I want to travel more. It's a well-documented desire of mine. Specifically, I want to plan my own trips, because I've historically been pretty terrible at it. I even made a "process", which I'll paraphrase here:

  1. Wait until a particularly whimsical mood strikes.
  2. Bike aimlessly until you find a book store.
  3. Enter the book store.
  4. Find the travel/travel guide section.
  5. Close your eyes.
  6. Spin around, preferably 3-5 times.
  7. With eyes still closed, pick a travel guide off the shelf.
  8. Buy the travel guide.
  9. Read the travel guide.
  10. Go there. Optional: Be merry.

Using this bulletproof approach, I had picked out a destination, Taiwan. I don't want to say I'm giving up on all of that, because I'm definitely still going to do it…I just went somewhere else first. To explain where and why requires the slightest bit of backstory.

Oregon (aka The Slightest Bit of Backstory)

In 2017, I saw my first total solar eclipse in Oregon, and it left quite an impression on me. The sky darkened over the course of a few minutes, taking on a weird, twilight-esque hue. The temperature dropped by 10 or 15 degrees. Birds started acting strangely. Suddenly, it was very dark, the sky ringed with light on the horizon. I looked directly at the sun (normally an ill-advised thing to do), my eyes meeting a black orb surrounded with the wispy, shifting tendrils of the Sun's corona. I can understand why ancient civilizations believed in some truly crazy gods. Needless to say, I was hooked.

The main barrier to my newfound addiction: total solar eclipses are finicky. They don't happen often (~less than once a year), and they happen over an effectively random stretch of the planet. Post-2017, the next one wasn't until 2019, and it had every intention of passing over a narrow strip of South America, visible in small parts of Chile and Argentina. Even more rudely, this narrow strip (in dark red below, call the "path of totality") had the audacity to avoid most of the major cities that would make viewing it easy.

Pretty and informative diagram from Time and Date.

That said, I wasn't going to let the machinations of a few stubborn celestial bodies rain on my parade. So, a few months ago, I traveled 6,000 miles for an event that lasts approximately, you guessed it, 2 minutes and 17 seconds.


Chile Chile Chile, where do I begin. It all started about a week before I took off…

Preparations (Or a Lack Thereof)

…because that's when I actually planned (and subsequently booked) the trip. I recognize that this was Not Smart of Me™ for no less than 13 different reasons. While I won't enumerate all of them, let's take a peek at a few here.

13 4 Reasons Why Booking My First Solo, Non-Work International Trip One Week Prior to Departure Was a Bad Move™
  1. Stuff gets expensive.
  2. One week isn't a lot of time to plan.
  3. I've made this mistake for every trip I've done in the past.
  4. I knew I was going to do the trip a year and a half in advance.

I've gotten into this bad habit of not really planning my trips, because they're usually for work. That means most of the blanks are already filled in for me: dates of travel, places to stay, itinerary, etc. None of that was true here, and I wasn't really setting myself up for success by not budgeting the time for it.

In spite of my best efforts however, I still managed to pull the trip together. I had churned through enough credit cards to pay for the round trip flight, even accounting for how inflated the prices had become. And I used my solitary week before departure to figure out the absolute basics:

  • Visa requirements (None)
  • National Language (Chilean Spanish, among others)
  • Season & Climate (Winter at the time, but not in the bitter New England sense)
  • Risk of danger? (Not particularly)

After one week of frantic and frenzied Googling, I had all my flights and accommodations and odds-and-ends booked, and a plan that looked roughly like the following:

  1. Get near the eclipse (San Francisco -> New York -> Santiago -> La Serena)
  2. Stay in an Airbnb in La Serena
  3. Watch the eclipse
  4. Take a bus to Santiago
  5. Stay in a hostel in Santiago
  6. Explore Santiago
  7. Get home (Santiago -> New York -> San Francisco)

Okay, I swear I won't make another list or trademark Another Random Phrase™ for the rest of the post.

A pretty basic plan, I'll admit, but it covered all the bases. I'd fly to near the eclipse (three flights), get used to the area, see the eclipse, take a bus to Chile's capital/largest city, stay in a hostel, (perhaps) meet some people, explore the city, and fly home from there (two flights).

The Arrival

My first couple days were fraught with all the hurdles Murphy's Law could cook up. Flights were delayed, phones weren't working, and for a brief, suspenseful, and utterly nerve-wracking moment, I truly believed my Airbnb didn't actually exist. Once everything was all sorted out and I got settled in, the adventures began.

My first order of business was getting some food. La Serena (the largest Chilean city where the eclipse was visible from) is fairly small as far as cities go, and not particularly known for its food. Accordingly, I opted to pick up groceries so I could cook for myself. The reason for this was two-fold: 1) it's a good way to save a few bucks while travelling, and 2) I never get to cook for myself, the truck being devoid of appliances…and electricity…and food.

I took a bus to the local Lider (a chain acquired by Walmart) and marveled at all the little differences and things entirely lost on me in my day-to-day life. Milk was in un-refrigerated boxes, as were eggs. Jelly came in little bags. You weigh your fruits and vegetables where you get them, not at the register. This last one got me good, it took a fraught game of charades for the cashier to explain the concept to me at checkout.

My second order of business was getting really familiar with the buses and the schedule. Because I booked so late, all the hotels in La Serena were booked and I ended up in Coquimbo, ~10 miles from La Serena. I wanted to make sure I didn't miss the eclipse because of my own ineptitude at catching the bus.

