How To Go On Vacay When You Are a Freelancer (Digital Nomad)

The whole idea might sound crazy, but actually, it's a new reality that we have right now. More and more people leaving their 9-to-5 jobs and start freelancing on their own, or doing their own business.

There are several types of people who work independently whether it's a client work or a startup. Let's combine both and call it a remote business.

The majority of people are still working from home or a co-working space in their hometown, but it's more and more popular to travel and do your business on the go.

The main reason for it is to reduce costs of living if let's say you go to a cheaper city or country. So you can bootstrap your business and have fewer expenses than in your hometown. This is something that allows you to experiment more and basically have more time for the development.

The second reason is to enjoy your life by traveling to new destinations. It includes seeing new places, cultures, meeting new people, trying local food and more.

This is something that makes your life more interesting and helps you to not focus only on your business all the time. It's a natural way of having fun from time to time. So you don't stuck in front of your computer 24/7 and trying to squeeze some results every minute. You need a break even if you don't want it. Because even if you go for a lunch on a new location it could be an adventure itself.

After some time of traveling continuously, you stumble upon one interesting fact that you no longer see the difference between workday and weekends. Especially, if you're doing your business solo. So you don't interact with too many people that have a standard weekly schedule.

Later on, you realize that you don't have such thing as a vacation time and holidays seem weird for you. Since you have important things to do and you think that you have to do it right away. But all people around you having fun at this moment and it feels like you're out of this planet.

I stumbled upon this issue many times and the longer you work and mixing it with your personal life the more time you need to switch off and just having your own time.

It's filling the void with more life that is hard. Finding excitement, as it turns out, takes more thought than simple workaholism. - Tim Ferriss

Do you even need a vacation if you have a dream lifestyle?

First of all, everyone has his own understanding of a perfect and so-called dream lifestyle. Secondly, living this independent or nomadic life it's hard to completely apply anyone else's experience or vision. So you're the only one who decides how to live your life, do your business, when to take a break and if you even need it.

I read a bunch of blog posts on this topic. Since it's a question I was looking for an answer on for a long time. But after some time I realized that I'm the only person who knows the answer. However, I had to make sure that I do understand alternative mindsets, schedules, ways how other freelancers and digital nomads mixing their businesses and travels.

Some people have crazy schedules like doing everything on the go, like literally on trains, flights, in airports, even standing in line for something. I did it myself and occasionally still do it that way. Because it's a time when you wait for something anyway.

A couple of weeks ago I had like 2-3 days on a new location and basically, I was strolling during the day and worked at night in AirBnBs. That's tiring and I feel like I can't do it forever. I've heard the same from other people.

Sometimes you need to settle down for a couple of weeks or a month to do the maximum for your business and then take a break for a week or two and go to explore the location or places nearby.

You can't live in the same pace all the time. We're not robots and linear way of living or doing anything is killing us mentally, or making us boring.

Whatever lifestyle you have you need to take a break from it from time to time. Just change anything for a week or so and you will open yourself for something new. Sometimes we need to change our routine to start seeing things differently. Or if we have a problem that we can't resolve on an everyday basis we can do it easily after breaking the usual schedule.

The word "vacation" might sound weird for freelancers and digital nomads, but you can call it whatever you want. The only thing that is important here is that you'll improve your life by making these breaks.

How can you go on a vacation if it feels like a vacation already?

People go to Thai islands or Bali to bootstrap their businesses and mixing with beach time, surf lessons, hanging out with other nomads. So how can you take a break from this? I mean what will you do then if you already on an island and going to the beach like every day.

I thought that having this lifestyle you don't need any vacation, but in practice, you need longer periods of time off the work than a couple of hours every day. It's just not enough to switch off completely from thinking about your business and enjoy other activities.

Answering the question I'd say that the best way to take a break is to plan it ahead of time.

You can say that in a month you're going somewhere and you're going to spend this time alone, or with family, or doing something not related to your business. Just block a week, 2 weeks, or 1 month of time in your schedule, tell this everyone who works with you whether it's a client or business partner.

Get everything done before your time off. So you'll not have anything urgent during your vacay and nobody will disturb you.

Arrange all the bookings you need, plan things that you want to do ahead of time. Because we tend to waste our time if we don't have even a basic plan of Do's and Want's during our vacay.

Let's say you want to read a book, or spend time with your family near the beach, or travel somewhere where you don't have access to the Internet. So you'll have time to think about everything without distractions like social media.

Even if your vacay started already some people can't switch from the work mode right away. And doing this time off is a good way of thinking about everything you do from another angle and eventually think about a better strategy, but don't actually do anything during that time. Just observe yourself from the side and think about actions you can do to improve your life in different aspects.

The last time I had a vacation I've cleaned up the mess I had in my planning system using Trello boards. I couldn't find a way how I can organize everything if I have more and more projects emerging in my life before I took a break. After a week and a half doing nothing and rarely opening my laptop, within one evening I found a perfect way of resolving my organization issues. I'll be writing a separate detailed blog post on this very soon. Also, I spent an amazing week with my family on the coast of Spain and almost finished reading the book I wanted to read for a long time.

I couldn't enjoy doing all these things being in a work mode and thinking about my business on a daily basis. So having a break like this helped me to spend all my time with family, personal stuff and thinking about everything. It's a golden time when you're busy with many projects like every day and doing everything as fast as you can to fit everything in your schedule.

Thanks for reading,



Join my personal email list and receive an email from me every 1-2 weeks.

So if you like the stuff that I write on the website then leave your email to get it right into your inbox. No BS, spam or tricks... just useful content: