I quit my job twice to travel.

First time around in 2008 I was a bit nervous since I was only one year into my career so wasn’t sure how easy it would be to get a job again. But it was a perfect moment, because I was still living at my parents home (planning to move out once back), had zero debt and few expenses and responsibilities to speak off. I worked at a small company and had a good relationship with my boss so I told him about my plans to go backpacking for 6 months in Latin America over a coffee and to my surprise he was very supportive and offered my to keep the job. If I remember correctly I didn’t actually ended up quitting, we just paused the contract.

Key learnings from that trip:

- After the first month, where I went to language school and stayed with a host family, I travelled way too fast. Barely staying more than 1-2 day in a place before moving on. Which is fun at the beginning but it quickly gets old to have the exact same conversations every day with other backpackers doing all the exact same routes. So towards the end I slowed down and e.g. almost stayed a month in Guanaja, a tiny island in the bay of Honduras which made a huge difference in actually experiencing the place.

- Learn as much of the local language as you can. Sure, if you stay on typical lonely planet routes, plenty people will be able to speak some English and these days with smart phones you can use translators, but it makes a world of a difference when interacting with locals, especially if you get out of the tourist/backpacker areas, if you at least try to speak their language.

- The more touristy the place (this includes “secret” tips from books and websites), the more you unfortunately have to deal with people trying to rip you off, pickpocketing etc. No different than in Europe in that regard.

- Don’t be overly paranoid. Yes, all those countries have a significantly higher crime rate than Switzerland where I’m from, but those tend to be focused on certain areas, so if you act sensibly the probability of something happening to you is actually low. Same for food. If you just go for vacation for 2 weeks you want to minimize risk to not ruin it. But for longer term travels I rather be sick for a bit and try things than acting like everything is going to kill me.

- Don’t plan too much ahead. I met people that had exact travel plans fir the entire trip, booking everything ahead of time, knowing which hostal their going to stay in 6 months from now, etc. But in most cases this either just didn’t work out, it robbed them
of flexibility, and also a lot of people only realize after starting traveling that it isn’t really for them. So better to stay flexible.

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The second time for traveling in 2012/2013 it was a bit more complicated, since I now had an apartment full of stuff, various subscriptions, insurances, etc and I planned to travel while working freelance for an unknown amount of time. I quit my job and started freelancing while still staying in Switzerland to build up contacts and starting to organize departure. I travelled for a bit over year in South America, mostly in Colombia and it ended basically by me deciding to just move here.

Learnings from traveling while working:

- Know what you need for working. There is this cliche of digital nomads working at the beach under palm trees, but to be honest it is way too hot/humid for me there to concentrate, and working in an AC’d hotel room is quite silly. So I prefer staying in more temperate climates while working and go to the beach for short trips.

- There is a lot of alcohol, drug use and partying in hostels. Your are not going to work productively if some teenagers are doing cocaine next to you at 10am on Tuesday morning. There are calm and relaxed hostels to be found everywhere, but you might have to look out for them and do a bit of try and error, but I still prefer them over airbnbs most of the time.

- Ergonomics still matter while traveling. While a well equipped co-working space might be less sexy than a hammock, after a while your back and arms will thank you to work more sensibly.

- Use a laptop that you can do basic repairs yourself. I phased out my MacBook because of this. There are more Apple Stores in Zürich than in all of Latin America. And those that can fix it unofficially might still be easily 10+ hours away from where you are.

- Large time zone differences are a curse and blessing. Make sure to align with your clients/employer up front to avoid them insisting calling you at 3am. Better to arrange something were e.g. you do development during their night so they can do testing, presentations, etc. during the day.