Planning a Workation

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How To Plan A Workation Like A Pro

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I’m in London typing today’s article from the comfort of my in-law’s cozy new couch. I’m on Day 2 of a 30-day vacation and couldn’t be more excited!

If you’re a US-based worker like me, I’m sure your first thought was, “How is she pulling that off?!” I’m not using accumulated vacation time, I’m not on medical leave, and I’m not independently wealthy (unfortunately). The secret to my month-long vacation is a booming trend called a workation.

Don’t have time to read it all?

A workation combines travel and remote work, allowing you to explore new places while maintaining job responsibilities. Benefits include increased productivity, improved work-life balance, and enhanced creativity, but potential drawbacks like distractions and connectivity issues must be managed. Proper planning, setting boundaries, and using tools like eSIMs for reliable internet access are essential for a successful workation.


What is a Workation?

A workation, also known as a “working vacation,” is a mix of travel and work. It lasts significantly longer than a traditional vacation and allows you to explore new places while fulfilling your job responsibilities remotely.

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After wrapping up work for the day, you can explore your new environment, sample local cuisine, or socialize with residents and fellow travelers.

Weekends transform into mini-adventures, where you can explore your temporary home’s culture, history, and attractions in greater depth.

It’s the perfect solution if you love to travel and want to keep your finances stable.


Benefits and Potential Drawbacks of a Workation

The benefits of a workation are plentiful. Aside from experiencing new cultures, you can also avoid the stress of taking time off from work and returning to a pile of tasks waiting for you.

Plus, it’s an excellent opportunity to enhance your productivity and creativity by changing your work environment.

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However, there are potential drawbacks to consider as well. Maintaining your regular home and paying for accommodation elsewhere can get expensive. The work-life balance may become blurred, time zones may become hard to manage, and you might never want to return home.

The Benefits of a Workation

Increased Productivity

Many people find that a change of scenery can invigorate their work habits. The new surroundings can stimulate creativity and enhance focus, increasing productivity.

Improved Work-Life Balance

Combining work and leisure helps better balance professional duties and personal relaxation. This balance is essential for mental health and overall well-being, and it’s a great way to combat burnout.

Enhanced Creativity

New environments often bring new perspectives. Being in a different setting can inspire innovative ideas and solutions that might not emerge in a familiar workspace.

If a workation isn’t in your near future, read my article on how to boost your productivity with inspiration from the world’s most creative cities.

Potential Drawbacks of a Workation

Distractions

The allure of a new location can sometimes be too tempting, leading to distractions that can hamper your work. It’s crucial to set boundaries to ensure productivity.

Connectivity Issues

Reliable internet and cellular service is vital for a successful workation. Poor connectivity can disrupt work and cause unnecessary stress.

Work-Life Blur

While a workation aims to balance work and leisure, the lines can sometimes blur, making it challenging to completely switch off from work. If you don’t have a dedicated workspace, you must rely more heavily on self-discipline and time management skills.


How to Plan a Workation Like a Pro

Planning a workation may seem daunting initially, but you can make it happen with organization and creativity. Here are some tips to help you plan your next workation:

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  1. Choose Your Destination Wisely: Consider places with reliable internet access, affordable accommodations, and cultural experiences that interest you. A hermitage in the Himalayas may be better suited for a vacation or sabbatical, while a three-month tour of Europe or a residency in Kenya might be a better fit for a remote worker.
  2. Plan Ahead: As with any trip, planning in advance is crucial. This allows you to book accommodations, secure necessary visas or documents, and arrange work-related tasks before departure. This doesn’t mean you need to book every tour and excursion before you leave – the beauty of a workation is that you can let your interests unfold naturally.
  3. Plan Your Schedule: Set a schedule for work and leisure activities to maintain a healthy balance during your workation. Take into account time zone differences and the needs of your client/employer. As much as a workation is about discovering new places and things about yourself, your priority is to keep working seamlessly.
  4. Set Expectations with Your Employer/Clients: Discuss your workation plans with your employer or clients and agree upon expectations and deadlines. If there are any days you need to be on Paid Vacation, state them clearly. I, for example, have booked PTO for days when I have flights, rest days, and special events, just as I would if I were working from home.
  5. Stay Connected: Research internet and cellular options at your destination, have backup plans in case of connectivity issues and stay in touch with colleagues/clients through communication channels.
  6. Have a Backup Plan: In case of connectivity issues, have backup plans for portable Wi-Fi devices.
  7. Pack Efficiently: Only bring essential work equipment and pack light to make traveling easier.
  8. Set Clear Boundaries: Workation can blur the lines between work and leisure, so it’s necessary to establish clear boundaries. Set specific working hours and stick to them, avoid checking emails during non-working hours, and schedule breaks and time for leisure activities.
  9. Disconnect When Needed: You might need a vacation, even on vacation. It’s perfectly reasonable to still feel stressed from work pressures and take some self-care days while you’re on your workation.
  10. Stay Motivated: Remember why you chose a workation in the first place and stay motivated to achieve your work goals while also enjoying the experience. Think of it this way – the better you succeed with your workations, the more of them you’ll be able to take.

How to Talk to Your Manager About Your Workation Plans

Communicate Your Intentions

Before embarking on a workation, discussing your plans with your manager, team, and HR is essential. Clearly communicate how you plan to fulfill your duties and maintain your productivity while away. While it’s unnecessary, you can get brownie points for offering your reasons for wanting a workation and how it can benefit your productivity and well-being.

