Don’t just set goals, instead take action

I’m a prolific goal setter. I create them with such zeal and determination. I dream into the future and imagine what it should be.

Here’s the rest of that truth, though. I plot and I plan and then ultimately go chasing after the next shiny thing.

The real story is that goals don’t really work for me. Maybe they don’t really work for anyone. At least not by themselves. Goals are sort of abstract to do list set far into the future. One that has by itself has no real plan and no real method of success tied to it.

Start my own business? No doubt.

Pay off all of my debt? Let’s do that tomorrow.

Plus, I would like to spend more time with my family.

The truth is, that just saying I would like to do these things does not make them accomplishable. Setting those things out for the universe does not make them materialize. What makes them occur in reality is strategy and hard work.

What makes them occur in reality is strategy and hard work.

In other words, action.

When I was your age

When I was first looking to break into web development I was in a pretty terrible place in my life. For years, I had been scraping by as a computer technician, cleaning viruses off of people’s PCs and trying to explain to parents the dangers of downloading things on the internet.

I was miserable. I absolutely hated explaining this thing that felt so obvious to me and was so repetitive. Every day was the absolutely same set of problems solved in nearly the same way.

In my own time, I had been programming. I was learning web development, but didn’t have a complete education, and didn’t really understand how to do it full-time.

Sure I had a ton of toy projects, but my real goal was to transition from doing repetitive work for near minimum wage to doing something that was more creative, paid better, and was overall more fulfilling. At the time, though, this felt completely impossible.

I didn’t have a college degree, I didn’t live in a digital hub, nor did I have any real experience to back me up.

What could I do? The answer as it turned out was to get the lowest paying web development job I could find and let that experience take me forward. And that’s what I did.

I searched around and found a small web shop that wanted to pay the kind of rates that we would pay to contractors overseas today and said, “I’ll take it!”

I did this because while it didn’t get me to my complete end goal, it got me closer. And over the course of the next 10-years, I went from near intern to having worked at several high profile companies and being the CTO of a small startup in New York City.

That wasn’t where I intended to go when I started, but that was where I landed.

Action is the real goal

The one thing that I can say for sure from my own journey, is that I got to where I wanted to go, not because I followed a plan the whole way, but because I knew the direction I wanted to go and I took action.

Recently I’ve been reading a fantastic book by Gary Keller called, “The ONE Thing.” As the title implies, the core concept of this book is that by nature we tend to focus on a full list of things we need to accomplish. That by checking things off the list that we will magically reach our goals.

What the book asks us to do instead is to ask the question, “what’s the ONE thing you can do such that by doing it everything else will be easier or unnecessary?”

This is such a simple, yet powerful concept. It challenges how we look at our long-term goals and how we seek to accomplish them by telling us, to just focus on ONE thing.

Perhaps instead of focusing on goals, we should be focusing on that ONE powerful action we can take right now. The one thing that will define the rest. That way we turn goals into simply the byproduct of action.

This simple turn of how we frame things has some powerful implications. It tells us that we need to be focused on what we can do today. Not what we want in the future.

Are having goals really a problem though?

The truth is, that having goals is a good thing. They provide useful guideposts. They tell us which direction to aim, however, by definition they don’t tell us much about which road we should take to get there. Instead, they distract us and teach us to focus too much on the unknowable future.

Yes, it is important to set goals. It is even important to set them well. To intentionally follow a framework such as S.M.A.R.T. goals to make sure that we’re defining them well. However, once this is done, it is important to take the next step and define how to get there.

What action can you take to reach your goal

Most people, myself included, tend to approach defining actions from the wrong direction. They will stand where they are now, in the present, and look toward the goal and say, “I will do this today.” They will repeat this over and over again and marvel at how their goal never seems to come closer and sometimes even gets further away.

The reason for this is really simple. You may know which direction to go, but you may not know how to get there yet. If you’re going to drive from New York City to San Francisco, California, do you just get in the car and drive west? Sure you could do this, but you’ll probably have some trouble getting there because you don’t know which roads turn where.

Luckily, these days we have software that makes navigation like this easy, but it wasn’t so long ago that the answer to this question was to pull out a map. Look at the start and the destination and draw backward from where you want to go, to where you’re leaving from.

You do this because you know where you are right now, so it is easier to trace back to there, then it is to trace to a place you’ve never been.

Let’s do a quick thought exercise

Let’s start with the goal “I want to start a business.”

First, we need to better define this goal, as technically I can just open a business checking account and I’ve legally started a business.

