In the summer of 2025, I took a solo motorcycle trip to Alaska and beyond. In the end, I spent 71 days on the road and rode 14,871 miles. I spent 11 nights in hotels/motels, 5 nights at a friend’s house, and the remainder of the nights were spent camping either in a tent or a hammock. Previous to this, the last time I had been on a motorcycle was ~10 years ago when we lived in Tulum. The bike was very small displacement and was only used locally to go the grocery store and the beach. Prior to that, I briefly rode a bike on sunny summer days commuting to work with the occasional weekend outing with a friend. All of this is to say that I considered myself pretty much a newbie to motorcycling. So, how does someone with very little motorcycle experience end up on a 15k mile motorcycle adventure? Read on…

Just to recap, Cate and I drove a truck/camper along most of the Pan-American highway from 2016-2019. We weren’t able to drive the Alaska portion. This was disappointing to me, but I accepted it. During that trip we met several folks doing the trip on motorcycles, and I often felt a twinge of envy towards those people. The thought of the motorcyclists stuck with me and I had it in my mind that I one day might be able to complete the Pan-Am highway on a motorcycle. In fact, a benefit of my employment at the time was a sabbatical and in early 2020 I was due for my sabbatical. My original plan of what to do with this time was to buy a bike and complete the journey. Then COVID-19 happened so I stayed home instead.

My mother passed away in late 2019, and my father in spring 2023. Of course the deaths of my parents caused me a great deal of grief, but there was also the grief of losing our lifestyle. There were a lot of adjustments. We now own a printer, and dryer balls, and a whole host of other domestic items that we had done just fine without for several years previously. We’re homeowners now, with all of the stupid bullshit that comes with that. Mowing grass and cleaning gutters. Additionally, my job became a real drag. The stress of it had caused me to hate it. I felt the job detrimental to my mental health.

Please excuse the brief interlude, but now seems like a good time to back up and explain the title of this post for those not in the know. There’s a hip-hop artist known as Aesop Rock. I have a lot to say about him and his work, but for the purpose of this story, suffice to say that one of the themes he explores in his work is grief. He’s also vociferously anti-capitalist. In one of his works, he describes taking a motorcycle ride at night as a means to deal with his grief. The title is a line from that song, and to me the line is validation that withholding my labor and using my arms for my own pursuit is the right thing to do.

By early 2024 my arms were no longer being farmed.

In the case of the deaths of both my mother and father, getting final closure was a drawn-out affair. Both of them donated their bodies to the University of Hawaii John A. Burns School of Medicine. Their remains were returned only after their contributions to the course of study were complete. In the case of my mother, COVID-19 measures at the time meant there was no in-person ceremony. Normally, the remains of program participants are spread in the ocean near Waikiki from canoes and this is what would have happened for my mother had there been an in-person memorial service. Instead the cremains were returned via mail. My father wished to take her ashes to be spread amongst the bristlecone pines on Mt. Evans in Colorado. Unfortunately, the road was closed in the summer of 2020 so our closure would be delayed until the summer of 2021.

When I received the notice that my father would be completing the program in early 2025; I, effectively retired and unmotivated to do any of the things I should be doing, started to plan a trip to spread his ashes with my mother’s. This seemed like the perfect excuse to also complete the Pan-Am highway on a motorcycle. Coincidentally, I had been in contact with an old friend and he suggested we try to get together sometime soon. The idea of a trip was hatched and I drew some lines on a map. Future me would come to realize that those lines were pretty flawed, but every plan has to start somewhere. Unbeknownst to me at the time, the Mt. Evans road was due to be closed during the summer of 2025, so there would be no trip there with dad’s cremains.

