Why email and vacations are incompatible and always will be

When you take a vacation, how many of you do what just did before I took my vacation? Even though I was secretly checking email while on vacation, through Exchange Server's Out of the Office Assistant (I'll call this OOA for short) I created an Out-of-the-Office email rule that replied to each email that came in while I was away with a message saying that I was gone on vacation, that I would not be checking email and that if the sender wanted to get in touch with me, to resend their email on or after Sept 5.  In other words, if their email was sent to me during my vacation, I wanted the senders of those emails to think their messages weren't going to get read.  Even when I returned. 

I wasn't completely truthful.  But, in what signals a complete failure of technology, I see no other way to keep my inbox relatively clear than to scare people into leaving it alone. And even then, they don't listen (in some cases, for reasons beyond their control).

Even though I took more than two weeks off (thanks in part to the the long Labor Day weekend here in the US), I wish I had more time to goof off. But with the psychological psyummer over and the hi-tech business clearly poised to move into full swing this week (actually, things didn't seem to pipe down at all over the summer), I guess it's time to dive back in with two feet.  Not that I totally tuned out.  Sure, I went to Maine (Point Sebago on  Lake Sebago if you must know) for some much needed R&R and firepit-side chat (replete with smore's) with the family. But the last thing I wanted to return to was a mountain of email to wade through this Tuesday morning.  So, what did I do?  In what is best described as the sad state of both vacations and technology, I managed it when I could. But not very deftly so.

For all the good it does, the mobile technologies (devices, networks, etc.) that result in the delivery of email to us anytime and anywhere have wreaked havoc on our vacations (and our sanity). What does it say about us when, even before taking off for some much needed decompression, we start stressing out about what we're going to miss and how we're going to deal with the motherload of messages (email, vmail, snail-mail) and action items that await us upon return? So far have we been pushed that we now use such inundations as excuses to pay attention to them when we're supposed to be recharging our mental batteries.  And the technology is very much there to answer that beck and call.  Well, sort of.

In my continuing long-term testing odyssey of Motorola's supposedly revolutionary Q smartphone, there are few opportunities like a long vacation in Maine to push such devices to their limits to see how they hold up under a real test of remote computing.  While I'll reserve the details for a separate blog entry to be published in the next day or two, let's just say that the Q did play an important role in remote email/vmail management (something that I would not have been able to do without the Q or something like it) but that it was not a pain-free experience (in fact, it was quite painful).

But, back to email itself for a moment, this vacation has taught me that, even after all these years email technology has had to evolve, email is still broken when it comes to handling something as ordinary as vacations. Or maybe vacations are just really good proof of how poor technology is when it comes to exception handling.  After all, who wouldn't want an email system that's nearly as capable as a human administrative assistant who knows what to do with everything that comes your way while you're supposedly unreachable. 

Think about it.  We jump through all kinds of stupid hoops (thinking it's normal) just to manage the exceptions.  For example, you can't set up a vacation "agent" (like I have in the past) that just deletes all email.  What if one of those emails is regarding a family crisis that needs your attention immediately? Oh, that's right.  Your family is supposed to use your Yahoo or GMail address when they need to contact you. Not the inbox you spend the majority of your time with.  And somehow, we think it's normal to use multiple inboxes from a variety of providers as a technique for segregating and managing email the way we need to.  That is, until you equip yourself with that newfangled mobile technology that's supposed to simplify your life (like the Motorola Q) only to realize how such complexity forces you into becoming your own personal systems engineer.

Sure. To handle the family emergency exception, you could program the rules engine in your email system to do certain things with some emails, and other things with others based on who the sender is.  Just make sure you've got a programming expert looking over your shoulder because, for various reasons, most such rules fail. It won't be long before what you thought was a simple rule becomes a labyrinth that turns into an exercise in pure futility.

And why do I want to automatically delete mails anyway?  Oh yeah.  It isn't just that I want less work to do when I come back from vacation. In an effort to keep a lid on storage costs, our corporate email system disables my email if I let my inbox take up too much hard drive space.  First, it starts with a little reminder that your inbox is exceeding the allowed size (which for some reason, is way less than the inbox sizes that Google, Yahoo, and others allow you for free).  Then, if you ignore those messages (as you should be able to do while on vacation), the ability to send mail is disabled.  Things can spiral downward from there.

