8 things that can go wrong with your workcation and how to prepare

The world is beginning to open back up and travel restrictions are loosening, at least for now. It’s finally possible to take the office out of your bedroom and work in all of these insta photo-worthy summer locations. 

The problem is that the reality isn’t like the photos. Most of the time you’re not sitting on the beach in a thong sipping on a margarita smashing out the blog posts. I want to tell you, from my own lived experience, what things can go wrong. My main advice is: Expect the unexpected. I will also give you some top tips to prepare and manage them.


  1. Intention

Why are you going on a workcation in the first place? (Just in case you need this word dissected work and vacation = workcation. Only in the capitalist world, right?!) Do you really need a holiday, but feel like you can’t take time off so you’re trying to smoosh the two into one? Bad idea. 

I did this once 7 years ago. I took a week off of work in London to go work at a bar in a festival outside Berlin. Fun right? NO. I needed an actual holiday and should have just gone to the festival and danced. But instead, scared of missing out on a week’s wage because I was a broke freelancer I worked on my ‘holiday’ and ended up resenting every minute of being there and got home exhausted, still needing a holiday.

If you need a holiday, take an actual holiday. 

It’s that simple. If your job won’t allow for you to be able to take time off, then you’re better off renegotiating the terms of your contracts or workload or even your rates, so that it’s possible to take an actual holiday instead.

Really think about the intention of the workcation. Are you just excited to go work from a new location, meet some new people, maybe do some networking and change your environment? Great! Do it, but make sure you also have a real holiday in the pipeline. It’s important that we make the time to truly disconnect. 

2.Priorities

This is a big clanger for many people. They get to their workcation and then treat it like a holiday. They prioritise holiday activities and let the work stuff slide and end up in a tangle trying to play catch up and feel stressed out.

What do I mean exactly? This could look like staying up late drinking at the beach with the new lovely people you met at dinner and getting swayed into a late night drumming circle that doesn’t stop until 5am and then realising you have a call in 3 hours and still haven’t slept. I hate to be the party pooper, but in this case your priorities are out of whack.

Work is work whether you’re in Bermuda or at home

Fortunately/ unfortunately whether you're working from the office, from your living room or Bermuda, work is work. If you have a job, people are expecting things from you. You still need to meet your deadlines, attend your meetings and tick those items off your to-do list. When you compromise all of this to have fun, you’re just giving yourself a mess to clean up later down the line. 

Have fun by all means, why work in the first place if you’re not going to enjoy your life? But think about your priorities and remember, again, it’s not a holiday. You’re going to have to compromise here and find some balance. 

Think about this when you plan your trip. Are you booking to go somewhere that’s so exciting that you’re going to feel like you’re missing out every day when you have to go to the cafe and open your laptop? If so, maybe go there for the actual holiday and not your workcation. You can also plan a real holiday at the end of the workcation where you have time to do these exciting things.



3.Internet

I think many of us in the western world have just come to take the internet for granted and think that we can and should be able to access it almost anywhere at any time. This taking it for granted has come back to bite me in the derriere on a few occasions. When you are a remote worker the internet is literally your lifeline and having a reliable, functional connection is essential.

Do not assume that you will be able to get onto the internet at

  • Your hotel

I cannot stress this enough. Even if it says online it has internet, double and triple-check. Read every review of that hostel to see if there is a weak internet connection comment. Call the place first and ask them outright and explicitly. Many places say they have wifi, then you show up and it’s been not working for weeks - you’ll kick yourself if this happens. 

I recently paid a little over my budget to stay at a hotel that said it had wifi and a desk in the room to work. The internet didn't work for my entire three days there, even after they tried to fix it. I left the hotel to stay at my friend's house instead, who runs his business from his spare room.  And day one, the fiber cable broke and we were without internet. I went to three local cafes, all had intermittent internet and could handle email but no calls. I was stressed to say the least.

  • A local cafe

See point above, often it can be fine. But it’s not always great for calls or downloads/uploads. You’re better off finding a co-working space. Don’t just assume you can work from a cafe. Do some research before you go.

  • Your mate’s house

Again, yeah it might work, but it also might not. Don’t assume. Ask them before you go what the connection is like. You’ve got no idea if it will work or not, so have a back-up. It’s not fun to then have to demand your friend call the technician and ‘sort it out’ when you’re meant to be there having a friendly catch up. 

