Retire Smarter Newsletter

Feb 12 • 2 min read

A Few Questions to Help You Spend Money Better


My job obviously isn’t to tell you how to spend your money, but I do enjoy helping people better align their spending with what matters most to them. And since what brings one person joy might do very little for someone else—and vice versa—there’s clearly no one “right” way to spend money.

That said, there are a few simple questions we can ask ourselves to help guide our spending toward things that truly add meaning to our lives.

I’ll share two of those questions along with a bit of commentary below, and then I’ll leave you with a few additional questions to keep in mind whenever you’re making big (or small) spending decisions. Here’s the first question:

· Will this purchase create an environment that brings you closer to the people you love?

Spending money in ways that generate more time with the people we care about is one of the most reliable paths to happiness.

Intuitively, we know this to be true, given that our best memories almost always include our family and friends. So, how might you spend such that it brings you closer to the people you love?

As an example of a big purchase, it might mean choosing a new home—or improving the one you already have—that encourages more gatherings, shared meals, or time together.

On the smaller end, it might mean spending money on experiences such as trips together, shared hobbies, comedy or Broadway shows, or dinners out. Ideas here are endless and don’t need to be expensive to be meaningful!

Regardless of the cost, this type of spending tends to pay what Bill Perkins calls “memory dividends,” which are returns that compound not financially, but emotionally, as we revisit these experiences in photos, stories, and conversations for years to come.

Whenever a purchase or experience creates more time with people you love, there’s a good chance it will be money well spent.

Let’s look at another question.

· Does the purchase itself promote enduring joy?

In his book Things That Matter, Joshua Becker offers a definition of minimalism that provides a good starting point for this discussion:

“Minimalism is the intentional promotion of the things we most value and the removal of everything that distracts from it.”

We may not be minimalists, but I think you’ll agree that abiding by this idea can help direct our time, money, and attention toward the things that matter most to us, whatever those are.

Author Ramit Sethi shares a similar philosophy, encouraging people to spend extravagantly on the things they love while cutting mercilessly on the things they don’t.

The challenge, of course, is that we live in a world that’s constantly persuading us that we should have the best of everything. The unfortunate result of this cultural fallacy is that we waste money on things that don’t meaningfully improve our lives.

The goal here isn’t necessarily to eliminate—or even to reduce our spending—but simply to intentionally direct our money toward areas that could make our lives better. By removing the things that distract us, we create room (both financially and mentally) to double down on the few areas that truly matter.

Rather than offering more examples, I thought it might be helpful to leave you with a short list of additional questions to ask yourself next time you’re considering a purchase:

  • Will this purchase make your daily life calmer, healthier, or more energizing in a noticeable way?
  • Does it support a hobby or skill you want to grow, rather than distract you from it?
  • Does this purchase reflect the kind of person you’re striving to be?
  • If you already owned it, would you be excited to use it this week?
  • Would you buy this if no one else ever knew you had it?
  • Will you still be glad you bought this a year from now?

I hope these questions help you spend your money a little more intentionally and, ultimately, a little more meaningfully.

Tony Matheson, CFA, CFP®
Fiduciary | Commission-free | CFP® Professional
tony@slalomwealth.com



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