1. Decide on your goal at the outset. Do you want to make money or get rid of as much stuff as possible? Your answers will affect pricing and outcome. Remember that you’re selling stuff you don't want, so it's all good.
2. If you don't LOVE it or haven't worn it in a year (2 years if you've been pregnant), sell it. If you think you'll miss it, take a photo to remember it. Clearing out the clutter will make you feel great and is better than seeing your "skinny jeans" sneer at you in the closet every time you look at them.
3. Find neighbors/friends to join you. Bigger sales are a draw for shoppers, more fun for you, and give you someone to watch your stuff if you need to take a break.
4. Advertise. Place ads on the PSP Classifieds by Thursday at noon (so it makes the Stoop Summary list) and post on Craig's List. Flyers around the hood can also work, but realize that they may be ripped down. Ads should include: day of week, date, time, address, cross streets, types of items being sold (e.g. appliances, furniture, clothes, books), sizes of clothes and shoes, and brand names (if significant). Finally, be creative with brightly colored chalk and arrows on the corners (kids can help!).
5. It's all in the presentation. Use tables so things are easier to see, get a clothes display if possible (or hang a clothes line between 2 trees), and hang as much of the nice clothing as possible (go through your pockets). If you have 'like' items put them in Ziploc bags (e.g., dinosaurs, Hot Wheels cars) and price as a set. If you can, pull out a bookshelf to display books and CDs so titles are easy to read. If you have to use the ground (avoid if possible), get a sheet or blanket. A brightly colored dress at the end of a clothing rack can attract someone way from down the street. Keep valuables and breakables safe and in plain view and away from kid hands.
6. Clearly price each item (unless you like to haggle). You'll spend less time answering pricing questions and more time chatting up your items. Have the cost on the top rather than the bottom of items. Pricing guidelines range from 20% to 33% of the retail price (if your goal is to make money), but remember, no one is going to pay you $50 for a 5 year old digital camera. Books are easier to sell if you have a standard price per book: they generally sell best when priced no more than $1 for hard backs and .50 cents for paperbacks. If you've got a ton of clothes consider having a "fill a bag for $X" price. You're better off selling large and expensive items on the PSP Classifieds than at a Stoop Sale. If you've got great clothes consider a consignment shop.
7. Have $1 and $2 boxes for items - it makes people feel like they are getting a deal. Make sure it's easy to differentiate what is in which box because things can get mixed up during the day.
8. Have a "Free for Kids" box with small toys. It can keep kids occupied while parents shop (and makes them feel beholden as well!)
9. Let kids help. Involving kids teaches them about finances and gives them a sense of responsibility. Give them their own area, discuss selling strategies, have them figure out change and let them keep money that they make. Make sure they know what you're selling and not selling; there's nothing worse than the "but I wanna keep that!" discussion in front of a buyer. Having kids run a lemonade stand is another way to draw customers on a hot day and keep folks staying longer.
10. Be respectful of the neighbors. Have adequate room for people passing by (and ask people to move strollers to the side if there's a traffic jam), keep dogs inside, and only use someone else's stoop if you've gotten permission to do so.
11. Have cash and bags on hand. $25 in 1s, $50 in 5s, $50 in 10s and a roll of quarters should get you through. (Don't forget to subtract this $135 when you count your loot.) Keep your money on you rather than in a cash box. Have various sizes of shopping bags as well as newspaper for wrapping items on hand.
12. Be friendly. Use the stoop sale as an opportunity to get to know your neighbors. Greet people as they come, chat with them if they are chatty, and avoid being on the cell phone or reading a book if there's someone there. Who knows - you may find your next friend. If there are other sales in the area, it's great to tell them about those sales too.
13. Play fun music to liven the mood. If you're selling CDs, make a playlist of the artists you are selling and play it during the day.
14. Make it easy to buy. Have an extension cord plugged in for people to test electronics. Consider putting up a sheet for people to try on clothes, print out specifics of things people will ask about (e.g., computer equipment, cameras).
15. Expect some people to want to haggle. Some people won't buy unless they feel like they're getting a good deal. Be firm when you want to be, and if it's early and someone doesn't want to pay your price, take down their name and phone number and tell them you'll call them if it doesn't sell.
16. Tidy and organize through the day. Fill in empty spots, remove a table if there aren't many items left in one area.
17. Drop prices about half-way through the day. That way you'll be left with fewer things to put deal with after your sale.
18. Figure out what to do with leftovers. "FREE" boxes are great, but make sure to follow through and clean up the next day. As for donations, CAMBA at the Armory will accept almost any household and clothing items if you can haul it down M-F, 9am-5pm and Vietnam Veterans of America http://www.pickupplease.org will pick up.
19. Gimme shelter. Remember sunscreen, hats or other sun protection if you and your kids are going to be sitting out all day.
20. Check games and puzzles. Only sell board games and puzzels if you have all the pieces. Mark them to say that they're complete.