Anyone who has sent emails to a sizable list of people lives in fear of the day that they misfire, sending out an email that’s inaccurate, incomplete, or ill-advised. Maybe it’s like paddling a canoe—it’s not a matter of if you’re going to tip over, it’s a matter of when.

Each time I load up an Idealware email, the last thing the broadcast platform does is show me the number of recipients on our mailing list. “Are you sure you want to do this?” it asks. No pressure, right?

We take steps to mitigate the risk of typos and other errors, but sometimes they slip in anyway. If you’re human, mistakes happen. I’ve been both perpetrator and victim of such mistakes. In fact, last month I sent out September’s Best of the Web with the subject line “Best of the Web: August 2018.”

Which is why I found the story about the U.S. Embassy in Australia accidentally sending an email with the above photo of a cat dressed like Cookie Monster hilariously relatable. The email went to an “unknown number of recipients,” inviting them to a “cat pyjama-jam.”

“Sorry to disappoint those of you who were hoping to attend this ‘cat pyjama-jam’ party, but such an event falls well outside our area of expertise,” said U.S. Mission to Australia spokesman Gavin Sundwall. He told the Australian Associated Press that the email was a “training error” made by new staff testing out the newsletter platform.

Not all our mistakes go viral, but sometimes they do. Let’s all hope it doesn’t happen to us.

In no particular order, here are some of the best things we read about nonprofits and technology last month…

No Cash Needed At This Cafe. Students Pay The Tab With Their Personal Data

NPR had a recent story about one commercial enterprise’s unabashedly open request for data about its customers. At the Shiru Cafe, near Brown University in Providence, R.I., students can get free coffee in exchange for their names, phone numbers, email addresses, birthdays, fields of study, and professional interests. The café gives that data to corporate sponsors.

I’m not giving away the ending here if I say that other organizations are collecting information on you, too—most of them are not so open about it. Social media platforms, search engines, the L.L. Bean newsletter in your inbox, the YouTube cooking videos you watch, the music you stream, when and where you use your credit card…like it or not, you’re being tracked.

Does that sound ominous? Maybe it should. While you might reasonably expect nonprofits to not use your data maliciously—at least not intentionally—should you have the same expectation of for-profits? As we’ve seen with the GDPR and Right to be Forgotten legislation, some countries believe that—but the U.S. lags far behind in that regard, so you’d be smart not to.

Why Are CVS Pharmacy Receipts So Long?

In another example of data gathering, over at Vox, Rachel Sugar has a piece about the ludicrously long receipts that unfurl from pharmacy registers targeting you with ads, coupons, surveys, and more based on all of your purchasing data that the store has access to.

Google Exposed User Data, Feared Repercussions of Disclosing to Public

Still riding the data train, last week the Wall Street Journal reported that Google+, the social network Google introduced in 2011, suffered from a major bug that may have exposed user data. Google opted not to disclose the incident to the public. (What happened to “Don’t be evil?”)

Now, the site is being shuttered.

Does this affect you? Did you even know Google+ still existed?

How to Get All Your Stuff Out of Facebook Before Deleting It

Not to be outdone by Google, Facebook has had its share of privacy concerns (Facebook Data Privacy Scandal: A Cheat Sheet ) and other disturbing accusations (Myanmar Military Said to be Behind Facebook Campaign That Fueled Genocide). This week it was revealed that Facebook overinflated video engagement statistics to sell ads—which, the argument can be made, led directly to many media outlets “pivoting to video” and laying off a good number of career reporters. (Facebook Hid the Fact That No One Watches Video Ads).

If you’re looking to flee the troubled site, Rob Beschizza tells you how to get all your data out before you delete your account.

Brands Are Not Our Friends

Writing for the Atlantic, Ian Bogost tells about the time Comcast sent him 10 pizzas based on a tweet he made. “This isn’t nice,” he writes. “It’s manipulative.” Social media has made it easier than ever for companies to connect with people. But those relationships can feel uncanny—the brands are not real human friends, but no longer are they faceless corporations.

“Isn’t that the point, though?” he asks. “Branding’s purpose is to get under your skin, to make you remember an otherwise forgettable company or product. When the surprise wanes, that feels a lot less delightful.”

For nonprofits looking to connect with followers on social media, and trying bolder moves to stand out among the noise, this piece is worth paying attention to.

Why Technology Favors Tyranny

Also in the Atlantic, Yuval Noah writes about how artificial intelligence could erase many practical advantages of democracy and erode the ideals of liberty and equality by concentrating power among a small elite.