Looking out from my Airbnb in Coquimbo. Off in the distance, just barely visible, is Coquimbo's main attraction, Cruz del Tercer Milenio, which is a ~270ft concrete cross.

Settling In

After a few days of learning the ropes, I had a couple basic takeaways:

1) My single, meager year of high school Spanish was no match for literally any conversation I attempted to navigate. Chileans speak far too quickly for my untrained ears, and the Chilean accent kinda drops the trailing sound off a work (like in French), which means things just sound different. Two of my most commonly used phrases (in Spanish) were "More slowly, please" and simply "What?". Hand gestures abounded.

2) Chilean money is infinitely entertaining. A bunch of bananas cost $616, because Chilean pesos use the same dollar sign ($) used for US currency. Technically they do have cents (centavos), but in practice, I didn't see any coins for less than 10 pesos.

3) Chilean buses are wild. I drove buses for four years in college, so I like to think I know a thing or two about them. Chilean bus drivers are on a whole 'nother level, and clearly competing in some bus rodeo that I'm not privy to. They whip those buses around like it's nobody's business. At one point, the bus I was on hopped a median because it didn't want to wait in traffic. My terror was matched only by my admiration.

El Eclipse Solar Total

Perfect eclipse-watching weather.

The day of the eclipse (July 2nd) rolls around, and I'm ready for action. I get to La Serena with plenty of time to spare. My lack of planning (see above) meant that I had forgotten one crucial tool: eclipse glasses. No problem though, everyone and their grandpa is selling cardboard eclipse glasses downtown, at a 10x markup. I fork over the cash and continue onward. Such is life.

Walking around with my eclipse glasses in hand, freshly divorced from ten US dollars, I decide I want to watch the event in relative quiet. There's a big eclipse festival going on downtown, so I start to head away towards a quieter residential area. The city slope downward from downtown to the coast, which means there are plenty of uninterrupted views of the sun. I walk a few miles, then sit down on a stone ledge alongside the sidewalk. And I wait.

I lied (multiple times) when I said that the eclipse only lasts two minutes and seventeen seconds. In actuality, the eclipse was nearly two and a half hours. It's just totality, the part people travel to see, where everything gets dark, that's so fleeting. When I sat down, the partial eclipse was just starting, so I had nearly an hour until the main event.

So there I was, sitting alone on my stone ledge, staring at the sun, paper glasses on my face, when an older lady strolls by pushing a small folding cart, clearly puzzled as to what I'm doing. I've since forgotten the smaller details of our interaction (such as her name), but she was Mormon, and had lived in La Serena her whole life. She was delighted to hear I came from California: her Mormon friend, who she kept an old picture of in her purse, lived there too.

We conversed mostly in Spanish, with very heavy use of a notepad that she would write down words in, and I would translate on my phone. She was infinitely patient. We spoke of the eclipse, the current goings-on in Chile and the US, the weather, and of family and religion. She initially tried to watch the eclipse by putting her flip phone's screen to her eye with the camera app open, which was an ultimately unsuccessful approach. We sat on the ledge for two hours, passing the glasses back and forth to watch the progress of the partial eclipse, sometimes in total silence, sometimes just pointing in delight at the progress the moon was making in its journey towards totality.

She had never seen a total solar eclipse before. In fact, she hadn't even realized one was going to happen then and there. To this day, I'm not sure what I enjoyed more: the eclipse itself, or the look on her face when it finally happened. She was so completely in awe and overjoyed, it was truly a special moment, and I couldn't have asked for (or planned) a better eclipse experience if I had tried.

Eventually, totality passed. My new Chilean friend and I parted ways, the brief intersection in our otherwise disjoint lives now over. I bused back (in obscene traffic) to my Airbnb, reflected a little on the experience, and packed my things for Santiago.


My bus to Santiago was scheduled to leave at 10 am. Out of an abundance of caution (and partially by accident), I ended up at the terminal at 8 am. With plenty of time to spare, I ordered a coffee, opened a book, and partook in my favorite pastime: people watching. Transit hubs are great for people watching, because they're frequently where people are beginning (and ending) different chapters of their lives, and they're full of people from diverse backgrounds.* It makes it easy to come up with grand backstories.

The six and a half hour bus ride was mostly uneventful. My seat was in the front row of the second-floor of a double-decker bus, which afforded me some pretty incredible views as we barreled down the Chilean coast. The TVs were playing clearly pirated rips of some straight-to-DVD movies, featuring such blockbusters as The Christmas Chronicles and The Crucifixion.

Eventually, we arrived in Santiago, and suffice it to say, I was unprepared. I had been disarmed by my few days in the quaint, laid-back La Serena. As it turns out, Santiago is a bustling metropolitan area, with a population larger than Los Angeles. When I got off the bus, I was wholly overwhelmed. It was loud, crowded, dirty, and I was legitimately thinking of shortening my trip by a few days and just heading home. Then I realized that every bus terminal in every major city in the world is loud and crowded and dirty, and it wasn't particularly representative of the rest of the city.

