In the interest of full disclosure, let me say up front that this column might not be for everyone.

If you’re an IT manager who has no trouble scheduling or going on vacation—if you can leave the job for a week at a time without fielding dozens of phone calls or worrying about what’s happening in your absence—well, then this column’s not for you.

On the other hand, if you’re like me—reluctant to take a vacation and dreading the time immediately before you leave and after you return—this column is definitely for you. Judging from the poll results in Figure A, this is a real problem for many of us. If nothing else, in this column, I’ll give you the chance to profit from my mistakes, which should help you when it comes time to plan your next vacation.

Figure A
Taking a simple vacation is difficult for many IT professionals.

Don’t do it this way: My vacation “planning”
If you’re looking for a way to plan your next vacation, just look at how I prepared for my last vacation—and do the exact opposite. Now, I’m not asking anyone to feel sorry for me. I just got back from a great week with my family in Florida. However, no matter how great the trip, the truth is I really screwed up when getting ready for it. Looking back, here are the major mistakes I made:

  • Planning? What planning? To be honest, I didn’t have any vacation plan, per se. I treated my weeklong absence from the office like a long weekend, assuming I would just pick up where I left off when I got back. I did send out an e-mail with contact information and mark myself “Out of the Office” in Outlook, but that was about it.
  • Working right up to the gun: Belatedly realizing I was behind the curve, I stayed at the office very late the last couple of days before my vacation, and I dialed in from home even later. I got a bunch of stuff done, but at the cost of spending the first part of my vacation catching up on the sleep I’d lost working. It seems rather silly to go all the way to Florida just to get a good night’s sleep.
  • Not prioritizing assignments: I’ve got a great group of directors and managers working for me, but in retrospect, I needed to do more than just say “Please handle everything while I’m gone.” I should have gone on to say something along the lines of, “Look, I know that you’ll be covering a ton of things for me while I’m gone. Here are the three things that really must get done.” I should have provided more direction.
  • Being unrealistic about deadlines: As I mentioned earlier, I just assumed that I could pick up right where I left off when I got back in the office. This means that I left some Monday deadlines for projects that I couldn’t possibly finish as soon as I walked back in the door. I should have pushed back some of those deadlines so that I wasn’t setting myself up for failure.
  • Bringing work on the trip: If you’re on vacation, you’re on vacation. So why did I commit to writing two columns while I was ostensibly not working? In this case, I can’t even blame the editor who runs IT Manager Republic. She offered me a postponement or a guest columnist to substitute. I should have accepted her offer.
  • Bad luck on the timing: Well, this wasn’t really my fault, but it turns out that last week was a terrible time for me to be out of the office. Of course, I couldn’t have known that six months ago, when we made the reservations.

Things I did right—or will do next time
Someone once said that you learn more from your mistakes than from your successes. In that spirit, here’s what I either did well during my vacation or will do better next time:

  • Make a plan: Next time, I’m going to treat my vacation just like any other project. I’ll have deadlines for the different tasks that I need to complete, and I’ll monitor my progress.
  • Resist postponing my vacation: As I said, this was not the best time for me to be out of the office. If this vacation involved only my immediate family, I might have been tempted to postpone. However, since my extended family (including spouses and children) had scheduled this trip months in advance, I went ahead. That was clearly the right call. There is always going to be a reason to cancel or cut short a vacation—but you need to resist that temptation as much as possible.
  • Keep the laptop closed: I only booted up the laptop twice on the trip and did as little work as possible—and only after the rest of the family was asleep.
  • Bring my BlackBerry: Faithful readers will be amused by my advocacy of the RIM BlackBerry, since I was so reluctant to get one in the first place. However, there is no denying the fact that having a BlackBerry on vacation made it easier for me to quickly respond to e-mails that were time critical, without having to boot up my laptop and dial in to the VPN. The time savings were substantial. Even better, I avoided the psychological urge to do more work, “since I was already connected to the network.”

As you can see, even with the mistakes I made, I consider my vacation a success. With all the pressures that technical managers operate under, time away from the office is essential. My message to you: Find a way, any way, to take your vacation.