Dealing with email embarrassment

By | December 20, 2024
Photo by Ivan Aleksic on Unsplash

I assumed that by now we’d be using something better than email. (Remember Google Wave? No, I don’t either.) But we aren’t. So it’s probably time for me to make a confession: I’m still struggling to find the perfect email app.

After a recent spate of embarrassing moments when important emails just passed me by, I vowed to come up with a system that didn’t let that happen again.

For years I’ve been using Apple’s stock email program (‘Mail’) and souping it up with rules, extensions and smart mailboxes. It looked good. I had at least 40 different smart mailboxes, a dozen or so rules, and everything seemed to be under control.

It was an illusion. By automatically directing things into smart mailboxes I cleaned up my inbox but to the point where I missed messages. Sometimes it’s not even clear why I missed it. Was it a bad rule I set up? It drove me nuts. An email from an accountant. Missed. An email from a teacher. Missed. An email from the guy who does, well, I’m not supposed to tell you what he does. Missed.

So I went back through the email apps I had played with in the past. There must be something better out there by now. It’s been 35 years we’ve been playing around with email apps (very happy to see Pegasus, my first email love, still going strong); surely we’ve got something solid and dependable to sink our teeth into?

Not really, is the answer.

I’m a Gmail user but not that’s one of four email accounts I need to have regular access to, so it couldn’t just be a Gmail client (like the discontinued Mailplane, and Mimestream.) Airmail is OK, but it looks and feels a bit dated these days. The same with Thunderbird. It’s great to see Mailbird with a MacOS version, noting the work Andrea Loubier did to get the app going, but it didn’t seem to add much to what Mail and others already do for free. Postbox is another dead man walking, having been acquired by eM Client in October. (eM Client is more of a productivity tool, and while it’s competitively priced, it fell outside my zone of candidates.)

Photo by Lucia Sorrentino on Unsplash

The field ranges from an all-singing, all-dancing app at one end that promises to do everything except clean the coffee machine, to ones that strip everything away and keep a tight focus (by hiding everything from the user, like a zen Marie Kondo apartment where everything has been stuffed in a cupboard.) I needed something half way between the two. In the end I settled on Spark (both the iOS and MacOS versions are available on SetappCanary is another email on Setapp worth a look.). There were, and are, things I don’t like about it, but I’ve tried to focus on what I need the email app to prioritise.

In short I need it to make sure I know that an important email has arrived. Spark is pretty good at that, allowing the user to mark sender(s) of a message as a priority sender. That means that anything from them will be shunted to the top of your list.

Then you’re able to assign an email thread as a priority, which colours it in a subtle orange. (A little Harry Potter scar appears alongside the thread to help you identify it.)

Everything is shunted into one of three categories Personal, Newsletters and Notification (a sort of half way between the two.) It actually works pretty well, although I’d love to be able to have more control with tagging (works with Gmail, not with other email services) or folders and filters.

And there’s also some AI guff that I really could do without. I never want anyone who receives an email from me to think it might have begun life as an AI prompt. All this kind of stuff is going to seem embarrassingly lame in a year or so and I wish development dollars weren’t spent on this when there are better things to work on.

Security, for example. Spark’s owners Readdle have been criticised for storing email on their servers, something they argue is necessary for some of the features. I don’t like it, though, and I wish there was a way to avoid this. It’s one reason that you can’t access Protonmail with Spark even through the former’s mail bridge (which works with apps like Apple Mail.)

I’m pretty happy with the outcome, and while I don’t have any use of the team-based functions, where you can presumably work on drafts with others, there’s clearly ambition to make the app better and smarter. Which is good: the app does crash, and sometimes the little x’s that you click on to close a mini-window don’t respond. And I’m not happy they only offer an annual billing. It’s $60 a year though there is a free version which I think offers most of the features that make it work. So try that first if you’re interested.)

Spark’s inbox

Given I’ve been writing columns about email for nearly 25 years, I’m a bit shocked I’m a) still writing about it and b) have had to admit I screwed up with lost emails enough to take action.

So I’m probably not the person to offer advice on the topic. I’d rather hear from you. But in the meantime, here are some lessons I’ve learned:

  • be a good emailer: acknowledge when you receive an email if you don’t intend to respond in detail immediately. You may save a lot of misunderstanding;
  • build your email world around the people you care enough about to not leave them hanging. Tags, folders etc are fine but if you’re missing emails, or forgetting to reply to those that deserve a reply, you’re doing something wrong.
  • think about email as the start of things. Spark has some pretty good extensions to help you connect with other apps that do a better job of handling tasks, calendars etc (my favourites: Agenda for contractual and project-level discussions, NotePlan for calendar+ and personal tasks, TickTick for assigning tasks to and managing others.)
  • don’t, whatever you do, use AI to write your emails unless the person you’re sending them to deserves it.
  • belt and braces might be a good way to go: I’ve kept my Apple Mail app going, and use that for digging around and organising the many newsletters I subscribe to.

Thanks for reading and let me know what I’m missing — either in terms of apps, or of the greener pastures of Windows.

Next time: Revisiting RSS

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