The “50% off” sign is staring me down. It’s bold. It’s red. It knows what it’s doing. And for a split second—before my brain kicks in—I think, Ooh, that’s a steal. But here’s the thing I’ve learned after years of analyzing price drops, writing shopping guides, and clicking “add to cart” more times than I’d like to admit: not every deal is a good deal.
Sometimes it’s marketing magic. Sometimes it’s a markdown on an item that was overpriced to begin with. And sometimes, it’s just not a good fit for your life or your wallet, no matter how tempting the discount.
So, when people ask me, How do you know when a deal is really worth it?—this is the article I send them. Because smart shopping isn’t just about snagging a sale. It’s about knowing your own buying patterns, asking the right questions before you click “buy,” and getting real about what value actually looks like for you.
Let’s get into the five core questions I always ask myself before calling something a good deal—and how they’ve saved me from a drawer full of regrets.
1. Do I Actually Want This—Or Am I Just Reacting to the Discount?
This is where it starts. You spot a sale and get that little jolt of adrenaline—the retail version of FOMO. But pause and ask: If this were full price, would I even be considering it? If the answer is no, that’s your first red flag.
I’ve learned that some discounts create urgency where there was zero desire before. It’s not about the item—it’s about the rush. A good deal should still feel good when you remove the price tag from the equation. If it’s not something I’d seek out independently of the sale, it probably doesn’t belong in my cart.
Sometimes I even step away for 24 hours. If I forget about it? It wasn’t love—it was impulse.
Pro Tip: Price isn’t the only metric. Use is. If something is 80% off but will sit untouched in your closet or kitchen, it’s 100% a waste of money.
2. Is This the Best Price or Just a Lower Price?
Not all “sales” are created equal. I’ve tracked enough products to know that retailers play games. A price may look lower, but it’s often marked up before a major sale, then “slashed” to make you think you’re saving big. Classic promotional theater.
That’s why I always do a quick price history check before I buy anything labeled as a deal. Tools like Honey, CamelCamelCamel (for Amazon), and even Google Shopping’s price comparison feature help reveal whether it’s truly a rare discount or just part of a pricing cycle.
And here’s the kicker: sometimes the biggest markdown isn’t the best value. I’ve bought “cheap” versions of things that cost more in repairs or replacements later. Which brings me to the next question...
3. What’s the Cost Per Use?
Cost per use changed how I shop. It helps me stop asking How much does this cost? and start asking How often will I actually use this?
Let’s say I’m eyeing a $200 coat on sale for $120. If I wear it three times a week for three seasons a year? That’s pennies per wear. But a $25 sequin clutch I’ll use once for a party? Not so much.
This mental math isn’t about being joyless. I still buy the occasional “just because it’s fun” item—but I know the difference between a smart splurge and a fleeting thrill. And when I evaluate based on cost per use, I feel way more confident in where my money’s going.
Think long-term value over sticker shock. Your favorite jeans may have cost more upfront, but they paid you back in confidence and cost per wear.
4. Does It Solve a Real Need or Upgrade an Existing One?
A true “good deal” adds value to your life. That might mean solving a problem you’ve been putting off (hello, meal-prep containers that actually stack) or replacing something that’s worn out or frustrating to use.
Here’s my gut-check test: Does this improve my life in a meaningful way—or just add more stuff to manage?
I recently passed on a discounted milk frother because, honestly, I drink one latte a week and my French press works fine. I said yes to a cordless vacuum that was 20% off because it replaced an old model that required way too much dragging and bending.
The best purchases usually make you go, Why didn’t I get this sooner? If the answer is more like, Where am I going to put this?—you probably don’t need it.
5. Will I Still Be Glad I Bought This a Week (or Month) From Now?
Impulse is fast. Regret is slow. This question is my future-proofing mechanism. It pushes me past the excitement and into the reality of what happens after the box arrives.
Ask yourself:
- Is this going to clutter my space?
- Is it aligned with how I want to spend my money this month?
- Will I actually use it more than once or twice?
Sometimes, I even picture the item six months from now: Is it in a donation pile? Still in its packaging? Or in my daily rotation? That visualization alone has saved me hundreds of dollars in “meh” buys that only felt exciting in the moment.
How Marketing Tricks You Into Thinking It’s a Deal
A big part of shopping strategically is understanding what’s happening behind the scenes of those discounts. These are the top tactics I watch out for:
- Artificial urgency: Flash sales, countdown clocks, “only 3 left” alerts—they’re designed to bypass your better judgment.
- Anchoring: Marking an item “originally $129.99” when it was never sold for that price.
- Bundles: Pairing a useful item with extras you don’t want—making you feel like you’re getting more.
- Price masking: Selling something at a “discounted” rate that’s actually the average market price.
Once you see these patterns, you can stop falling for them. And honestly? It makes shopping more fun because you’re in control.
So... What Is a Good Deal?
For me, a truly good deal checks all these boxes:
- It’s on something I already need, want, or have been planning to buy
- It’s at a price that’s better than usual, not just lower than the fake original
- It adds value to my life and aligns with my lifestyle or goals
- It won’t be forgotten, returned, or regretted later
That’s not to say I never buy something purely for fun. I’m still a human who loves a good seasonal candle and an overpriced coffee mug. But I don’t call those good deals. I call them what they are: little splurges that I choose with intention—not because they were “on sale,” but because they bring me joy.
Deal Delights!
1. A quality white tee on sale at Everlane or Quince
Because wardrobe basics you actually wear weekly are always worth upgrading.
2. A discounted robot vacuum from a reputable brand
If it saves you hours of cleaning, the ROI is real, and steep holiday discounts often appear.
3. A multi-cooker or air fryer at 40% off
Appliances that simplify meals and don’t gather dust? Solid investments.
4. Refillable skincare systems (when bundled at a true discount)
Look for brands that offer future refill discounts—not just introductory hype.
5. Designer denim on seasonal clearance at trusted retailers
One well-fitting pair of jeans that lasts 5+ years will beat five cheap ones every time.
Value First, Price Second
You know what makes someone a smart shopper? Not how many “deals” they can find—but how often their purchases actually serve them in real life. When your closet, home, and cart are filled with things that fit your needs and values, that’s the kind of wealth that lasts longer than any sale.
So the next time you’re tempted by a price slash or limited-time offer, just pause and ask: Would I buy this at full price? Will I use it again and again? Is this aligned with what I truly value?
That pause? It’s the most valuable deal you’ll ever make.