The SIM Hijackers

Writing for Motherboard, Lorenzo Franceschi-Bicchierai tells you about hackers who flip seized Instagram handles and cryptocurrency in a shady, buzzing underground market for stolen accounts and usernames. Their victims’ weakness? Phone numbers.

Selfies Kill More People Than Sharks Do

When I was a kid, Hollywood had me convinced that two of my biggest fears as an adult were likely to be shark attacks and quicksand. Of course, we had no way of predicting the actual future—that someday we’d have revolutionarily powerful computers that fit in our pockets, giving us access to the collective knowledge and experience of the entire world and all of history, but that instead we’d use them mostly to take pictures of ourselves.

“In 2015, 19 people were killed in selfie-related incidents, and many more injured themselves,” writes Dr. Richard E. Cytowic. “During the same period, eight people died of shark attacks. How did we reach the point where the need to show off on social media outweighs common sense for seeing danger and the instinct for self-preservation?”

The Way We Use Smart Speakers Continues to Evolve

Speaking of using powerful technology for trivial entertainment, streaming music is by far the most popular way we’re using smart speakers, says Christina Bonnington, but a new pastime is gaining popularity—talking to your assistant for fun.

Some 68 percent of smart speaker owners admit to chatting with their Alexa, Google Assistant, or Siri digital assistant just for kicks.

Personally, I won’t put one of these speakers in my home or office. Why? Because it’s not just a speaker, it’s also a microphone—and we’ve already discussed companies gathering and misusing personal data.

This MIT Tool Can Erase Anything or Anyone From Your Old Photos

Back in the day, if you wanted to cut an ex out of a photo, you used a pair of scissors. After digital photography came around, you could use Photoshop—but it would take hours of work and create a wildly imperfect result. Now, an MIT Media Lab project led by Matt Groh has invented a tool called Deep Angel that can disappear anyone or anything from your pictures.

“The reality distortion field is real,” Fast Company explains, “and it’s getting better every day.”

These Magical Sunglasses Block All the Screens Around You

From smartphones and tablets to laptops, TVs, and touchscreens, screens are everywhere these days—even on airplanes, taxi seatbacks, gas station pumps, and airport gates. While there’s some research encouraging us to carve out screen-free time for our children and ourselves, there’s a better reason. Sometimes you just need a break.

When Scott Blew read about a film that blocked the light emitted from screens, he wondered if the technology might work on a pair of glasses. It did.

There’s Nothing Dystopian at all About These High-Tech Blinkers for Humans

In my previous career as a journalist, I worked in a few newsrooms that were big open spaces filled with desks, hives of activity with a dozen simultaneous phone calls and conversations competing with police and fire scanners and TV newscasts. Concentrating on your work could be… difficult. (I wore a pair of these.)

Taking my solution to the next level, Panasonic has invented a pair of blinders—not unlike the ones fitted to horses—that block peripheral vision to help you concentrate in the office. At The Verge, James Vincent has the scoop.

Counterpoint: Writing for the New Yorker, Maria Konnikova says, “Don’t build open offices.”

Smart Glasses, Apps, Talking Appliances: How Tech For Blind People Is Getting Better

In what is, in my opinion, a much better use of technology, Here and Now’s Robin Young looks at some of the best new technology for people who are blind or visually impaired, from smart glasses with an integrated camera for reading to apps that offer more independence and freedom.


This remarkable piece of journalism is a difficult read, but reporting for ProPublica and Time, Finlay Young reports that an acclaimed American charity that said it was saving some of the world’s most vulnerable girls from sexual exploitation was actually perpetrating it.

The New Hotness for Tech Billionaires? Do-Gooder Investments They Can Write Off on Their Taxes

Finally, a one for the development directors: “Silicon Valley’s one-percenters have long flocked to tax loopholes to try and keep the IRS out of their lives,” writes Theodore Schleifer at Recode. “When you’re as rich as Mark Zuckerberg or Jeff Bezos, you have legions of highly paid lawyers and advisers who specialize in taking advantage of every subsection of the tax code to keep your billions your billions.

“The rage in recent years has been the rise of Donor Advised Funds, limitless pools of cash that earn a tax break since they are earmarked for philanthropy but have drawn criticism because there is little accountability to ensure the money is actually spent. That’s old news. This is the new toy—’impact investing on steroids.’”

Thanks to everyone who sent me links for this month’s roundup of the best things we read about nonprofits and technology in the past month. As always, if you come across something you think would be a good fit for Best of the Web, send it to

See you next month…