For a long time, I thought being good with money meant spending as little as possible.

I'd compare prices, look for cheaper alternatives, and convince myself that saving twenty dollars automatically meant I'd made the smarter decision. If something wasn't absolutely necessary, I'd usually talk myself out of buying it.

Sometimes that was the right call.

A lot of the time, though, I realized I wasn't actually saving money.

I was just delaying purchases I'd eventually make anyway or buying cheaper versions of things I'd have to replace a year later.

Over time, the question I asked myself started to change.

Instead of asking, "Can I afford this?" I started asking, "Will this genuinely improve my life?"

That sounds like a small shift, but I think it completely changes the way you spend money.

When I recorded this week's podcast, I realized almost every purchase I recommended passed that test. None of them were about buying expensive things for the sake of buying expensive things. They were purchases that made everyday life easier, saved me time, built confidence, or created experiences I'd remember years later.

I think this sums it all up in one sentence:

"A lot of these things improve your life because it improves... they improve the way you think about yourself. And they make you feel better about yourself."

Looking back, I think that's become my filter for almost every purchase I make.

I Don't Buy Things. I Buy Outcomes.

One of the biggest changes in how I think about money is that I rarely evaluate the product itself anymore.

I evaluate what it's going to do for me.

A gym membership isn't really about access to weights.

Quality cookware isn't really about owning a nicer pan.

A good pair of shoes isn't just about the shoes.

Each one creates an outcome that's much more valuable than the object itself.

The gym gives me structure and energy.

The cookware makes me more likely to cook at home.

The shoes become something I can rely on every time I leave the house.

I've written before about in How Do You Start Going to the Gym? (A Beginner's Guide), and that's exactly why I think it's one of the best investments you can make. The real return isn't measured by how many workouts you complete. It's measured by how much better you feel during the other twenty-three hours of the day.

That way of thinking has changed almost everything about how I spend money.

Instead of comparing price tags, I compare long-term value.

According to Consumer Reports, well-made everyday products often provide better long-term value because they last longer and perform more reliably than inexpensive alternatives. I've found that's true in my own life too.

The purchases I appreciate most are almost never the ones that felt exciting when I bought them.

They're the ones that quietly keep making life better every single day.

The Best Purchases Usually Pay You Back More Than Once

One thing I've noticed is that the purchases I value the most aren't the ones that impressed me when I bought them.

They're the ones that continue making my life better months or even years later.

Take TSA PreCheck, for example.

It's not something anyone gets excited about.

You don't post about it on Instagram or tell your friends you finally signed up.

But every time you walk past a long security line, you're reminded why you spent the money in the first place.

"Time is the only resource that we can't get any of back. And that should be enough of a reason for you to get TSA PreCheck."

That idea has started to shape almost every purchase I make.

If something saves me time every week, makes a daily task easier, or removes a recurring frustration from my life, I don't really see it as an expense anymore.

I see it as buying back part of my day.

The Transportation Security Administration reports that millions of travelers choose TSA PreCheck because it makes the airport experience faster and more predictable. You're not really paying to skip a line. You're paying to spend less time waiting and more time doing the things you actually care about.

That's a return that's difficult to put a price on.

Some Things Are Worth More Than Their Price Tag

I've also realized that the most valuable purchases aren't always practical.

Sometimes they're experiences.

I've spent money on concerts that lasted a few hours but gave me memories I'll probably have for the rest of my life. I've taken trips that felt expensive at the time but completely changed my perspective afterward.

Those purchases never feel like money wasted.

"I've never regretted spending money on a concert. I've never been like, I shouldn't have gone to that."

I think that's because experiences continue giving you something long after they're over.

You look forward to them before they happen.

You enjoy them while you're there.

Then you carry the memories with you afterward.

Researchers writing for Harvard Business Review have found that experiences often create more lasting happiness than material possessions because they become part of our identity and are frequently shared with other people.

Looking back, that's been true in my own life.

I've forgotten plenty of things I've bought.

I've remembered almost every great experience.

A Good Purchase Should Make Tomorrow Better Than Today

I don't think every purchase needs to change your life.

Most won't.

But I do think the best ones make tomorrow a little easier than today.

Maybe that's a gym membership that gives your week more structure.

Maybe it's quality cookware that makes you want to cook at home instead of ordering takeout.

Maybe it's finding clothes that fit well enough that you stop thinking about them altogether.

I've written before about The Little Upgrades That Make Everyday Life Better, because I've found that improving your life usually isn't about making one huge change. It's about making dozens of small decisions that quietly improve your routine over time.

The same idea applies to confidence.

Buying a quality trimmer or a bottle of cologne isn't really about the product itself.

It's about how you feel when you leave the house.

That's why I also think What Should Every Guy Invest In During His 20s? is ultimately a much bigger conversation than money. The purchases that are worth making are usually the ones that help you become the person you want to be.

And Here's The Thing

These days, I don't really ask whether something is expensive.

I ask whether it's valuable.

There's a difference.

Some expensive things aren't worth buying.

Some inexpensive things improve your life every single day.

The goal isn't to spend more money.

The goal is to spend more intentionally.

If a purchase saves you time, helps you build better habits, strengthens your relationships, improves your confidence, or creates memories you'll still be talking about years from now, it's probably worth considering.

Those are the purchases I've almost never regretted.

Not because they were cheap.

Because they kept paying me back long after I bought them.

Frequently Asked Questions

How do you decide if something is worth spending money on?

Ask yourself whether it will continue improving your life after you buy it. If it saves time, builds better habits, improves your confidence, or adds lasting value, it's often worth the investment.

Is it better to buy quality or save money?

For items you use regularly, buying quality often provides better long-term value because they last longer and improve your everyday experience.

Should you spend money on experiences?

If they're within your budget, experiences can be some of the best purchases you make because they create lasting memories and meaningful relationships.

How can I spend money more intentionally?

Focus on purchases that solve recurring problems, improve your daily routine, or help you become the person you want to be instead of buying things on impulse.

What's the difference between an expense and an investment?

An expense ends when you spend the money. A good investment continues creating value by improving your life long after you've made the purchase.