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,

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 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.

Source: Get it? It's a Red Solo Cup™. The amount of effort I put into selecting or drawing a post picture is based on nothing and varies wildly from post to post.

I'm completely going to ignore the fact it's been four month since I wrote last.
Writing is hard sometimes.

When I started the blog, I talked a lot about my travel ambitions, mostly about my romantic and hyper-idealized fantasies about perpetually travelling. My thoughts on the topic have shifted a bit, but the core reasoning still stands: I think travel is the best way to expand your understanding of the world and the people in it.

While I've definitely stepped up my travel game in the past few years, most of my trips have been planned by other people (friends, work, significant other, etc). Even though they've all been great trips, I want to start doing solo trips, which means being a more active participant in the whole trip planning process. The logical first step is to figure out some sort of process for planning these new Big Boy Solo Trips™ of mine. After much thought (read: no thought), I came up with the following proposal.

The Proposal

I'll take (roughly) two solo trips a year: one will be domestic, one will be international. The domestic trip(s) will probably be decided by what flights are on sale and/or fair dice roll. The international trip will be chosen via the following Very Serious™ 10-step system:

  1. Wait until a particularly whimsical mood strikes. If you're also feeling wanderlust-y, that helps too.
  2. Bike aimlessly until you find a book store. Try to find a different book store every time you do this, for maximum whimsy.
  3. Enter the book store. Act casual.
  4. Find the travel/travel guide section. If they don't have a travel section, the cooking section will do just fine restart at step 1.
  5. Close your eyes. Bear with me here.
  6. Spin around, preferably 3-5 times. Trust me, this is very normal and won't look weird to fellow book store-goers.
  7. With eyes still closed, pick a travel guide off the shelf. You can probably see where we're going at this point.
  8. Buy the travel guide. Money can be exchanged for goods and services.
  9. Read the travel guide. This step might take some time, you can exit the book store at this point, leaving patrons to wonder what just happened.
  10. Travel somewhere entirely unrelated. Just kidding, travel to the location in the travel guide.

If that system sounds weirdly specific, it's because I already did steps #1 through #8, and I'm retroactively formalizing it. Last month (on a particularly whimsical and wanderlust-y day), I went on a post-work bike ride to nowhere in particular, and ended up at a book store, in the travel section, with my eyes closed, feeling slightly dizzy. I ended up walking out with the following:

The fruits of my first-ever Very Serious™ 10-step system run-through, naturally under sketchy box truck lighting.

As you can see from above, my first solo, personal, international travel destination will be Taiwan, and I'm looking forward to learning about it over the course of the next few months. Turning my short attention span to domestic travel, I actually recently went on my first solo, personal, domestic trip, which was to Austin, Texas, and was a genuinely wonderful time.

Why Austin though? That's a long story, perhaps for another post. Though I will say, the choice was based not on price nor dice. Don't worry, a fair amount of whimsy was still most definitely involved.

Source: This isn't the house I bought, but if I was going to design my own, it'd probably look something like this. Small, lots of natural light, hopefully mostly self-sustaining, out in the middle of nowhere, but biking distance to civilization. House from Architectural Digest.

My life may or may not consist of a series of questionable (and sometimes poorly thought out) choices that are ever so slightly outside my comfort zone. Even with a long line of shaky choices to choose from, a recent choice (and the topic of this post) might mark the climax of my personal brand of impulsive opportunism.

Since I'm wholly unable to structure my posts for dramatic effect and gave away the surprise in the title, what I'm trying to say is: I bought a house. Don't worry though, the house is 3,000 miles away and I still totally live in a truck.

Wait, what?

It's a sad fact of reality that despite having a decent job and pocketing/investing all of my rent-savings by living in a truck for the past three years, I'm not anywhere remotely near the realm of having the luxury of considering the idea of potentially almost thinking about purchasing a home in the Bay Area.

But, with that same decent job and rent-savings, I'm perfectly well-equipped to buy a home many other places in the country, including around my hometown, for example. In fact, if you squint a bit, three years of Bay Area rent is a pretty solid down payment in a lot of places. So when a close family member lamented their frequently rising rents and frustrations trying to get a mortgage, I had an idea.

