Many people can conduct their entire business or work from a laptop nowadays, and so there’s a new term:
A “Workcation” is a vacation you take to do work.
Work + Vacation = Workcation
To some people this sounds horrific, to others (like me) it’s heaven.
A workcation offers a bunch of benefits:
- Working in a new environment makes you think differently.
- You get to work but also goof off. This makes working much more pleasant.
- You can brainstorm with others on the trip.
- Can get lots of reading in.
- A leisurely work pace makes work more fun.
- Goofing off guilt-free!
As someone who’s taken several workcations, here’s a bunch of my personal recommendations:
1.) Make sure everyone on the trip knows work comes first.
This might be the most important part.
If you go with someone who wants to party the whole time, and you’re more into working 8 hours a day, it can be a problem.
For example, I’ve been on two workcation trips with my buddy Noah. We both know that working and reading is the primary goal, but some fun is of course involved. For this reason we’re good workcation buddies:
Just make sure you don’t go on a workcation with someone who purely wants to vacation.
Curating the crowd of people or making sure everyone is on the same page is very important.
2.) You shouldn’t jam-pack your calendar.
The point of a workcation is to leisurely work. This means not planning extensive trips or tours during the trip which take up all your time and energy.
On a vacation it might seem like a waste of a trip not to plan anything on certain days, but that’s totally acceptable for a workcation.
3.) Choose a place where you’ll get solid internet.
Without internet it’s unlikely you’ll get tons of stuff done. Unless you’re writing a novel and don’t need internet, not having good internet will severely cramp the amount of work you get done.
In my last workcation to Puerto Rico I purposely selected a building because one of the AirBnB reviews said the unit had good internet!
Beach + Desk + Internet.
Beach + Desk + Boats + Laptops + Internet.
So long as the wifi is good, you’re in business, no matter where in the world.
4.) AirBnB tends to be an awesome experience.
I love a good hotel, but there’s something about getting a solid AirBnB that’s better for work. Hotels are designed for entertainment and distraction, whereas a nice HOME can be stayed in for long hours.
Getting an AirBnB allows you to live more like a local rather than a tourist which is pretty fun. However this is more of a personal decision.
In a hotel I’ll get small spurts of work done, but usually not a lot. I’ve really enjoyed all the AirBnB’s I’ve stayed at for workcations.
One big distraction in a hotel is eating. You’ll tend to go out for every meal at a hotel, which means you have to get ready, select a place, go out, do the whole eating out thing. It can also EASILY lead to more distractions.
Whereas in a home-like environment with a proper kitchen you can always eat at home for a lot of meals.
One time we did a workcation in Napa Valley and a bunch of people rented a ginormous house and worked:
5.) Try to eat clean and workout so you can concentrate longer.
If you eat clean, your mind stays clean. Buy groceries the first day you get to your location and lots of healthy fruits and snacks. If you eat like crap, it’s unlikely you’ll be able to get long periods of work done.
Laptop + Book + Banana = Productivity.
You should definitely NOT eat delicious street food on your workcation like I am ;)
Make sure to get a good workout at least 2/3rds of the days you’re on workcation. It’ll help concentration and give you more ideas.
6.) Write it off your taxes ;-)
I’m no accountant (although I’m Indian so I might as well have a diploma), but you can write off elements of your trip. I’ll leave this up to you to figure out how much you can claim.
My favorite is if there’s a conference in a cool location. I recently went to a conference in San Diego that was semi-relevant to my industry. I didn’t really wanna go, but hanging out in San Diego for a while as an “expense” was appealing!
According to my taxes this is my “office” for the day!
“Ummm I’m listening to a BUSINESS podcast on headphones, therefore this is a BUSINESS expense right!?”
7.) Bring good books (not just business-y books)!
I’ve noticed through experience that sometimes you JUST DON’T WANNA DO YOUR WORK FOR A BIT during a workcation, but you DO want to get some solid reading time in.
Bill Gates routinely takes workcation style trips where his goal is to just read the whole time:
There’s something very relaxing about sitting by a beach and reading the entire time (although I take intermittent breaks to go pee in the ocean) :-P
I noticed that if I bring purely just educational or business-y books I sometimes get bored with them. Therefore I’ve made sure to always take at least one easy reading book. Some great suggestions are The Martian and Ready Player One.
For my recent workcation I partially read The Power of Habit, then made a big dent in The Kid Stays In The Picture. It was just an autobiography that was fun to read.
Reading a bunch for long periods of time helps increase your concentration and is just plain fun!
8.) Go during a “Slow” season to get great deals.
Obviously if you go during peak seasons to a place, the prices go up big time.
If you’re going on a vacation you’d definitely want to go during peak times.
If you’re going on a workcation you have the luxury of going whenever you want. This means better prices and less crowds.
Un-crowded streets to wander.
Endless un-crowded bike lanes.
We went to Puerto Rico when it was pretty slow so we had miles of clear bike lines and non-crowded beaches. It was great!
Obviously there were still a lot of people around, but in a slow season it’s just easier to do stuff than with big crowds.
9.) Workcations don’t have to be far, they can be close by.
One time on a workcation we went to Thailand. It was about 30 hours of transit each way, and we also had to deal with jet lag. You also have to stay longer because “you’re all the way on the other side of the world, we may as well see some other cities.”
This meant the workcation turned out to be a minimum of two weeks. Just look at the amount of flights I had to take JUST to get to Thailand. This didn’t include all the other flights within Thailand:
To be honest, after that many flights I wasn’t really in the mood to get work done. For this reason I prefer taking workcations a bit closer to home.
You can even get together with a couple of buddies and throw down on an AirBnB near town.
I once rented a sweet golf villa for super cheap on the outskirts of Austin. It feels like a whole different place, but it’s just a short drive away.
On my last workcation I went to Puerto Rico which is a domestic flight from the U.S., same time zone, and only 5-ish hours of transit. It felt like a whole different country, but is just a domestic flight.
Hope this helps you take a succesful workcation!