I eventually got my act together, purchased a bus card (bip!), and bused to my hostel. I started researching what there was to do in Santiago, and quickly realized Santiago was basically made for me. It's walkable, and chock full of sprawling public parks, high-quality (and frequently free) museums, cute little coffee shops, and even nearby hiking opportunities. I totally could have spent a month there and barely scratched the surface. After an hour or two of researching, I cooked up the following rough itinerary:

  • Thursday, July 4th
    • Plaza de Armas
    • Museo Chileno de Arte Precolombino
    • Museo Historico Nacional
    • Santiago Metropolitan Cathedral
    • ProntoMaticwhich is a laundromat, because I ran out of clothes.
  • Friday, July 5th
    • Hiking at Cerro San Cristobal
    • La Chascona
    • El Hombre Araña: Lejos de Casa
  • Saturday, July 6th
    • Parque Forestal
    • Bellas Artes

I'm not going to tackle each item one by one, because this post is already criminally long. So here are some pictures I took with my standard potato-quality smartphone camera:

From top-left to bottom-right: (1) Palacio de los Tribunales de Justicia de Santiago, where Chile's Supreme Court sits, (2 + 3) the mind-bogglingly massive Santiago Metropolitan Cathedral, (4 + 5) statues in Plaza de Armas and Parque Forestal, (6) the view from halfway up Cerro San Cristobal, and (7 + 8) posters at the movie theater.

Those three days were an absolute blur: I spent a dozen (or more) hours exploring museums and churches, learning a bit about Chile's history (both before and after Europe came knockin'). I checked out book stores and coffee shops and caught a movie and, at one harrowing point, got lost on my hike and stumbled onto someone's haphazard settlement in the woods. They were not happy to see me. Safely back down the mountain, I reached a serious milestone when I successfully ordered an empanada (sin carne), and was then able to pay without having to look at the register display (dos mil dos ciento = $2.200 CLP = ~$3 USD). I made some Brazilian friends at the hostel and we went out for dinner/drinks/dancing. The night included several glasses of a Chilean drink called Terremoto, which literally means "earthquake". It's some unholy concoction of alcohol and pineapple ice cream, and I look forward to never drinking another one again.

When I started planning the trip, it was originally "the Eclipse trip". After my whirlwind tour of Santiago, it's now "the Chile trip". I had dramatically underestimated Santiago as a destination unto itself, but I'm happy to report that it proved me wrong (over and over) in the best way.


Now that I've got my first solo (non-work) trip under my belt, I'd like to refine my travel philosophy a bit. In no particular order:

Doing the mundane things is just as important as doing the attractions. Shopping for groceries at Lider, doing laundry at the local ProntoMatic, or struggling through ordering an empanada, it's all part of the experience.

Pictures aren't a bad thing. I've always shied away from taking photos when I travel (or go to events). In the past, my rationale has been that I want to be present and live in the moment and all that other romanticized garbage. I'm also just cognizant (read: self-conscious) of looking "too touristy" when I pull out my phone and stand awkwardly in the middle of a crowded place to snap a pic. But photos can be useful. For one, they keep my blog posts from being uninterrupted black-and-white-wall-of-text tirades, adding a bit of color and space. And for two, my memory is total garbage. It doesn't matter how "present" or "in the moment" I am if I forget everything a few days later. Pictures last much longer,** and they'll help me remember when my mind fails me.

Learn the damn language. I eked by with my limited Spanish, but I could have had a bunch of more meaningful interactions (and been less reliant on my phone) if I had studied up beforehand. I'm certainly not saying I should be fluent, but ~a month of practicing the basics for nights and weekends would have gone a long way.

Don't book first, ask questions later. I had a great trip, don't get me wrong, but I could have made it even better by planning things out. If I had booked farther in advance, I could have coordinated a hike through the Elqui Valley and sampled local pisco brandy and watched the eclipse from a remote hilltop. But then again, I had a pretty great eclipse experience as it was. I'm still all for spontaneity, but it doesn't work well for events that attract a lot of people.

Obligatory Housekeeping Item

The small-to-mid-sized elephant in the room is just how long it's been since I've last written. I actually started this post while I was still in Chile, over five months ago. My defense: I've been busy. In the interim, I've been to Shanghai (twice***), Chicago, Boston, Orlando, and Boulder, and in the next few weeks I'll be in Boulder (again), Boston (again), Chicago (again), Malawi, and Kenya. I've spent my free time updating the blog infrastructure, reading my usual cocktail of self-help and sci-fi, and getting side-tracked building low-quality novelty sites.

That said, and armed with a new arsenal of organizational techniques, I plan to write more frequently and clear through my backlog of blog email. Well, maybe when I get back from Africa.

*After all, the need to travel from point A to point B cuts across all demographics. Certainly more interesting for people watching than your average yoga studio.

**Barring bad personal data hygiene, of course.

***Technically, my first trip to Shanghai was right before I went to Chile, but let's not get stuck on the specifics.

This is a story about my poor life choices and where they sometimes take me. It all started when I was a little boy a few months ago. It's President's day weekend*, and I've got some grand plans, at least in relation to how quiet I usually like my weekends.

Friday night was catching up with some friends

Saturday was a holiday party (¿in February?)

Sunday was exploring San Jose

Monday was supposed to be snowboarding, since I'm fortunate enough to have had work off (thank you Mr. Washington)

We made it until about Sunday evening before things went pear-shaped.

Setting The Scene


It's Saturday evening, about 6:45 PM. I've quite successfully nerd sniped myself, having spent the last 6 hours travelling down an infinite rabbit hole of configuring my servers.** I get dragged back to reality by my friend, who's texting me to say she's ready for the holiday party. Now, strictly speaking, I'm not late at this point, but I'd definitely lost track of time and was caught a bit off-guard.

