How to End Regrettable Spending: 9 Questions to Ask Yourself Before Buying Anything

We all want homes that are decorated with lovely things, closets that brim with stylish clothing, and social media feeds brimming with evidence of fun nights out with friends.

If those don’t fit your spending style, feel free to substitute with whatever inspires swiping. But, no matter what strikes your fancy, we all long after stuff—or experiences—that stress our budget.

And, as nice as it feels to splurge, no amount of telling yourself “I totally deserve this!” can stand up to the realization that your spending repeatedly goes towards things that you regret.

So, in hopes of helping you redefine your personal relationship with spending and happiness, we’ve compiled nine questions to ask yourself before every purchase, along with some examples of different motivations behind regrettable spending.

Note that the purpose of this isn’t to completely overhaul your budget or tell you how to save money, but to help make sure that what you do spend is a direct reflection of what makes you happy—not just another item that will sit there collecting dust.

1. Is It a One-Trick Pony?

Can you wear that sweater with several other things in your closet? Can you use that kitchen gadget to make soup and hummus and coleslaw? Can you use that cute (but overpriced) bottle of Mrs. Meyer’s concentrate to clean every surface in your home?

Figuring out if a purchase fits your spending profile starts by determining if it will have multiple, ongoing uses of if it’s going to be a one-trick pony.

See Also: 6 Top Tips to Buying Pre-Owned Designer Clothing Online (That You’ll Actually Love)

If the garment doesn’t go with anything else in your closet, or the kitchen gadget can only be used to make one recipe, consider leaving it on the shelf.

2. Will I Use It Right Away?

Is whatever you’re considering so amazing that you’ll wear it, display it, or use it the minute you get home?

You’ll have a much easier time reducing clutter and regrettable purchases if you honor the idea of the “immediate yes.”

For example, we’ve all seen something in a shop window that’s to die for, or tried on shoes that you feel compelled to wear out of the store. These are the items that make you think “YES!” before even spotting the price tag—and you’ll probably love forever.

But, those placemats you found while browsing out of boredom? Chances are, you’re not dying to go home, clean off your dining room table, and swap them out.

Bottom line: If the only thought in your mind is “I guess this’ll work,” then you’re probably better off leaving it in the store.

3. How Much Is It Worth to Me?

I’m the absolute worst at buying clothes that aren’t ever worn, so I learned to play a game that’s helped to reduce regretted purchases exponentially:

When you’re shopping, check out the inner tag for your size, then try items on. But, don't look at the price. Once you’ve decided that it fits, set a mental limit on how much you’d be willing to pay for it before ever looking to see how much it costs.

When deciding how much an item is worth, try to think about the cost-per-wear. For example, amazingly comfortable shoes that’ll go with everything you own should be allotted more than a pair of strappy sandals that’ll get less than one or two wears a month.

Similarly, a gorgeous winter coat that you’ll wear for six months gets cheaper each time you wear it—as long as it’s cozy enough to keep you warm.

Once you’ve set a mental price, stick to your guns! Not only will it help reduce the number of purchases you don’t need, but doing so helps quell aspirational purchases—the kind that makes you desire a product or item just because it has an exceptionally high price tag.

4. Do I Already Own Something Similar?

Stop me if you’ve heard this one before: You see the absolute perfect kitchen appliance, black sweater, lipstick, or tech gadget and purchase it immediately. Except, the minute you get home to unpack your bags, you realize that you already one something almost exactly like it.

Avoid duplicate purchases by making a shopping list. It seems obvious, but listing out what’s needed beforehand is the best way to avoid being lured by the siren song of a sales rack, only to realize that you already own something oddly familiar.

5. Is This Well-Made Enough to Last?

If it’s a piece of clothing that costs less than $25 new, the answer is probably “no.” Sure, you can make cheaply-made clothes last longer by washing them less, washing them in cold water, inside out, and then line-drying them. But just remember that having to repurchase basics gets expensive.

If you’re buying appliances or electronics, read reviews before you buy it—even if you’re reading them on your phone while you stand in the aisle at Target. If you’re shopping on Amazon, sort your search results by ‘average customer review’ and then read what people have to say.

6. Can I Just Borrow or Rent It Instead?

Supposedly, the average power drill is used for somewhere between six and 20 minutes in its entire lifetime. I imagine that statistic holds true for many tools and well-intentioned hobby purchases.

So, ask yourself: Do you need to buy a bike rack for your car if you only use it twice a year? Or a tent when you camp once a year? Or that super tall ladder for a one-time paint job? Probably not.

If you’re just starting a new hobby, make sure it’s something you really, truly love before you buy all the gear. If you’re making one-time home repairs or taking a once-in-a-lifetime trip, consider borrowing or renting some of the many things you’ll need to reduce both your initial cost and long-term clutter.

