Every time I take a vacation, the day before I return to the office is tinged with regret for taking time off. I enjoyed my time off, oh yes. But I know that when I come back, I'm going to have to tame the email beast. I always set my OOF message before I go. I add recurring all-day events to my calendar for the days that I'm gone. I have to admit that I do check my email at least a couple of times while I'm gone, but I don't read it nearly as much as when I'm in the office. In January, after the holidays and Macworld Expo, many people have this collective fear.

I've adopted a few strategies in Entourage that help me get through all of that email. First, I check everything by priority to make sure that there's nothing in there marked urgent or that is flagged, and deal with those from most recent to least recent. If I've been gone for awhile, I've found that items that were marked urgent but sent more than a couple of weeks ago have usually resolved themselves, often by the sender following up with someone specified by my OOF message.

Next, I take care of my calendar invites, to make sure that no-one has scheduled something for me early in my return. There's always someone who schedules a meeting with me a couple of hours into my first day back, and I'd rather that they get a response from me instead of radio silence.

Then, I sort my inbox by sender. Some senders are more important than others —-- for example, emails from my manager are the most important ones. This also lets me delete all of those Facebook emails that arrived over my break. I get a lot of email for stuff that I need to do, but those tasks are often pretty quick, so this usually lets me pick off those low-hanging fruit quickly and easily.

After I've done this, I sort my inbox by conversation. Next, I scan through them and prioritise the conversations. Some of that is simply by reading subject lines. Also, I usually check conversations with lots of responses first. Then, I read the most recent email in that conversation. This often means that the whole email thread has been taken care of by the time that I got back, so I can just delete all of the emails in that conversation.

Between these, I've usually deleted lots of emails, and dealt with the highest-priority and easiest-to-handle stuff. Now it's time to really dig in. I have a lot of projects going on at once, so the next thing that I do is sort my inbox by category. I have an extensive address book, and all of the senders in there are categorised, so the vast majority of what ends up in my inbox already has a category (if you're not like me and don't like that, you can turn it off). I start off with the email that isn't categorised and take care of it as quickly as I can. Then I decide which of the categories is the most important, and I work through those emails. I tend to work from most recent to least recent for long vacations (more than a couple of weeks), and the reverse for short vacations. And so on and so forth, until I reach the goal of Inbox Zero (no emails at all in my inbox).

I just got back from vacation today, and have been employing this method on all of the new mail in my inbox. I'm not going to get to Inbox Zero today, since I'm working on my Macworld Expo presentation. Speaking of Macworld, and if you're going to be there too, don't forget to swing by the booth to say hi!