Good Questions Can Change Everything

“Sometimes the best financial decision you can make is not about the math; it’s about asking yourself the right questions before you make your choice.”

So often, financial decisions look like math problems.

Can we afford it?
Will the numbers work?
What’s the return?

But some of the most important financial decisions you’ll ever make have less to do with numbers and more to do with the questions you ask before you say yes.

I learned that years ago through a conversation about a ski house.

The House That Almost Happened

Years ago, when I was still working as a financial advisor, I got a call from a couple I’ll call Bob and Jane.

They were smart, hardworking professionals, building successful careers, raising young kids, and doing a lot of things right financially.

They had just returned from a ski trip with friends where they found the perfect property:

• Ski-in, ski-out access
• Shared ownership with another couple
• Rental income potential
• A “great investment”

And the math worked. At least on paper. Their CPA liked the idea. Their friends were excited. The realtor made it sound easy.

But before making major financial decisions, Bob always called me to talk things through. So I listened. Then I asked a few questions.

The Questions That Changed a Choice

I asked:

• What happens if the other couple runs into financial trouble?
• What if rental income doesn’t cover the costs?
• What if you can’t sell the property when you want to?
• What happens when your kids get older and priorities change?

None of those questions were really about math. They were about wisdom, stewardship and understanding the hidden cost behind the opportunity.

Because there’s a place where the math stops…and you begin.

The Decision They Didn’t Make

After a lot of conversations, Bob and Jane decided not to buy the ski house. Instead, they took their extra resources they would have spent and began to pay down their mortgage.

Years later, I received an email from Bob. It simply said: “We sent in our last mortgage payment today. We are 100% debt free!”  They were in their early 40s when they sent that email.

No mortgage.
No lenders controlling their future.
No financial pressure tied to a second property.

For them, less truly became more.

The Bigger Lesson

Most of us don’t wrestle with ski-house decisions every day. But we all wrestle with questions. I see so many people who chose their lifestyle before they chose their life they actually wanted.

People who bought houses before they thought deeply about their homes. People who slowly built lives that looked successful, but felt exhausting.

Questions Worth Asking

The right question has great power. So here are a few worth sitting with:

• What are you building with all this hard work?
• Could something important be slipping away while you chase more?
• What will your kids remember—the stuff or the moments?
• Are you controlling your money, or is it controlling you?
• Is your house serving you/your family… or are you serving your house?
• Whose approval are you really seeking in your financial decisions?

These questions aren’t meant to create guilt and not all of them apply to each of us. They’re simply invitations to pause, to reflect, and to be more intentional. Because financial decisions are rarely just financial.

They reveal what we value. What we fear. What we trust.

Less Can Become More

I’ll be honest—there was a season in my life when I made financial decisions based largely on how things looked. I even wrote about it in my book He Spends She Spends. I thought “more” would create peace. But over time, I discovered something different:

Sometimes having less creates more space for what matters most. Less distraction. Less pressure. Less striving.  And more room for more:

• God
• Peace
• Generosity
• Relationships
• Contentment

Sometimes the right question, at the right time, changes everything.

Next Steps

Listen to Money Made Faithful podcast Episode #220: Good Questions Can Change Everything (22 minutes)

Apple: #220- Good Questions Can Change Everything

Spotify: #220 - Good Questions Can Change Everything