Trail Overland: How we left everything to drive to Alaska

We’re Nico, Lina and our dog Dexter. Traveling North from Chile to Alaska. You can follow our adventure in Instagram, track our position with Garmin and read our travel journal here.

“Man cannot discover new oceans unless he has the courage to lose sight of the shore.” — Andre Gide

A few weeks ago I published on Facebook something like: “I’m leaving to Alaska!” and it was by far the most popular post of my entire life. This made me think about how many people want to explore the world and all the difficulties along the way. It’s not easy but is doable if you commit to it. This post is about our start, our planning and how we’re planning to live on the road.

700 people react to this post. That’s more than 30% of all my friends on FB. (Probably all my real friends)

The decision

Life trajectory sometimes is very clear to me. I was living in Chile, having a kind-of-successful company but we were running out of new ideas, and I was settling down. It was very clear to me where my life was going, and I didn’t like it, I was deep into my comfort zone.

I had some money, the company was doing O.K, but I was tired of not having time to try new things because of the routine and daily situations that drained all my energy. I wanted to build something bigger.

I knew that I needed to change my trajectory and thought a lot about all the times that I had upgraded my life, always was by taking a long trip. I shared the idea with my girlfriend, Lina. What if we drive to Alaska by Jeep? She thought for a moment and said yes right there. That moment was the beginning. It was seven months ago.

The planning

1. How we make our Jeep a mobile home

We needed to move to a new home. Our Jeep. I had a Jeep Wrangler seating on my garage, so I decided to take it to the next level and explore the possibilities of an off-road machine turn into a mobile adventure home. The work took like eight months, and I will share with you guys later the complete build, but a rule of thumb: Don’t try to find the perfect car, just used whatever you have in your garage and build upon it.

2. Leaving our apartment

First of all, we sent an email to our landlord saying we were leaving our rented apartment on January 1st, 2017, three months before. Lina took pictures of everything, and we sold plenty of stuff. Our terrace furniture, bikes, chairs, fridge, washer, etc. and the rest moved into a rented storage room we paid for a year. Easy. We didn’t have to worry about things.

Good bye house

3. Making our Job possible.

I’m an entrepreneur, and I run a software company that serves the ticketing and event industry in LatAm. We’ve worked on it for six years now, and it hasn’t always been easy. The first two years we didn’t know where we were going. Years 3–4 we almost broke the company and finally years 5–6 we found some stability to grow big and better.

I started to think and read a lot about remote working and management, and my conclusion was that the best way to run a company from abroad is to take you out of the picture and do what CEOs should always do: Hire great people, coaching and set the vision/direction of the company. I planned accordingly:

  1. I hired four developers to grow product
  2. We created a workflow using JIRA Cloud and Confluence. Obviously, we already used Slack, Google Hangouts, and Github.
  3. I coached our existing team to grow inside the company by making themselves more valuable to our product.
  4. I chose 2–3 people inside the company and made them our executive team. So I could delegate most of my daily duties to them. (work in progress).
Special thanks to our entire team at Welcu!!! thanks for helping me with this adventure.

Now, after more than one month into this adventure, It seems to be working. Business flow continues, new product features are getting into our customers more frequently and I’m thinking more than ever about new opportunities to grow our business. It’s possible, but I will give you an update if a few months to see if we’re still alive.

4. Personal affairs

My recommendation to everybody that is still hungry is to try to keep your backpack light so you can walk away without second

thoughts. We don’t have many things so leaving them was easy. Our more valuable piece of property is with us and is the Jeep. Having our dog with us totally worth it but it has its challenges especially with all the paperwork you are required to get him in and out of countries.

But I still have some stuff that I need to take care of especially when they need my signature on things like banks, credits, renting properties, etc. So I gave my mom, who is one my best friends, complete power (by law) to sign and do whatever is needed, as if she was me.

Our life on the road

This is not a vacation as many people think. This is Life travel. Our life must continue to be productive, and we divided our life into three areas: Family, work, and experiences. When spending all the time together avoiding working on improving this area is totally impossible. So we need to work hard to make it work.

BONUS: Things that I’m working on but can’t fully share because is too early are:

  1. Working on a daily routine that I can follow every day.
  2. Making my job remote.
  3. Trying to get stronger as a family.
  4. Eating better by eating at home and not outside. (Impossible in Perú)
This is home now. Not always as great as a lonely beach but most of the time works.

So this is it. Our life travel. I’d love to hear your ideas, your dreams, and your next travel adventures.

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