I’ve often heard that running periodic sales just trains customers to wait for a sale before buying. Well, that’s very true for one of the online stores that I purchase from regularly. Their shipping charges are substantial, causing me to wait for the free shipping specials that they run every few months.

So when I got an email about the latest free shipping promotion, I filled up my cart and went to find the free shipping discount code. The trouble was, they didn’t have one. Instead, the email said to just get your total over $75, and the discount would be applied automatically. Well, I did just that, but the shipping charges remained on the ordering page. I even opened a live chat with their customer service folks, who insisted that the shipping would be taken off once I finished checkout. I followed their instructions, and was rewarded with a receipt that showed a hefty shipping charge.

Long story short, I had to call them to get the shipping costs removed. The person on the other end of the line said the automatic discount wasn’t working, so everyone using the offer presumably had to call to get the charges taken off. Lame.

Of course, there’s a lesson here. Don’t try to reinvent the wheel or do unusual things just because they seem a tiny bit simpler for the customer. In this case, the store abandoned the tried-and-true discount code in favor of an automatic removal of shipping charges. As I described above, it was a total failure.

The next time you’re given the opportunity to make something simpler, be sure that you’re not introducing all sorts of other problems just to save the customer a few seconds. When things work as expected, they certainly won’t be complaining about a tiny amount of time savings, anyway.

When I receive a really nice bottle of wine as a gift, I tend to keep the cork as a memento. Typically, these corks just have the name of the winery printed on them. But the bottle I uncorked on Saturday took a much smarter approach. Instead of just a brand name, the cork also provided the phone number and web address for the winery.

This is a brilliant move on their part. Sure, I’ve read about some retailers that include a sticker or magnet with each bottle of wine, making it easy to reorder the product later. But this takes it one step further, turning the most basic wine keepsake (the cork) into a marketing piece. For people who collect corks, it’s a great way to stand out and earn repeat business months or even years down the road.

Any company that sells a tangible product can benefit from this way of thinking. Just figure out which parts of the product that consumers are likely to retain long after the product has been consumed, and put your brand name, product name, web address, and other relevant info on there. To make this even more effective, include a coupon for some type of discount or free gift, perhaps that doesn’t become valid until after the usual reordering period. For example, if loyal buyers usually reorder every month, make the discount valid 60 days after their last order.

By making your mementos more relevant and coupling them with special offers, you should be able to increase brand equity among already loyal customers, while turning infrequent shoppers into repeat buyers. And for people like me who received the product as a gift, you make it that much easier and more enticing to become a paying customer for the first time.

Chicago’s Michigan Avenue is home to some of the priciest stores you’ll find anywhere, along with hundreds of mainstream retailers and restaurants. Generally, the city puts a lot of effort into keeping the area clean and upscale-looking. But there’s one glaring exception: the incredibly annoying “musicians” that park themselves in front of the high-traffic stores, and bang on plastic buckets while asking for handouts.

Since the city won’t do anything about it, I would expect the stores to take some action. But judging by the looks of the offending parties, there’s no way a store employee would risk their health and sanity to confront them. So, the idiots continue creating noise pollution and scaring away customers without anyone to stop them.

I wish someone from the corporate HQ would commission a little experiment, designed to see if sales are lower when there are flagrantly obnoxious people parked right by the door. And once the obvious conclusions are reached, they can hire a private security force to properly deal with the problem.

If you live in a city where Peapod is available, you’ve probably seen one of their delivery trucks. You might also have noticed that the online grocery retailer does a great job at turning each truck into a moving ad for their website. In particular, they have prominent branding and a call-to-action right on the truck itself. There’s even a special coupon code that you can enter after seeing the truck. For instance, I saw one that said “Save $10 off your first order by entering discount code TRUCK”.

But once you look beyond Peapod, delivery trucks are rarely used for customer acquisition. Companies like FedEx have thousands of trucks, but all they put on there is a web address — no enticement for new customers to sign-up or a coupon code to help track them.

In fact, there’s no reason this approach is limited to delivery trucks. Anything that customers use outside your physical place of business — from a rental car to a shopping bag — is a strong candidate for inexpensive customer acquisition. Add a little call-to-action and a special discount code, and you’ve got a cheap and effective way to gain more customers.

Though I rarely travel during the holidays, people always talk about how Christmas Day and New Year’s Day have low passenger traffic and cheap flights. Well, I checked out some flights for a potential trip to Florida anytime from mid-December through early January, and everything on Southwest was at least $400 per ticket. That’s about twice what it would cost for the same flight outside the holiday period.

Absent any other data, I would have to assume this is the result of the airlines’ efforts to reduce capacity and more closely meet actual “demand”. But I wonder: at what point do fewer flights and higher prices end up shrinking the market size? How many people will stop flying entirely, or at least cut back their trips by a significant amount?

