How To Take A “Workation”

Screen Shot 2014-08-21 at 10.36.07 AM

The days of taking a carefree vacation are gone. It’s no longer our parents’ working world, and very few people other than the President take real vacations anymore. Some of us take the “workation,” where we either schedule meetings while in a certain region and throw in some down time or we attempt to go on vacation but spend the mornings working and responding to emails anyway. In all fairness, if it wasn’t for the advancements in technology, people in this economy may not even get workations, so I’m thankful for any workation I get. In fact, if you plan them right, you can have a damn good time.


During a workation, you are going to try to pack in as much fun in as possible, because you honestly have no idea when you’ll get the opportunity again. Less work, more -“ation” is your goal, and you will have to pack accordingly. If you are going to schedule meetings, pack one pair of dark slacks, two ties, two dress shirts, and one pair of dress socks and shoes. That’s it. You’re going to pack all your meetings into a couple of days, anyway. Make sure to bring plenty of Hawaiian shirts and shorts with elastic waistbands because your corporate gut is nothing compared to what your vacation gut will be. A proper workation Hawaiian shirt to dress shirt ratio is 5:2. Throw in a pair of American flag sunglasses to complete the casual zero fucks, I’m-here-to-get-rowdy-and-maybe-close-some-deals look.

Work Preparation

Wake up early and get all your emails out of the way, first thing in the morning. Check it every three hours on your phone and pray no emergency requires your attention after your fourth margarita. You can always answer non-emergencies the next morning. If you’re too drunk to handle a work emergency, have a sober person articulate your need for a favor to a coworker from whom you’ve never drunkenly requested a favor. Pick someone who doesn’t drink, odds are they won’t ask you to return the favor when you return to the office.


If at all possible, schedule any meetings you may have within the first two days of your workation. Why? Because the amount of alcohol and local food you are going to consume are going to leave you too hungover to function for a meeting and with too much gut for your work clothes. Trust me on this. I woke up from a drunk nap today and blew a .08 in my iPhone Breathalyzer. There’s no way I could function in a meeting tomorrow. If you have one or two meetings you couldn’t schedule at the beginning of the week, schedule them on Friday afternoon. Why? It gives you Friday morning to sober up after 2-3 consecutive days of getting drunk in the sun.


I’m not actually advocating a workation workout regimen here. You sit at a desk over 40 of your waking hours per week. If you’re on workation somewhere walkable, like coastal Los Angeles, the Las Vegas strip, or New Orleans, try to walk wherever you go. I can tell you firsthand that a high BAC, an open Hawaiian shirt, and a slight breeze can make a few mile walk down the beach feel like nothing, and it definitely counts as exercise. Trust me, I have friends in med school.

Email this to a friend


"Technically, Pablo Escobar was in sales."

1 Comments You must log in to comment, or create an account
Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More