Instead, following the S.M.A.R.T. paradigm for goal setting, I’m going to rephrase this as:

“By December 31st of 2018, I want to have started a business that pays me at least $10k per month, has done so for at least 6 months, and have transitioned from being an employee to an owner as a result.”

Already this goal simultaneous feels far better defined and somewhat scarier due to the immensity of what needs to occur to make that happen. Both of these are good things, because they’re both real, and you should be a little scared by something this big.

Visualization and the art of right to left thinking

The next thing to do is to better understand this goal. What will life look like when you’ve reached this goal? What do you do in the morning when you wake up? Do you have more or less time? Are you energized to go to work on your business? Do you work from an office? From a coffee shop? From home? Do you work with clients? Are you working on a computer?

These are all important questions because they ground you in that future moment so you can stand there instead. The more details of that life that you can visualize, the better you can draw yourself there, stand in your future shoes, and look back on this moment and imagine, “how did I get here?”

Once you’ve placed yourself firmly in that future, “what needs to occur just before this, for this to happen?”

This question is key because it acknowledges not only the cause and effect that will result in it but begins to ground you in the actions needed to get there. Likely a long series of actions, all that lead a trail right back to where you’re standing right now.

For this, you need to disconnect yourself from the doubt of “but I don’t have that yet” or “I can’t do that right now,” because that is sort of the point. You’re identifying what you need to do to be able to do those things. So every time you hear that voice tell you those things, simply ask, “what would I need to be able to make that happen?” and you now have the preceding step.

After which, you will have a map. A series of guideposts to mark your way to your destination. A series of smaller steps to take that are more attainable and less overwhelming.

This brings us back to the ONE Thing.

Once you know where you’re going and have an approximate map, you should be back to standing in the present moment. From this moment, it is your job to cut down on the noise and take action. You will likely have a thousand things on your mind. A thousand potential actions, but your only goal right now should be to get to the next point on your map.

Every day, the one question you should ask comes back to, “what’s the ONE thing you can do such that by doing it everything else will be easier or unnecessary?” Ask this when you’re looking at your long list of things to do and focus on your next point on the map you’ve drawn.

The answer won’t always be easy, but the reality is, that most of the things on your list are probably not as important.

Is the first post on your list to have one client? Then why are you reading a book about marketing? Get out there and sell yourself on a site like Upwork until you get that first client. Use the experience from that to tell you what you need to learn. Your book is just a distraction.

Once you get to this first milestone, you’ll be able to see more easily how to get to the next one. The cycle will repeat on and on. There will always be distractions, but there will always be ONE thing that you can do right now that will move you forward.

Focus on that.

The goal is not the destination

Remember, the goal is not what you’re really looking for. It is the actions you take that will define where you’re going. Be open to the fact that your destination may change along the way. That as you repeat this exercise, your destination may change many times. This is not only okay, but it is also a good thing.

I write all of this, not to state my own expertise on action-taking in general, but instead to distill what I’ve learned in the past in my drive to become a web developer.

I do this because I am not repeating this journey and relearning these lessons as I go forward. That goal from the thought exercise, that one is mine. It is one of my destinations and from it, I have set a series of nearer term destinations to aim at along the way.

Maybe it will change along the way, that is okay because the destination doesn’t matter.

Your destination doesn’t matter.

Your actions do.

What is the ONE thing you can do today, such that by doing it everything else will be easier or unnecessary?

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 street A.” You need to have a deeper understanding of things and really stop and ask a lot of people, “which way is 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, 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.

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 10 am 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, 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 coworking 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

I met a (potentially) homeless ex-convict named David yesterday, as I exited my favorite Gumbo Bar on the Strand, in Galveston, Texas. When I had entered to eat lunch the sun had been shining and it was a balmy 55 degrees (Fahrenheit). As I exited, listening to a podcast on my iPad, massive headphones over my ears and rain pouring down outside,  I paused under the overhang to consider my options.

That is when I met David.

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 car packed tighter than anticipated and my dog, I left for the long drive from Brooklyn, NY to Galveston, TX. The intention up until the night before was slightly different.

Our intention with getting a car in New York rather than in Texas, was so that Lauren, Bear, Walter, and I could make the journey together. We assumed a need to maximize available space, so I purchased a soft top carrier and a bike rack. The reality of our spatial needs, however, was well beyond our imaginings. 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 Bear 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.

The long way around

The next morning, 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 they ultimately would meet me in Austin, TX. There we would spend Christmas before completing the drive together (somehow) to Galveston, TX.

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. 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. It was 55 degrees Fahrenheit, near the end of December, and I was wearing shorts and a t-shirt. 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.