7. Will This Make My Life Significantly Better?

Answering “yes” can justify even the most expensive purchases. For example, if you have pets, children, or allergies, then yes, a Roomba will likely change the quality of your day-to-day and is worth the hefty price tag.

Depending on what aspects of life’s daily chores drive you a little crazy, there are plenty of purchases that will make your life significantly easier or more awesome. For example, an Amazon Prime membership, a gym membership, or the right chef’s knife are great examples of stuff totally worth spending your money on.

However, that $25 scarf you feel lukewarm about? Probably not so much. Just remember to ask yourself, if a purchase isn’t going to improve your life in any way, why are you buying it?

8. Can I Afford to Buy This Without Credit?

Credit is a wonderful last-ditch method of paying for things like medical emergencies or a new transmission. What isn’t wonderful is having an emergency or broken car, and no available credit because it’s all been used up to pay for stuff you regret.

See Also: Americans Are Bad at Budgeting and Great at Making Excuses

Sure, that product or service you’re eyeing might offer a payment plan, but ask yourself: Is there any way you can wait until you’ve saved up to buy this thing in full? The chances are that the answer is that you can.

9. Would I Want It in 30 Minutes?

Have you ever finished your shopping, turned to see a checkout line that’s dozens of people long and thought, “Oh heck no!” before putting down your basket to leave?

Whenever this happens, I’m always surprised to realize how little I’ll tolerate to make my purchases. Which begs the question: How much did I want this stuff to begin with?

The next time you’ve filled a basket with clothing, home decor, or other odds and ends, pretend you have to stand behind a stranger for half an hour before getting to leave. Chances are, you’ll save yourself some money.

Tailor Your “Should I Buy It?” List to Your Spending

Cleaning up your spending habits doesn’t always mean focusing on the kinds of purchases I’ve listed above. I use shopping for clothing as an example multiple times above because that’s my weakness—each might need a little shifting to be totally of use to you.

Maybe you’re not the sort of shopper who gets lost in Target’s home decor section. However, you do systematically overspend on eating out towards the end of each week after running out of groceries. Or, perhaps you’re regrettable purchases are in the shape of sports equipment that’s done nothing but collect dust.

To help you take a closer look at what behaviors can cause your budgeting to go awry, consider if any traits and examples describe your spending:

You regularly spend in ways you didn't expect because you’re disorganized or unprepared, including:

  • Buying duplicates because you lost, forgot, or can’t find the first one.
  • Didn’t anticipate the traffic, meeting to run long, or dress code.
  • Didn’t buy enough groceries, so eating out again.
  • Ordering something online without researching.

You easily succumb to social pressure (whether direct or indirect), even though it isn’t stuff you wanted:

  • A neighbor’s kid is asking for fundraising support again.
  • A second-cousin is inviting you to an out-of-state wedding.
  • It feels like everyone has this cool, new thing and you feel a twinge of jealousy.

Money regularly “disappears” from your account because you didn’t keep track of your balance statements:

  • Forgetting to cancel 30-day free trials before they’re up.
  • Not noticing when you didn’t get a refund.
  • Failing to check your receipts to see if you’ve been overcharged.

Your purchases regularly sit on the shelf (or in the closet) collecting dust because you’re shopping for the life/ figure/ hobbies you wish you had:

  • Buying clothes that don’t fit because you swear you’ll slim down soon.
  • Stocking up on supplies for crafts, when there are already unfinished ones at home.

You confuse purchasing something with taking action:

  • Instead of getting a gym membership, you spend money on workout clothes.
  • Instead of applying for an internship in a field you like, you spend $500 on home courses.
  • Instead of cooking, you buy fancy kitchen gadgets that never get used.

There are plenty more reasons that are the real root of regrettable spending, whether shopping to stop from being bored or because you had a bad day, or telling yourself that “Of course I need new throw pillows, I’m hosting a party!”

The bottom line is that we all have different reasons behind why we’re buying what we don’t need, which is why it’s so important to ask yourself “Why am I buying this, really?” Are you avoiding something? Chasing a feeling? Trying to fit in?

Answering “yes” doesn’t always mean that it’s a bad choice. However, understanding what triggers that spending is crucial to shaping your own “Should I buy this?” list of questions.

A Quick Recap: The One Simple Question That Can Save You Money

Before you perfect your should-I-buy-it list of questions so that they’re useful during your weakest moments, you need to first identify what those are by:

  1. Figuring out where your money is going.
  2. Identifying which purchases or areas of spending you regret most.
  3. Understanding why you keep making those regrettable purchases.

Once you identify the above, it’s much easier to help shift your spending purchases that reflect items or experiences that actually bring you joy.

Read Next: The Top 7 Money Mistakes: How Many of Them Have You Made?


Autumn Yates

Autumn draws from a reporting background and years of experience working remotely, while living abroad, to focus on topics in travel, beauty, and online safety.


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