Autumn 2021 Email Links

Summer is long over, so it’s time to publish some links about email for Autumn. I thought about calling it Fall 2021 Email Links, but “fall” sounds too close to “fail”, and email is never a failure. Plus, as anyone whose watched 500 Days of Summer knows, Autumn comes after Summer.

If you liked my article on why instant messaging is no longer instant, you might like L.M. Sacasas on instant messenger over instant messenger, in which tech philosopher L.M. Sacasas (of The Convivial Society newsletter) talks with Uri Bram (of The Browser newsletter) about the unusual cultural friction and communication challenges of instant messaging. They did the interview over instant messaging itself and published their chat. An excerpt from Uri:

meanwhile, email often frustrates me because there is TOO much time to polish, it feels like I can’t just say what’s on my mind and work things out, whatever I send feels “final”

in some sense I really dislike and sometimes there’s very long “silences” between my email and a reply, where I’m torn between feeling “this person secretly hates me” and “they just haven’t got around to answering yet”

Closing email with “thanks” gets the most replies (although technically it was “thanks in advance” that won out). Tech app Boomerang, which makes add-on ‘productivity’ software for email, such as a writing assistant and scheduled email sending (all of which I oppose, but to each his own; you might find them helpful), actually wrote this post in 2017, but as you know with links, if it’s new to me, it gets posted when I discover it, not necessarily when they post it. Strangely, their main site is partially insecure, so I’d recommend they fix that before asking people to trust them with email integration tools. But they do have an interesting, albeit aging and infrequently updated, blog (which is fully secure) so check them out.

After doing some sleuthing, we realized our findings actually reaffirm a 2010 study published in the Journal of Personality and Social Psychology titled “A Little Thanks Goes a Long Way.” In this Grant & Gino study, 69 college student participants got one of two emails asking for help with a cover letter. Half received an email that with a line that included “Thank you so much!” The other half got a similar email, sans an expression of gratitude. The study found that recipients were more than twice as likely to offer assistance when they received the email that included “thank you.”

Email: the future of messaging is not what you think. Yes, it promotes email, but it’s really to sell you on yet another wrapper over Gmail (called Shortwave) to change your inbox so you can finally “get things done” and keep you “organized by default” and “understand your inbox at a glance”, all of which any thinking person should be able to do with almost any normal email client but Gmail. The founders have some money and will live a short and mild life, as all other Gmail wrappers do, but as I’m often fond of saying, you must learn email, not ask software to do it for you. It isn’t hard if you Just Use Email and spend less than an hour learning about its superpowers and mastering your email client. Unless that email client is Gmail, in which case, maybe Shortwave can help you. Still, I can’t help but love this sentence:

We believe that email, despite all of its flaws, will eventually win as the way we communicate online, displacing iMessage, WhatsApp, Slack, WeChat, and every other messaging app in your pocket today.

Nice interview with the Fastmail’s CTO, Ricardo Signes, on Privacy and the Future of Email. He promotes a new podcast that Fastmail started this summer called Digital Citizen (5 episodes so far). I’ve been increasingly attempting to do just this below (when appropriate) so I was happy to see Ricardo discuss the unusual friction that should not exist within email:

The other thing that needs to get better is tiny messages. Sometimes I get an email, and I just want to type “yes,” then hit send—but that makes me the weirdo! We need mechanisms that let us get the things we want out of instant messaging and Facebook-style reactions – to let us interact in a simple, efficient way that doesn’t feel like we’re subverting the idea of what email is.

Ricardo spends most of the interview talking about privacy and then ends talking about using email as identity, and why most of us need more than just one. There are those who promote using only one single email address for everything, and that may be a working model for some, but in general, I agree with Ricardo:

If we want to talk about email, it’s that your email address is your identity. Email is the way online services know who you are, and so you should think about how many identities you need. Most people need more than one—work, family, friends, bills, etc. Separating these identities beyond just privacy can help you lead a life in which you compartmentalize your concerns intentionally and have a way to think about how you’re dealing with these aspects of your life.