Buying a Motorcycle

Before a motorcycle trip was going to happen, I would need a motorcycle. Back in the days when I was fantasizing about doing this on my sabbatical and drawing from knowledge I had gained while we were overlanding the Pan-Am, I had decided that the Kawasaki KLR 650 was the proper bike for this trip. Nine years ago, perhaps that was the case. In 2025…maybe not so much. The thing about the KLR that really stuck with me was its legendary reliability. Generally speaking, this was true of many Japanese bikes, but the KLR occupies a special place in the lore of motorcycle reliability. That said, many of the reliability issues in the days of yore have been solved by replacing carburetors with electronic fuel injection. I have a lot of thoughts regarding how to select a motorcycle, but that’s not really what this post is about, so I’ll skip all of that. To make a long story short, I had a list of makes/models that I thought would be appropriate for the type of rider I anticipated I would be that would also work for a trip like this. One of those was the KTM 390 Adventure. I opine that this bike is a really, really great value and nearly perfect for someone like me doing a trip like I did. When one came up for sale on the used market, I got in touch with the seller and we struck a deal. Given that the KLR 650 was my baseline, the bike I bought makes 1 fewer hp, but weighs 120 pounds less. It’s got a six-speed vs. the five in the KLR. It comes standard with ABS (optional on the KLR) and traction control, and a TFT screen with a tachometer (new generation KLR has no tach). The lower weight was really the spec that made the difference for me. In all of my years on earth, my back is still in good shape. I’d like to keep it that way, so lighter seemed much, much better in case I’d need to pick it up (I did need to pick it up a few times).

Planning

I hatched the idea for this trip and then spent money on it before doing a great deal of research and planning. I knew it would be possible to ship a bike to the continent, but I wasn’t really aware of any of the ins and outs of the process. As it turns out, there’s really only one choice. I would need to ship to San Diego, CA. My initial plans assumed a start/finish in Seattle, WA. Southern California is a long way away from anywhere I wanted to ride. At any rate, this gave me a defined starting point, and without putting too much thought into it, I just figured this would be my finish point as well. At this point the lines on my map connected San Diego, CA, Prudhoe Bay, AK, Green Bay, WI, and back to San Diego:

This was just kind of a rough idea. I eventually decided that I wanted to maximize visits to various national parks, you know, enjoy them before they get sold off to Paris Hilton or whoever. I also decided to follow parts of the historical Route 66 back to San Diego.

I would also need gear appropriate for riding in all conditions, suitable camping gear, and a well thought out set of tools and spare parts. Suitable luggage for the motorcycle would need to be acquired and installed. I really wanted to limit the number of batteries I would need to manage, so this meant no camera(s), drones, tablets, computers, heated riding gear, bluetooth earbuds, etc. I did end up getting a helmet brake light that required charging daily, though it is not possible to charge while riding. The air pump that I purchased for the trip also serves as a power bank, so I decided I would charge it while riding during the day and use it to charge the helmet brake light at night. I would use my phone as a navigation/music system and it charges on its mount while riding.

The Trip

Prior to setting off, I tried to get as much riding experience as possible. I ended up putting over 2,000 miles on my bike. All of that is on two-lane roads with speed limits of 55 mph or lower, and secondary roads/gravel/dirt. There’s no eight lane superhighway through a mega city near where I live and I was extraordinarily nervous about riding through Los Angeles on the first day of this trip. I wasn’t sure if my tiny adventure bike would keep up with LA traffic. I was pretty sure I’d be run over and devoured by it before I even got to my first camp site. I decide to depart at 3AM in an attempt to get through LA before traffic became bad and also to get through Bakersfield before the heat of the day. As it turned out, the little adventure bike goes plenty fast for LA. I got through LA and Bakersfield which was confidence inspiring but I felt much more relaxed when I got on the secondary roads and made my way to Sequoia National Park, where I would camp for the first night.

My camp neighbors at Sequoia were a lot of fun. They were a group of retired or getting ready to retire ladies. They invited me over to eat with them and then we went for a little hike in a nearby meadow where we saw a black bear which was a reminder that I needed to purchase bear spray still.

