7 reasons why you probably should NOT make a Workation

Christian Krammer
Digital Global Traveler
7 min readDec 22, 2022

Please take them with a grain of salt as I’m not always totally serious.

What a look for my colleague when we had this call. The main square of Klagenfurt. Photo by author.

Here are some reasons why you may want to make a Workation after all and to get a primer on Workations please check this article.

Not sure when I had the idea of doing a Workation and what made this thought appear in my head, but I can say with total confidence that these times were the best in my life (besides the birth of my son and meeting my wife). Still, there are reasons why a Workation probably isn’t something for you.

1. You are afraid to try out new things

The whole reason of a Workation is to go out, try new things, visit unique places, just leave your comfy home office for once. I’m certain that this takes a lot of courage and procrastination (not sure how much time I wasted until I found the perfect train, Airbnb, or restaurant …). And some people are just not willing to make this first step, and I don’t blame anyone for that. There’s a lot of comfort in doing the same stuff every day, sticking to routines, eating the same food, getting up and to sleep at the same time. But come on, where’s the fun it that. YOLO, for once!

2. You hate to plan things (including your days)

Let me be straight with you: Going on such a trip takes a lot of planning. It’s not like you hop into the next best train, get off at a location that looks nice and spend some days in a hotel that you find by accident. Sure, there’s also some fun in not planning too much, but if that’s your first time, and if you really want to get some work done too, thinking a couple steps ahead is certainly a prerequisite to have a good time.

You need to find some appropriate train connections, an Airbnb (or multiple, if you want this to be a multi-city trip) or hotels, make a list of things to take with you (and probably even buy some new things), think how you arrange all of that with your workday, where to eat in the evening, what to have for breakfast, which sights or places you’d like to visit, etc. I’d love to help you with that, just send me a message on Instagram (https://www.instagram.com/chris.kram.070379) and I will guide as best as I can and answer all your questions, or just share some tips.

3. You hate public transport

Actually, public transport is an essential part of Workations. Who wants to take the car for such a trip? Come on! Trains, buses etc. give you a lot of flexibility and freedom, also to work for example while reaching new destinations. And it’s a lot cheaper and relaxing. With that, you will spend A LOT of time in public transport — not only to reach your destinations, but also to explore the surroundings. We are still in the middle of a pandemic, and if the thought scares you to share a compartment with some strangers for a couple hours, then you may want to spend your life doing other things.

4. Walking and exercising is not your type of thing

Another thing you probably will do A LOT on Workations, besides taking public transport, is to walk. How else would you explore all the lovely places, sights, restaurants, lakes, beaches, hills, cafès, museums, exhibitions, castles, historic cities, parks, markets, shops, streets, alleys, that just wait for you to be discovered in these strange and exciting new cities you will visit?

Why I also mention exercising? What about going on a small (or long) hiking trip, take a walk in the evening, swim a lap, go jogging in the early morning in this city you never have been to? Doesn’t sound so exciting? Well, I warned you …

5. You don’t speak Italian, or German, or whatever the spoken language of the place is you go to

The actual language is actually just a placeholder. If you are uncomfortable to have a lot of people around you that don’t understand a single word of the spoken language in your head, then you will have a very hard time in any city. That’s another essential part of a Workation. Get comfortable with being uncomfortable and if nothing else helps communicate with gestures and signs.

Usually, you get by with English quite well, but I highly recommend to learn at least the basic vocabulary of the country you go to. That’s why I love Italy much: A couple of years me and my wife went there for the first time and we spent the evenings two weeks before that to cram Italian. In the end, we were able to ask for a table in a restaurant or food and drinks, go shopping, greet, ask for the name, how the other person is doing, generally to know everything to find your way around in any Italian place.

This helped me a lot when I went on my two Workations in Italy, as it makes a difference if you try to order food in Italian or you just go the easy way and use German for example, which is also understood in touristic regions in Italy. But that’s pretty lame …

6. You don’t speak English (well enough)

Now we’re getting into the danger zone. If you just speak your mother tongue and no other language at all, then you should reconsider if a Workation will be an enjoyable experience for you. As I had mentioned, English is pretty common no matter where you go (that’s my experience at least, but I wasn’t at that too many place to be honest) and you can always find your way around even if you don’t speak it all too well. If you don’t speak it, then, well, good luck ordering food in a restaurant where you can’t read a single word from the menu.

The good thing: In our digital world, your cell phone might be your savior. Dict.cc is opened permanently on my mobile phone as there’s a lot I don’t understand and even for English stuff I use it regularly. (There’s no shame in that). There are even apps out there that translate as you talk, or give you the meaning of the word you are pointing your cell phone’s camera at. Lucky you …

7. You don’t have enough money

With this one I’m pretty serious. A Workation can be pretty costly. First there are the train tickets, which luckily get cheaper the sooner you book. Then there are the Airbnbs or hotel rooms, which can quickly cost you up to 1.000 Euros for a week depending on your living standard and the neighborhood. Of course you can also get some bargains if you search long enough. Then there’s food, oh boy, this will cost you a fortune if you are eating out every day (and wouldn’t want to do that when being on a Workation?). Of course you can also save some money here by going to the local (super-)market, buying some fresh ingredients and cooking your own meals. As mentioned, Airbnbs are usually well equipped.

Furthermore, you surely also want to enjoy the nightlife and go out for a drink in the evenings (there’s actually no shortcut for this one). Then there are entry fees to sights (which can range from “are you kidding me” to “OMG, I’ll never come back”) or museums. What about renting a bike or a motor scooter, having breakfast or one (or three) coffees in a coffee shop, or fees for public transport. Of course there’s always a way to travel on a budget and being low on money shouldn’t prevent you from a Workation at all, I just have found that have at least some money will make make such a trip much more enjoyable.

8. Sightseeing doesn’t fill you with you

Nobody ever said that sightseeing is a prerequisite for going on a Workation, but don’t you want to enjoy the place your are going to a bit? And typically, sights, or old castles and museums, are the best way to learn more about the place and its history and to discover a lot of different places. Although, I have to admit, that just walking around in a city without a plan is by far the most joyful thing for me to do and usually the first thing on my todo list.

Soaking in the flair of the streets, café and restaurants, hearing natives talk and laugh around you, smell coffee and food from food stalls, marveling at old buildings, sitting in a park and enjoying the silence or strolling on the beach or the riverside. Not to forget witnessing a sunrise or sundown. Live can be so beautiful if you seek joy in the little things.

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Christian Krammer
Digital Global Traveler

Program/ project/ product manager, Scrum Master, father, and husband. Addicted to reading, spirituality, and meditation. Proud author of The Sketch Handbook.