Sometimes you just have to start

I know from personal experience that one of the most crippling forces that one can encounter when starting something new is what they call analysis paralysis.

In short, this is what happens when you have access to so much information and so many variables, with so many unknowns, that you simply run through your options over and over again. Telling yourself why you’re not ready to start.

It is a game of second guessing and pretending. Believing there is a perfect solution out there. Hoping that if you just keep thinking about it and researching, that you’ll find it.

To this, I call bullshit.

You’ve probably heard this one before, but there is a famous Chinese saying that goes, “a journey of a thousand miles begins with a single step.” The one thing that needs to be remembered is that when you’re analyzing your idea in your head and going back and forth on why it is good or why it isn’t, you’re really just standing still. Maybe you’re even going backward. What you’re not doing is going forward.

It doesn’t matter if you don’t get it perfect that first time. Here’s a protip for you, no one gets it perfect their first time and next to no one gets it right either.

What they do see is progress.

They learn something from both success and failure. No longer are there those “well maybe” type questions about everything in their head. Instead, those are replaced with more definite “this works” and “this doesn’t.”

Each step you take forward teaches you something new and helps inform the direction you need to go. The goal is to just keep moving. Keep doing. Keep trying new things. Most importantly, keep learning. The worst place you can do this is in your own head.

Instead, get out in front of people.

Write something and get people to read it.

Want to sell a product, but haven’t built it yet? Talk to the people you think would be your customer, and pre-sell it to them. If your idea is good enough, you’ll end up with the motivation to get your product built. If you can’t sell it, then take each failure as an opportunity to learn what your product should probably be instead.

The point is, you’ll always be in a state of limbo if you don’t take that first small step. You’ll always wonder what could be. Instead, the idea you have and pick one thing that you can do every day to move that idea forward. It doesn’t matter if you don’t know if it will work yet. That isn’t the point.

The point is to do. There will never be a better time than now. So get started.

Finding gratitude in difficult situations

Yesterday started out like just about any other day in Bali. You wake up, make some breakfast, make some coffee, chase the baby around, and then load up on the motorbike and decide where to go for the day. Unlike other days up till then, we decided to go a little further out and head down to the beach in Canggu, specifically, Echo Beach.

None of that is really the point of the story, though.

To fast forward a bit, we rode for about an hour, got slightly lost, but ultimately made our way to an amazing beach, where we got some sun, played in the water and sand. We had lunch, walked around a bit and let Bear play with some fish in a little pond in the middle of an amazing little cafe.

On the way home though is where we ran into some troubles.

In the United States, when you’re going somewhere somewhat far away, you generally take the main road or a highway. Here in Bali, it is quite different. Most of the roads are very small, with one lane going each direction and traffic runs considerably slower. So distances that you think of in minutes in the US, become much longer.

The other thing is, many of the roads are unmarked and feel more like side streets in many places. Really, this is a country where most of the roads were created around the villages, as the villages needed and then were later connected. Because of this, going to someplace big from someplace else big that is 15 miles away isn’t a case of “go down X road, turn left on Y road, and Z will be on your right.” Instead, it is a complex journey that requires 10-15 turns down roads that are poorly marked and in some cases look too small to be a road you’d consider going down.

I’ll start by saying that none of this is unsafe, just that the American way of thinking about navigating simply does not apply here. It is not easy to simply pull out your phone every once in a while and say, “I need to turn left in about 100 meters at A street.” You need to have a deeper understanding of things and really stop and ask a lot of people, “which way B?” and then just do that over and over again until you understand the roads.

That was one of the lessons from yesterday. Here are the rest.

On the way back, it was immediately apparent that the amazing sunshine we had enjoyed all day was coming to an end as clouds began to cover the skies. It had already been a tough afternoon, with Bear seeming tired and grumpy, not to mention I wasn’t entirely happy either. Then on the way home, it seemed like nothing could go right.

First, we had trouble finding gas (or petrol as it is called just about everywhere else). In the many places we’ve been to here, outside of city centers, it seems very common to purchase a bottle of gas and just pour it in your tank. This weirds me out, so I kept driving past the 100 stands offering gas like this, hoping to find a pump. Luckily, just as we were going into the deep red, we found a single manual pump operated by a small shop that helped us fill our tank and we were off.

