What I learned about money as a kid was simple:

It was freedom.

My parents never showered me with gifts. In fact, my mom clipped coupons religiously, even though we were a solid two-income household, and my dad was a partner at a law firm.

If I wanted something, I had to save for it.
Air Jordans? Save.
My first computer? Save.
A dog-walking job and a paper route gave me the money, and I learned fast: if you want it, work for it.

We were frugal but not because we had to be. And while that taught me responsibility, it also planted a subtle seed of scarcity. It taught me to work for what I wanted, but it didn’t teach me how to give. I had friends who had to explain to me that splitting the tab or picking up the next round was just how relationships worked.

My dad left the house every morning at 7:15 a.m. and got home around the same time each evening. He worked hard. One job, his whole life - stable, steady, silent about stress.

I learned that money came from consistency. That success came from stability. That safety and freedom came from being the guy who stuck with it.

Fast forward to now:
I’m a dad. I’ve built my own business. I’m trying to raise emotionally healthy kids.

And I’m still untangling all of it - the scarcity mindset, the "play it safe" story, the belief that “providing” only comes from long hours and steady employment - especially in a world of career pivots, market collapses, and runaway college costs.

And I’m not alone.

We’re the First Generation of Dads Redefining This Role

For most of our fathers (and grandfathers), being a provider was the whole job description.
They didn’t get asked to do bedtime.
They didn’t talk about emotional regulation.
Their value wasn’t linked to how present they were. It was how consistent the paycheck was.

But today?

We’re being asked to lead at work…and show up with empathy at home.

As one Ambitious Dad explained, “what keeps me up at night is being able to financially and emotionally support my family.”

To make time…and money.

We’re still providers, but what that means has changed radically.

And Here’s the Catch...

We want to provide more than just comfort.

We want to give our kids options.
We want them to have access.
We want them to pursue purpose, not just paychecks.

But also…
We want them to know how to work hard.
We want them to understand responsibility.
We don’t want to raise entitled kids who fold when life gets hard.

So now, we’re stuck in the middle, between tectonic plates of expectation:

• Don’t be absent like our father’s were, but don’t drop the ball on being the provider.

• Be generous… but don’t spoil them.

• Be present… but don’t sacrifice the future.

No wonder so many dads I talk to feel like they’re never doing enough even when they’re trying to do everything.

The Questions We’re Wrestling With

After asking several hundred Ambitious Dads what keeps them up at night, money comes up again and again, but not in the form of 529 plans or crypto portfolios. It’s something deeper:

• “How do I give my kids the good things in life without making them entitled or spoiled?”

• “How do I build wealth without letting it define me?”

• “How do I model healthy ambition… without modeling burnout?”

• “What if I’ve tied my identity too tightly to what I earn?”

• “What if I’m providing the wrong thing?”

These are the conversations that matter. And they are not financial planning ones. They’re emotional questions disguised as economic ones.

So Let’s Be Honest

If you grew up believing that love = provision = productivity then you probably:

• Feel guilt when you’re resting

• Say “yes” to work when your heart’s aching for connection

• Equate net worth with self-worth

• Work harder when you’re scared

• Get tight when your kids ask for something big

That’s not failure.
That’s programming.
And it can be rewritten.

Here’s What I’m Learning (Slowly)

I want my kids to believe that money is a tool, not a scoreboard.
That they are enough, even when they don’t produce.
That generosity and stewardship matter more than accumulation.
That we can define wealth in terms of freedom, alignment, and time.

But if I want them to believe that…I have to start modeling it.

One Belief to Keep. One to Let Go.

So here’s a question I’ve been asking myself:

What’s one belief about money or providing I want my kids to inherit?
And what’s one belief I hope they never absorb?

My answer:

Keep: Money is something you can learn to manage.
Let go: There’s never quite enough, so hold on tight.

I’ve had to keep unlearning this inherited belief in scarcity, even when I know there’s enough. I’ve already experienced that it stifles generosity and leads me to believe that generosity = risk.

5 Ways to Teach and Model a Healthier Relationship with Money

Given that most of us have certain fixed mindsets around money, here’s a list of simple actions we can take to model healthier connections to providing:

1. Narrate Your Choices, Not Just Your Spending
   “We’re saving for a family trip right now. That’s why we’re not buying this toy today.” This helps kids understand priorities, not just limits.

2. Talk About Enough
   Let them hear you say: “We have enough.” Say it often. Say it like a value. Say it like a prayer. It teaches sufficiency rather than scarcity or constant striving.

3. Give Them a Role in Giving
   In my family we have three piggy banks in the boys room. They are labeled Give, Save, Spend. The boys equally divide their savings or cash gifts from kooky grandma into them. When we had a huge flood last fall, we talked about donating money from the Give bucket.

4. Separate Self-Worth from Net Worth
   Catch yourself (and correct yourself) if you use success language that’s all income-based. And see my last article on (re)defining success.
   Instead: praise courage, effort, thoughtfulness, integrity.

    

5. Let Them See You Use Money With Intention

   Don’t just save. Instead, show them how to spend in ways that align with your values. Talk about why you donate, why you invest in family trips, or why you tip well.

The New Provider

I’m still providing but not just paychecks.

I’m trying to provide calm.
Curiosity.
Structure and tradition.
Clarity.
A sense of enough.

Because in the end, it won’t be my income they remember.

It’ll be the way I spoke about what matters.
The way I modeled generosity without fear.
The way I showed them how to live fully with or without financial certainty.

Providing, it turns out, isn’t just about what you give.
It’s about what you leave behind in the people you love most.