Cal Newport shows how misuse of email between a risk analyst at Credit Suisse and an accounting manager at hedge fund Archegos cost Credit Suisse over $5 billion dollars. That isn’t meant to be a slam against email, but really about the insipid way we communicate in the modern era. This same foible could have occurred over Slack, Microsoft Teams, or even by postcard (although I doubt it). There’s something in the air that seems to prevent many modern workers from picking up the phone and insisting on a conversation, and even if one person does it, there seems to be a general hesitancy and anxiety on the part of many would-be telephone answerer to accept or answer an incoming call if they didn’t previously agree to it and be given all the information upfront via some other method first. Cal quotes Matt Levine at Bloomberg on the fiasco:

It’s just that they sort of kept each other in the loop as a substitute for actually doing anything. The processes were all moving along nicely, which gave everyone a false sense of security that they would produce the right result.

Sound familiar? In 2021, a solid third of emails and Slack messages I received at work were exactly that. The problem isn’t email. We need to train people on how to communicate and write effectively.

Clo, a project manager and UX designer, writes about 8 ideas for a calmer inbox. I like the title, and although the tips are mostly run-of-the-mill, it’s a well-written piece that some may find helpful, especially if they are graduates of the University of Oregon. Clo makes a good point about notifications (although I’d argue that unless you’re a field worker, you shouldn’t have work email on your phone at all):

Free your mind from notifications and calm will follow. Notifications get in our way by interrupting and distracting us, sometimes with information we don’t even care about. Turning them off allows you to regain control over your attention… I’ve recently turned my professional email notifications off on my phone: I can still check them, but I do it on my own terms. I find this setup to be way more relaxing.

If you didn’t know, Apple now allows using custom domains with iCloud, if you subscribe to iCloud+.

Florian pontificates frustratedly on an agreeable anti-meeting post where he reworks the meme This Meeting Should Have Been an Email in a blog post, but with a few added tips. He emphasizes that email isn’t always the right solution for meeting replacements, but effective structured writing is, which would include wikis, documents, and text files. He correctly and humorously footnotes at the end of his list of meeting alternatives:

Please note that interactive chat (like Slack) is not in this list. It fails the “formulate complex thoughts and reasoning” test.

Paul Ohms, the creator of MailPlace and an email aficionado, asks developers to consider using email as a way to monitor production sites. He compares the advantages of just using email to building custom dashboards, some of which are “doesn’t consume any resources, very easy to extend or customize, almost no maintenance, and everything is time-stamped and archived by default”.

ProtonMail details a recent Swiss court ruling (where ProtonMail is located) that strengthens privacy for email providers. Good to see some email providers fighting for privacy rather than fighting to monetize our email communication.

As part of these efforts, in May 2020, we launched a legal challenge against the Swiss government over what we believe to be an improper attempt to use telecommunications laws to undermine privacy. In a ruling this week, the Swiss Federal Administrative Court confirmed that email services cannot be considered telecommunications providers, and consequently are not subject to the data retention requirements imposed on telecommunications providers.

I missed this announcement this summer. Stanford Libraries announced that Ted Nelson’s email archive is available to the public. Included are over 230,000 messages. Nelson was known for his work on organizational and hierarchical thinking and often emailed himself with custom abbreviations (we’d call them ‘tags’ today) in his subject lines to help himself find his own emails.

One common thread found throughout Ted Nelson’s work seems to be a deep interest in how information is organized, related to other pieces of information, and presented to people who need to make sense of it. As an inventive thinker on matters related to information and technology, it should come as no surprise that Nelson wouldn’t be content to simply use his email account in the conventional way. His email account served many functions beyond communication: a note keeper, a log of daily activities (or “drungs,” a portmanteau of “daily” and “running” coined by Nelson), and a repository for important reference documents (search for “refx” to find these).

Lastly, this one’s a bit wonky, but for a life lesson on how not to migrate an email domain (related to a business email account used for transactional emails), Will Hankinson shares a recent foible. I like articles where people openly share their misunderstandings and mistakes to help others. That’s the kind of boldness the internet and blogosphere used to have. Can we still say blogosphere? I think we can!

I forgot to migrate the bounce list from the old domain to the new domain (and, less important numbers-wise but still important: the spam list).To make matters worse, my newsletter algorithm prioritizes sending emails to more recently active users first. This includes on-site activity as well as a prior history of opening emails. I purge that data after about 6 months (less data is a good thing these days). After an initial burst of “good” emails, I started hitting around a 5% bounce rate and Mailgun gave me the ban hammer.

For more boldness, scroll down to Will’s footer on his website. Then enjoy what’s left of autumn in your area and prepare for winter ahead.

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