Drew Butler

How I got to work from everywhere

December 16, 2015

It was about two and a half years ago when Lauren told me that she wanted to go on a trip to Asia. It was the early part of June and the trip would be in about 4-weeks, just after school got out. Being a teacher definitely has its ups and downs, but no one can deny the amazing perk that is summer vacation. Pretty much as soon as school was out, her plan was to go to Asia for 2-weeks, then head back to Texas, to go on vacation with her family in Colorado.

In the sudden weeks leading up to her impending departure to the far east, Lauren started to impart the bug in me. The idea of endless travel. Of being a vagabond, an expat, a location independent nomad.

Before this time it had never really occurred to me that this would be something that I wanted. Travel seemed so expensive. However, as I began to research all those fun buzz-words, I started to see a pattern, traveling could be cheaper than living just about anywhere.

So I got the bug.

At first, we started planning on waiting a year

The plan was to build up some savings before finally leaving everything behind. The timing would give me enough time to close up a lot of loose ends, vest some stock options at Tumblr, which had recently sold to Yahoo! I even thoughts to perhaps even get a few residual income opportunities going on the side. The goal was to help propel us through this journey.

At the same time, I also began looking to a book I had read years before by someone I had grown to admire greatly, Tim Ferriss.

In The Four Hour Work Week, Tim talks at length about the idea of creating muses. Generally speaking, a muse is a project that can be used to generate enough income to live in these types of far away locations. The idea is to automate the vast majority of a project so that you’re working only as much as you want to. This way, you become far more effective at what you do, by building playbooks and passing tasks off to others. It all sounded great and I started to plan for our departure.

Then she returned and talks changed. Instead of traveling, we began talking about home ownership.

In New York City.

Ah, the naiveté.

As time went on talks about buying an apartment continued, but it was becoming more and more obvious that we may never be able to actually execute.

The market in NYC was just too crazy and while we could maybe afford the payment itself, getting the down payment needed to put 20% on one of those tiny places was just too much for the average person. So, we kept renting and our future plans became to continue to rent.

Fast forward 2-years: we got married, traveled to Southeast Asia for our honeymoon/wedding, and finally our son Bear was born earlier this year.

It has been a packed few years and doing a bit of traveling in there showed us one thing, we definitely want to travel more. Maybe some extended travel, but more than anything, we want for travel to be a part of our lives.

Most jobs require you to be in an actual office

As a web developer, it seemed bonkers to me that I needed to be constrained to a desk in an office to get work done. Theoretically, I don’t need anything but a laptop and an internet connection to build websites. The office itself tends to be more of a distraction than an asset in my case.

Could it be that it is actually more harmful to have an office to go to every single day?

I had read for a while about these mythological creatures known as “digital nomads”. Location independent workers. Some of which were entrepreneurs, running their own businesses from all over the world. Others, everyday people, whose jobs offered them the flexibility to work from anywhere. Their metric for success was not their time spent in the office, but the work they produced.

And it made sense. This is what I wanted. But how?

This concept was what they talked about in the 4-Hour Work Week. Streamline your life and processes, focus your time, and you’ll get more work done in less time. You’ll also be able to take back your time as your own. As your asset, not your company’s asset.

Then I found Automattic.

Strictly speaking, I’ve known about Automattic for years. I became super impressed with their VIP WordPress hosting service several years back when I helped transition one of my previous companies to use their service. I even, for a brief period of time, thought about applying there. On top of that, I’ve been aware of and somewhat of a user of WordPress since it first came on the scene a decade ago.

What I didn’t really think about previously was that Automattic checked off a lot of the boxes on my list. They’re a fully distributed company, which means their employees live all over the planet. There is no home office where most people work. People work from where they want, when they want, using web technologies to work together effectively. Travel itself is built into the culture of the company, with several trips to different parts of the world built in to meet with teammates a few times a year. On top of that, their core technology stack happens to be perfectly aligned with my expertise.

So, when I heard Automattic founder (and one of the founding developers of WordPress itself) Matt Mullenweg on the Tim Ferriss podcast in early 2015 it sparked something new for me. I could have what I wanted and it wouldn’t require as massive of a life shift as I’d imagined.

So, I started talking to Automattic

Ultimately I knew, this was something that I needed to do. It helped me come into better alignment with who I knew I was and needed to be. I wasn’t leaving my job for some other company because I didn’t like it. I was very strategically creating a new chapter in my life. Not only for me but for my family.

It took the vast majority of 2015, and I had many doubts along the way. Not because I doubted Automattic, but because I felt very guilty about the possibility of leaving the company I was helping to build.

So, when I finally talked with Matt Mullenweg in late October (he does every final interview himself), it didn’t take long for me to accept the position he offered.

It has taken me a while to write this post. To talk about how I got to this place, because where we go next, while exciting, feels very hard to accept.

As I’m writing this, I am in my 3rd week as an official employee of Automattic. I’ve stayed on as an advisor to my previous company Onevest and I’m thrilled about being able to maintain such a close ongoing relationship. This week also marks my last week in Brooklyn. We’re leaving New York City, at least for now.

Over the last month or so, Lauren and I have been packing and preparing. Our lease is up at the end of the year and we’re taking this as an opportunity to go see new places. Earlier this week we moved most of our things into storage. In just 2 days, we’re leaving the city.

We’re going to be staying with family for a little while in Texas, before ultimately heading to Southeast Asia and eventually South America for a short stint. The plan, for now, is to come back to Brooklyn at the beginning of 2017 and settle into a more permanent apartment that our family can grow into. Some place to act as a home base for further travels.

For now, the world is before us and we plan to see as much of it as we can.


Drew Butler

Written by Drew Butler who lives and works in Brooklyn, NY building useful things. You should follow him on Twitter