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How Far in Advance to Plan as a Digital Nomad

What is the perfect combination of planning vs. being open to new friends and new possibilities?

Bali 2019

Some people like to fly by the seat of their pants, and other people like to plan months even years in advance, but which one is better for the Digital Nomad lifestyle? Like most great questions, the answer is... it depends. But what I can give you are the tips and tricks I have learned and what works best for me.

To Give You a Little Background

I have been traveling full time since May 2019, and before that I had traveled to about 15 countries on different breaks from college or vacations. Based off my previous traveling experience, I figured it would be nice to plan about 1-3 months in advance, and otherwise see what opportunities pop-up.

I had always had such a fun time buying a one way ticket, and seeing what the universe put in my path. Needless to say when I started nomading I followed the same strategy.

I started in Bali, and booked three months worth of accommodation there, and figured I would let the rest play out.

What I Learned

Being whimsical sounds fun in theory. In practice it was stressful as hell!

I realized, when I would travel before, I was on vacation mode. So it didn't matter to me when I would arrive, leave, or anything in between. But traveling as a working digital nomad is completely different.

My old whimsical ways caused myself and Andres quite a bit of stress around the end of month three in our journey.

We were coming to the end of our time in Bali, and we knew we wanted to stay in Lisbon, Portugal to check out the Digital Nomad scene there. And then meet my family in October to travel around a bit as well. But other than that, we were pretty open to see what possibilities came our way. However, traveling around Europe gets more expensive the longer you wait, so we saw trains and flights we had looked at in May cost almost double when we checked back in August.

Another issue we had to consider was wifi capabilities. I work in graphic design, so the typical run of the mill wifi isn't usually powerful enough for me. So when I was trying to plan out my next three month stent in Europe it proved to be more difficult than I expected trying to factor in not only working time, phone calls, but also wifi I could count on.

The cherry on the cake was that I was trying to research, make decisions, and book everything my last week in Bali.

So the stress was compounded by the natural stresses that come with leaving one part of the world and moving to a completely new one.

My hat goes off to travel agents who book travel for a living. Trying to balance and coordinate planes, trains, buses, luggage requirements, checking if airlines allow surf bags, timezones, and business calls, all while trying to stay within budget was enough to make my head spin (and may have lead to multiple bottles of wine thoroughly enjoyed).

It also causes me to not enjoy the moment and where I was at. My last week in Bali was a blur, and my first week in Lisbon was even more hazy. Between getting settled and trying to book the rest of the next 3-6 months, my mind was tapped out. Luckily I spent four weeks in Lisbon so being mentally exhausted for the first week wasn't a catastrophe, but if I was only going to be in Lisbon for a week, that would have been much more upsetting.

The conclusion I came to is that as a digital nomad, I prefer to plan 3-6 months in advance on a rolling basis.

So I will never again wait until a few weeks before my next chapter to start planning transportation and accommodation. I think there is still room for some spontaneity when to comes to weekend or short trips, to visit the surrounding areas with friends. But for me, I like knowing I will have a place to sleep, leave my stuff, and work efficiently.

Like all great questions though, the real answer is it depends on YOU!

To help you make the right decision for yourself, here are some pros and cons to consider.

PROS to planning more in advance:

  • Less stress

  • Potentially cheaper

  • Ability to ensure high quality wifi easier

  • Ability to coordinate travel plans with friends

  • Ability to have a home base and go on smaller shorter spontaneous trips with new friends

  • Able to research and overlap travel with large national or ceremonial events (like Carnival & Oktoberfest), with conferences and learning opportunities, with networking opportunities (like the Nomad Cruise).

  • Able to pack better because you know what types of weather you will be in

CONS to planning more in advance:

  • Less flexibility and spontaneity

  • Not able to plan large trips on short notice with new friends you meet

  • Spending quite a bit of money upfront. For example the down payments on accommodations on Air BNB, flights, etc.

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