"Free shipping" is often advertised as attractive bait for you to take action and buy something! That is, until you find out it's not free after all. In other words, an absorbed charge. For example, I love Amazon.com. Their selection is generally excellent and their service is unrivaled (over the holidays, I got a reply on Xmas day when I enquired about undelivered goods). But if you've compared their prices with other online stores, you'll notice unless it's an especially killer deal, they'll factor shipping into their at-face cost.

The same has applied to Zappos (which has prominently advertised "free overnight shipping" and tried to differentiate with no-hassle support), eBay (where it's determined per-seller) and other places: whenever you see "free shipping", take a closer look at that total number and discern whether it's really gratis, or if you're paying a few bucks on top. It usually doesn't amount to more than a tip at a fine restaurant, but nonetheless, it's best for you to be aware.

Amazon has also had great success with their Prime program. Here's where they advertise "all-you-can-eat", free 2-day shipping for $80/year. Plus, $4 extra for each item gets you 1-day shipping. They're savvy enough to lure you in with a free month trial, and that's exactly what happened to me. My subscription just ended yesterday, and I'm going to renew — I've noticed better deals are on the horizon like this 3-month trial w/eligible textbooks.

Before answering:

"Is it worth paying more for faster shipping?"

First ask yourself:

"How much is my time worth?"

As bitter as the economy can be, the fact nevertheless remains: you can make more money. You can't make more time. This is a hard rule of how the universe works. Sometimes this traps us, like people paying more for guaranteed before-Christmas delivery because they procrastinated. It's times like these where it's advantageous to have a flexible lifestyle: not paying attention to social pressure when it comes to holidays, and setting your own rules. Not everyone has that luxury, especially if you have to dig yourself out of a hole of awkward family traditions.

That being said, here are some tips worth applying:

  • There's often a huge cost jump between 2-day and 1-day shipping, and that price often isn't worth it unless something is "mission-critical". (We aren't talking delivering organ transplants here.) You can easily observe this cost jump by visiting any web store that lets you preview shipping before checking out. (Some places are awful and require you to sign up for an account, or get to the final stages before checkout.) Other World Computing is a fine example of informing you about shipping beforehand. There, 1-day shipping can be double (~$22) what 2-day shipping costs, but the gap between 2-day and longer periods is less.
  • It's best to buy in the morning. Or more accurately, before the day's cutoff date: if you place your order too late, it doesn't get processed until the next day. Amazon has a handy countdown clock on numerous items, something I wish more places had: I've tested this by placing an order within the last 1-2 minutes, and got my goods on time. Other stores offer a rush processing fee, like Newegg's $3. General consensus is this isn't worth the minimal trouble if you order fresh to begin with. Like shopping in the supermarket, be early in the queue.
  • A little cost is worth a lot of convenience. Don't be foolishly thrifty. This guideline is especially true if you're putting together a new computer with accessories and expansions, as I experienced with my Mac Pro last month. I didn't want my performance to be bogged down waiting for RAM (which is far cheaper to install yourself than from Apple), so I selected 2nd Day Air @ OWC. Saving money is good, but spending money selectively where it makes a substantial improvement to your experience is even better. I find this is reinforced if I'm ordering something expensive. I get anxiety waiting too long for it to arrive, because even with today's tracking systems, I wonder, "Is it alright?"
  • Arm yourself with good package tracking tools. Even if you've paid for faster shipping, there's still a chance it may take longer than expected. Check the store's shipping policy ahead of time: in Amazon's case, if they can't live up to their $4-for-1-day guarantee, they'll refund the shipping cost. I've done this twice and they've been very prompt about it. After you get an order receipt, it's common to see tracking numbers in there. Go to the right link and bookmark it, and check it daily (if it's important). On Mac, I favor the Delivery Status Dashboard widget. It's nice and elegant, altho I wish it could autodetect the shipping service from the #. There are also cross-platform websites like TrackThePack.
  • Amazon Prime has no weight or dimensional restrictions. I wish I could apply this broadly, but I don't know of anywhere else that has a model like Amazon. If you buy a 200-lb. piece of exercise equipment, it's still $4 for 1-day shipping with Prime. Those moments are really worth it, because many places charge shipping by weight or dimensions. But remember, Prime only makes sense if you order regularly from Amazon — say, over a dozen times a year or if Free Super Saver gives you too much of a headache to push just a wee bit over $25. Also, items must be "Prime Eligible", meaning Amazon, not a 3rd-party retailer they list, carries it. Again, consider convenience over cost and what you're willing to dish out.
  • Keep gas costs in mind. This was more of a factor months ago, but with black clouds still looming overhead, and if your vehicle is a gas-guzzler, I think the lesson's well-burned into you: if it's going to be a long drive to a store that's got something in stock, it may be worth both the time and money to have it delivered to your door instead. Once more, contemplate what might be a better use of that time — relaxing, painting, reading the Wise Driving Guide? :)
  • Don't put it off. It's the most obvious thing in the world, but unless you can time-shift your holidays and aren't under familial pressure like me, plan and execute with extreme lookahead. Rushing also leads to poor decisions and compounds buyer's remorse, since you have less time in which to make sensible decisions. Remember that procrastination is average, not an exceptional outlier, and all that waiting and lazying around will cumulatively clog up the pipes at Xmas, Valentine's Day, etc. You, on the other hand, should be ahead of the game.

Do you think it's worth paying more for faster shipping? Share why or why not!