After that first day, I settled in to a routine pretty quickly. Most days were a variation on getting up and breaking camp, loading the bike, and hitting the road as early as practical. I decided I would try to keep my daily mileage under 250 and stop early in the day. I wasn’t carrying any cooking equipment. I couldn’t even make a cup of hot coffee in the morning. I mostly relied on gas station coffee and pastries for breakfast.

From Sequoia National Park, I made my way towards Yosemite. The view of El Capitan as I rounded the corner was incredible. Tonight’s camp site would remind me that I still needed to purchase mosquito repellent.

The next noteworthy destination was Crater Lake. Unfortunately, sections of the road around the lake were closed so I was only able to see part of it, but the part I did see is incredibly beautiful.

From there, I headed to the Oregon coast. I had reserved a camp site at Coos Bay. This turned out to be a bit of a mistake. The campground mostly caters to motorsports enthusiasts who are there to ride various off-road vehicles in the sand dunes. This results in a layout that isn’t optimized for enjoying the peace and quiet of the nature around you. It was also windy and cold.

I followed the coast north until I got the Olympic National Park. I spent a day exploring there and then pointed the bike east and rode through some spectacular scenery in North Cascades National Park.

After North Cascades National Park, I crossed into Canada. I had called ahead to a motorcycle shop and had some tires waiting for me. I wanted to replace tires before getting to Yukon, since opportunities would be few and far between the further north I rode.

Kelowna B.C. was my first hotel night. I found out I don’t much care for hotels while on a motorcycle trip. It’s much more a pain in the ass to offload everything and bring inside than it is to just sleep next to it, and the neighborhood I found myself in was definitely the “secure everything” kind of neighborhood. Seriously, Kelowna. Shit’s bad. Anyhow, my plan was to get my tires changed and get back on the road. I ended up having a bit of a time with it, but was ultimately successful enough so that I could leave this shithole. Unfortunately, during the course of changing the rear tire, the reluctor ring for the ABS system got bent. This meant that I would not have ABS, traction control, or cruise control until this problem was resolved. It was Friday and this was a job I didn’t have equipment to do myself. I had no interest in spending any more time in a city overrun with tranq zombies so I pushed onward without the aid of fancy electronics. During my departure ride, I experienced my first downpour of the trip, dropped the bike for the first time, and ended up camping near some railroad tracks with noisy ass trains all night.

The weekend was spent cruising wide open straight highways. Would have loved to have cruise control here. By Monday I reached Vanderhoof, B.C. where there is a machine shop. I stopped in to see if they could help me with my bent ring, and shortly after was leaving town with a straight ring, ABS, traction control and cruise all working as expected.

I camped at a lake. When I arrived and was setting up, there were a couple guys getting their boat on its trailer. We got into a conversation and they’re pretty cool guys. They’re just out jackassing around, enjoying all the great outdoors of Canada has to offer them. They reminded me a lot of me and the buddy I would be visiting in Wisconsin.

The next day, I started on the Stewart – Cassiar highway. Not long after turning on that highway, it seemed like shit got real. The landscape is definitely wilder here. Very large. Lots of bears.

At the northern end of the Stewart – Cassiar highway, I entered Yukon and turned on to the Alaska highway. Strategizing for the rain was an impediment to progress here. In hindsight, I was not well prepared for being rained on while on a motorcycle. Remarkably though, even with the indecisiveness regarding how to deal with rain, I rode nearly 400 miles, which you’ll notice is more than the 250 I wanted to try and stick to but with lots of daylight, it wasn’t a problem. I arrived to a place called Teslin. I mention it because there’s a really long metal grate bridge on the way. That bridge had been rained on all day and there was opposing truck traffic on it. If you’ve never ridden a motorcycle across a metal grate bridge, it’s freaky. It feels like the motorcycle is on ice skates or something. The sensation is very unsettling and I don’t care for it. The combination of everything broke me. The Teslin fuel pumps/restaurant/campground were on the side of the bridge I was traveling to and I was happy to stop for fuel/food and a break. I spent much of the evening trying to figure out how many more bridges of this type I would have to cross on the remainder of my trip. Thankfully, the number I came up with was zero. I’d have given serious consideration to ending the trip right there if there were more of these in my future. Given that I’m writing this after having crossed the bridge going the other direction, I can say that I wasn’t nearly as bothered by it or any other subsequent metal grate bridges now that I’ve gained that much more experience riding.