I quickly head back to the truck to grab my suit and pack my bag, then head over to the gym for a quick shower. I make myself pretty, pick up my friend, and we head off to the holiday party.

Looks like I can add "giving people bunny ears" to the list of things I'm not good at, alongside "snowboarding", "dancing like Beyonce", and "knowing where my truck is".Foreshadowing!


It's Sunday afternoon. The holiday party was a blast, my friend and I are in San Jose eating avocado toast and drinking overpriced lattes like the Hipster Millennial Trash™ we are. We finish our discussion on the merits of heated Vinyasa flow goat yogakidding, and check out the Tech Museum, conveniently across the street from our hotel.*** After a few hours of pure educational bliss, we say goodbye to the museum and San Jose.

The next item on my grand weekend agenda is snowboarding. A few months ago, I got a season-long snowboard rental, and I keep it in the truck (usually just leaned against the wall). I call my friends in SF and tell them that I'm going to grab my board and I'll head up after. I get back to my usual stomping grounds and…

The truck isn't there.

Searching for Answers…and my Truck

There's something uniquely strange (and strangely unique) about losing track of your home. I wouldn't describe it as bad, just a bit disorienting. I try not to take too much for granted, but I guess I've come to expect the truck to be, you know, where I left it. So I'll be honest, I wasn't prepared for the truck's disappearing act, even if I'm always joking about the truck burning down having a negligible impact on my day.

At first I thought I had done something wrong, even if I couldn't say exactly what. I did a lap around the block, as if the truck would suddenly and miraculously reappear once I rounded that last bend. Much to my chagrin, it didn't. Had I parked it somewhere else perhaps? On a few previous occasions, I'd gone on a bike ride and absent-mindedly returned to the wrong place, but even after racking my brain, I couldn't remember moving it before I had left.

At this point I assume it's been towed or stolen, but which, and why, and when, and how? I have the only set of keys and I always habitually lock the doors. Plus, the area I was parked in isn't known for auto thefts. Plus plus, I had seen it ~24 hours ago, so there's a fairly narrow window of time to consider. I conclude that it probably wasn't stolen, which I guess is a good thing. I put on my sleuthing hat and get to work.

The first thing I do is knock on the door of my nearest "neighbor", and explain I'm the guy with the decrepit white box truck, and ask if they might perhaps know where it is. They (quite helpfully) explain that it was towed earlier in the day (Sunday), and even recount their (much appreciated, but ultimately unsuccessful) attempt to convince the towing company that they probably have the wrong vehicle. They suggest I check in with the police department and find out what happened.

Cool, so the truck's been towed. At least that eliminates a whole swath of hilarious-but-probably-messy-and-annoying-to-deal-with truckjacking situations. I call the local police station, they look up my vehicle, give me a case number, and tell me that I can pick it up tomorrow morning, they open at 7 am.

My first thought was, "Damn, guess I can't go snowboarding."

My second thought was, "Damn, now I'm even more houseless than usual."

I call my friend and give them the bad news: my house has been towed away, which means I have no snowboard or gear. Worse, I have to go pick it up tomorrow morning, so I can't go to Tahoe. They suggest I come up to SF anyway to hang, and save on the cost of the hotel room I likely would have rented. I think this is a great idea, and I drive my car to SF.

Picking up the Pieces

After a night in SF chock full of gourmet garlic bread and Pitch Perfect 3, I head back to South Bay, ready to get my affairs back in order.

My morning looks roughly like the following:

  1. Wait for police station to open
  2. Drive car to police station (7 am, sharp)
  3. Pay $155 vehicle release fee (ouch)
  4. Request a copy of the police report (because why not)
  5. Grab a leisurely breakfast, wait for tow yard to open
  6. Drive car to tow yard, ask for a copy of the police paperwork they received
  7. Pay $500 to get my truck back (big ouch)
  8. Drive truck back (I've yet to assess "the damage")
  9. Walk back to car at tow yard (~2 miles, but it was a gorgeous day)
  10. Drive car back (Thus ending my rousing game of Vehicle Juggling™)
  11. Assess the damage

The Damage

At this point, I'm down $655 and up one box truck. Speaking of the box truck, it has definitely seen better days:

The lock on the back had been cut, and there were marks from the slim jim the towing company had used to get into the truck, but those (thankfully) wiped away.

The truck looked like a cyclone hit it, my mattress thoroughly divorced from my bed frame among other things. All in all, a confusing state of affairs. Why cut the lock and hack open the front door? Either one alone would have been just fine, thankyouverymuch. Let's see if the report from the towing company answers any questions:

I can add 'scanning documents' to my list of things I'm not great at, but I'm pretty proud of my redacting work.

  1. My truck is described as a '2010 CHEVY'. In reality, it's a 2006 Ford. Close, but no cigar.
  2. The officer values my humble abode at between $501 and $4000. I personally take offense to this.
  3. The 'REASON FOR STOP' section has something scribbled out, then says '72 HRS PARKED'.
  4. The condition of the tires is marked as something that's hard to make out (even before my questionable scanning job), but appears to say 'POOR'.
  5. The highlighted section says 'SNOWBOARD IN BACK'.

My first thought was that they mistakenly towed the wrong vehicle, given the year/make/model were wrong. I'm usually pretty good about driving the truck at regular intervals, mostly to charge the battery, help folks move, and generally make sure things are in working order. That said, I very well may have been parked there for 72 hours, I have no evidence one way or the other.