In other words, let's say a few overly ambitious senders of email send you something with a giant attachment like a video.  You may have thought you left your inbox before vacation with enough room to accommodate everything that comes in while you're gone. But you didn't anticipate an idiotic email that, in one fell swoop, shuts down your inbox so badly that even your especially programmed vacation agent stopped auto-responding on your behalf while you're out of the office.  Even worse, your anti-spam technology is set to funnel emails that come from anyone supposedly named "System Administrator" into your spam folder and it isn't until you check your spam folder where those messages are hiding that you realize that some of them were actually from your system administrator and that you've got a major problem. 

The problems with integrating email and vacations don't stop with storage.  The way Exchange Server (what we run here at CNET) works -- or, at least the way we have it configured -- the only time you'll get a message from me that I'm on vacation is the first time you send me email after I've turned my OOA on.  After that, you won't get any more reminders that I'm out of the office.  You're supposed to remember.  This results in several failures, most of which I think can be corrected. 

A lot of email comes to me by way of my inclusion in some distribution list. Some of these distribution lists are internal to CNET.  Others are external to CNET.  Many such lists are managed by an administrator or designated list manager and not the actual senders that use them. For example, most public relations agencies distribute press releases to the media by way of distribution lists. With a few keystrokes, a single press release gets blasted to hundreds if not thousands of journalists in true form letter fashion. It's probably a good thing for someone who is sending mail to a distribution list (whether they are internal or external to my company) to know that some recipients are on vacation.  But here's where the technology completely falls apart. 

One of the reasons I use the OOA in the first place is so that people will stop sending me email until I'm back from vacation.  Recall from the beginning of this post that inbox management (while on vacation) actually requires some cooperation on the sender's end as well.  Once they're notified by my OOA that I'm out until some date in the future, the hope is that they'll stop sending me email until that point.  Unfortunately, if those senders are reaching you by way of distribution list, there's really no easy way for them to cooperate even if they wanted to.

How, for example, is someone supposed to temporarily remove my name from a distribution list when they don't have the necessary security rights to do so? And, just supposing they had such rights, how could they make that change temporary so that it automatically reverses itself when I'm back from vacation?  Even better, why should something so straightforward need to involve the manual attention of the sender in the first place? Why can't email standards be updated so that my OOA can remotely instruct a distribution list to exclude me from future distributions until a certain date? Just supposing this capability existed, then, wouldn't it be great if I could tune it so that it leaves me on some distribution lists, but not others? In many ways, my ability to temporarily stop an external server from sending me email overlaps the idea of a "relationship termination" protocol that I've discussed in the context of dealing with spam. The idea of recipients remotely controlling external distribution lists in such ways is probably a pipe dream. But is it too much to ask when the distribution lists are behind your own firewall?

I could keep going about the incompatibility between email and vacations, but you get the picture.  They're like oil and water and one of the reasons it's this way is that senders are the ones that are ultimately in charge of what happens in your inbox which, to me, is a problem.  If the question is how to put recipients in charge, then perhaps RSS is the answer.  As I've written before, RSS could be made into an integral part of the email system such that the only things that show up in your inbox are things that you subscribe to. So, if PR Agency XYZ wants to send me press releases about ABC company, they can send me one such release and on my end, the first time I get an email from PR Agency (or domain) XYZ, the system can notify me that XYZ domain is requesting that I subscribe to its email system.  I can look at the email and decide for myself whether I trust the sender and whether I want to subscribe to emails coming from that domain.  If I say no, from that point forward, future solicitations from that domain are refused (and perhaps a polite message is sent back) and I never see email from them again.  If I agree, from that point forward, all emails from that domain come to me by way of RSS subscription (automatically processed in the course of agreeing).

Once all email is coming to me by way of RSS subscription, then, with the right client-side RSS tools, I can very finely tune my OOA.  For example, I can say turn off all RSS subscriptions until Sept 5 except for these people in these domains (eg: Dan Farber in domain CNET.com).  And, as I use my OOA to exercise this degree of granular control over my subscriptions, it can proactively (instead of reactively, the way things are today) notify the senders with whatever standard message I've written that I'll be out of the office until a certain date.

Unfortunately, such tools (for exercising time-based RSS subscription) are completely non-standard today (even though they should be built-in to every RSS reader out there).  If they did, I could use them to turn off any subscription including ones to all the newsfeeds I watch. This way, not only might my email inbox be pretty much clear of non-critical content when I return from vacation, but so too might my RSS inbox. Instead, and sadly however, such tools are uncommon and we must take time -- often, valuable vacation time -- to manage both.  Either that, or tell our employers that they won't be hearing from us during the first two or three days were back on the job as we clear our virtual desks.