My plan from here was to go to Skagway and then catch a ferry to Haines. I made this plan without having any knowledge of ferry schedules and just assumed it was a daily thing. My assumption was wrong. I did ride to Skagway. I arrived after campground offices had closed for the day. I ended up finding a spot and set up a tent and promptly set out to find a bar. When I did, I noticed a bottle of Clase Azul tequila on their shelf. I opted to make this a celebratory drink. My first time to Alaska!

The next morning, I broke camp and loaded the bike. I stopped by the campground office only to find out that the spot I had occupied the previous night comes with a price tag of $75. I could have totally slipped right out. Honesty cost me on this one. Fuckin’ robbery, but whatcha gonna do? Skagway and Alaska proved to be quite unwelcoming in plenty of other ways. You go there for natural beauty, and there’s endless amounts of it but I encountered a very high concentration of straight up entitled assholes in Alaska.

Anyhow, given that I was feeling unwelcome, I was happy to arrange for my departure so I headed to the ferry terminal to find out what time the ferry for Haines would be leaving. I was told that it would be leaving on Tuesday. It was Saturday. I had already had my fill of Skagway so I wasn’t hanging out waiting for the ferry. I retraced the previous day’s ride until rejoining the Alaska highway and I set my sights on Whitehorse.

Just outside of Whitehorse is a pretty famous motorcycle camp. The place is set up very well for motorcyclists. It has a workshop with a motorcycle lift, a tire machine, and plenty other tools/supplies. My bike was due for an oil change so I got that done while here. The place also has laundry so I got some of that done. I met a few other riders, some of whom I would continue to see at various places on the route.

I departed the Yukon Motorcycle Park with the general idea of riding towards Fairbanks and waiting for an ideal weather window to ride to the northernmost motorable place in North America. The ride was nice. Mostly favorable weather and nothing too remarkable happened.

Research had shown me a promising hostel/campground in Fairbanks so when I arrived, I checked in there. Sven’s Basecamp hostel in Fairbanks turned out to be a great choice for me. There were other motorcyclists there. Some who had just completed the trip to Prudhoe Bay, and others who, like me, were waiting for a weather window. There were also other adventurers of various pursuits. Evenings around here were just great. I really liked this place.

After three nights at the hostel, the weather forecast was looking very favorable. During the stay there, the motorcyclists who were riding north had made a pact to stick together and help each other out along the way. Pretty fantastic camaraderie, I thought.

We all departed on the same morning and met up again at Coldfoot camp which is about halfway between Fox, AK and Prudhoe Bay (Deadhorse), AK. The Dalton highway was built to service the oil fields in Prudhoe Bay. It’s an industrial “haul road” first and not really maintained for the purpose of recreational travel. Surface conditions vary from not very good to absolutely horrible. From Coldfoot to Deadhorse is 250 miles with no services whatsoever. If your fuel range is less than 250 miles, you need to carry extra fuel to make the trip. There’s no restaurants or repair shops between the two.

Accommodation in Prudhoe Bay is expensive. Access to the Arctic Ocean requires one to book a tour a day ahead and is also expensive. I had no interest in staying in expensive lodging or taking a tour that would require me giving up personal information that surely won’t be safeguarded so I made alternate plans. From Coldfoot, I rode to a campground at Galbraith lake and spent the night. The next day, I rode to Prudhoe Bay and then back to the lake to camp again. This strategy ended up requiring an additional day on the Dalton Highway, but since I have more time than I do money, the trade-off was acceptable.

