The Silicon Valley Voice

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Work Daze – Get Out of Town

You may find this difficult to believe, but not everyone loves his or her job as much as you do.

It’s true! The working world is full ungrateful malcontents who actually want to take vacations. Instead of taking advantage of the opportunity to spend their vacation days crammed into a cozy cubical, or aimlessly wandering an open office, these losers would prefer to bake their bodies on talcum powder beaches, or party through Provence, or just stay home and do nothing.

There’s only one obstacle to living out these frivolous fantasies.


Vacations are not only expensive, exhausting and often require shots — especially if staying home — but they also require permission from your boss.

In her recent post on The Muse website, Michele Herrmann addresses the risks of asking for the vacation time you are owed. Her article, “The Right Way to Ask Your Boss for Time Off,” is designed to help workers get the vacation time they deserve, or, in your case, the vacation time they don’t deserve.

Checking up on your company’s vacation policies is a good first step to making the big ask, according to Herrmann. Any good HR person will be happy to tell you how exactly how many vacation days you have accrued. And after you leave their office, any good HR person will be even happier to tell your boss about the disloyal employee who hates their job and needs to be fired, stat.

Another important preparatory step is to “try to get a feel for how vacation time is perceived in your department.” This makes sense. Do you really want to raise eyebrows and attract eyeballs by asking for two vacation days in a row? (Remember the funny looks you got when you took a whole sick day to recover from Dengue Fever?)

Job search expert Amanda Augustine recommends that you also consider if “there any major projects, events or deadlines during or directly after the time you want to take off.” Since you haven’t completed any project since starting with the company, this shouldn’t be a concern. Just make sure that one of your sneaky workplace enemies doesn’t jump in and finish your work while you’re away. If there’s one thing you don’t want to hear when you and your third-degree burn return from two weeks in sun-kissed Bongo-Bongo, it’s, “Gosh, everything went so well, we didn’t even notice you were gone.”

“Give plenty of notice” is another piece of reasonable advice, but I’m not sure it will work for you. You might try to schedule a vacation for two or three months ahead, by which time your ditz of a manager will surely forget you asked and be too embarrassed to say no. On the other hand, you are not likely to be employed two or three or even one month ahead, so you risk losing your vacation altogether.

That’s why I recommend the “pop-up” vacation notification. Swing by your manager’s office on the way to airport with news that is so unsettling that you will be long gone by the time they get over the shock.

“Just found a great deal on an flash-sale, economy-minus seat to Moldavia,” you breathlessly announce. “Please take care of my Great Pyrenees while I’m gone. They need to be wormed.”

If you have a fixed date — your sister’s wedding, or your own — Lynne Sarikas, the director of Northeastern University’s MBA Career Center, advises that you come up with solutions for coverage.

The strategy here is to show your manager “that nothing will fall through the cracks.” This is a good idea, though, in most cases, the only thing that falls through the cracks at your job is you.

It will take time and effort, but be prepared to show your manager that you are a responsible employee, and well aware of the unique skill set you bring to your job.

“Don’t worry about my being away,” you confidently tell your boss. “I’ve arranged for my work to be done by a trained orangutan.”

The final piece of advice is tricky. “Pick a good day” when asking for vacation, suggests executive coach Kathi Elster. “Find a time when you know your boss would be in a good frame of mind.”

This is a daunting proposition, but it’s not impossible. Your boss may be a grouch of prodigious proportion, but there was one day when your manager was definitely in a good frame of mind.

It was the day before the company hired you.

Bob Goldman was an advertising executive at a Fortune 500 company, but he finally wised up and opened Bob Goldman Financial Planning in Sausalito, California. He now works out of Bellingham, Washington. He offers a virtual shoulder to cry on at


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