entrepreneur on workcation

A common dilemma for modern-day entrepreneurs is that they don’t want to sacrifice their lives for work, but they don’t want to fall short on income at the same time. 

The solution? 

A workation ‒ a little bit of life experience, a little bit of work ‒ a perfect work-life balance, or is it?

For present-day entrepreneurs and executives, with remote teams spread across the seven continents, always being connected and ready to contribute as needed is a compulsory part of the job. It’s hard to unplug, no matter how much you may crave an escape. 

As such, “workation” has become a popular buzzword, a phenomenon that strives to combine the best of both worlds and offer a welcome escape for entrepreneurs who feel too guilty to take a break from work. 

In its simplest form, a workation is when you take a trip somewhere (usually for an extended time) and work remotely from that location. This type of setup can allow you to experience new cultures and try out new things without falling massively behind at work. 

In 2018, the idea of a workcation didn’t appeal to 70% of Americans. Compare that to 2021 — according to a Harris Poll, 74% of remote workers feel ready for a workcation. However, workcations may not be for everyone. Since business owners and entrepreneurs are already working around the clock, experts caution against further blurring the line between work and vacation. 

So, before you buy the next plane ticket to Bali, ask yourself the following questions and analyze your responses carefully. 

1. Do You Get Bored During Vacation?

Nick Vujicic Instagram post


Time to unwind is CRUCIAL, there’s no doubt about that. However, not every person likes to lie on the beach all day long for weeks on end. After a couple of days of sipping and dipping, some people get bored and crave a creative outlet. 

As they become more rested and relaxed, these types of people feel an increase in their creativity and want to make use of it. For most entrepreneurs, their business is a labor of love that they don’t want to stay away from for too long. I know some of my best ideas come to me while I’m staring at the sea.

If that’s you, you will definitely enjoy a workcation because it can inspire you to approach things in unusual ways that may actually benefit your business. 

2. Do You Like to Immerse in the Local Culture?

Some people don’t like rushed vacations—myself included. They want to stay at one place for at least a couple of weeks and really get to know it. They want to explore, meet the locals, hang out with them and eat where they eat. Immersing yourself intimately into the local culture can be an extremely rewarding experience. However, that’s not really possible on a weekend or even week-long vacation and most people can’t stay cut-off from their business any longer than that. 

The ideal solution? Take the work along with you. Workationing is your ticket to staying longer at a destination and temporarily living there. Work for a few hours, then explore the area for the rest of the time and get to know the world around you. Who knows, you may even forge lifelong friendships or open up new business opportunities

3. Is Your Team Ready to Manage in Your Relative Absence?

Workationing isn’t just about work; it’s equally about vacationing as well. However, it means you’ll likely be clocking fewer hours than usual. You can pre-plan some tasks that don’t require your active involvement, such as social media automation, but it’s handy if you have a trusty team that can step in for you on some tasks. You should designate a person to be in charge of managing the team in your absence or to alert you to any emergencies.

If you haven’t designated this type of role on your team, maybe it’s time to look into it. Lay down standard operating procedures (SOPs) for all critical tasks as well. These SOPs, training, and automation will also come in handy as your business progresses and you’re ready to scale. 

4. Can Unexpected Circumstances Affect Your Productivity?

Travel can bring about many surprises. There can be connectivity issues, power outages, phone service issues, or several unpredictable situations due to natural disasters ‒ like a global pandemic! If these unfavorable situations can frazzle you easily and hamper your productivity even after everything’s back to order, you should think carefully about going on a workcation.

Choose your destination carefully. Maybe join a retreat or co-living space if you’re going alone or with your team to make sure everything’s as reliable as possible when you sit down to work. A workcation can be an excellent opportunity to meet like-minded entrepreneurs and forge relationships, too!

5. Does Your Travel Partner Understand Workcation Limitations?

It’s crucial for you and any travel buddies or partners to be on the same page and understand typical workcation constraints. Like the fact that you’ll actually need to work sometimes! You will need to block a few hours every day to catch up with your team and attend to clients. You may not always be ready for an impromptu event or fun opportunity, and anyone you’re traveling with needs to be OK with that.

When everyone is on board with the idea, everyone’s expectations will be met and you can get to work with peace of mind. Workcationing can be an enjoyable way of spending time with a partner or friends at an exotic place longer-term without feeling guilty and stressed about neglecting your business. 

6. Do You Understand the Tax and Other Legal Implications?

Your workcation destination could be in another US state or another country across the globe. From unemployment to taxation, each state has its own laws that you should be aware of before packing your bags and leaving. Similarly, some countries have detailed legislation for digital nomads and remote workers, while others may not have clear policies. Before selecting a destination, you should make sure you understand all policies to avoid penalties and fines. 

If you’re feeling stuck in a rut of routine work from the confines of your home office, ask yourself if a workation might be the right solution for you. If you find that a workation suits you as a remote entrepreneur, don’t wait another minute, pack your bags and go!