to raise adults who recognize mistakes, learn from them, and adjust.

And maybe that lesson is not just for our kids.

Maybe all of us could benefit from looking at our financial lives every once in a while and asking the same question.

What do I notice?

That is part of being built for life, not just wealth.