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When to Tell your Boss you are Becoming a Digital Nomad

Updated: Sep 15, 2019

How soon should you propose working 100% remote, without loosing your job in the process?

There is a fine line when determining when to strategically tell your employer that you are becoming a digital nomad.

On one hand your employer might decide to keep you on, working 100% remote. And in that case it would be nice to have a few months in your home country to perfect the new work environment and expectations.

On the other hand your employer might decide since you are essentially quitting anyways to walk you right then and there. This could be problematic if you where counting on those last couple of pay checks before leaving the country.

How soon should you propose working 100% remote, without loosing your job in the process?

I have decided to tell my boss two weeks before I plan on being "unemployed". That way, if my employer does decided to "walk" me, missing one paycheck won't kill me. But if my employer decides to give the remote work a try, I have 4 weeks left in the country and can organize myself appropriately for success.

Here is the rough timeline I have worked out:

  • April 15- Tell my employer I am going remote

  • May 1- Stop working (potentially) in order to finalize any loose ends before I leave the country

  • May 13- Hop on my one way flight to Bali

There is a 50/50 chance that my employer will want to keep me on, even only part time because of my expertise and niche skill set. Because of this, I think those extra two weeks between May 1 and May 13 will be very helpful to streamline the expectations and the software I will need to be able to perform my job around the world.

But this is just theory, I will let you know how it all pans out! And you can learn from my success and mistakes.

UPDATE: (4 months later)

I ended up telling my employer the first week of April, giving my full time employer over a month's notice. I realized that the traditional two weeks wasn't going to be enough time, and I wanted to show the immense amount of respect I have towards this company in my actions. It turned out great, I presented the idea on a trial bases, and my bosses were willing to test out this new concept. Fast forward four months, and I am still working with this company remotely and it is going exceptionally well!

To learn more about how I successfully presented this idea to my full time employer read this blog post here.

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