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Hey there, ambitious one!

Thank you for dropping in to this article. It tells of the ups and downs I ran into while transitioning from office job to remote life.

I boiled down the 7 months it took me to go from idea to boarding a plane into 10 “steps”. Are they in order? Eh, kinda.

Hopefully these help you with whatever decision you may be trying to make!

Here we go:

Most importantly, I decided. Period.

So I had this thought: “I am going to work remotely and travel the world!”

Then what happened?

  • My employer said no when I asked. That path to my dream was cut off.
  • My travel-group invitation expired (because my employer said no). Another dead end.
  • Friends and family questioned and disagreed with me. Support didn’t come so easy.

If I wasn’t convinced and sold on my idea, I might have caved. Had I caved, I never would have left.

Obstacles will get in your way, and the only way to get what you want is to push through them.


To decide, I weighed the options.

Before I was fully decided, traveling the world was just an idea. Just a dream that I really really really wanted.

I’m the type of person who analyzes everything.

“Just do it” is so much easier said than done. I questioned my own thoughts and wanted to know I was making the best choice.

So I compared my options:

  1. Stay at my current company.
  2. Get a remote job.
  3. Change jobs to another company in the area.

I had pros and cons on white boards, I wrote out lists on countless pieces of paper, I did 80/20 analyses of my happiness, I made spreadsheets.

Basically, I worked to get to the point where there was no doubt this was what I wanted. I worked to get to the point where I decided.


I made it easier on myself.

Traveling the world alone is was a scary thought.

Add in working full time and there were a lot of decisions I would have to make on an going basis.

  • Where should I go next?
  • Where will I stay?
  • Will there be good enough internet?
  • Will there be flushing toilets?
  • And on, and on…

I eliminated most of these concerns by choosing to travel with a nomad group.

This put the responsibility on them to choose the city, to find the place, the WiFi, find the sights to see, and best of all, the people to travel with!

Paying “rent” to them, which I’d have to pay anyway if I went alone, seemed totally worth it to take a load off my mind.


I started adopting minimalism.

This podcast definitely changed my mindset on life in general, but a lot of what they talk about prepared me for the jet-setting life.

Own less things.

Consciously choose your life.

Do what fulfills you.

Goodwill got many donations from me in the months before I left. I wanted to store as little as possible so I sold what I could. You can’t carry an entire bedroom in a backpack, and I didn’t want to!

Do more with less.

I looked for anyone that would allow me to go.

In this case, a remote job.

My employer shot me down when I asked if I could go remote. So what did I do?

I accepted it wasn’t going to happen, laid down on my bed, and cried.…Just kidding.

I started applying to remote jobs!

How many?
So many!

Every remote job I felt eligible for, I applied to. Every interview I had I asked, “Do you allow your employees to travel while they work?”

Each application, each interview, I told myself, “This could be the one!”

Eventually, one was the one.

I was open minded…whatever that really means 😀


I pushed past the mental doubt.

I worried SO MUCH about what I was getting myself into.

  • How would I do my laundry?
  • What would I do if the WiFi went out?
  • What if I didn’t recognize the foods at the grocery store?
  • What if I got injured?
  • Would I get robbed?

Doubt creeps in so easily when we’re thinking of making big changes. If you give in to it you’ll never change.

Understand that you don’t have to listen to that voice in your head telling you not to.

This was a BIG one for me. My friend Diego of www.wifitribe.co can tell you all about the million questions I asked before I got on my flight.


I accepted I would figure things out as I went.

My Spanish is half decent and I was heading to South America, so I could ask for help if I needed it.

Yet, I still had the feeling that I needed to know everything I possibly could about where and how I would live.

Looking back now, it seems like I wanted the same level of certainty about where I was going compared to where I had been living the past three years.

It wasn’t going to happen!

Accepting this, and realizing I would learn as I go calmed me down and made me whole lot more ok with the idea of living in another country.


I trusted someone I barely knew.

Letting go is hard.

It’s one thing to trust yourself to figure things out. It’s another thing to trust someone else to provide you what you need.

I was about to fly to another country to join a group of nomads, trusting the travel company to provide a work friendly environment, and most important, solid WiFi!

“What ifs” are so overwhelming that eventually I thought to myself, “WiFi Tribe has done this for years, I’m going to trust they know what they’re doing and will provide what I need.”

It felt much better to mentally “let go” like this. I’m so glad I didn’t let that hold me back.


I prepared for the journey.

Every country is different and every city is different.

I needed clothes for all types of weather. And all that clothes had to fit in luggage I could personally carry and move easily.

Questions were running through my mind like:

  • What’s better, a backpack or a duffel or a roller bag?
  • Ok, it’s a backpack. What’s the best backpack that’s not crazy expensive?
  • What size backpack should I get? How much stuff am I even going to take?
  • How much warm clothes is enough? What about shoes?
  • What about…?

I read countless articles and websites about what to pack. My wardrobe was planned for a mix of comfort, efficiency, and weight. Eventually, I believed I had everything I needed.

There was only one thing left: to go.


I didn’t look back.

Crossing the finish line of a life-changing decision is an indescribable feeling.

My body is tingling now just thinking about it.

This was right for me. This was the right decision.

All the obstacles along the way (mostly mental!) I overcame and I got what I wanted.

I boarded a plane not knowing when I would return to this city. And if I did, it’d likely be only to visit.

I was more excited about what was ahead of me than what was behind me. That remains true to this day.

It’s so easy to stay where you are yet want for more. It felt so good to change my comfort zone.

When did you last change yours?

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