The most humiliating moment of my life happened during a recent attempt to be thrifty. My sister often sells old or unused items on eBay, and so I figured I would give it a shot.

I had two Lily Pulitzer dresses that were no longer my size or style, and so I decided I would put those up and see what I could get for them. I estimated that I could sell each of them for around 50 dollars. That would give me a nice cushion for my monthly budget.

For those of you who have never forayed into online selling, here’s a tip: Read the fine print.

I didn't. I clicked a few boxes, uploaded my pictures, then sat back and waited for the money to pour in. A few days later, I received an email that both items had sold! Huzzah!

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I basked in my superior budgeting strategies until I read the details of the transaction. My dresses had been sold to the same user, who had bought both of them for 99 cents each.

A dollar ninety-eight for two Lilly Pulitzer dresses. That’s not even the best part, though. The kicker? I had to pay for shipping.

At the end of the transaction, I had lost three dollars and essentially paid another person to take these dresses off my hands. How could anybody be so incompetent? I amaze myself. At least I could make someone’s day while ruining my own.

It took me a few hours of shameful sulking before I pulled together the text message to my sister asking for some eBay tutorials. She got a substantial laugh from it as she drove me to the post office to mail the two pieces of clothing that I hoped would pay for two Friday nights out.

Since then, I have learned some handy tips on how to sell on eBay successfully.

How to Sell on eBay the Right Way

How to Avoid Rookie Mistakes When Selling on eBay. Got tons of things you don't want? Learn how to sell on eBay and make some extra dough. Just be careful of certain rookie pitfalls. #eBay #sidehustle #technologyblogIf you want to make money on eBay, you should first make sure that your items are worth selling. Are they in good condition? Would you let your friends use them and still be okay being seen with them in public? If the answer to either of these questions is no, then maybe these clothes shouldn’t be put on the digital market in the first place.

If they’re fabulous clothes that you’ve just outgrown, then these methods will help you get the best possible price for them.

  • Don’t Be Lazy. Use high-quality photos (and lots of them!) and in-depth, well-written descriptions to assuage people’s fears. No one's going to spend big money lightly. Make them trust that you’re giving them exactly what they’re looking for.
  • Labels Matter. Designer clothes will sell better, dresses are easiest to sell, and pants seem to be the hardest. Think about it — the fit for jeans is much more specific than it is for a dress. Be clever.
  • Time It Right. A wool coat is unlikely to sell in the middle of the summer. Be smart about when you sell.
  • Be Informed About Price. Research what similar items sell for, and raise your price only if your clothes are in pristine condition. Wear and tear mean that you'll need to adjust the pricing accordingly.
  • Prepare Your Items for A Photoshoot. Remove dangling threads from clothes, find an uncluttered, uniform background, and use natural light for your photos. And de-wrinkle your items!
  • Show What You Would Want to See. Snap pictures of the front, back, label, flaws, and any unusual details. Decide if an on-body shot makes sense.
  • Keep Original Tags and Receipts. Photos of these a must, though obvs don’t include personal information. Also make sure your title is exact with the brand name, color, and size.
  • Calculate Shipping. Don’t offer free shipping if it’s going to cost you twice the asking price. If you’re selling a shirt for $15 and it costs $25 to post it, it’s not worth it.
  • Get PayPal or Venmo Verified. When you make a sale, make sure you can receive your money safely.
  • Ship Quickly. Don’t leave your customer waiting two weeks for their purchase because you’re lazy and forgot you left the package by the door multiple times. To save yourself a headache, use a tracking number so you know where your package is at each stage.

Also don’t forget that eBay will charge you an insertion fee, which will vary depending on how much you list your product for, as well as a final value fee, which runs at a minimum of 12 percent of the final selling price.

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Final Thoughts

The eBay failure, though tough to swallow, was a serious learning moment for me. The biggest takeaway was that you need to be careful in the how you attempt to save or make money. Buying the cheapest, crappiest cut of meat at the butcher may not be worth the three dollars in savings.

I was so excited to gain a hundred dollars that I was careless and ended up losing money. (Seriously though, how did I do that?) Another takeaway for me was the importance of being careful with how I engage with the internet. The best deals can often be found online, for sure. Digital tools can even help you get discounts when you shop.

But still, it’s important to always read the fine print and know what you are signing up for. I learned that you can pay dearly for trying to get creative with your frugal living.

Additional reporting by Kelly Meehan Brown