Next, it seemed like I couldn’t make a single correct turn. We’d drive for 10 minutes, I’d stop to look for directions on Google Maps and curse as the GPS just seemed way, way off (protip: GPS basically doesn’t work here, or at least not in a reliable way.) After awhile Lauren just started asking people “which way Ubud?” to which people would point us in a direction, and we’d go. Every time we’d stop I’d pull out the phone, curse at the GPS, “I just need to know where we are!?!”

It felt a lot like the movie Stargate (not the show) where in order to dial home, you needed to know your origin point and they spent the whole movie trying to figure that out. Yesterday felt like us spending all day trying to figure out where we were so we could figure out where we were going. Long story short, we ended up driving way out of our way. Oh, and I forgot to mention, it was pouring rain.

Finally, we turned around, turned down another road and it seemed like we were going the right direction. To counteract my driving for too far without asking, I basically just started stopping every few minutes, or whenever I’d see someone, in order to confirm we were going the right way. It was raining, we were wet, but we were at least on our way in the correct direction.

Then, on one last stop to check our direction, they pointed the way we were going and I merged back on the road, only to find my back tire was sliding back and forth. I hit the brakes and pulled to the side. We hopped off to take a look and it seemed like maybe a water bottle had been caught in the wheel (weird,) so we dumped that and jumped on again with the same result. This time, I checked the tire itself and it was flat. Pouring rain, on the side of the road, surrounded by mostly rice paddies with a couple of small restaurants, I turned the bike around to ask for help.

The first people we talked to were the ones who had just pointed us in the right direction. Unfortunately, they didn’t speak any English, so couldn’t understand much more than “Taxi,” to which they pondered a moment and said no. We waited around for a minute as a helpful person who had just stopped for a bite to eat, who spoke a little English, tried to help and translate, but it seemed to be going nowhere. She wanted us to follow her to Ubud, thinking we were just lost. And as grateful as I am that we could have had someone guide us, we were stuck.

At this point, all I wanted to do was leave the bike for the night, get a car, and get home. I could deal with the bike in the morning. That didn’t seem to be happening, so we said thank you and I walked the bike a little bit up the road to what seemed like a bigger restaurant (the other place wasn’t much more than a stand on the side of the road) where they might be able to help.

It took a moment to explain what was going on. They didn’t speak great English, but they knew enough to know we had a broken bike, and that I was hoping to leave it, get a taxi home, and get it the next day (today.) At first, it seemed like they might not be able to help, but amazingly they started calling people to enlist friends and family to help us. Maybe it is just because we’re traveling with a baby, but everyone just wanted to reach out and help us. No one seemed put out either, even though they were obviously going way out of their way to help.

What happened next was just amazing and we are so grateful.

First, they offered to take the bike to a mechanic for us that night and we could pick it up in the morning. Next, they called a man, who we still don’t fully know the relation, but he showed up with a jeep-like vehicle and offered to drive us the rest of the 30+ minutes home, in the now torrential downpour.

So we left the bike, with the key, in the hands of total strangers. All the while, every bit of American in me was screaming, “don’t do it, they’ll cheat you and steal your bike.” But I ignored that voice and left it anyway.

Then we got a ride home with the kindest man, who apologized to us the whole way for not having a better car or A/C. His car was a 1982 Suzuki 4×4 and while definitely not the kind of car I would expect were I to call for an Uber, given the circumstances, it was amazing and dry and warm. We couldn’t have asked for anything more.

In the end, we made it home safe. Lauren tried to hug the man out of appreciation, which he thought was a bit strange (I guess they don’t do that here.) We ended up walking to dinner that night, but we were home, in our neighborhood, so we didn’t mind.

This morning, I hired a local taxi to take me back to pick up the bike and sure enough, they were there at 10am as promised. The brother took me on the back of his motorbike down the street to the mechanic and there my bike was. Tire fixed, ready to go. I tried to give them money for their help, but everyone refused it. The only money I paid was for the taxi back this morning and 10,000 IDR (less than $1 USD) for fixing the tire.

This is a situation that had it occurred in the rural parts of the US, I can imagine may have gone much, much worse. Instead, we were greeted with a sense of community and social responsibility from everyone we encountered who took it as a matter of personal pride to protect and help us. It was truly inspiring.

We’re taught in the US that everyone is out to get you. That the world is unsafe, especially the world outside of the US. The longer I’m away, though, the more I see the flaw in this logic. The more I experience, the more I see the fear that has been so nurtured and perpetuated by our news media for what it is. For years I’ve heard people lament when they hear I don’t watch the news. I’ve always thought I was better off to not hear the horror in its contents because, in my opinion, it is mostly a manufactured view of the world. One meant to drive ratings and create a sense of xenophobia through distrust in the outside world. Now that I’m out in the world, I believe this even more strongly.