I got the full police report a few days later. It's covered in scary watermarks that indicate I shouldn't post it here, so I'll just grab a few entertaining excerpts:

There was a padlock on the back of the truck, which I attempted to saw through, but my department issued electric saw ran out of battery power to finish the cutting.

Well, that explains the padlock nonsense. They had cut the wrong side of the lock. If they had cut the other one first, they would have been able to open it before their battery died.

After the fact, Sgt. [REDACTED] noticed an opening between the front and the storage area. Sgt. [REDACTED] and I had never seen this set up before.

I'm flattered I can add some novelty to humdrum of routine police work. But this was also a misstep on my part. In my rush to get to the holiday party, I hadn't closed my new(ish) interior door, so they could see straight from the doorway into my living/bed room, so to speak. That's certainly cause for them to investigate further.

[Towing company] arrived to store the RV per [some regulation]. The tow driver unlocked the truck, where I entered to do an inventory check of the back. There was a bed, new snowboard and miscellanous (sic) items in the truck.

"Unlocked" is quite the euphemism here. Up until I read this report, I hadn't realized they had actually explored the back of the truck. Aside from the general icky feeling you get when other people rummage through your things, I was surprised they could, from a legal perspective, just go into the truck and look around. But I checked with a few legal-type folks, and the general consensus is that 4th amendment protections don't apply as strongly to vehicles, even if you happen to live in them. I've heard similar stories from friends who have had their RV doors pried open by police.

The Depressing Part

There are a lot of things that went right with my situation. The truck disappeared and reappeared within a day. The impact on my life was minor and short-lived. I stayed at a friend's house, paid a fee, and picked up a new lock. Hell, I had a great time tracking down and retrieving the truck, it was a mini-adventure for me. But all of this is only true because I have the resources to not care about it. After all, crimes where the only punishment is a fine are effectively legal for those who can afford it. As an absurd example, the cost of living here means that I could park somewhere convenient and illegal, and if the only punishment is a parking ticket, it'd still literally be cheaper for me to pay it every single day than renting anywhere in a 15 mile radius.

I've talked about how my story is only entertaining because I'm doing it for fun. The fact of the matter is that most people living in vehicles are doing it because they can't afford housing, or paying for housing would dramatically reduce the quality of life for them, and sometimes their families as well. What happens to someone in that situation when their vehicle gets unexpectedly towed?

They find themselves truly homeless. Not only that, they now have to come up with ~$650 just to get their home back. That's a scary situation to be in, and it's not obvious to me what they should even do at that point. In a world where 40% of Americans can't cover a $400 emergency expense, this isn't even just a hypothetical example, and people living in vehicles are already a particularly vulnerable population.

Playing devil's advocate for a second: you could argue that, if their vehicle is so important to them, they should make sure it doesn't get towed. But life happens, mistakes happen. And in my case, it's not even obvious to me that my vehicle had been parked the requisite 72 hours before being towed.

In any case, homelessness and affordable housing are hard problems, and there's no silver bullet solution to fixing them. I plan on dedicating a full post to discussing this at some point.

*Feb 15-18 for those who don't keep tabs on American holidays.

**More specifically, I was setting up my own personal Athens proxy server to go with my own personal Drone CI/CD server to go with my own personal Gogs server, where I store the code for all of my personal programming projects (like this blog). I was also documenting the new proxy setup on my own personalwiki server.

***If you've never been, the Tech Museum is insanely cool. Their exhibit on human anatomy is beautiful and nightmare-inducing, and their 'Living Colors' exhibit on growing multi-colored bacteria is as captivating to me as it is for the 10-year old children it was designed for.

Source: Actual footage of me trying to write an essay to win this contest.

I can't remember where on The Internet™ I originally saw it, but at some point in the past few months I came across an article about a woman selling her preposterously picturesque home in Canada for the low, low price of $19 and an essay of (at most) 350 words.

The catch here (because houses usually cost more than nineteen dollars) is that you have to win the contest (i.e. have the bestest essay), and the woman running the contest needs to receive enough entries to cover what would normally be the asking price of the house, which happens to be $1.3 million USD. Crunching the (two) numbers here, that means ~68,000 people need to enter to effectively subsidizing the cost of this home for one lucky (and probably Canadian) duck.

As a dude who, uncoerced, writes rambling essays for random internet strangers, and regularly spends more than $19 on way worse things*, entering this contest seems like a no-brainer. There's even a prompt, which is like adding mental bowling bumpers to keep me from getting too sidetracked. Without further adieu, I present to you my answer to the question:

Why would moving to this lakefront dream home change your life?

The Entry

I don't have a lot of words to spare, so let me cut to the chase: I live in a truck, I'm very happy with it, and I have no intention of living in your home.

My claim: Houses are expensive, it's overwhelming likely that whoever wins your contest will have to sell it to pay the (inevitable) small fortune in taxes, which kinda defeats the purpose and spirit of the contest.

My proposition: If I win, I'll place the home in the care of a property management company. They'll find a renter, take their cut, and I'll donate the rest to charity. No strings attached. If it can be made legally binding, I'll happily sign on the dotted line before taking ownership of the home. If I ever sell the home, I'll donate those proceeds too.

Okay, with that out of the way, let's preemptively answer some questions.

Why do you live in a truck?

