The trip is planned. Everyone is excited. The money is there.

And then you hesitate.

Not because you cannot afford it. But something inside you pumps the brakes anyway. A little voice whispers: Should I really be spending this? 

Sound familiar?

If you have spent most of your life being careful, saving faithfully and making sure everyone else was taken care of first, this hesitation is not a stranger to you. It shows up at the checkout line, at the travel website, in a restaurant, at the moment you finally have permission to enjoy what you worked so hard to build.

Here is what I want you to know about that hesitation moment: It is not really about the trip.

That hesitation is an internal cue. If you allow money to be a mirror, it is reflecting something much deeper than a budget decision. It is showing you what you believe. About security. About worthiness. About trust. And sometimes, about God.

Jesus talked about money more than almost any other topic. Money has a way of getting right to the heart of things. It is a material representation of finances, health and work. In a practical word: security. Therefore, it exposes our fears faster than almost anything else. It shows what we value when no one is looking. It reveals whether we are living from a place of trust or of scarcity. 

Most of us did not come to our money beliefs on our own. We inherited them.

Waste not, want not. Make hay while the sun shines. Many hands make light work. A penny saved is a penny earned. You probably heard the voice of a loved one just now. 

These sayings carry real wisdom. They were often born in hard times, passed down through ancestors who knew what it meant to go without. These were statements that helped generations survive.

And . . . today’s daily realities have shifted. Therefore, what was wisdom can quietly shift into fear.

This is when saving becomes hoard­ing. Caution becomes paralysis. Frugality becomes the belief that we do not deserve to enjoy what we have. And the rainy day we were saving for never quite feels distant enough to relax.

I call this “making do like the Millers” (the opposite side of the coin of keeping up with the Joneses). If you identify with responsibility, as I do, then you know the tension I am talking about.

On one hand, you feel the pull to ever be a good steward. To not be wasteful. To protect the future. All good things.

On the other hand, you feel a quiet longing to actually live. To take the trip. To give the gift. To say yes without lingering guilt.

A person with the making-do-like-the-Millers mindset lives with this tension their whole life. They feel like they are doing all the right things yet never feel truly free.

What if responsibility and joy are not supposed to be opposites? What if faithfulness with money includes enjoyment of this life God gave you?

Here is what I have come to believe: Responsibility alone rarely creates joy. But responsibility paired with personal clarity often does. The problem is not usually the money. The problem is that we have never stopped to ask what actually brings us satisfaction and fulfillment.

There is a woman in the Bible who did something that made everyone in the room uncomfortable. She walked in carrying an expensive jar of perfume. And then she poured the whole thing out. On Jesus. All of it. Not a portion. Not a careful, responsible amount. All of it.

The people watching were upset. That perfume could have been sold. The money could have gone to the poor. What a waste!

And Jesus said: Leave her alone.

That story is powerful because it challenges something deep in those of us who were raised to be careful. The woman’s act was not good stewardship. It was not practical. But it was aligned and faithful.

Sometimes the most aligned financial decision is not the most responsible one. Sometimes it is an expression of love, gratitude or worship. Sometimes it is booking the trip, buying the gift or giving in a way that does not make sense on a spreadsheet.

Not every dollar needs to be optimized. Some need to be offered.

A few years into my career, the way I financially planned for others began to shift under my feet after a friend died in an accident. I was just at his employer giving a presentation about why it’s important to save for retirement. 

But he never got there.

Simultaneously I was having conversations about retirees who had decided not to spend their IRAs “just in case,” only for the money to pass on to a person who spent it freely. Poof. Gone. 

I am not telling you this to scare you. I am telling you this because I want you to think differently about what it means to be a human with money.

Yes, save for the future. But don’t forget the beauty of now. Don’t withhold permission from yourself only to sit in a recliner, reflecting on life with regret.  

Permission may never come in the form you are expecting.

What is ready to be experienced by you that opens your life to more freedom?

I’m not advocating reckless spending. I’m suggesting giving yourself permission to let your money be well-spent now, not just someday.

Anyone who’s paged through the More-With-Less Cookbook knows this intuitively. Thrift creates margin. Margin makes generosity possible. And generosity gives meaning to money in a way nothing else can. In that sense, thrift and generosity aren’t in conflict. They’re partners.

After years of working with women and couples, here’s what I’ve noticed: The thrift-and-generosity partnership doesn’t always feel complete. Thrift and generosity come easily for many in the Anabaptist faith. The nonprofits are funded. The needs around them are met. And yet something still feels

. . . off. Like the life they’re living doesn’t quite match the life they imagined. Meaningful, yes. But not always satisfying.

What’s often missing isn’t more giving. It’s generosity turned inward.

Thinking specifically of women, I’ve noticed that giving comes naturally to those who’ve spent years caring for others. Receiving or even allowing yourself to enjoy what you’ve been given — that’s harder.

So the question becomes: What does generosity toward yourself look like? Not over-indulgence. Not exclusion of others. But care that reflects your values, your season of life and your needs.  It’s a self-generosity that compounds generosity with others. 

When I see someone hesitate (whether it’s giving to others or allowing something for themselves) I often ask: What story are you telling yourself right now? Because that story is the mirror. And the mirror is showing you something worth paying attention to.

As you face the mirror, ask yourself if it is time to reorient your story. 

The freedom you seek is to become someone whose financial choices align with your soul-driven desires and beliefs. About yourself. About God. About our world. About enough. About what this life is for.

If money is a mirror, what is yours revealing?

Liz Hand is a Certified Financial Planner, Associate Certified Coach and member of First Mennonite Church in Canton, Ohio. She is the co-owner of Pleasant Wealth, dedicated to empowering women nearing retirement.