Having reached the end of the road, I had no choice but to turn around and do some backtracking. On the return to Fairbanks, I managed to pick up a massive piece of iron in my tire. I got it plugged and air back in the tire, but as time would tell, the lifespan of the tire had been significantly reduced.

Back at Sven’s Basecamp in Fairbanks, myself and the rest of the riders did some celebrating and made revelry. I may have overdone it a bit and I ended up needing quite a bit of rest the following day. After a rest and some light errands in the relative civilization that is Fairbanks, I set off to explore around Alaska a bit before heading back south.

I rode to Denali National Park and was treated to a rare sighting of the peak that the park is named for. I rode to the Matanuska glacier and camped nearby. I rode to Seward. I had high hopes for exploring around the Kenai Peninsula, but alas, the weather was not favorable for motorcycle riding or glacier viewing. I ended up rained in my tent in Seward.

When I departed Seward, I was headed to Whittier where I would board a ferry that I had checked the schedule for and purchased a ticket on to Valdez. Getting to Whittier is a unique experience. There’s a tunnel. The tunnel is shared with railroad tracks and trains. This necessitates timed passage through the tunnel. It’s a bit of a different world on the other side of that tunnel. It’s possible the tunnel is some kind of wormhole to another dimension. I don’t think I’ve been the same since having gone through it.

The ferry trip to Valdez was a nighttime affair. It was particularly meaningful in this instance as it was the first time I had seen stars in a few weeks at this point. At this latitude and this time of year the sun never gets far enough below the horizon for the sky to get dark. The return of darkness and stars was welcome.

From Valdez I made my way to McCarthy and the Wrangell – St. Elias National Park. It was an awesome ride with more views of really big mountains and wide open spaces. Beyond McCarthy, I made my exit from Alaska via the Top of the World highway that took me to Dawson City, Yukon then to Whitehorse again and a tiny bit of backtracking along the Alaska Highway.

The weather turned cold after I left Whitehorse. So much so that I opted to stay in a hotel in Watson Lake. That didn’t improve for a few days and several miles south. I ended up skipping a few of the things that I wanted to do due to being low key miserable so I just kept riding south with the hope of getting to warmer weather.

On the trip north, I didn’t really notice when the restrooms went from running water to pit toilets but I definitely noticed the first roadside restroom with running water on the trip south. Where there are flush toilets, there are families with children. It felt a bit like a return to civilization or something. Would I need to seek out some kind of training to be able to reassimilate?

I visited a couple of the famous parks in Alberta. Saw some glaciers. Saw a fat family pulling a wagon full of fat pugs. As I rode south in Alberta, I noticed a never ending stream of “oversize” loads moving equipment north. I can only assume that this equipment is directly related to the extraction of energy whether natural gas or oil or whatever else. I also noticed what was surely a beautiful pine forest that had been recently devastated by wild fire exacerbated by climate change. I noticed the shrinking glaciers. This juxtaposition was a real mind fuck for me. I don’t like it.

I made my way to Glacier National Park in Montana and then generally eastward across the northern plains. I rode through North Dakota and Minnesota before arriving in Wisconsin to visit my buddy. I crashed my bike in a mud puddle one morning. It turns out that a motorcycle air bag doubles as a flotation device.

By the time I got to my buddy’s house, my bike was screaming for some maintenance. While still in Alberta, I ended up needing to replace my chain but a correct replacement was not available so I replaced it with an incorrect one and its life was nearly over. Also, the aforementioned reduced life span of my tire was a dire concern by this point in time. I ended up staying longer than I had planned but I’m glad I had a place to attend to these necessary tasks. It was an absolute pleasure to hang out and catch up with an old friend.

Having achieved all of the things I wanted to achieve on the trip, it was functionally over, but I still needed to get back to San Diego for return shipping. I made my way towards Chicago for the start of Route 66. I caught up with another old friend on the way. It was awesome!

I more-or-less followed what I could of Route 66 across Illinois, Missouri, Oklahoma, and New Mexico until Santa Fe where I turned north with Mesa Verde National Park in my sights.

