Your Guide to a Productive Workcation

2020 threw us some major curveballs. Stay at home orders due to the COVID-19 pandemic led to millions of people around the world working from home – some of the first time (me!). Two weeks of working from home have turned into almost a year, with no sign of heading back to the office anytime soon. I’ve used the time to create better boundaries (and integration!) between my work life and my personal life. I’ve also been lucky enough to transition from my makeshift desk to a more permanent office in our guest room.

It wasn’t all pleasant though. Cabin fever is real, and I felt it bad. While I appreciated the new found freedom in working from home, I longed for some semblance of normalcy. Days spent researching our next adventure left me feeling more down and out, as we had no idea when it would be safe to travel again (or who would even let us in their country!)

Spring turned to Summer. Summer to Fall. And as the temperatures cooled, days shortened, and COVID-19 cases soared in the U.S., I didn’t know how we would endure a long winter stuck inside with little interaction with the outside world.

And then, an idea hit: we work from home. “Home” can be anywhere. Our offices could be anywhere. We weighed the pros and cons of leaving the country for an extended trip (pro: mental health; con: COVID-19 knows no borders). After careful research and consideration (especially regarding staying healthy and safe), we embarked on a five-week workcation.

Okay, so what exactly is a “workcation”?

A workcation is just what it sounds like: a trip where you work by day, and vacation by night and weekend. Workcations can vary in purpose. You could take a workcation in your hometown during the holidays, allowing you to stay longer and have more quality time with family and friends. Or, you could take a workcation to a typical vacation destination (like the beach, mountains, or a big city), allowing you to get a little taste of the location each day. Unlike a typical week of vacation where you try to fill your schedule with all the sights and activities, you can spread them out and experience the location at a slower pace – all while still earning a paycheck!

Is a workcation for you?

A workcation may be for you if…

You conduct your business primarily from a computer, you have an already-established strong work ethic, and if you’re not easily distracted. If you’re like me – you can put some headphones in, crank out projects, and look up three hours later and wonder where the time went – then a productive workcation may be for you. The worst would be getting so distracted by the beauty and fun of your destination that you dread the “work” part of your workcation.

A workcation may not be for you if…

You stick to a strict schedule everyday, are easily distracted, or find it hard to shut down your work brain each day. If you’re someone who answers email, IMs, and texts on your phone 24/7 for work, you’d be robbing yourself of the “vacation” part of your workcation. If you’re easily distracted or need to stick to a strict schedule to remain productive, workcations might not be ideal, as the whole goal is to integrate the two parts of our lives we’ve traditionally thought we needed to separate. And, remaining productive on your workcation is paramount.

All that being said, if you think you can remain productive while working poolside, then read on and don’t think twice about scheduling a workcation!

Key to a productive workcation is high-speed wifi throughout your accommodation.
Key to a productive workcation is high-speed WiFi. Even better, if your accommodation provides high-speed Internet throughout the property so you can unchain yourself from a desk.

Research and preparation are key!

I’m a chronic over-researcher, over-packer, and just general nightmare when it comes to preparing for a trip. For workcations though, you gotta take it to another level, because this isn’t just a vacation – this is your livelihood, your job. While you might book a week-long vacation with little thought or consideration, planning a productive workcation is the time to, well, do the work in advance.

Run it past your boss

Unless you’re a freelancer or work for yourself, chances are you’ll need to run this idea past your boss and/or company. Every company, relationship, and situation is different but nothing would suck more than having to deal with the fall out (and guilt associated) once your boss finds out where you’re working (because they will!). Chances are, they’ll be totally cool (like mine), but give them the courtesy up front. Be prepared to make your case if this type of work arrangement is unique in your organization – ultimately, they’re going to want to know: what’s in it for them and how you’ll maintain your productivity during your workcation?

Consider WiFi and equipment needs

Nothing will make your stress level skyrocket other than not being able to connect and check-in when you need to. Before you book the first cool Airbnb you find, message the host and ask for a screenshot of their internet speeds. The posting might advertise high-speed WiFi when it’s really just enough to stream some music – good luck hosting a Zoom call! What type of equipment do you need to continue doing your job? In my case, I wish I could work solely from my laptop, but I’ve been spoiled with dual monitors my whole career and I feel like I am more productive with more than my laptop screen. We brought two LED monitors in our luggage, along with HDMI cords, docking stations, wireless keyboards, and laptop stands (in addition to the usual mouse, headset, and other basic office needs).

Prepare, prepare, prepare

If you know me, you know I am the Queen of Checklists. I have a checklist for everything – target and grocery shopping, morning routines, Netflix shows to watch – the list goes on. One I added for our workcation is a “Remote Work Checklist”. I created this over a few weeks. Anytime I found myself reaching for a highlighter, a USB, a notebook, pen, Post-it Note, you name it, I put it on the list and that list became my packing guide to make sure I had everything I could possibly need to be productive on my workcation. I also planned my calendar for the five weeks away – walks, lunches, and real vacation days, to make sure I had enough vacation time sprinkled in throughout.

Master your productivity…

I could literally go on and on about productivity. During the height of the pandemic, I found myself really slipping in motivation and, thus, productivity. I randomly signed up for a Lifehack Method webinar, and my work day has been forever changed. Maybe I’ll do an entire post about the crew at Lifehack Method, some of the hacks, and why I think their Tribe membership is the best money I’ve spent in 2020. But for now, below are some basic productivity suggestions to adopt before your workcation.

