1. Send a memo to Bob, asking him if it’s okay for you to take two whole weeks together, and informing him of the date and perhaps asking whether it fits with his vacation plans. This will not only serve the function of informing him of your potential non-presence and coordinating it with his own, but also remind him that he, too, will be taking some time off and that others might be entitled to some also. 

2. Inform your colleagues and, if you are a manager of some sort, your reportees that you will be away, telling them when, and making sure that your functions are covered during your absence. If any important subordinates were planning to take the same time, and it would destroy your peace of mind while you are away if they did so, simply tell them that they’re out of luck. Establishing a bona fide vacation is a war. There are going to be casualties, one of which should not be your vacation. 

3. Make sure you have your passport up to date, if you are traveling abroad. Once you ascertain that all is in order, make sure to drop the fact that you have done so to Bob, employing a breezy and informative style that let’s him know that your vacation is proceeding according to plan and that you’re happy about it and hope he shares that happiness, seeing how he’s so tuned in to other people’s feelings and all. 

4. Make sure that your electronics work at the location to which you are going. Cell phones are not as important as BlackBerrys. This is not because you will be doing e-mails all the time or that you wish to be reachable 24-7, but because by doing half an hour of messaging first thing in the morning and at the end of the day, you will be avoiding the nightmare of returning to 8,756 e-mails in your inbox, some of which were marked URGENT! even though you put up an away message. After you have done this, by the way, you may observe to Bob in an offhand way how incredible it is that BlackBerrys work in the mountains of Wyoming. 

5. Get any shots that you require if you are going to places like Belize, which has bugs as big as footballs, and jungles that sport diseases that haven’t been invented in humans yet. Don’t forget to complain that those inoculations hurt within earshot of Bob. 

6. One week before your vacation, take a look at your schedule. People will have stuffed it with things to do for the two weeks you are planning to be away. There is no logical reason why this happens, but it does. “What’s this meeting with Beanie and Cecil doing on my calendar?” you may ask the person who put it there. “I’m going to be away, as I told you sixteen times already.” To which they will reply, “You’re going away? Really?” In all cases, set about clearing your time and delegating the important stuff to other people. 

7. If you are a manager, a few days before your departure call in each of your key people and once again inquire what they are planning to do during your absence. At least one will mention that he or she was planning to be away, in spite of the fact that you have ensured that nobody was going to be doing so. There is no logical reason why this happens, but it does. Be kind to this person, because they are likely to be a future boss and you have to be careful how you treat people when they’re on the way up, because they may be the ones who are treating you on the way down. But do make sure that your ducks are in order for your time away, which means that they are all present and accounted for. Don’t forget to complain to Bob about how hard it is to do this. 

8.  Wednesday before your last Friday, Bob will inform you of an important meeting/project that will have to be done “next week.” This is a critical moment. Fools and wimps will in a trembling voice remind Bob of their vacation plans, but promise to be “reachable” when necessary. Do not do this. Executive amnesia is a form of authoritarian terrorism that must be fought. “Bob,” you may say as calmly and inoffensively as possible, “As I told you several times, I’m out next week and the week after.” Bob will look confused and hurt. He may even lightly question your loyalty or dedication. That’s all right. A display of spine is seldom out of place in what we do. Of course, if the corporation is being sold, or you are about to be named to a big new position, all bets may be off. Organizations can spoil the best of plans and often do. But 99.99% of the time, the ability to disregard other people’s needs is pure executive brain flatulence. Manage it. 

9. On Friday morning, as you begin the process of packing up to leave, a host, a myriad, a phalanx of problems, challenges and effluvia will fly up and hit you in the face. In some cases, this will be just bad luck and you will have to work your head off to get rid of them. Sometimes it will be other people’s anxieties surfacing in the knowledge that you are actually not going to be there, a notion that is making them freak out. You may soothe them by telling them quietly that you will be on BlackBerry now and then, but that if they bother you with little stuff you will rip off their noses when you return. Make sure your desk is clear. Leave an away message on your e-mail. Say goodbye to your colleagues and thank them for covering your butt while you’re away. Then wait for the inevitable phone call. 

10. At 5:45 in the evening of the day you are leaving the office for the last time in the next couple of weeks, Bob will call. It will be about nothing. You will laugh and scratch for a while. He will mention that he’s looking forward to the weekend. You will say NOTHING about your vacation, but allow how you can’t wait to get out of the office either. Then, as you are wrapping up this pleasant conversation, Bob will say, “So, I’ll see you Monday, then.” Breathe. Let the silence grow between you on the phone line. “Bob,” you may then say, but that is all. Nine times out of ten, that will be enough. “Oh, right,” Bob will reply after some time, very sad, very hurt, a tiny puppy being abandoned by its owner, “You’re flaking out for a couple of weeks.” To which you may say, “Right.” He will then wish you bon voyage, and probably tell you all about his vacation plans. The one time out of ten that he gives you a hard time? What can I say. Do what you have to do. The guy’s a madman. But even madmen need limits, maybe more than other people, even. 

Now… breaking your desire to stay in touch while you’re away? That’s another story.