Quit your job and freelance on this island… Or should you not?

Freelancing on an island is the dream of almost every non-freelancer. “I will quit my job, and freelance on this island for as long as I can.” The idea of being in such a beautiful place while working seems attractive to many.

Truth is, one’s brain is the player in this situation. Your brain associated your corporate office in the city with discomfort and unhappiness. Thereby, when you’re being presented on an island like the one in the picture (which is in Bali, Indonesia btw.), your brain goes into ecstasy and tries to be convincing.

I’ve been a freelancer for around 10 years now. I’m now based in Zurich (which is quite the opposite of an island.) Yet, there were times where I went to islands and worked there for a few months. Here’s what you should know:-

1. You get used to it.

You are starstruck by the beauty. But after a while, your brain associates this location and view with indifference. Yes, it’s the beach. Yes, we saw it yesterday, and it didn’t change. It could eventually lead to situations where your brain would actually connect the island with stress and unhappiness. In that case, it’s probably neither the island nor your office in the city, it’s your work.

2. You need discipline.

It’s highly dependent on the person and her/his discipline. If you’re working as a freelancer in an organized hourly fashion, and you know when to shut down your devices, then you could possibly find joy in your new paradise. However, if you’re the type of person who would need to keep checking the phone every hour or so, it’s almost useless to be there. You’ll miss out.

3. Beware of the mix.

The pickle would appear when a person would quit her/his job just to fulfill that dream and freelance on that beautiful island. There’s a chance that your brain will start feeling worried after a few days/weeks of excitement. You’ll constantly have an inner feeling that you’re doing something wrong. That you’re failing in life. That you gave up something amazing. This line of thought could be poisonous, and will eventually lead to a non-pleasant experience.

4. It could be the best decision you’ve ever made.

If done correctly, living in a paradise, especially if you don’t work that much, will expose you to a different world within yourself. You’ll be able to appreciate the small things compared to the fast-paced surroundings in cities. The only obstacle to bypass is the contradictory life of an island minimalist compared to a city workaholic.

At the moment, you see it as a fantastic option, and your mind, to access the ecstasy, is blocking your thoughts. You won’t be able to get that coffee cup from your favorite coffee shop. It doesn’t sound like a problem right now. Nonetheless, you’ll know how much you love that coffee cup the more you stay away from it.

5. Should I just do it? Quit my job and freelance on an island?

That would probably not be the wisest idea. If you’re thinking clearly, the best decision would be to ease it in. Initially, if you’re unhappy with your job, find a freelancing venture and start with it parallel to your job. If you believe you won’t be able to do this because of your “time”. Sort out your time management skills, and do it. The more you freelance, the more you’re confident that it’s a safe journey to get into.

When you’re ready, you’ll know it. You should go for it then. Get that flight ticket, relax in the hut, work a few hours in the morning with your mojito. Then, after a few months, if you dislike it, the choice is yours. You can try somewhere else. Alternatively, you can live in the city and work in your favorite coffee shop. You can return to your corporate job. Your options are endless then. What you did was check the weather, before flying your plane.


There are a few things to consider in such situations. A person is not her/his job. When you choose to freelance on a beautiful island. You need to assess yourself as a person outside of work. It takes incredible self-discipline to be able to live a minimalist’s life. You’re currently unaware of what your subconscious mind would prefer to live with or without.

In order to embark on such a journey, you need to get to know yourself better. Only then, when you’re fully aware of what you can and can’t do, will your mind have the clarity to undergo such a decision. I’ve met people in my freelancing world who are doing this. Hands down, they’re some of the happiest people I know.

I’m Al, a business consultant in Zurich, Switzerland. I believe in providing readers with value. Hence, I created Learn, a section on my website purely dedicated to guides and articles providing value in the fields of Freelancing, and Entrepreneurship. Alternatively, you could visit my journal for all my articles, or my Medium profile.

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