Spend, Save, or Enjoy? The Real Cost of Living the Life You Want

“Money is a terrible master but an excellent servant.” — P.T. Barnum

Money’s a funny thing. You work hard to save it, and then what? You spend it and feel guilty. You don’t spend it and feel deprived. You help your kids, and it stresses your retirement. You don’t help them, and you feel selfish.

I’ve been thinking about all of this lately—after buying a car I probably shouldn’t have bought.

When a Shiny Toy Turns into a Tough Lesson

I bought a vehicle. Collector-style. Custom mods, candy-apple red paint. A real looker. Paid for it, paid tax on it, paid to ship it, license it, insure it, fix a few things, house it. Then—sold it.

Sold it for more than I paid, technically. But by the time I added everything up? I lost money.

Was it a mistake? Maybe. But maybe not. Maybe it was just the price of a hobby.

We don’t usually think of things like boats or motorcycles or weekend trips that way. We tell ourselves, “If I sell it for what I paid, I didn’t lose.” But even when we do lose—was that really a mistake, or just the cost of living a little?

Is It a Waste—or Worth It?

Here’s a few real-life questions I hear from clients:

• Should I have just gone to McDonald’s instead of the steakhouse?
• Do I really need this big of a house?
• Why am I still driving this 10-year-old car when I can afford a new one?
• Why am I driving something so new and fancy—do I even need this?
• Should I be helping my adult kids more? Or less?

There are no universal answers. But there are better questions.

The Real Test: Can You Afford It Without Derailing the Plan?

Here’s what I tell people—and what I remind myself, too.

If you’re on track with your goals, and you’re not carrying debt that hurts you long-term, then yes—maybe it’s okay to spend the money. Even if it looks ridiculous to someone else.

But if you’re behind, or relying on credit, or skipping contributions to your retirement plan just to make it happen… that’s a problem.

Quick Litmus Test: Should You Buy It?

Use this to gut-check your decision before you spend on something big.

Still unsure? That’s what I’m here for → Let’s run the numbers together.

You Can’t Judge Someone Else’s Spending—Even If You Try

Here’s the thing:
I know people think I’m foolish for how much I spend on boating and travel. I know it. I’ve cringed when I’ve told people. And guess what? I’ve cringed at what they spend money on, too.

We all do it. We look at someone else’s life and think, “Why is he doing that?” or “That’s such a waste.” But you know what? It’s their money. Their plan. Their priorities. And mine are mine.

The only thing that matters is that your financial choices line up with your long-term goals. If they don’t? We need to talk. But if they do? Enjoy the ride. Even if it’s in a bright red custom-mod car.

Some Common Spending Traps (I See These a Lot)

Helping the Kids Too Much

If you’re constantly stretching your own budget to help adult children—and you’re dipping into retirement savings—you may be doing more harm than good. You’ve got to take care of yourself first.

Driving a Car That’s Too Old

If you can afford something safer, newer, and more reliable—get it. You worked hard. And newer safety features aren’t just luxury anymore; they’re protection.

Being Overly Frugal for No Good Reason

You’ve paid off the house. You’ve got savings. You’re debt-free. So why are you eating saltines for lunch and skipping the vacation? You’re allowed to enjoy what you’ve earned.

The Spend-Save-Enjoy Balance

Here’s how I think about it:

It’s Your Money. Live on Your Terms—But Be Honest About the Math

If you’re crushing your plan and still feel guilty spending? Let it go.

If you’re spending to feel better but quietly falling behind? Time to face the numbers.

And if you’re not sure where you stand at all? That’s where I come in.