The more I’m out here, the more I see the inherent goodness in everyday people. I’m grateful to have this opportunity. I’m grateful to have had such amazing people help us out of the kindness of their hearts, in what felt like such dire circumstances. In retrospect, all of it was minor, and all of it was a reminder that we’re all just people and that at the end of the day, we should all reach out to help the small family, with a baby, caught in the rain with a flat tire.

I’m grateful that Bali never built a wall to keep people out. That we’re able to live here, even if for a short while. So we can experience and understand that the world is such an amazing place and that the people in it are equally amazing.

Our next adventure begins tonight

Ever since we made the decision 9-months ago for me to change to a more location flexible job and to relinquish our apartment in Brooklyn, NY, we’ve been somewhat on the go.

First, we left New York for Texas. The plan was to live with parents for a bit and make some small trips in between. Truth be told, just the travel time between Galveston, TX and Austin, TX multiple times a month was enough to feel like we were travelling a lot. But between that and trips to Belize, Costa Rica, Ireland, Las Vegas, and New York, we’ve been busy.

Finally, though, we have made it to the next stage of our travels. Tonight we embark on a near 24-hour set of flights that will land us in Tokyo, Japan, where we will spend a few nights before heading to Kyoto, Japan, then Bangkok, Thailand, after which we will ultimately be settling into Chiang Mai, Thailand for about 6-weeks before moving onto Bali.

The idea is for me to take about 2-weeks off from work in the beginning and spend a few days in each of these locations as a vacation. Afterward, I will be working a regular schedule from a co-working spot in Chiang Mai.

It is interesting that after all of the planning that has gone into this, it still feels like it has come too soon and that we are nowhere near ready. In some ways, we are probably over prepared, however, I have no question that there will be dozens of things that we will realize that we have forgotten and will need to either buy or send for once we settle into life in Chiang Mai.

None of that really matters, though, because we will figure it all out. We always do.

What does matter is that this is going to be a fantastic adventure and I cannot wait to experience all of it with Bear who has just turned 1 and is just getting to the age where he is starting to experience more of the world. I cannot wait to get to show him a different kind of life in these earliest of years.

My hope is that it will leave an impression in him that although the world is big and full of different people, that it can still feel very small when you realize that everyone, at their core, is really the same. Though I want him to always remain curious about the differences people have, I also want him to see that they don’t separate us, instead, they make us unique and interesting. More than anything, I want him to know that he can learn something from everyone he meets, no matter where he goes and no matter who they are.

For now, though, we have a plane ride with a 1-year old to tackle. That promises to be an adventure all and of itself.

You should start a travel agency

As a New Yorker, I’m used to the spiel. “I’ve got these kids who need …” or “I need money for …” or simply, “can I have a dollar?” Usually, all but the last are total BS, so it is easy to brush them off and say, “sorry, I’m broke too.” This time was a little different. Instead of starting with the story, he started with an introduction.

“Hi, I’m David,” he said, as he stretched out his hand.

Such a simple gesture, one that you might see just about anywhere else, but rarely do you find with a disheveled man on the street, smoking what seemed to be the butt of a cigarette.

My first reaction, of course, was to step away. Not because he was (potentially) homeless, but because I have a horrid aversion to cigarette smoke. I think having been a smoker myself, once upon a time, has given me a super sensitivity when it comes to burnt tobacco. That and a general fear of the asthema that it inevitably triggered causes me to avoid even a hint of the stuff. The irony of how staunchly I used to ignore my own cigarette smoke as I pushed it on others was not lost on me as I almost reflexively backed away.

Feeling slightly ashamed, I reversed positions and met his hand with my own. “I’m Drew,” I said in return.

Then came the story. He began to relay to me about how he had just been released, was still trying to make his way, and was hoping I had some change. It wasn’t much different than the thousand stories I had heard before, so reflexively my inner New Yorker came forward and offered, “sorry, but I’m broke too.” Almost as an aside, I added, “I don’t even have a home of my own right now.”

Not entirely true, but if there is one thing I can say about myself, it’s that I have a penchant for dramatic statements.

So then he started talking. He asked me where I’m staying. He told me that I look like a smart guy, the kind that likes to read. Not that fantasy or science fiction crap, but good heady stuff.

He asked me if I had ever thought about starting a business.

I told him I had.

