How I Handle Awkward Situations



I hide. I don’t answer my phone or return calls.  I’ll turn the other way or act like I didn’t see the person coming. I’ll turn around and go to another restaurant. I’ll leave an anonymous note. Anything to avoid an awkward situation.

Then I started buying and selling items on Craigslist. This provided a great opportunity for me to face my fear of awkward situations by fire. You see, every time I sell something, the buyer always asks questions. Questions such as “How long have you owned it?”, “Did you buy it new?”, “Why are you getting rid of it?”, “Have you had any problems with it?”, and all the way to “How much did you pay for it?”.  What did I get myself into?

At first, I would slither around each question. “Why are you getting rid of it?” would be answered “We just need the money.” which was true, just not all of the truth. I would answer the questions, just without volunteering ALL of the information. “How long have you owned it?” would be answered by a terse “Not too long.” I would then immediately start talking about the various features etc.

Then one day I changed. It wasn’t because I had climbed to the top of a 40 ft tree without a harness, thus gaining fearless courage.


I just gave up. A man was asking about an appliance that I was selling, and I was sick of blathering out creative answers. I also may have had 5-6 washer and dryers in my garage.

I explained how I buy and sell (in this situation) appliances on Craigslist.  I told him how I clean them up and do basic maintenance on them etc. I then plugged the dryer into the wall and let him see it work. His response?

“That’s really cool.  I’ll take it. Can you help me load it into my truck?”

He didn’t walk away. He didn’t frown. He got the item he wanted, clean and in great working condition at a great price. He was happy as a clam.

I’ve haven’t tap danced around a question since.  My fears of awkward situations were completely overblown. In fact, I feel like the fear at first actually made the situations more uncomfortable, as people are very discerning. They can smell when you aren’t quite telling the whole truth. If it wasn’t so awkward for them to walk away, I think many more of them would have in my early days of buying and selling.

Hundreds and hundreds of times I’ve told people exactly what I do. Maybe 1 in 200 leaves without purchasing the item. The rarity of people not buying the item from me is pretty mind boggling.  More often than not they end up fascinated and inspired by how I’m not only providing for my family, but thriving.

They don’t want negative surprises. Instead, blow them away by under-promising and over-delivering on your product. They want to buy from someone that they can trust.  Become that person.

I’d love to answer more questions with more specifics in the comment section below.


  1. Haha, nice. So what do you say when they ask where you got an item or how much it cost? I have found the opposite scenario more often then not with buyers telling me their life story and all the reasons why they need the item. That aspect is fun and interesting but also requires patience.

    • I’ll do my best in the moment to remember where it came from. Often times it’s from someone that moved, upgraded etc. Sometimes it’s from a trade-in. When they ask how much it cost, I tell them I got a good deal. That’s the one question that I don’t answer. It’s not going to help anyone in the moment and there is no benefit to answering it.

      Michael, I love talking with the buyers. It’s sadly been one of the few ways to actually get to know more of the people that live in the city. It’s a great way to connect with people in your area. Especially if you buy/sell items around your hobby, like surfing, certain outdoor sports etc.

  2. The fact that you fix up the appliances should eliminate some of the questions. Before I started fixing up the bikes that I picked up, I would get similar questions from prospective buyers that you get. Once I explain that I fixed up these bikes because I didn’t want to see them going in a landfill they decided that I was doing a good thing and not just flipping a bike that I got on the cheap. You should do a story on the dumbest questions that you and other sellers have gotten. I know I’ve gotten a bunch.

    • Absolutely. The more value you add to whatever your selling, the easier and less awkward the questions are.

      I’ll start writing down some of the funniest questions. There’s been some good ones! One example that comes to mind was a couple that had come to look at a refrigerator. They asked for a few moments to themselves to talk. When I came back out, I see they had opened an upright freezer, looked at it’s contents, asked me about all the food inside and then expressed that they actually wanted to buy the freezer instead. It gets even better! I’ll give that it’s own post! 🙂

  3. I just have to say that your dog is absolutely adorable! How long have you owned it? Did you buy it new? Why are you getting rid of it? Have you had any problems with it? How much did you pay for it? (Sorry, couldn’t resist!)

    • Hahah. I was thinking no way. We actually did adopt a dog off Craigslist. He was not house broken at all and peed everywhere the moment you spoke to him. I literally would run outside with him in the front yard and then start talking to him. We eventually found another home for him that could put the time it was going to take to train him. We will get a cat soon and I’m going to name him Mr. Higgins. You can then expect at least half of the posts here to contain pictures of him.

  4. This is still something I’m working to overcome in flipping electronics, and it’s gotten me into trouble a number of times.