I went to stay with my mum for a week thinking I could work only to arrive and find out the internet only worked in one corner of the house and even then it was intermittent. She’d been having problems with it for months, but I didn’t ask and so she didn’t tell me before. I would have brought a dongle had I known.

  • The beach or the top of a mountain

If you think the internet will really work and the tasks you have to do aren't so important and you can risk it, sure go ahead. But if you have deadlines and calls, just play it safe and go to the beach afterwards. I think we’re all adults here, just be sensible.

From the other side of the screen there is almost nothing more annoying than someone who shows up for a meeting from the beach with crappy signal: hey keep dipping in and out and you can’t actually discuss anything because they spend the whole time trying to get a better signal shouting “Can you hear me now?”. 

So how do you prepare?

Data roaming package

Make sure you have data roaming packages on your phone as backup in case it drops out. And in order for this to work, research your provider and how good the data signal is in the area you are going. It’s dull, but you will be forever thankful you didn’t book that hotel on the edge of a mountain when a monkey pulls the cables from the roof and you're in your mobile provider's blank spot (real life ladies and gentlemen).

Pick your location carefully

Prioritise somewhere with a good signal.  Try and stay in an area with cafes and coworking spots so that if all else goes wrong you can run through the street, laptop in tow, and not be too far from your solution.

Coworking resorts

There are also more and more coworking holiday resorts popping up. There are literally places being built for people who want to work in a great location with a desk and stable internet. They can be pricey but they exist and have considered all of these problems. Why not check one out?



4. Electricity

Even if you have a stable internet connection it’s meaningless if your phone and laptop have run out of battery. There are some pretty simple solutions here.

  • Don’t stay in the outback

  • Take a battery power pack with you (worth every penny)

  • Always sit near a power outlet

  • Take every opportunity to recharge your battery

  • Check if you need a power adaptor

If your laptop has a battery that lasts 20 mins before it dies and your work depends on your laptop, upgrade the battery. It will pay off in the long run.


5. Time zones

I’m sure you do not want to miss your important meetings. I did a clever thing once where I had two time zones on my google calendar so I could see my schedule in local and home time. I’m being sarcastic, it was a terrible idea. I missed two meetings because it mixed up my brain so much and also confused other people who got times written from different zone’s on their event invites.

Double-check and communicate

Double-check what time zone your calendar is in. Double-check you know the actual difference between where you are and where your meeting participants are. It can be confusing, so if you’re confused, check again.
Write it out

Write it out

Always write the time zone next to the time for clarity when writing emails and arranging events with people. Over-communicate and just ask again if needed. 

Check it daily

Check your schedule daily and if you can’t change it into local time, write it out for yourself in local time and add reminders into your phone. Better safe than sorry.



6. Noise

I don’t think I need to dig too deep here. Get a decent pair of headphones that have a built-in mic. If you can afford it, get noise-cancelling ones. The builders might be at your friend's apartment whilst you're trying to deep dive into the monthly analytics.

It’s a small price to pay to just be able to hear in a meeting, be heard and block out the inevitable noise of working in a local cafe.


7. Travel plans

Unless you run your own business and you have no meetings, deadlines and your work doesn't affect anyone else, you'll need to plan well. 

I’ve found it’s always best to err on the side of caution and assume you will have delays and it won’t work out like you think. Especially if you’re travelling somewhere for the first time. 

If your flight lands at 9:00 and it says it takes one hour to get to your hotel, don’t book a meeting for 11:00. It seems safe, but it’s not safe. I’d even go so far as to say, try and not have meetings booked at all on travel days to save yourself the stress. If this isn’t possible, at least leave a large buffer zone.



8. Well-being

I think we should be looking after our wellbeing on workcation or not, but it often happens that when we’re away from home we let things slide. Much of the time it can be ok, but it can have serious consequences if you have deep focus work or tight deadlines. 

Getting four hours sleep a night for 3 days in a row because you just need to stay up and watch the stars seems innocent, but when you’re only half awake for your client calls, it’s going to look bad. People are, after all, paying you for a service and you need to show up at your best.

Maybe you know that you need to do vigorous exercise each day to release stress and get out of your head and when you don’t you end up agitated and cranky. Plan in advance, see if there’s a local gym or track you can work out on, take your skipping rope or resistance bands in your suitcase and carve out the time to stick to the things you know work.

Well-being doesn’t stop just because you're away from home.



Have you had any workcation mishaps? Have we missed any top things that can go wrong? Let us know below we’d love to hear from you.


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