Housing in San Francisco is expensive. My [REDACTED] employer has all the amenities (gyms, food, laundry) I could ever need, so when I moved out to California nearly four years ago, I bought a box truck and threw a bed in the back. The rest is history, documented (sporadically) on my blog, FromInsideTheBox.com.

What charity will you donate to?

My personal preference is GiveDirectly, but that's too easy. My first order of business as New Canadian House Owner™ will be building a silly website (ala my day job) where people can vote on what charity to donate to. I'll call it HomelessHomeownerDonations.com or hopefully something catchier. Since the contest has already generated a bit of fanfare, I don't imagine I'll have a problem finding people to suggest and vote on charities.

What about your family?

Aside from having to endure harsh(ish) Boston winters, my family is doing just fine. I bought my [REDACTED] a house last year (so I'm already technically a homeless homeowner), meaning [they're] not really in a position to complain.

Anyway, let me know what you think, happy to discuss further.


If you've been here before, you're probably familiar with most of the contents of my three-hundred and forty-three word essay above, but I had to catch our new Canadian friend up to speed. Probably the only new/surprising thing in there is that I'd be willing to donate the money, rather than, well, keep it for myself. There's roughly two reasons why I'd opt to donate the proceeds:

  1. It'd help me win the contest.
  2. I've been trying to get into Effective Altruism.

The first reason is pretty self-explanatory. If my answer to the question "Why would moving to this lakefront dream home change [my] life?" is just "I like money and want even more of it", that's not particularly compelling or inspiring.

The second reason is probably the more interesting one, so let's talk about that.

A Philosophy on Giving

Effective Altruism is a philosophy centered on maximizing the good you can do in the world with the resources you have. I'd heard about the idea before, but was more formally introduced when a friend gave me a book on the topic for our yearly Secret Santa (thanks Joy!).

To be clear: I haven't actually finished the book yet, so I'm really not that well-versed in the details of Effective Altruism. The parts that I have read discuss different tools you can use to help evaluate how 'good' different (and seemingly incomparable) causes are. If nothing else, that seems pretty useful.

The main criticism I've heard of Effective Altruism is that it sucks all of the fun out of donating. For example, a strict adherent probably wouldn't donate to an animal shelter, or even give money to a homeless person, knowing that that money could literally save human lives in a third-world country.** Really strict adherents might choose careers to maximize their impact, which seems pretty hardcore to me (but power to them). I've also noticed that people I personally know who subscribe to Effective Altruism tend to also subscribe to fringe philosophies and movements that border on cult-y. That could just be because I know weird people in general though.

Circling back to my essay: having a side income (i.e. rental property in Canada) that I can dedicate wholly to donating is an easy way to increase my impact, outside of the (admittedly limited) donating I already do. The other (decidedly less altruistic) thing that would be nice about winning the contest, which I didn't have enough words to explain, is that I get to claim all of those donations as tax deductions, which is great for a dude who accidentally underpaid his taxes by $17,000 this past fiscal year.*** Then again, there's no reason I can't donate on those tax savings as well.

In any case, we'll see what happens…as soon as I figure out how to send $19 to Canada.

*Like mermaid costumes, hotdog onesies, and a small armada of novelty websites.

**Wikipedia informs me that lots of effective altruists do indeed care about animals. I don't think I've read that chapter yet.

***The proximate cause of my tax kerfuffle is a combination of changing tax laws and me having my withholdings set too low, which I've fixed for 2019. I didn't have to pay a penalty because the amount I paid was >100% of my previous year's taxes. Interestingly, the house purchase had a net zero impact on my taxes.

Recently, a reader of this blog tracked me down on Facebook and asked me a very interesting question. Just to be clear, I don't recommend doing this (even if I am indulging this behavior by writing this post). I may be terrible at answering questions, but I'm somewhat responsive over email, so maybe try me there first.

Anyway, the question went something roughly like:

And by roughly, I mean exactly, given that I took a screenshot of the question.

There's a few reasons I find this question interesting:

  1. I spend a lot of time thinking about my money.
  2. I spend a lot of time thinking about what I want out of life.
  3. I'm not sure I agree with the premise.

I responded on Facebook with an incoherent wall of text, as I am wont to do. For this post, I'm going to attempt to organize and format my ramblings into a semi-intelligible post.


The core of the question assumes that 'saving money' and 'experiencing life' are fundamentally ('somewhat') in conflict, which makes sense, to a certain degree: Doing stuff costs money, doing stuff is a key part of experiencing life, so it stands to reason that experiencing life costs money. The counter-argument I'd make here is that we're in control of how much those two things are in conflict.

Our lives are made of a billion different knobs that we can tweak: how many jobs do we want to have, what hobbies do we pursue, who do we spend our time with, what shows/books/media do we consume, etc, etc. I think that one of the most important sets of knobs we can tweak are the knobs that control how we define success* within our own lives. Once you define what success is, 'experiencing life' is just the vehicle we use to be successful.

For example, if success for you means 'having lots of nice things', experiencing life is probably going to involve buying lots of nice things, which will limit your ability to save. On the other hand, if success means 'challenging yourself to be better', experiencing life can be done pretty cheaply.

I'm obviously oversimplifying things, and everyone's idea of 'success' is going to be different and way more complicated than my examples above. That said, the premise is still true, we can control how much experiencing life impacts our ability to save.

To what end?

