5 Steps to Planning the Ultimate Workcation

When you started your journey as a freelancer or remote worker, I’m sure you imagined working on a beach with your laptop and a Piña Colada. Maybe you imagined taking a road trip to a new city and working out of a local coffee shop or co-working space. Now think of this last year, how many of those trips did you actually get to take? The idea that you can work anywhere in the world as long as you have a strong wifi connection is certainly a perk and benefit to this lifestyle, however, with the demands of life we often forget to take advantage of it.

So what’s the difference between a workcation and a vacation? Typically you have two weeks per year for vacation time. During this time, you should be relaxing and not working AT ALL. Most people actually feel guilty about taking vacations and will often check emails and work, which ultimately does more harm than good.

Vacation is your time off to relax and rejuvenate, so that you can return to work refreshed and more productive. I have a strict rule of no work and limited phone use on my vacations.

Workcations are trips you can take anywhere as long as you have wifi and can still do your work. You must be able to do your work. This is not the time to miss a client meeting because your friends want to go zip lining. You should be doing work as if you were in your office back at home.

Workcations aren’t meant to replace your vacations but should be taken in addition to your vacations. With proper planning, budgeting and scheduling, you can ideally take as many workcations as you want. Unlike vacations, you do have to work your normal set hours, communicate with your clients and team and quite possibly conduct meetings via Skype, Zoom or some other type of online meeting app.

As a former freelancer and now remote worker, I love taking mini-trips throughout the year. I recently took a workcation to Dubai from January 18-24. It took lots of planning. I also had major anxiety and nightmares over the loss of wifi, but it all worked out perfectly. Here are five tips that helped me to plan the ultimate workcation.

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1. Create a Separate Workcation Budget

When assessing your annual budget, be sure to first set aside your budget for vacations or trips to be used during your paid time off. Workcations are not replacing your vacations. So, you don’t want to spend money budgeted for a vacation on your workcation. Does that make sense? Then budget for one or more workcations, whatever you can afford. Workcations can be costly; so, you want to plan and budget properly.

2. Choose the Right Location

When looking into locations for a workcation, there are several things to consider. Are you going to stay local or visit a nearby city? Are you going to take a road trip or fly to a different state, island or country? Are you traveling to visit friends or family? Your workcation can be anywhere near or far, as long as there’s wifi and you can properly communicate with your team or clients.

Also, you may not want to pick a location where you ultimately should be vacationing. There’s no need to waste money on flights or an expensive trip if you will not have the opportunity to really explore the destination.

Even so, a workcation can still be enjoyable. Last year, I took a workcation to Puerto Rico and worked on the rooftop of different hotels overlooking the water. Then I made sure to grab lunch at different local restaurants.

Another tip, try to extend your trip to include a full weekend, so that you have at least one or two days to explore and do activities.

3. Research and Convert Time Zones Ahead of Time

Timezone changes are going to be a huge factor when planning your workcation. For my workcation, I still had to be up working during our normal business hours of 9 a.m. to 5 p.m. EST. Luckily in Dubai, those hours are 6 p.m. to 2 a.m. This was ideal, because I had the entire day to take tours and do activities with my friends. Then, I worked at night. I used a time zone converter to help calculate the difference prior to leaving for my trip.

While you’re choosing locations, be sure to check the times you will be required to be available to your team and clients. You want to make sure ahead of time that these are hours you feel comfortable working.

4. Plan your Travel

Traveling also took a lot of planning and research. I thought I would be able to use the plane’s wifi to work, but read reviews that wifi was slow and unstable on Emirates from LAX to Dubai. I couldn’t afford to not have wifi so I opted to fly between work. This had some interesting challenges. Let me illustrate this for you. I live on the West Coast so my normal hours of work are 6 a.m. to 2 p.m. PST. Here was my travel and work schedule from Wednesday to Friday:

Wednesday, January 18
3:00 a.m. Leave for LAX Airport
5:00 a.m. Arrive to LAX. All coffee shops were closed and it was too early to check-in so I just had to find a seat in the terminal
6:00 a.m. Work
10:00 a.m. Find a restaurant in the terminal to work out of so that I could have coffee and breakfast
12:00 p.m.  Lunch break. Time to check in and go through TSA early. I then found a Starbucks near my terminal.
2:00 p.m.  Off work. Time to eat and prep for boarding.
2:30 p.m.  Take off; 15-hour flight. I mostly slept and watched movies. I also tested the wifi and it was down! (Whew, dodged a bullet.)
Thursday, January 19
5:30 p.m. Landed and found a spot in the Dubai terminal near baggage claim
6:00 p.m. Work
Friday, January 20
12:00 a.m. Took lunch break and caught taxi to hotel
12:30 a.m. Checked back into work
2:00 a.m. Off work. Time for late dinner, shower, and bed.

Madness, right? Yes, and very exhausting, but so worth it.

5. Wifi and Communication

I’ve mentioned wifi above a few times, but it’s obviously really critical. In order to effectively take a workcation and continue to take them as you please, you have to be able to get your work done. Arrive at locations a few minutes before you start work and meetings to test your connection. The last thing you want is to miss meetings or that critical email because your internet was too slow or not working.

Also if you travel out of the country, you may not have cell phone service. Call your service provider and add an international package so that you can continue to make calls if needed. This can get pretty pricey so an affordable option would be to use Slack, Skype, Zoom or GoTo Meeting to chat and communicate with your team or clients. Remember, you still want to be dependable and responsive.

With these five tips, you should be well on your way to planning the ultimate workcation. It honestly doesn’t matter where you go, as long as you get from behind your desk once in awhile and experience new environments. Below are some photos of my recent trip to Dubai. I was also there on a Saturday and Sunday so I had plenty of time to do all of the tourist activities that I would have done if it was a vacation, without using any vacation time.

Posted in General and tagged with freelance remote vacation workcation

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