I don’t have the answer to these questions, but I think it’s interesting to look at the point where higher prices and lower supply don’t just bring supply in line with demand. Rather, this point might also mark the point of no return, beyond which you start making the entire market smaller in the long run.

When you call a company on the phone, they’ll sometimes tell you that you’ve tried to reach them during a very busy time. For instance, they might say that call volume is highest on Monday morning, and recommend that you call at another time if you don’t feel like waiting. While this isn’t a perfect system, I think the approach has merit. You’re giving customers additional data that otherwise wouldn’t be available, and helping them make better decisions about their time and resources.

Ok, so that covers the telephone. But what about physical stores? Have you ever seen a sign that indicates when a store tends to be the busiest? I’ve never come across anything like that, so I’m always forced to make my own judgements about good and bad times to shop, at least in terms of the crowds and lines.

Unless there’s some business advantage to having long lines at the same predictable times every week, retailers should put up signage that shows when they are busiest. Then, customers who want to avoid the lines can plan their shopping for off-peak times. Sure, there’s a chance that enough people will shift their shopping behavior and alter the historic trends. Just use a dry-erase board or some type of digital sign so that changes are easy. Either way, by giving customers the power to alter their shopping habits if they want to avoid the crowds, you’re improving their experience with your store and fostering long-term loyalty.

Even though we’re in the middle of fall, I did some spring cleaning recently. In the process, I was reminded of the incredible variety of documents that we tend to acquire over the years. And if you’ve ever read up on the matter, you know that most of these papers are of little value after a few years. Yet we tend to horde them much longer than that.

Why the disconnect? Well, there’s no obvious way to tell how long to keep something. You can ask a friend or look it up online, but that takes work. Even a small hurdle means a lot more junk is kept in closets around the country. I think there’s a better way: put an expiration date on the document itself.

Much like the expiration dates on food packaging, I would like to see a universal standard adopted for documents. On every bill, statement, or receipt, there would be a little line on the bottom that says something like this: “We recommend keeping this document for 7 years, although your needs may vary.” Sure, the guidelines may change occasionally. But having basic advice close at hand would help people fight the urge to keep every document forever, enabling us to free up space and unclutter our lives just a little bit more.

After a few recent conversations about the rapidly increasing cost of healthcare, I learned that many people are unfamiliar with a very useful math shortcut. It’s called the Rule of 72, and it helps you quickly calculate how long it will take for your investment — or your expenses — to double.

To use this trick, take the number 72 and divide it by the annual rate of increase. For example, if you earn 12% a year on an investment (lucky you!), the number of years it will take to double your money can be calculated as 72/12, or about 6 years. Similarly, if your health insurance costs rise by 18% a year, then those costs will double every 4 years (72/18).

I’m sure there are some details I’m leaving out. For instance, I believe the formula assumes that annual compounding occurs, and the estimate tends to be less accurate when interest rates get very large. Regardless, I think everyone should take a few minutes to learn the Rule of 72, since it helps you perform a valuable reality check on how good an investment is — or how awful an expense is becoming.

Last weekend, I went shopping for a new winter coat. I’ve been wearing the same coats for almost a decade, so I figured it was time to find something new. In particular, I wanted a mid-weight coat for when the temperatures are in the 30s or 40s.

I located a good match rather quickly. But there was an odd problem: it had no pockets. My wife said that maybe they were just sewn shut, so we tried to open them. No luck. So I asked a sales rep, who proceeded to rip open the pockets and tell us they were sewn shut, as if we didn’t even think of that. The enormous effort required to tear the pockets open was obvious to her, but not to a customer.

I ended up buying a totally different coat at the store, but the pockets thing still bothered me. And I think the solution is rather obvious. When your product has some unusual attribute that defies expectations, find a way to attach a tag or notice that tells prospective buyers about it. After all, if people don’t know about the pockets, they may as well not be there at all.

During the warmer months, many of Chicago’s restaurants set up outdoor dining areas. Normally this works out fine, and there’s plenty of room to walk around the makeshift patios. But sometimes the restaurants go too far, blocking more than two-thirds of an already narrow walking path.

In the absence of any regulations, they have every incentive to create as much dining space as possible. More tables means more meals served during peak times, and thus more revenues. But this comes at a cost to everyone else: the sidewalks are more crowded, and there might even be more accidents as people step into the street to avoid congested areas.

What’s the solution? Well, I’d like to see the city pass some limits on how much space the restaurants can take up with their seasonal patios, and make it easier to report those who are cutting into public space. Or, the city can just charge rent for the right to use the sidewalks, with the rate increasing depending on the scarcity of space and other factors. That way, the offenders would be forced to pay for obstructing everyone else’s walking path.