He leaned in, whispering to me as if he was going to suggest something elicit that no one else should hear, “you should start a travel agency.

Confused by the juxtaposition of how he told me and what he told me, I must have given him a funny look. He explained further. A lot further.

“See that over there?” He pointed to the building across the street, though, I think his intention was just to point in the general direction of the docks several blocks away. “Think about all those boats, what is the easiest way to go on vacation? You take a cruise.”

While I mostly disagreed with his point, I didn’t really get a chance to object as he continued on. “If you were to start a travel agency, you could make bank around here. You open one up on every corner. Different names, all around the country.” Seemed more like a Ponzi scheme than a business, but I listened on.

“Think about all the hotels. They sell a room for $100, you get it for $30, that’s pure profit. Or hell, maybe the room is $300 and you get it for $75. I don’t know what the prices are like, but you get my point?”

His math definitely made sense, however, I was starting to wonder how long he had actually been incarcerated and I wanted to ask, “have you ever heard of the internet?” But instead, decided to keep that one to myself. His heart was in the right place and I enjoyed that he honestly thought he was helping out.

Unfortunately, I had to leave and decided it was time to brave the rain.

Before jetting across the street, I said to him, “David, it was great to meet you. I’ll definitely take your words under advisement. Have you ever thought that maybe you should start a travel agency? Best of luck if you do.”

And I was gone. I didn’t want to be completely rude, but the fact was, I did need to get back to work, even if work was just in the coffee shop down the street.

As I hurried down the opposite sidewalk, I heard David shout to me as he shadowed me from the other side. “Hey man, best of luck. My name is David. I’ll see you again.”

Taken out of context, that could sound creepy, but I think he genuinely thought we’d talk again some time. Maybe we will. Maybe he’ll take his own advice and start a travel agency. The idea was out of date, but at least he had some enthusiasm and zeal for it. In the end, that is all that really matters.

The long road traveled

I embarked nearly alone on a Friday morning. One week before Christmas with a packed car, and a dog, for a long drive from Brooklyn, NY to Galveston, TX. The intention up until the night before was slightly different.

The assumption with getting a car before leaving, instead of upon arrival in Texas, was so that Lauren, our son, and I could pack up the car and make the journey together. We assumed a need to maximize available space, so in anticipation, I purchased a soft top carrier and a bike rack for the back. This was to ensure the maximum amount of available space for our crew to cross half of the United States. The reality of our spatial needs, however, was well beyond our imaginings. In fact, within the first attempt to load the car up, I was left with the reality that I had filled the whole of the top carrier and trunk, with only half of what we had to take.

We were out of time and the plan was clearly flawed and needed to be changed. So, we adjusted. In the final moments, before leaving it was decided that Lauren and our son would fly ahead the next morning.  She would be able to take a couple of the bigger items, like the stroller and car seat with her, not only freeing up space from those things but allowing me to flip half of the back seat down, gaining us more valuable space in the car. Since we were going to be staying an additional night, it also meant I had an opportunity to take a few more things to our storage unit before we left.

This would mean that I would be driving with just our dog, alone, for nearly 2000 miles. But it gave us a chance.

When Friday morning came along, I took Lauren and a sleeping Bear to the airport. The departure was quick, at least from my point of view. They would fly to Nashville, TN, where I would meet up with them, before ultimately meeting me in Austin, TX. There we would spend Christmas, then ultimately complete the drive together (somehow) to Galveston, TX. I was taking the long way around it would seem.

After the airport, I moved more of our things down to our storage unit in southern Brooklyn. Next, I repacked the car, with barely an inch of space left to space. Added the dog with his bed, into a small corner of the back seat. Said goodbye to our empty apartment. We were homeless, and by 12 pm I was off.

See you later Brooklyn.

As I crossed the Staten Island bridge, it was unseasonably warm. At 55 degrees Fahrenheit, near the end of December, it was nearly shorts and t-shirt weather. In fact, because of the near warmth and the fact that I wanted to be comfortable for my long trek, that is exactly what I wore. My plan was to drive all the way to Tennessee in one shot. I estimated that with doggie and human breaks, it would likely take until 4-5 am before I would get there, but that was okay. I’d rather have the extra downtime in between legs of the trip, than to sleep. In the end, though, the choice was hardly mine to make.

Pennsylvania took nearly forever to cross, or so it seemed. However, when I finally did the weather started to take a turn for the worst. For the previous few hours, I had seen small flurries of snow here and there, but it was so light, that I assumed it was melting far before it even hit the ground. As I crossed into West Virginia, though, the story changed, as the roads became treacherous.