Understand Your Companies Guidelines and Policies on Remote Work

Familiarize yourself with your company’s guidelines and policies on remote work. This will help you understand any limitations or expectations for working remotely and ensure you follow company protocols.

Create a Workation Plan

Outline your workation plan, including your destination, duration, and how you intend to manage your responsibilities. Discuss your communication plan and how you will create a suitable workspace at your chosen location.

Be Prepared to Address Concerns

Your manager may have concerns about your workation, such as potential distractions or lack of availability. Anticipate these concerns and come prepared with solutions, such as setting clear boundaries and having a backup plan for internet connectivity.


Tools to Achieve a Successful Workation

Project Management Tools

Tools like Trello, Asana, and Monday.com can help you manage your tasks and collaborate with your team, ensuring you stay organized and productive.

Communication Platforms

Stay connected with your team using communication platforms like Slack, Zoom, and Microsoft Teams.

Time Management Apps

Apps like Toggl and RescueTime can help you track your work hours and ensure you stay focused.

An eSIM

In case I have yet to say it enough, connectivity matters. For local internet and data connections, activate an eSIM like GigSky on your mobile device even before your trip.

What is an eSIM, and Why is it Beneficial to Global Travelers?

An eSIM (embedded SIM) is a digital SIM card that allows you to activate a local cellular plan without using a physical SIM. This technology is particularly beneficial as it offers the flexibility to switch between different carriers and plans without the hassle of changing SIM cards.

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Benefits of eSIM for Travelers

Convenient

With an eSIM, you can easily switch between carriers and plans, making it convenient for frequently changing locations.

Cost-Effective

eSIMs often offer more competitive rates than traditional roaming charges, helping you save on international data costs.

Space-Saving

Without a physical SIM card, eSIMs offer one less thing to keep track of.


Why GigSky is My Preferred eSIM Provider

GigSky is a leading provider of eSIM technology, offering unparalleled access across the globe. Here’s why GigSky stands out from the competition:

Global Coverage

GigSky provides coverage in over 190 countries, ensuring you stay connected no matter where your workation takes you.

You’re also covered while in the air and out at sea. With coverage on roughly 200 cruise ships throughout the Gulf of Mexico and the North Sea, you can save a fortune with GigSky instead of buying small data bundles from cruise lines.

There are currently over 20 different airlines where GigSky operates seamlessly. No eSIM competitor can boast the same land/sea/air combination.

Heavy MVNO

Almost every eSIM company on the market today is just a reseller of someone else’s services, but as a ‘Heavy MVNO,’ GigSky is an actual network operator, meaning that if a particular network goes down, GigSky simply shifts users to one that is not down. eSIM resellers are not able to do this.

My favorite feature of GigSky is since they are an operator, I only require ONE eSIM. GigSky automatically shifts my plan to the country I’m in.

Each plan generates a new eSIM for resellers, requiring a fresh download and activation each time I change countries. Ugh!  

Access and Customer Support

Confession Time: I am technologically challenged. If I had a superpower, it would cause glitches in glitch-free technology. Luckily, GigSky offers 24/7/365 live support. Yes, live. What a relief!

The GigSky app also acts as a captive portal, meaning you can always access their services, technical support, and app if there is internet or cellular service in the area.  

Free Plan Option(s)

GigSky is the only eSIM company that offers a free plan, allowing users to test the service before committing to a paid plan. When creating an account, simply select “free 100MB plan,” activate your eSIM, and that’s it. You’re set.

Additionally, they are partnered with Visa. Now through November 2025, when you download the GigSky app, you can redeem 1GB of data, valid for 15 days, which can be used in more than 125 countries.  


Where to Get GigSky

To start enjoying GigSky’s seamless eSIM service, visit their official website or download the GigSky app from the App Store or Google Play.

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For an exclusive offer, use my affiliate link here and enter the code CHIOMA10 for a discounted rate. By using this link, you’ll get the chance to explore the benefits of GigSky’s service and support my work.

Step-by-Step Guide to Installing a GigSky eSIM

1) Check Compatibility:

Ensure your device supports eSIM technology. Most modern smartphones and tablets are eSIM-compatible.

2)Download the GigSky App:

Visit the App Store or Google Play Store to download the GigSky app.

3)Purchase a Data Plan:

Choose a data plan that suits your needs and purchase it through the GigSky app.

4)Activate the eSIM:

Follow the in-app instructions to activate your eSIM. This usually involves scanning a QR code or manually entering a code.

5)Enjoy Seamless Connectivity:

Once activated, your eSIM will connect to the local network, allowing seamless internet access during your workation.


How I Plan to Use my GigSky eSIM on my Workation

GigSky now offers unlimited data plans, and it was tempting to purchase one so that I would not have to think about data while I’m out here. However, I chose their 10G/30 Day Europe plan covering 44 countries.

I’ll visit four countries this summer, all covered by the Europe Plan. Mostly, I will have internet access in hotels and resorts, so I can keep in touch with work, family, and friends through Wi-Fi-enabled apps.

I’ll use my cellular data to check in from museums and beaches, call taxis and Uber, and video call my bestie from the store to help me decide between the red dress and the blue one. Hint: I’ll buy both.

Fortunately, if I’ve miscalculated my connectivity needs, I can seamlessly top up my available data through the GigSky app. They really do make this too easy.

Have you taken a workcation before, or is it something you’re planning to do? Share your best tips or biggest concerns in the comments. Happy workationing!


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Hi, I'm Chioma Ikoku, a spirited explorer and a peace-loving homebody. I founded Casa Diem Life to help you combine the excitement of travel with the comfort of home, because I believe that adventure begins at home.

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