How to Plan a Successful Workcation

  • By Jodi West
  • August 31, 2021

For a freelancer, the world can be your office. Sometimes that means working from home, but other times it means the freedom to travel the world—as long as you can get your work done. Freelancers all over are packing up their laptops and hitting the road, mixing their work and vacations into a workcation.

Whether you are looking to take a short trip or hoping to dive into the work-travel lifestyle, having a plan will keep you productive and make the most of your time away. Here is what you need to know to plan a successful workcation. 

Pre-cation planning 

Like most things, a good plan is the first step to quality results, and getting ready for your workcation is no different. You can break down your travel preparations into three categories.

1. Picking a place

Deciding where you want to go may seem like an obvious first step, but location plays a big part in getting work done. For example, if you know you’ll need high-speed internet for a Zoom meeting with an important client, being in a remote mountain cabin may not be the best idea.

At the same time, if you need some space without distraction for a big writing project, a major city could interfere. If this seems like a challenging task, don’t worry, there are resources to help you narrow down your options.

Sites like NomadList can filter a location search with features like wifi speed, cost of living, and ease of public transportation, while AND.CO provides you with the tools you need once you sit down to work. 

After you have decided where you want to go, it’s time to figure out where to stay. When choosing your home away from home, there are a few things to keep in mind, and it’s all in the details.

Finding a place with internet is a must for most freelancers on the go, but not all broadband is created equal. The internet requirements needed to check your email are different from what you need for video meetings, so checking in with the place you plan to stay can save a lot of frustration down the road.

Another thing to keep in mind is where you will be working. 

Having a functional and designated workspace is key to accomplishing quality work and staying productive. Making sure your Airbnb or hotel room has a place for you to set up your computer is a great start, but think about what else you may need. For example, if you are a designer that needs to send out hard copies, check where the nearest print shop and post office is.

No matter what your work is or where you plan on doing it, picking a destination and accommodations that suit your individual needs could make the difference between a successful workcation and a lot of missed deadlines and catching up to do. 

2. Allocating on-the-road responsibilities

Making your workcation work is not just about the where but also the when. For example, going away during the busiest part of the year, when you have the most deadlines coming up, may be a less than ideal time to travel.

On the other hand, if you have a creative project that you need to finish, getting away could give you the focus you need.

Either way, making a clear outline of the work you will need to do while on your workcation is a must before you head out the door. 

3. Packing

As all seasoned travelers know, packing is an art. Getting ready for a workcation is a balance between a vacation and a day at the office, so push your sunscreen and beach towel to the bottom of your bag and make sure you have all your chargers and devices ready to go.

Having already allocated your on-the-road responsibilities will help you know exactly what you need for your upcoming tasks, but it’s worth double-checking everything. Some things to think about are external hard drives, tablets, stylus pens, or a wireless mouse and keyboard—a few power adapters and some extra batteries never hurt anyone either. 

The work in workcation 

Once you have arrived at your dream destination, put your plan into action. This is all about setting a schedule, and most importantly, sticking with it.

The goal is an actionable work-vacation balance, so depending on how long you are away, you may want to break your time into weeks, days, and even hours. However you choose to schedule your time, there are a few essential components to keep in mind to make the most of your work time and your vacation time.  

1. Scheduling

Setting a goal for what you will accomplish every time you sit down to work is always important, and even more so when on a workcation. First, you should already know everything you need to do by the end of your trip. Next, consider mid-trip deadlines and map out your days.

Using a task management tool is a great way to stay on top of your work. That way, all you need to do is focus on one task at a time, and you can be confident that on your return trip home, everything will have gotten done. 

2. Work-life balance

The most important aspect of setting your work-life balance is the balance. That means knowing when it’s time to work and when it isn’t. A workcation without the vacation is just work, so be sure to plan your relaxation as much as your work time.

Think about your high-priority vacation activities and make space for them, keeping in mind the downtime created that can be used to send emails or hop on a conference call. 

3. Staying productive

Achieving a good work-vacation balance is the basis for staying productive on your workcation. But that doesn’t mean it will always be easy. The draw of the beach is powerful, and staying focused and motivated, wherever you are, can be challenging.

One of the best things you can do is get some help. Tools like a time tracking app can help you manage your time, stay on track, and keep you from getting burned out. 

Next stop, anywhere 

One of the greatest parts of being a freelancer is the flexibility it provides. From those thinking about their first work trip to seasoned freelance travelers, there are many strategies and tools that can help your work take you anywhere.

Like most things, a little planning goes a long way, so think about these tips for success on your next adventure and feel assured that you can handle whatever unanticipated curves may come your workcationing way. 

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