It was dark at this point, nearly 8 pm. I had been delayed by far more breaks across Pennsylvania than I had anticipated and by the time I was starting to go through the mountains of West Virginia, I could feel the car slipping on the road. My speed started to dip down from the 75-80 mph that I had been driving before, to a terrified 20-30 mph. The roads were covered in a thin layer of white and traffic was proceeding in a caravan of unsettled travelers. Any fear of falling asleep while driving was gone at this point as the combination of Starbucks coffee and adrenalin from my white-knuckled drive was more than enough to keep me going.

It was becoming clear though that I had two options in front of me. Either keep white knuckling it at the crawl I was proceeding at and perhaps end up in a ditch somewhere in the middle of nowhere, all to add likely several more hours to my total drive, or stop at a motel and call it a night. I chose the more sensible of the two.

The next morning, after a nice warm night’s sleep, The dog and I embarked once again. The roads were still a little dicey, but it was light out. The morning sun was already doing its work and I was off. Within an hour or two, I was far enough south, that the roads were completely clear.

West Virginia went on for longer than I expected, then it was onto Kentucky. While the initial intent was to stop at Lauren’s grandparents for a couple of nights in Clarksville, TN, a combination of lost time and the realization that I should probably take the next leg to Austin, TX a tad slower sunk in. As such, when I was told to stop at her other grandparents’ house in Bowling Green, KY. I took it as a blessing that I would get to the stopover that much sooner.

One night in Bowling Green meant happy times for a pent-up puppy in the back seat. He got to run around a bit, jump all over some family members, and lick a very happy and mostly smiling baby, before ultimately landing back in the car another 24-hours later.

The road between Bowling Green, KY, and Austin, TX was luckily uneventful. The plan was to make it to Texarkana, Arkansas by nightfall, before ultimately stopping for the night. This meant having only 5-hours of driving left, but it also meant not showing up at somewhere between 3-4 AM and messing with my still undamaged sleep schedule. The reward was definitely worth the small price of the somewhat sketchy Motel 6 that we stashed ourselves in.

One thing that I had always heard but never really understood was how empty the drive through northern Texas could be. From Texarkana to Dallas, the road was almost a blank slate. A canvas someone forgot to finish painting. Brownish green and flat, and missing that all-important element that gives it emotional purpose. Maybe Dallas itself was that purpose, as for as flat and boring the previous 3-hours of driving had been, the eastern approach for Dallas was quite spectacular.

Looming in the west as I drove across the causeway across a small lake, it was perhaps the most impressive entrance into a city that I had seen in my whole trip. New York City itself really only rivals it because of its immensity and the amazing skyline. Dallas, however, seemed like a transition from pointlessness to vibrancy. Something that seemed missing throughout the rest of my trip.

The rest of the trip to Austin, TX was uneventful. We eventually landed in my parent’s driveway. Unpacked the car, unwound, and awaited the arrival of my better 3/4 later in the evening.

The plan from that point was to spend a few days with my family, work from coffee shops, have some Christmas fun, before ultimately packing the car again and finishing the final leg of our journey to Galveston, TX.

Luckily for the final leg, we had some relief in the baggage department, as Lauren’s sister was making a similar journey home a couple days before and was able to take some of our things with her. This meant that the car, just barely, had enough room for all of our things, leaving the backseat for mommy, baby, and doggie, while I drove the final 4-hour stretch east across Texas.

In the end, we’re temporarily transplanted. Homeless, but with family in the most positive and purposeful way. We’ll eventually land back in NYC, most likely in Park Slope, Brooklyn. Until then, the plan is to allow our families to spend as much time as possible with our son, save some money along the way, and eventually travel for a large part of 2016.

It is hard having given up a piece of our independence. To once again be living with family. To not get to wake up to the city we love. However, the opportunity that we have before us is an amazing one and in 10-years, I know we’ll be happy we made this decision.

For now, our lives will be filled with beaches, biking, and running along hopefully warm beaches throughout what might be a very cold winter for our normal home. I can’t say that I’m sad about this one facet of our journey. I’m, in fact, incredibly grateful for this opportunity to share our son in his formative years and to experience a different side of life for a little while.

The road to get here was a long one. Where it leads in the long term I cannot fully say. I do know that it will steel us in our resolve for the life we choose for ourselves.

2016 is going to be an amazing year.

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, 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, 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 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 one of 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.