How I got to work from everywhere

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, ex-pat, location independent, nomad. Before this time it had never really occurred to me that this would be something that I wanted, travel is so expensive after all, but 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, building up some savings, and 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, and perhaps even get a few residual income opportunities going on the side, to help propel us through this journey. I began looking again to a book I had read years before, from one of my personal idols, 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 the 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. Until it didn’t.

The overall plan stalled upon her return. Instead of traveling, we began talking about home ownership.

In New York City.

Ah, the naiveté.

As time went on, we still talked about buying an apartment, but it was becoming more and more obvious that we may never be able to. 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, we had our son Bear earlier this year.

It has been a packed couple of 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. The only problem, most jobs require you to be in an actual office for most of your time, giving you only a few weeks a year to go do (not so) crazy things like go see the world.

That doesn’t seem right, though. I’m a web developer by trade. I don’t need anything but a laptop and an internet connection to get my work done. My greatest asset as a web developer isn’t the office I work in, it is the time I have to focus on my work. 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

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,

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 basically 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. 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.

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.

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 was up at the end of the year and we’re taking this as an opportunity to go see new places. Earlier this week we move most of our things into storage. In just 2 days, we’re leaving.

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

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

The time I moved to New York City

Just over 5-years ago, I made a pretty big decision in my life. I had for years before dreamed of one day leaving my home state of Michigan, but lacked any real motivation or grit to actually create a plan and put it into action. There are many reasons why that was the case, but chief among them were two of note: fear and complacency. Worst of all, these two feelings fed off of each other and made the other stronger.

When I first dreamed of moving to another state, it was back sometime around 1998. The tech boom was at its height and I was at the bottom of things. I looked at cities like Seattle and the stories how IT professionals could pretty much write their own ticket. How people could work at a company one day, and the next, walk out and get a job across the street.  The stories were surreal and full of hope. Something I sorely lacked at the time.

At the time, I had hardly begun my journey as a software developer. While I had minimal experience in this field at the time, instead what I knew was more general computer tech knowledge. I knew how to build computers and troubleshoot issues people were having. I was a computer technician. The lowest of the low. Even worse, while I was pretty good at it, I was not incredibly motivated to go beyond the working at a big box store phase of this part of my career. I dreamed of working for a bigger company, where I could fix real problems, instead of removing viruses and explaining why it isn’t my fault people lost everything because they didn’t keep backups. These types of jobs were very hard to find in Kalamazoo, Michigan, where I was living at the time. So instead, I dreamed of better places. However, I did little to fix my problems.

Time went on and I went through some major ups and downs. Mostly downs.

Eventually, I started teaching myself web development and after a moving home to live with my parents, after the previously mentioned down times, I landed my first real job as a developer. In retrospect, having had almost no experience nor education, I can’t help but feel like I conned my way into this first position.

Why would they hire a nobody with no experience like me?

Probably because I was cheap and unbeknownst to anyone at the time, I actually had some good potential. Thankfully they saw enough in me to take advantage of my lack of options and to give me my first foot in the door in a brand new industry.

And guess what? I actually did pretty well.

Over the next few years, I flourished in my new found career. I went from barely scraping by, to supporting myself quite well, and leading many engineering efforts for a very large financial company. Life was pretty good for a while, at least when it came to my career. Personally, though, I was at the bottom of a very deep a dark hole.

It was near the end of 2009. Over the course of the prior 2-years, I had gone from being engaged; to getting dumped; to drowning myself in video games. My personal life went from a lifelong high, to non-existent, and I felt like there was nothing else for me.

I dreamed of how I would get out.

I dreamed of other places.

I dreamed of being anyone but who I was.

Eventually, I found myself at the bottom of that deep, dark hole, and I dreamed of the end.

Instead of giving up, though, I clawed my way to the top.

I decided that if I wanted to be someone else, I would become someone else. Still Drew, but a different version. One who fought, instead of one who gave up. Someone who took action, instead of lamenting his failures and blaming circumstances, as if they were outside of his control. I got better. I became better.

It started with a dedication to lose weight. I started a diet. I started exercising several times a week. Eventually, I joined a gym and got a personal trainer. I started thinking about how I could be the best version of myself. I looked at the things I didn’t like about myself as variables that could be tweaked, instead of as constants that couldn’t be changed.

Because of this, over the course of 2010, I lost weight. I started to feel as if I was in control of my life and my destiny. I also traveled for almost the first time. I visited Chicago, Seattle, and New York City. Places I had never been but had always imagined were the pinnacle of urban life.

Over that year, one thing became incredibly clear to me: I didn’t just want to dream about living somewhere else, I wanted to actually try it. At first, I thought it might be Seattle. I dreamed of a place where I could work for one of the many amazing companies that I so idolized. I also dreamed of a place where I wouldn’t have to own a car. Where it was normal to walk down the street, instead of driving ridiculously short distances, to avoid the scorn of people you don’t know, who naturally assume you’re poor or homeless because you’re walking.

Walking is not a mark of failure. Walking is the most basic form of human transportation and should be a direct part of everyday life.

Eventually, I ended up finding a small company in New York City who was looking for a developer to join them. They were a brand new startup, just out of the accelerator program YCombinator. It took me moments to decide to apply, a week or two to land the job, and a few weeks later I was saying goodbye to everything and everyone I had known and was driving my life halfway across the country in a U-Haul.

The why of New York City was simple at the time. It represented a far extreme of life to me. One where you were a part of something so much greater than yourself. Where life was active by default and the only limits you had were placed on you by yourself. If you could dream it, you could make it happen.

If I were to put together a list of the top 5 most influential moments in my life, easily 3 of them have occurred since I moved to New York City. It was one of the best decisions I have ever made. I will never regret making that change in my life.

Change is an inevitable part of life. It is both a catalyst and result of growth. For me, a life without growth is a life devoid of meaning. For that reason, I will always seek to try new things.

So here I am, just over 5-years into my New York City experience, married with my first child, and I choose change once again. Next week Lauren and I will be putting all of our things into storage, driving with our son to live for a while with family in Texas, and we’ll be then be traveling for a large part of 2016. This next year will represent the most significant change of our lives.

It is a scary proposition, but I will always choose change when so much growth is possible as a result. Our goal is to eventually come back here. To raise our son, and perhaps more, here in New York City. For now, though, there is a world to see and we plan to see as much of it as we can.

It took a lot of work to get here, but 2016 will be an amazing year.