My thought went something like this: I could buy a home, and they could live in it and fix it up to their liking (their significant other is a contractor, who fixes houses for a living). When they move elsewhere, I can finish paying off the mortgage in one lump payment and start renting it out, or even sell it if I so desire.

So that's what I've been up to for the past few months: making offers on homes in the Greater Boston area. About two months ago, one of my offers was accepted, and a few hectic weeks later, I flew out to Boston to sign my soul and first-born child away close the deal and help the aforementioned family member move in. It's definitely weird to say, but as of May 24th, 2018, I'm officially a homeowner. Just to reiterate, I still live in a truck though.

The Process

Not that I ever intended for it to be this way, but the blog tends to be pretty family-friendly. I mean it makes sense, I'd really have to go out of my way to make a blog about box trucks overtly risqué or indecent. Allow me to trample all over that for a brief second with some PG-13 language:

Buying a house is a f***ing process.

Not only is it a process, but (as one might expect) living in a truck and being 3,000 miles away doesn't make it any easier. If you've never bought a home (3,000 miles away) (while living in a truck) before, the process looks roughly like this:

1. Find an agent.
2. Find a real estate attorney.
3. Put in offers.
4. Get offers rejected.
5. Put in more offers.
6. Get an offer accepted.
7a. Panic, existentially.
7b. Panic, financially.
8. Shop for a mortgage.
9a. Get inspections done.
9b. Be horrified at the findings of the inspections.
10. Panic again financially, for good measure.
11. Negotiate a closing credit based on inspection findings.
12. Sign the purchase + sale agreement.
13. Choose a lender, sign a million mortgage-related papers.
14. Get a loan commitment.
15. Explain to the bank that you live in a truck, but it's totally not weird.
16. Fail to convince them it's not weird, but get them to approve your mortgage anyway.
17. Fly home for the closing, sign a stack of papers that is quite literally thicker than the boards your new home is made of.
18. Breathe, deeply.
19. Be a homeowner, and be stuck enjoy doing homeowner activities forever.

Whew, that was a doozy. I'm convinced that buying a house is made intentionally convoluted and counter-intuitive to make it as expensive as possible. If buying a house was straight-forward, our GDP would probably plummet. At every step of the process, it feels like there's a group of used car salesmen-types eagerly waiting to take your hard-earned money, and you can't help but laugh at the literal dozens of different fees itemized at closing. I can understand why people put in "all-cash" offers on homes, and why they're so attractive (the offers, not the people making them, though I guess being rich is attractive to some people).

In any case, it's over. It's done. Salient details:

  • Loan/insurance labelled as for a "second home". Because I won't be living in the home most of the time, except when I come home for holidays, none of the banks I talked to were willing to classify this as a "primary home" loan, which I find ironic, seeing as I don't have a primary home.
  • ~$2,300/month mortgage payment (including tax + insurance) on a 15-year loan. For a bit of perspective, this is less than what some of my SF-based friends pay in rent. I opted for a 15-year loan, instead of a more traditional 30-year loan, because I wanted to get a better rate. I bought the house at a bad time, just after mortgage rates skyrocketed. Since I knew I'd be holding onto the loan for a while (probably the whole lifetime of the loan), I opted to optimize for lower rates, at the expense of a higher monthly payment and slightly higher closing costs.
  • 20% down payment. To avoid private mortgage insurance, lock in a better rate, yada yada.
  • 4.125% interest rate. Not bad, though not great compared to rates even a few months earlier. Still a significantly better rate than if it had been classified as an investment property.
  • Total out of pocket: ~$80,000. I sold a bunch of my index funds to cover it. Luckily, I'd had all of them for more than a year, so I'll get to pay for the gains at the long-term rate come tax time next year. I also used the opportunity to consolidate all of my investments into the Admiral Share variants of the funds I invest in, which sometimes have slightly lower expense ratios and support buying fractional shares.
  • Total home cost, after closing credit: $320,000. When discussing with my family member the price range I was willing to put in offers on, I think we agreed on $275,000 to $350,000, and this was comfortably in that price range. Though at one harrowing point in the home shopping process, I did put in a $370,000 offer on a home, nearly 10% over asking, and it was (perhaps thankfully) rejected.
  • Two bedrooms, one bath. The home itself is pretty small, about 1,000 sqft. It sits on a ~9,500 sqft lot, and has a in-ground pool and a patio.