The choice wasn’t mine to make

Pennsylvania seemed to take forever to cross. When I finally did make it to West Virginia, the weather took a turn for the worst. For the previous few hours, I had seen small flurries of snow here and there. It was so light I assumed it was melting before it even hit the ground. As I crossed the border the story changed, as the roads became treacherous.

It was dark at this point, nearly 8 pm. After a few missed exits and a few more breaks than I had anticipated, I was running further behind schedule than anticipated. 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 that I had two options in front of me. Either keep white knuckling it at a crawl and perhaps end up in a ditch in the middle of nowhere or stop at a hotel and call it a night. I chose to cut my losses and opt for a warm night’s sleep.

The next morning

The sun was already doing its work as Walter and I embarked once again. Though the roads started a little dicey, within an hour or two I was far enough south that roads cleared completely.

West Virginia went on for longer than I expected before I finally made it to 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 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.

Onto Texas

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 parents 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 of 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, 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.

The time I moved to New York City

Just over 5-years ago, I made a pretty big decision in my life. For years I had dreamed of one day leaving my home state of Michigan, but lacked any real motivation or grit to 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 each made the other stronger.

When I first dreamed of moving to another state

Sometime around 1998, the tech boom was at its height and I felt like I was at the bottom. 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 hadn’t yet begun my journey as a software developer. Instead what I knew was more general computer technical knowledge. I knew how to build computers and troubleshoot issues people were having. I was a computer technician. Which at the time, felt like 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 my career. The problems I face at the time were of the every day variety. Viruses from kids pirating software and music, crashed hard drives, and general problems with technology just being harder than it needed to be.

In my mind I thought often of what it would look like to work for someplace that did something that felt meaningful. To have my own desk, my own computer, my own contribution beyond the same 10 problems and solutions repeated day in and day out. In retrospect, I lacked the drive and imagination to see my way up.

Instead, I was locked in a loop, dreaming of what it would look like to move somewhere else, but seeing it as nothing more than the fantasies I read in my own time.

Time went on, from down to up

Eventually, I started teaching myself web development. I was lucky to have made a friend who showed me a world beyond HTML and CSS. I started learning Apache, MySQL, and PHP. I started building my own sites, my own CMSs, and teaching myself as much as I could. After some very down times, I moved home to live with my parents. I went back to school for a short time, cleaned up my finances a bit, and eventually landed my first 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 eventually 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.

Climbing back to the surface

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. At the same time, I also started to travel.

An exit strategy emerged

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 I was from if you saw someone walking down the street, you’d naturally assume they were too poor to own a car. Instead, I wanted to be where it was normal to walk down the street, instead of driving ridiculously short distances.

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.

New York on pause

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 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.

To the guy who bumped into me on the subway stairs this morning

It was busy this morning.

Heck, it is busy every morning in New York City.

As usual, I was turning down the stairs of the Atlantic Station D/N/R platform, to find them full of people going up. So full, that there was almost no room to go down.

This is a normal thing.

In fact, it is such a normal thing on this exact stairway, that I long ago gave up the feeling that I should somehow be meek when people give no lane for opposite travelers.

When I first would encounter this I would press myself against the railing, turn my shoulders aside, and try to give everyone else room. I was trying to be courteous. However, after 2-years of this exact stairway, with this exact situation, I eventually stopped. I’m not saying I instead turned into an asshole who throws people out of his way, but I instead took the stance as I went down those stairs that I belong there. That I’m not in your way, that you are in mine. The right side of this stairway belongs to downward traffic.

Unlike a busy street, there are no police officers to enforce traffic in these situations. However, that doesn’t mean that you have the right to the whole stairway. Traffic, in order to move efficiently, moves in two parallel streams. Just like a street, you should keep to your right and I will keep to mine. If you violate this, then you do not have the right of way.

So, instead of being meek and attempting to take up as little space as possible, I simply walk down the right side, next to the railing. It is honestly not an unreasonable assumption to make, that this 1/4 of the downward stairway can belong to myself and my fellow downward travelers.

It is the least we deserve.

Today, though, you didn’t agree with me. You, upward traveler, took to the right side, my right side, and tried to own that too. So I stood my ground, in perhaps the lamest of ways and simply walked down, expecting you to move further to your right, as social norms expect you to. Instead, you turned your shoulder, expecting me to do the same. To get out of your way, on my side of the stairway.

I declined.

Instead, we collided shoulders. The smallest of connections between us. In my mind, it was par for the course, for you though it was an infraction of the highest order.