From there, I visited the Navajo National Monument where I enjoyed the coyotes yipping through the night. I rode to Grand Canyon National Park, then to Joshua Tree National Park and finally returned to San Diego for shipping the bike and celebratory libations.

If I were ever to do something like this again (and I plan on it) here’s a bit of an after action review:

What Worked Well

• Timing and length of the trip. I had as much time as I felt I needed. I wasn’t rushed.
• Positive experience. Overall the trip was fantastic. I’ve found a passion for motorcycling and feel great for having done it.
• Tools. The tools I took were the right tools for what I needed.
• Camp chair. This is a point of debate it seems, but for me, it was important enough to have back support when seated in camp that I packed a large chair with me.
• Tent/sleep system. Easy to set up. Was sufficiently durable for the trip. Kept the water off.
• Packing. While I certainly overpacked a bit, for the most part, everything that I took proved useful.
• Food/coffee strategy. I didn’t carry any cooking equipment. Couldn’t even make a hot cuppa in the morning. There were only a few mornings when I wouldn’t be riding by somewhere I could get coffee and in those cases I just purchased and carried canned coffee drinks to get my morning fix. Cold food on rare occasions was fine.
• The bike. I feel I made a great choice for the kind of rider I was when I began and the kind of rider I became while on the trip. It was economical and did everything I asked of it.
• Hippo Hands. I installed these on my handlebars. They look stupid so I avoided putting them on until the first time I encountered rain, but once they were on, I left them on and I never had to put on wet gloves the next day.
• Prioritizing a dry sleeping bag. I kept the bag dry which contributed significantly to my comfort at night.
• Short riding days. I feel I did quite well with the 250 mile “limit”. There were a couple of days where I rode much further but I could and that’s kinda the point. Limiting my days to 250 miles kept me from getting fatigued and burnt out. I had time to stop and look at things and enjoy the trip.

What Didn’t Work Well

• Rain gear. I was ill-prepared. My helmet fogged up horribly, making me use goggles in the rain. The rain paints I started with were snow boarding pants. They were a pain-in-the-ass to put on and the bottoms got hung up in my footpegs causing a hazardous condition if I needed to move a foot off the pegs, e.g. when stopping and putting a foot down.
• Phone as navigation system. The phone gets hot with that much sun exposure and so won’t charge then it needs to go in a pocket where it also doesn’t charge and is less than ideal when navigating cities. Repeated exposure to rain will eventually break it via water intake in the USB port.
• Hotels. I found I’d rather camp than unload the bike and take everything inside. The luggage works well enough on the bike. Once it’s removed things become more difficult to find and put away. This is, of course, contextual. If I were staying in Latin America style posadas or whatever where I can take the bike inside the courtyard or other indoor/walled parking that might be different.

I don’t do challenges. And when I say challenges I mean the types of challenges that go viral on social media. You know the ones. I didn’t dump a bucket of ice water on my head. I’ve never planked. And I most certainly have not done the Harlem Shake.

In fact, if you challenge me with something I’m not getting paid for I’m more likely to duck and run than I am to take you on. I’m lazy that way.

However, if I come up with a challenge on my own that’s a different story, and this story is about 96 books.

As you can imagine Will and I have a lot of time to talk when there are miles and miles of empty road in front of us. A few days ago Will asked me about the Nobel prize for literature. Specifically if the prize was given to a single published piece or to the author (we later learned it’s awarded to an author based on their body of work). We had no G’s at the time but this led to a discussion about literary prizes in general and the Pulitzer specifically.

Then I got an idea.

Anyone who knows me knows that I read like my ass is on fire. I read when I’m bored, I read when I’m anxious, I read when I’m supposed to be doing other things. And reading is such an integral part of my sleep routine that if I don’t get my eyes on at least a few pages the chances are good that I won’t sleep at all.