Plan, plan, plan

No matter how long your workcation – five days or five weeks – I suggest planning your time in advance. Plan broadly: what time will you start working? what time will you have lunch? what time will you end working? when will you take a true vacation day? Block out all of those times on your calendar so those hours and days aren’t gobbled up by someone else’s needs. And then plan specifically, day by day (or week by week). Make a list of all the projects you need to complete that day (or week) and use your task list as motivation to move as efficiently as possible.

The quicker you complete the to-do list, the quicker you can get back to the fun. I’m all about rewards, and vacation has many enticing rewards. In my case, I reward myself with some time at the pool, a walk, or a cocktail when I’ve completed all my tasks for the day.

Reduce notifications

Anyone else look up from your computer at 5 pm, only to realize you didn’t actually accomplish anything that day? You just IMd, emailed, and talked with people on the phone? Same. Until I removed my notifications on my phone and my computer. If you work with desktop with applications like Microsoft, Slack, or Zoom, I highly suggest removing notifications when you receive new messages. That notification or “ping” is there for a reason: it’s supposed to get your attention! But when it grabs your attention, it interrupts whatever task you were working on at that time. When you remove notifications, you can answer correspondence on your terms, instead of always making yourself available to others.

The same is true on your phone. Your family and friends are (hopefully) interested in your workcation and want to know everything. Instead of getting distracted by the numerous texts throughout the day, put your phone on Do Not Disturb, and answer them on your terms. Reducing notifications all around really allows you to take ownership over your day, helping you to accomplish the things that are most important to you first, and then address the needs of others.

Wake up earlier

Iiiiiiiiiiii know. I get it. No one likes to wake up to an alarm on vacation (unless you’re going to scope out sunrise, then in that case, wake me at whatever time needed). But remember, this isn’t only a vacation…it’s a workcation. And the sooner your day starts, the sooner you can transition from working to playing. I like to wake up before the sun, around 5:30 or 6 am, and get a full hour or so of work in before going on my first walk of the day to watch the sunrise at 7 am. It’s all about blocking your workday around things that matter to you. For me, I love watching the sunrise and the sunset, so I bookend by day with walks to go watch both.

Pro tip: Workplaceless is a remote work training provider with a great blog on tips to work and manage teams remotely. They even have a remote work certification program if you want to really prove you can be productive on your workcation!

Remember to take time for yourself during a productive workcation, like watching the sunrise!
Remember to make time for yourself during a workcation. For me, sunrise and sunset are important, so I bookend my days with walks to go watch both.

…so you can get back to the fun!

Anyone else tend to over-plan vacations, cram so much activity into each day that it all becomes a blur, and before you know it, it’s time to head back home? Guilty! The beauty of a workcation is that you won’t feel the pressure to do all the things. Instead, you’ll find time to cook a homemade meal using local ingredients, check out some of the local spots without feeling like you’re missing the best of TripAdvisor, and sprinkle excursions throughout. The freedom and spontaneity are refreshing and a luxury we don’t typically have on a standard one-week vacation.

Productive workcation destinations

Okay, so you’re convinced, I’m sure, that a workcation let’s you have your cake and eat it too. Now is the tough decision of where to workcation. Being based in the U.S., anywhere in North, Central, or South America is ideal. You won’t have to fight time zone differences back at home, and your work day will largely align with the typical workday of your company and coworkers.

When I asked a friend of mine the best places to be a digital nomad, he told me about the Starbucks test. It’s the idea that, if a town has a Starbucks, it likely has all the amenities you’ll need for a successful workcation: established Internet infrastructure, restaurants/coffee shops with WiFi, and any other creature comforts you find important (grocery stores, gym studios, Uber, etc.). This doesn’t just apply to more off-the-beaten path locations in Latin America, for instance. Even the mountain towns in Colorado can vary drastically in their amenities to help you work from home.

Where would I go for a productive workcation?

  • Mexico, but specifically places like Mexico City, Puerto Vallarta, Guadalajara, Tulum, Monterrey, and Cabo. Either metropolitan cities, or vacation destinations with established infrastructure. Now is not the time to venture to the up and coming beach towns. Save that for your real vacation or long weekend while on workcation.
  • Ecuador. With a huge expat community, the country will have what you need in terms of accommodation and infrastructure to experience a productive workcation.
  • Colombia. Bogota and Medellin are booming at the moment. Sure, it still has some shady areas, but Colombia has experienced a resurgence in the past decade and is now a top travel destination for digital nomads looking to stretch their dollar.
  • Peru. I’m not sure if this would be on most people’s list of workcation hot spots, but I just love the country so much, I would be smitten with spending an extended amount of time there. The infrastructure is surprisingly modern in most of the tourist parts, and with a little research, I know you could find a location that meets your needs. Check out our top five cities to visit in Peru for inspo!

The best thing about a productive workcation? Stretching your precious and valuable vacation time. Conduct your business as usual during the day, and then you’re free to vacation each evening and weekend. You’ll have the chance to live and experience local life, and there’s truly nothing better.

My only regret? Not going sooner!


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