Here’s why I have trouble buying things quickly online

Like many of you, I’ve been doing a fair amount of online shopping. But I’ve probably been much slower at it than most of you.

Not “slower” in the sense of taking forever to pick one product over another (although my indecision-making there is considerable), but in the sense of deciding how I’ll pay for it and which third-party site I should click through before making the purchase.

Picking a credit card is the easier part even if I’m not buying stuff for my job (work expenses go on a separate card to ease my accounting). Most of the time, the 2% cash-back rebate on the Citi Double Cash Mastercard makes it the obvious choice. It’s been an even easier call when Citi’s offered extra cash back in promotions with various merchants.

But other card issuers have their own extra incentives. American Express and Chase offer extra cash back and do so much more often, but you have to sign up for each such offer on their sites or in their mobile apps. So I need to consult both before any purchase–and then hope the merchant in question doesn’t drop one of these deals the week after my purchase.

(Note that Amex and Chase also have tiered cash and points rewards for categories outside of online retail; a proper discussion of them would require a separate post.)

Not too many years ago, my shopping decisions would have ended there. But then I had to start considering shopping portals, the points-for-purchases sites most frequent-travel programs provide for members. By itself, a mile or a point for a dollar spent somewhere is barely worth thinking about. But that incremental addition does deserve your time if you’re nearing an award-redemption threshold or have miles or points that will expire without new activity in your account.

These portals don’t all offer the same rate or each offer the same rate over time. To verify which one offers the most return, I use a site called Cashback Monitor that tracks these deals and lets you set up a custom page with your favorites. (For more details, see this concise how-to by One Mile At A Time’s Tiffany Funk.) JetBlue consistently offers some of the best earn rates; fortunately, TrueBlue points have not seem the same deflation as other frequent-flyer currencies in recent years.

You may find no future-travel benefit for a potential purchase. Best Buy, Target and Walmart recently seem to have dropped out, while I can’t remember seeing any travel incentives for Amazon. In those cases, I’ll go to one last site before starting a purchase: my client Wirecutter, which often tells me what to buy and makes a decent chunk of its money off affiliate payments from Amazon and other retailers. If I can’t treat myself to a little kickback on a purchase, helping one of my favorite clients seems like a decent fallback.

Weekly output: encrypted DNS in Firefox (x2), expanding rural broadband, business turnarounds, optimizing business travel, travel tips

My calendar this week is much less cluttered than it was a week ago, between SXSW’s cancellation clearing out Friday and (also coronavirus-related) postponement of the DC Blockchain Summit freeing up Wednesday and Thursday.

3/2/2020: Your internet provider knows where you’ve been. How to keep your browsing more private, USA Today

I tackled a fairly esoteric topic–encrypted domain name service–in this column. I don’t know how many people read it to the end, but at least my tweet about the piece seems to have done well

3/3/2020: Why ‘rural broadband’ may no longer be an oxymoron, Fast Company

I wrote up a new study from the Pew Charitable Trusts that offers reasons for hope about expanding rural broadband, plus useful lessons learned from states that have managed to make progress on that front.

3/3/2020: This Morning with Gordon Deal March 03, 2020, This Morning with Gordon Deal

This business radio show had me on talk about the Firefox browsing-privacy news in my column. My bit starts at the 12:45 mark.

3/4/2020: Four companies that reinvented themselves the right way… and won, Signal 360

A friend edits a newsletter Procter & Gamble publishes and asked if I could write about a few examples of companies turning themselves around. That’s not a genre of story I usually do, so I thought it would be fun to write. The results: this look at how Lego, T-Mobile, Yelp and Best Buy managed to dig themselves out of various holes.

3/8/2020: From Bookings to Bandwidth, How to Supercharge Your Business Travel, Frequent Traveler University

I did this talk with travel blogger Tess Zhao twice: a more beginner-oriented version in the morning for attendees of the Travel & Adventure Show at the Washington Convention Center, and then an expert-mode version in the afternoon for FTU DC ticket holders.

3/8/2020: Closing panel, Frequent Traveler University

This gathering for miles-and-points travel enthusiasts wrapped up with almost all of the FTU DC speakers fielding questions from the audience about various flight and lodging hacks and tips.

Updated 3/9/2020 to add a link the Signal 360 post I didn’t find when I did my usual Google News search for pages featuring my name over the last week. 

Weekly output: mobile payments, Black Hat security, travel tech

I left Black Hat feeling a little overwhelmed–not because of how little time I had to take in things between my arrival in Vegas Tuesday afternoon and my departure Thursday night, but because of how many fascinating briefings I had to miss because I was attending others. And then there’s everything I missed by flying home before DEF CON

8/6/2018: Hang on, Apple: Phone payments still need work, USA Today

Seeing all the hype over Apple announcing that CVS will finally succumb to reality and accept Apple Pay (meaning you can also pay with any non-Apple phone that does NFC payments) got me feeling cranky enough to write this reality-check post. I’ve since received an e-mail from a reader saying he’s had no problem paying for stuff with his iPhone in Mexico, contrary to a statement in the column based on an incorrect reading of Apple and Google support documents. I’ve asked my editors to correct that part.

8/9/2018: Black Hat attendees are surprisingly lax about encryption, The Parallax

As I was putting together my Black Hat schedule, I got an invitation to tour the network operations center supervising the conference’s WiFi. I thought that visit would allow me a chance to look at a lot of blinking lights, but instead it provided up-close evidence of some horrifyingly slack security practices among a minority of Black Hat attendees.

FTU DC badge8/11/2018: Welcome and Keynote with Rob Pegoraro, Frequent Traveler University Washington, DC

After years of profiting from tips shared in various frequent-flyer forums, I had a chance to give back when FTU host Stefan Krasowski asked if I’d like to talk about my travel experiences to open this two-day program of seminars about airline and hotel loyalty programs and other sorts of travel hacking. We had a great conversation about freelance business-trip economics, the gadget accessories I take on the road, two underrated virtues of United elite status, and my worst airport-transit experience ever. My only regret: Since I couldn’t stick around for the rest of the day, I didn’t have a chance to meet the other FTU speakers, a few of whom I’ve been reading for years.