So you stopped. Rapidly slapped my shoulder in the weakest (and perhaps weirdest) of ways, and asked what was wrong with me. Why didn’t I say excuse me? What was my problem? You acted as if I had purposefully run into you, when the reality was, I simply didn’t get out of your way.

Here’s the truth, I’m not going to fight you. Not on a busy stairway. Not anywhere. Especially not for bumping shoulders. So don’t pretend like you’re going to fight me. It is just unnecessary.

Instead, I wonder, what is wrong with you? Did you have a rough morning? Was it something else in your life that you were bringing to that moment, the smallest of collisions, to make it into something more than it was. More than it should have been.

New York is a hard place in this way. Finding the balance between not getting stepped on and not stepping on others is hard. Preferably you want both. And most of the time it works out, but other times it turns into something unnecessarily more. My goal in these situations is to let them slide and not make it into an excuse to be the person they need to fulfill their own narrative.

Some days it works out better than others.

Finding my voice through writing

I used to dream of being a writer. At first, I would write in a notebook every day. You could have called it a diary of sorts. Maybe that’s what it was, but for me, it was how I was learning to tell my story. My attempt to find what made me unique.

Eventually, I graduated to writing stories involving D&D characters, taking the things that would happen in our games and trying to bring another depth to them. My dream was always to write stories, to create fiction, and this was one of my first attempts.

Then something happened, I became a web developer.

I didn’t necessarily stop having the dream of writing, but my effort and focus moved from channeling my creativity through one craft and into another. In writing software, I found a faster way to bring ideas to reality, one that provided an immediate source of good income. So my dream of being a writer stayed just a fond dream.

Eventually, I found my way into blogging (not too different from what I’m doing here), however, it wasn’t something I ever took seriously for its own sake. Instead, it was a companion for my other efforts, losing weight and getting fit. While I think many people might have used it as an opportunity to do both, I stayed focused on only one piece and eventually the writing stopped.

Over the last 2-years or so, one thing I’ve realized is that when I’m not writing, it creates a hole in my life. Not the dramatic woe is me sort of hole, but the kind where reality makes less sense to me.

Writing is in some ways a meditative exercise. One that allows me the time to really explore ideas, without reacting to them. It gives me the means to find the me in between all the things that happen all around.

However, one thing I’m learning about myself is that I don’t want this space to be a blog like I’ve done before. While I need that medium to figure things out, I’m starting to miss the original pen and paper approach. Where I can say anything and not feel afraid of judgment.

So one thing I want to note is that I don’t plan to go as fully personal with this blog. I want to use this as a place to develop my writing style, specifically around my abilities with storytelling. Not to say this blog will be full of fiction, but I want to learn to hone the art of storytelling through life itself.

For all the other stuff, I’ll keep that to myself. Not to say no one wants to see it, I’m sure someone will, but it just doesn’t match what I want to do with the next chapter for my life. For that next chapter, I want to see what it might look like to be a writer. Maybe not professionally, but I’d love to at least earn the moniker.

What type of stories would you like me to tell?

I’m going to be a father

Yep, that’s right, I’m having a child. We’re almost 17 weeks into this and it is crazy to even try to rationalize this news against the person that I’ve always been in the past.

In many ways, I still feel like I’m a child myself, even though I’m very clearly not. Being able to fool myself with this line of logic though, has been sort of a mental get out of jail card when I was looking to make excuses to be lazy or to just not make important things a focus. I have a feeling though, that this part of my life needs to be sunsetted.

If I’m really honest with myself, though I have trouble expressing it, I am truly excited about this. The fact that I’ll be able to discover who this person will be is fascinating to me. At the same time, still being a bit of a child myself, it seems nice that in the not so distant future that I’ll have a very valid reason to start playing with toys again. I’m especially excited about Legos.

Please, oh please, like Legos.

I’m not sure who they will be yet. We find out the sex in just a few weeks, so I’m super excited for that. However, I’m committed to the fact that I need to come into this new relationship without any preconceived notions of who they will be. As much as I may hope for certain aspects of who their personality might be, I’m most excited for the pieces of their personality that will ultimately surprise me.

Sure, I hope they enjoy games as much as I do. I wish that they will be imaginative and that they’re able to hold on to that imagination for as long as possible. I hope that they love stories and love to read. I hope they love to create, I’m not sure I even care what, so long as they love to take a piece of themselves and see it expressed in the world. However, I promise not to be disappointed if one or more of these isn’t true.

Whoever you might be, I just hope for one simple thing, that you be happy. And I hope that I can play a role in making that true.