    There was an iphone that I had repaired and then sold (after giving a dishonest history of my ownership of the device), and later the buyer left me a message saying the speaker didn’t work. Rather than calling back and saying it was a broken device that I had attempted to repair, I ignored the voicemail, justifying to myself that “all sales are final”. All was well and good until his wife started leaving me threatening voicemails on my office phone. I had to bite the bullet and come clean and gave the guy is money back and then some just to put the situation behind me.

    However, I’ve found that when you say “I buy and sell used cell phones and electronics”, people will tell me of a family member or friend who is looking to sell their device, and I get two deals for the work of one. I’m looking to ramp up this networking effort by creating business cards to hand out to everyone that I buy or sell from, advertising myself on craigslist, and ultimately creating a website storefront. I’m the only one in my area doing this, so I’m looking to become the “go to” guy in town.

    • Dude, I’ve been there. When I first started, I would sell like 100 appliances and one person would call back saying there was a problem. The big temptation is to hide, and I did a few times. But, it’s not what we would want people to do to us, and it’s not worth the stress. If someone calls within the first day or two with a problem, I will swap the appliance out, and worst case scenario return their money. It’s extremely rare that this happens, but owning up to an issue in the first few days, even though I don’t offer a warranty is the stand up thing to do. They’re happy, your happy, less stress, better sleep, better word of mouth reputation about what we do. Even more so if your the main ticket in town.

      We might lose a little time or money on the short term, but the long term gains will far outweigh them. Thanks for sharing!

  5. Hi Ryan, I would love to know more about how you “Under Promise and Over Deliver”. What are some of the ways you do this besides just avoiding over promising? I do website design and application design, and often used to find myself over-promising to get a deal. Once I stopped life got a little easier each time. I guess I am mostly interested in your methods of “over delivering” more than anything. Thanks, hope to hear from you soon. Karl.

    • Karl, you’ve conquered the hard part by stopping the over promising. The over-delivering part is the easy side of the equation. I’m going to write a post on it today and it will be up tomorrow morning.

  6. I used to worry about turning people off to my flipping sales too. But I got tired of lying, just like you. Now I tell my CL buyers the truth: I yard sale shop on Fridays and Saturdays, up to six hours each day. I tell them I find nice things for my family and when I run across award-winning items (I specialize in toys and read lots toy-rating books, reviews, blogs, etc.), I purchase them for resale. I tell them that I only buy the best, items that I know a lot about, items my own kids might have had. I describe all the work involved in selling toys: cleaning/pressure washing, finding replacement pieces, photographing, listing, meeting buyers … and the clincher is when I tell them that I’m happy if I make four or five bucks flipping a few things, that it helps off-set the cost of my gas and weekend time away from my family. The only thing they don’t need to know is that I typically make a good bit more than four or five bucks per flip–that’s not their business! They love my honesty and readily admit they’re not going to put in the time I do to find these same items. They’re happy to buy from me!

  7. I love this site. I read it often. I had my first sale this week from an item that I received free from Craigslist. This post is what I needed to read before that attempt. I, too, felt like I wasn’t being honest because I was skirting around the questions. I didn’t like that feeling at all.
    I’m a stay-at-home mom that has always sold stuff here and there but more as a way just for extra money…selling the kids stuff to buy them more. This year, my husband and I calculated what it would take to pay-off my car this year. So, that is my goal. I have it calculated to what I need per day, on average. It feels so great! This is my first month working it like this and I’m thrilled to say that I have already exceeded my goal this month!
    Thanks for sharing all your insight!

  8. I’m really happy to find your site, Ryan. Thank you! Its neat to see the natural trend of people facing their own dishonesty or “stretched comfort zone” mostly out of insecurity & fear in sales tactics. It’s encouraging, just like the documentary “Craigslist Joe”, to know that most people are good-hearted, & mean well. Its a growing experience to learn to sell in your comfort zone. We all have to find that…

    I have been selling virtually everything on CL on my way to live on an island, & have discovered with certain finesse & by being genuine, everyone I meet is positive, appreciates honesty, pays asking price & bottom line: now I too want to make at least a partial living on CL, as making $600 each day in 1 week & enjoying it has shown me its almost a way better option to eBay/Amazon for many self-starters …. More hands on, local, & social. I’m hooked & eyes open now & am excited to integrate long term CL-selling into my life in my niche. Thank you for sharing your tips & experiences! Viva working for oneself & having time to LIVE… however creatively we get there.

  9. I about fell out of my chair at the impact of the first sentence and picture. Great effect! I’d just read a couple of other posts and clicked on this one ready for the inspiration straight away. I love how real that first line comes across: “I hide.” Classic stuff.

    Keep it up and thanks for all you do.


Please enter your comment!
Please enter your name here