The other assumption baked into the question is that the questioner's idea of success involves saving money. Now, I'm all for saving money, but having money for the sake of money isn't all that useful. Money is a means to an end. If you have the means to reach that end, more money doesn't really do anything for you. This is largely in line with the idea that people don't seem to get any happier after they make about $105,000 a year. So for those cases where 'saving money' and 'experiencing life' are in conflict, it makes sense to ask what you're saving for, how much it will cost, and when you want it by.

Otherwise, the game of 'saving money' becomes an infinitely deep rabbit hole. Without a target or concrete motive, it's easy to drive yourself insane trying to optimize every little expenditure in your life. I try to focus on just the top three or so costs (or potential costs) in my life, like rent, food, and medical expenses**. I figure that once the larger expenses in my life are managed, I've done my due diligence and can cut myself some slack in other areas that account for a much smaller percentage of possible expenses.


Applying all of this to my own personal experience: I've tried to define what success means to me before. It's been a year and change since I wrote that though, so let's take another crack at it. Success to me means getting stronger/faster/smarter than I was before, cultivating the relationships I care about, exploring my hobbies (travel, blogging, etc), and eventually being financially independent.

Financial independence definitely requires saving money, but it's relatively easy to put an upper bound on just how much money. For example, I'd like to be financially independent before 40 and be able to buy a modest home in a relatively low cost-of-living area and support either a small family or a few large dogs.

Let's say that I'd need $60,000 a year to do that comfortably. Using a conservative safe withdrawal rate of 3%, I'll need to save $2 million before I'm 40 to make it happen. I can subtract how much I've currently saved from that $2 million, assume a 4% growth on my investments and get a rough idea of how much I need to save per year to reach that goal. Doing the math, it works out to less than I'm currently saving, which is to say I shouldn't let 'saving money' get in the way of my other success metrics.

One way that I want to 'experience life' is by catching the total solar eclipse in July, which means travelling to South America. I had traveled to Oregon with some friends to catch the total solar eclipse in 2017, and the experience was sufficiently life-changing that I'd like to make a hobby out of it. Knowing that I'm saving enough money to make my other goals work out in the long run means that they aren't in conflict with each other.

*I say 'success' instead of 'happiness', because I don't think that happiness is necessarily the goal to strive for. This Oatmeal comic explains it pretty well.

**I "control" my medical expenses by taking care of my body (and teeth) and just being supremely lucky that I don't have any chronic illnesses.

Source: Perfectly balanced, as all things should be.
I have no idea what this is supposed to be/represent, I just kept image search-ing random words until I found a few icons I liked.

ho·me·o·sta·sis (/ˌhōmēəˈstāsəs/) - the tendency toward a relatively stable equilibrium between interdependent elements, especially as maintained by physiological processes.

Recently, I've been more or less MIA, distracted by work trips, holidays, good books, and my random assortment of novelty website side projects.* Anyway, I figured this is as good a time as any for a general status update on the state of truck-related things. I'll try to avoid straying into retrospective/reflection territory, as I've already done enough of that this year last year, but no promises.

Finding a Rhythm

I'm a creature of habit. I like a healthy amount of structure in my life, and I have a routine that provides it. Even my spontaneity is usually structured; I set aside the same rough time frame every weekend to do something new and hopefully weird. Whether or not that's really sad is up for debate.

With that in mind, it's probably no surprise that my crowning truck achievement is how little has changed recently. It took me the better part of two years to figure out a winning formula for what I want out of the truck (and in it), but my setup has stayed largely the same since I threw out everything and bought new stuff, which was nearly a year and a half ago. In other words, I think I've reached Truck Homeostasis™**.

Truck Homeostasis looks something like the following: a small sunroof for ventilation, an interior door for security and slightly less sketchy ingress + egress, a giant storage cabinet (and associated organization system), and a raised bed frame for putting shoes and a few select items that don't fit in the storage cabinet.

Oh look, it's the vast majority of everything I own.

In recent memory, things have been pretty boring, but like, in a no-news-is-good-news kinda way. I've settled into my role as The Homeless Homeowner™, rolling with the ebbs and flows of mortgage payments and home repairs, and everything is on the right level of auto-pilot. As a result, there's really only a few vaguely noteworthy events worth rambling about, which is what I'll spend the rest of this post doing.

Seeing Double

An unfortunate side effect of being alive is consuming stuff, and sometimes that stuff hangs out for longer than you'd like. A pair of hiking shoes here, a sexy mermaid costume there, and on occasion, a birthday gift you don't quite have the heart to reject. Over time, even with the most diligent of cruft-control efforts, you end up with stuff you don't necessarily need. Luckily, the truck has no problem reminding me when I have too much stuff, just by virtue of being small.

This time around though, I noticed that not only did I have more things than I cared to, but more specifically I had duplicates of a lot of really random things. Like, for example, backpacks.


There are a few things I'm a total sucker for: good headphones, good notebooks/pencils/pens, and good backpacks. There's nothing like having a solid organizational system for schlepping around all of your garbage, which is extra important to me because I spend most of my time at places that aren't my "house". And one size doesn't always fit all, the system I use for carting around a full workday's worth of gym clothes, work clothes, and laptop(s) doesn't make a ton of sense for a long bike ride, which also doesn't make sense for organizing multi-week trips. Try to optimize for too many situations, and eventually you end up with this.

Five, count 'em, five different bags. From top-left, clockwise: one duffle for traveling, one steal-proof drawstring sack from a KickStarter, one everyday backpack gifted by my employer, one lightweight bag for hiking, and one for, well, everything else. Comprehensive? Yes. Entirely necessary? Not a chance.