Science says that reading is good for you. I know it’s good for me. So why do I need to undertake a reading challenge when I already read so much? The short answer is this: I read garbage. More to the point, I read books about horses that are geared toward younger people. This leads to Will receiving emails from Amazon suggesting YA books for him since we share a Kindle account. It’s funny but it’s not.

So, on that 12 hour driving day I scanned the Wikipedia page about Pulitzer prize winners and it came to me. I need to learn more about the world, my world, and the best way for me to do that is to read.

I’m going to read every fiction and nonfiction Pulitzer prize winning book published since the year I was born. I haven’t given myself a time limit but I have given myself some rules. They are as follows.

• I will start with the 1970 winners and read both books for each for year before moving on.
• I will read the nonfiction book first since I’m not a huge fan of nonfiction. The fiction winner will be my reward.
• I will write a report for each book, incorporating the social and political atmospheres of the year and decide how or if the literature reflects that.
• In the few cases when there was no winner for the year I will read one of the finalists or the National Book Award winner for that year.
• I have read 15 of the fiction winners. I will read them again. I will struggle mightily to finish The Goldfinch. I will reaffirm my sincere belief that no one can read Thomas Pynchon and make sense of it.

So, with that being said, this is what I’ll be reading.

As you can see I have my work cut out for me. Even typing the full titles of the non fiction books makes me a bit weak in the knees. However, I’m intrigued and excited to get started. I’ll also have to amend my list soon as 2019’s winners are announced. Then 2020, and so on.

And that, my friends, is how a habit grows its wings.

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on the Automattic yacht.

That’s my job title. Because at Automattic we pick our own job titles. I think that’s a really cool policy. Previously I have been a ninja and an alligator wrestler; and for the next few weeks and the previous couple, I am also a community guardian.

I haven’t really blogged about work much. I really don’t want to put that much personal information out there. Also, it has taken a long time for me to adjust to being full-time employed. If you’ve been following along on my adventures from the beginning of my journey, you know full well that I am very comfortable with being cyclically unemployed. I relished the freedom and the psychology of my employment having an “end date” did wonders for my morale. The problem was, that employment did require a physical presence for long stretches of time, sometimes in the worst ducking conditions known to man on earth. Yeah, the adventure aspect of that was nifty and so far as the Antarctic portion of that employment cycle, I’d be keen to do it again at some point. Maybe when I get old I can go be a shuttle driver or something, provided the whole damn thing hasn’t been flooded by sea level rise by then.

Anyhow, in addition to the requirement of a physical presence, I also found myself more and more at odds with my own beliefs and values. I know that me stepping away from the machine isn’t going to bring the machine to a grinding halt. There are willing people to do that type of work. Doesn’t mean I have to be a part of it.

In 2014, at the tender age of 45, I did a career 180. My first intention was to be a freelance software developer with a focus on WordPress plugins. Turns out I’m a horrible entrepreneur. I tried a few different approaches and failed miserably in all of them.

I was working on a client project one day. That project involved WooCommerce so there I was browsing the documentation when at the bottom there was some sort of “hey, want to work with us” type advertisement. I applied. Mark and Magnus must have taken pity on an old man or been very desperate or a combination of both and here we are today.

Something pretty significant happened along the way though. WooCommerce was acquired by Automattic. When I first got that news, I was floored. I looked up at that company and aspired to one day work there. In no way did I consider myself worthy at that particular point in time. But, fake ’til you make it I guess ¯_(ツ)_/¯.

This hasn’t been an easy year for me at work and otherwise. There were a lot of changes and I lost a lot of the flexibility that had drawn me to that type of work environment to begin with. I struggled. I really loathed the idea of trying to find another job this good and I have never lost site of how horrible I am at trying to be my own boss. I had to find other ways to cope. And I have. I have also found myself truly respected and adequately supported in my endeavors.

Which brings me back to my job title. There is no yacht but if there ever is, I have staked my claim to the engine room and adventures on the high seas. And the champagne.