How to Convince Your Boss to Approve Your Workation

Receive All Insider Tips 👇

The concept of a workation—blending work and vacation—is gaining traction. But how do you get your boss on board? This article breaks down the process into three straightforward steps, addressing potential concerns and highlighting the benefits for both employees and employers.

Step 1: Understand Your Motivation

Before approaching your boss, be clear about your reasons for wanting a workation. Here are some compelling reasons you might consider:

  • Mental Health Boost: Working remotely, say from a serene spot in Portugal, can rejuvenate your mind, leading to increased productivity.

  • Focused Work: The constant buzz of office life can be distracting. A workation can offer a peaceful environment, allowing you to concentrate on significant projects.

  • Extended Breaks: If your role doesn’t allow for long vacations, a workation can be a compromise, letting you relax without completely disconnecting.

  • Temporary Relocation: If you’re between homes, why not spend that transition period working from a picturesque location?

Step 2: Craft a Well-Thought-Out Proposal

Once you’ve identified your reasons, it’s time to draft a proposal. Here are some guidelines:

  • Be Transparent: Clearly state why you want a workation.

  • Provide Data: Back up your proposal with statistics showing the benefits of remote work for the company. For instance, studies have shown that digital nomads are 13% more productive than their office-based counterparts. Moreover, remote workers report taking fewer sick days, leading to cost savings for the company.

  • Suggest a Trial Period: Propose a short-term workation to demonstrate its feasibility and benefits.

Step 3: Address Potential Concerns

Your employer might have reservations. Here’s how to address some common objections:

  • “Remote work harms company culture.” Highlight the benefits of a diversified work environment and how remote work can introduce fresh perspectives.

  • “I want you in the office.” Propose regular check-ins and updates to keep your boss informed.

  • “I can’t monitor your work.” Suggest tools or software to track tasks and productivity. Emphasize the importance of results over physical presence.

Additional Benefits for Employers


Remote work is more than just a trend—it’s the future of work. If your employer is hesitant, use the data and arguments in this article to make your case. Remember, the key is to show how a workation benefits both you and the company. Interested in exploring more about workations? Check out our comprehensive workation guides!

Discover helpful tools for your workation


Visa finder

Please check if you need a remote work visa


Workation Wizard

Find your perfect workation destination


Work-friendly accommodations

Find the perfect workspace for your workation

Travel insurance check

Make sure you have the right travel insurance for your workation

Popular destinations

Popular articles

Share with Friends and Colleagues


Get All the Insider Tips (and a welcome gift!)


Need Help? Let's Plan!

We’re here to make your remote work adventure smooth and stress-free

Feature List

Personalized support and answers

Safe, reliable travel planning

No fees, just honest advice

One of our Remote Work Experts will respond to your question within 24 hours. We’re here to assist you on your workation journey!