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Perhaps you know how it begins. Somebody starts acting a little weird around you. Their tone of voice is different when you speak. Or maybe, out of the blue, you receive a strange, often angry email from someone you thought you were good with. “Well, I guess my emails aren’t important enough for you to open.” Huh? After a minute of bafflement you realise that this person has sent you an email that you didn’t bother to read. But wait . . . why wouldn’t I have opened it? I always open anything they send. So you go through your archives looking for the email and you can’t find it anywhere. Huh. So you write back, in words along the lines of, Sorry, but I don’t think I ever received the email you’re talking about. Resend it?

But the problem is that the person accusing you of not receiving their email (and it is indeed an accusation) doesn’t believe you and probably never will. Out of the blue, you, having done absolutely nothing, have been convicted, judged and sentenced to a reduced level of friendship. And the bitterness and anger on the other end just ramps up the more you try to exonerate yourself. Look, I’ve scoured my spam box and all my folders and email chains and there’s just nothing. What am I supposed to do here?

For some reason, this always seems to happen with emails that are important rather than quotidian. Last year I sent out a hundred or so invitations to a gallery opening and, as the day approached, I started sensing the tone change in some people’s voices. But it was only on the day of the opening that I got the standard hurt/bitter email saying, I guess I’m not important enough to merit an invite to your show. WTF? I trawled through my sent box, and yes, all my invites were indeed emailed out . . . So what was going on here?

And then I got another email from someone else, about not getting an invite, with the same hurt/bitter tone. So, after a wasted hour on a very busy day, it turns out that some email services, if they detect emails sent in bulk, deliver those emails into “promotional” folders instead of primary folders — and nobody ever opens the promo folder, which is essentially an electronic dustbin. It turned out that almost 20 friends didn’t receive invitations. So on the day I had the most to do, I had this bonus boring drama dumped in my lap.

Failmail need not always be personal. It occurs in the business world as well. Hi Doug . . . how’s it going with that file I sent you? We really need your changes by tomorrow.

File?

I once pursued a failmail to the nth degree and learnt that emails can sometimes contain toxic bits. I asked a friend who sent me a file that wouldn’t go through to me to send it to a third party. The third party then tried sending it to me but it wouldn’t go through, so I asked if he would send the first half of the email, which did get through — which meant there was something in the second half that was toxic. By trial and error we narrowed the toxic patch down to three banal words, “before next Thursday”, which, for whatever reason, made that mail unsendable. I was overjoyed to relay this info to my miffed friend. The result? I’m pretty sure they still don’t believe in their heart that I didn’t read the email way back when.

Sometimes it’s not just a single email that vanishes. A toxic relationship can develop between servers: for example, my own email provider, Gmail, and the servers of the FT Weekend Magazine that you find yourself reading here. Emails between me and the FT have been vanishing for months and it’s beyond a joke at this point, and it’s also really, really annoying. I’ve had to open a separate email account just for the FT, which still doesn’t always work and, in the end, emails have to be sent and received through an annoyed constellation of third parties. And because the server relationship is toxic, there’s still no way of being convinced that files have been sent or received. Trust me, I’ve checked my spam folders, I’ve called anybody who might have a theory, and still nothing explains the toxic server relationship.

So then, what is a failmail (non)recipient supposed to do? Actually, nothing. If you think about it, the onus is on the sender to figure out why it didn’t go through. It seems obvious enough but people really get insulted when you ask them to resend a failmail. Many won’t. I guess you don’t trust me. Was there an attachment to this failmail? Probably. Attachments are a major failmail trigger. And as attachments are usually about work, when they fail, the fallout is more than just someone being a crybaby.

This is a dispassionate account of experiences that can be very emotional. We’ve all sent emails that apparently never got through, and it’s very difficult to not think that the person on the other end is lying. Perhaps there’s an invitation you never received and you took it personally. Or maybe it was just a letter and a link to a funny Russian dashcam site. But the fact remains that failmail seems to be that magic equilibrium point where people will trust technology more than they trust a human being, and it seems to take very little for them to do so.

Douglas Coupland is currently artist in residence at the Google Cultural Institute in Paris. Twitter @dougcoupland

Photograph: Ken Mayer Studios @douglas coupland

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