That said, sometimes it's just plain hard to get rid of things. At some point in the past, I wholeheartedly believed I needed each one of these bags, despite knowing full well that having five bags is a bit silly. I managed to convince myself that I could get by with three, and I bit the proverbial bullet and donated the other two. I'll leave it as an exercise to the reader to figure out which bags I thought were superfluous and which were necessary.

Product area number two where I was seeing double (or triple, in this case): novelty outfits.

Erhm…"Novelty Outfits"

I wouldn't describe my wardrobe as "colorful" or "interesting" or "good". I wear a lot of black and grey and otherwise uninspired colors, mostly because I own like a week-and-a-half's worth of clothes, and I don't want them to be too memorable, lest people recognize how weirdly limited my outfit rotation is. If we're being honest here, the more adventurous parts of my wardrobe are all past years' Christmas gifts from my (Jewish) mother, who actually has a surprisingly well-tuned sense for men's fashion.

Boring wardrobe aside, I also own a few outfits reserved for special occasions. Not 'special' like weddings or white-tie affairs, more like Bay to Breakers or Halloween or the odd Ugly Sweater party.

Again, three novelty items here is looking a little crowded. The ugly sweater I got because I love pandas (in all their derpy glory), and wanted to be an active participant in each winter's barrage of Ugly Sweater parties. I also wear it once or twice in the middle of summer, just to make sure it doesn't get too lonely. The hotdog costume is reserved for races and onesie parties, and I bought the mermaid costume a few Halloweens ago as a protest against a good friend always having the flashiest costume. Personally, I like to think I did it justice.

Bringing back the BlurryFace™ treatment to showcase the more fringe items in my Seasonal Collection. Yes, I blurred out the octopus face.

In the end, I couldn't bring myself to actually get rid of any of these. They're all uniquely suited to a different subset of festive occasions, not to mention I haven't yet gotten my money's worth out of the mermaid costume. I have however resolved to not acquire any more pieces of novelty attire, if that counts for anything.


I had too many jackets.

A jacket for travelling to cold climates (featured here), a jacket for brisk days, a jacket for a motorcycle I don't own, and a jacket for reliving my ever-more-distant college days.

This one was easy. I think I've semi-successfully navigated my quarter-life crisis, so I donated the motorcycle jacket and the college sweatshirt. I still own a "UMass" shirt in case I ever need to pretend I'm a college student.

That concludes our tour through my closet/general spring winter cleaning efforts. Let's talk about vaguely noteworthy event #2.

An Old Enemy Returns

This was originally supposed to be the section of this post where I congratulated myself on not having any pest-related problems for over three years. Unfortunately that's an accolade I no longer get to give myself, because I recently came back to the truck and made the following mental observation:

"Huh, why does the floor look like it's moving? Weird."

This thought was immediately followed by an overwhelming sinking feeling and a sense of impending doom, as I realized my floor had been replaced (quite suddenly, might I add) with an entire army of tiny ants. I really cannot overstate how thoroughly they covered the floor, their intricate crisscrossing paths like the factory floor of a giant warehouse or sorting facility. Like, if I had a dollar for every tiny ant on the floor of the truck, I'd probably have bought a house in San Francisco that night.

Luckily (and perhaps unfortunately), this wasn't entirely unfamiliar territory for me: I have an entire arsenal of critter-killing cocktails that I keep in a small (and hopefully well-sealed) plastic bin in my storage cabinet. Given that there were ants coming and going every which way, I couldn't really tell where they were coming from (if it was indeed only one location), so I opened up my plastic death bin and liberally placed ant traps all around the truck. The saving grace (and reason I could sleep at all that night) is that the ants seemed content to stay on the floor; they weren't crawling up the walls or (**deep internal shudder**) on my bed.

What was particularly perplexing to me is that I had no idea what drew the ants to the truck. I keep literally nothing edible in the truck for exactly this reason. My best guess is that there was something about the wooden floor, perhaps something edible kicked up onto the underside of it. The onslaught came hot on the heels of the first (or maybe second?) rain of the season, so maybe that had something to do with it?

In any case, when I came back the next night, things were in much better shape, and the invasion was limited to a few hotspots along the walls. So I swept out a horrifyingly large dust cloud of dead ant debris, ripped out the insulation around the hotspots, did some more sweeping, then sealed the areas where the floor meets the walls with a heavy-duty construction adhesive, which I probably should have done years ago.

The infestation seems to be contained (knock on wood), as I haven't seen any ants in the past week or so, but I'll probably rip out the rest of the insulation and seal the rest of the floor just to prevent it from happening again.

In Conclusion

And that's about it, the current state of truck affairs all accounted for. Oh, and happy New Year! This obviously wasn't a New Year-related post, but that's probably fine. As my next order of business, I plan on catching up on my long-neglected blog email inbox.

*I haven't actually bothered to check this, but I'd be willing to bet that my output of blog posts trends downwards during the later months of the year, because I usually spend all of my free time August-December building a Christmas game/website for my hometown friends, where they fight for a varying number of inappropriately sized cash prizes. Past years' games have included clones of Cards Against Humanity, Texas Hold 'Em, Bomberman, Bananagrams, and Tetris.

**Tromeostasis? Nah never mind, that sounds terrible.


If you want to get emailed when I write a post, add your email here. Don't worry, you can always unsubscribe.