Some Hiccups

As noted above, there are a lot of moving pieces in the home-buying process, and not all of those pieces moved as smoothly as I might have liked. I'll talk about a few of the more entertaining ones.

The Clock is Ticking

Right off the bat, we had a pretty aggressive closing date, which was less than a month from the date of the offer. I'm told that this makes the offer more attractive because it means the dozens of middle-men get paid sooner the seller wants to be done with the sale as quickly as possible. This means that I had to be pretty quick in coordinating inspections and finding a mortgage and shuffling papers back and forth between interested parties, and that any subsequent hiccups had to be dealt with quickly.

Thoroughly Horrified

The next wrench in the works was the inspection report. In hot housing markets (like the Bay Area), buyers usually waive their right to inspections because it's so competitive. Buying a house in Massachusetts meant I had the luxury of having a home inspection performed. The inspection itself was extremely thorough, which was problematic in the sense that it highlighted an overwhelming number of problems with the home. For example:

This was the results of the "Exterior" section of the home report. You might notice that nothing was labelled as in "Good" condition, only "Fair" or "Poor". This was the general trend for other sections of the report as well, including the roof, basement, plumbing, electrical, etc. I probably shouldn't be surprised, given the house was built in the 1920s. In total, the report has 61 densely packed pages worth of findings (with pictures and diagrams and explanations, oh my!), each one enough to keep me tossing and turning at night with the specter of future home repairs looming over me.

In the end though, the problems weren't dire enough to warrant backing out of the purchase, even if I had the legal right to do so. Instead, I looked at the few most pressing and immediate repairs that would be necessary, and got some estimates for how much it would cost to fix each one. I ended up negotiating a $7,500 credit at closing (deducted from the closing costs). Originally, I had asked for a little bit more, but it turns out banks get spooked if you ask for more than a few percent of the total value of the home. C'est la vie.

The Elephant in the Room

Mortgage lenders (understandably) want to make sure you can pay back the money they're considering loaning out to you. As a matter of fact, this is so important to lenders that they have a whole department dedicated explicitly to this, called the underwriting department. They'll look at your income, assets, expenses, and various other aspects of your life to determine whether or not they think you can afford your mortgage payments for the foreseeable future. Particularly relevant to my case, they look at your current housing expenses.

When they asked me if I rent or own my current residence, I told them (in my most political voice) that I have an agreement worked out where I don't have to pay rent. It's technically true if you squint a bit, and I thought I was being pretty slick. Turns out it's their job to be slicker than I am, and indeed they are. They wanted proof of this alleged agreement, which naturally I couldn't furnish. So I had to spill the proverbial beans and tell them that I live in a truck.

At this point, I expected them to run for the hills. What respectable lender of sound mind and functional faculties wants to put hundreds of thousands of dollars in the unwashed hands of some truck-dwelling degenerate? But the underwriting department is far more pragmatic than I had giving them credit for. Instead of abandoning ship, they simply asked for proof that I owned the truck, and proof that I had insurance on it. It was literally written into the legal paperwork:

A snippet from the loan commitment document, redacted to protect my secret identity and highlighted to draw attention to the absurdity of my life.

I provided them a copy of the title, registration, most recent insurance policy, and a link to this blog for good measure (any new readers from Citizens Bank — hello!), and the process kept on rollin' along.

Home Insurance

This last hiccup I only include because I found it interesting, and it's not something I would have expected. Mortgage lenders want to ensure their home is insured in case of catastrophic acts of man or nature. That definitely makes sense. What makes slightly less sense, is that a few home insurers I spoke with won't insure a "second home" if they aren't also insuring your first home, probably so they can get more money from you. That means if you rent your main residence (or you live in a truck), there is no way to get insurance through certain providers (cough Liberty Mutual cough) on another property. Luckily, this isn't universally true, and I was able to secure insurance on the home after a few tries.

Okay, I think that covers most of the major hiccups/wrenches (or any other metaphor for unexpected difficulties you may prefer). Now let's talk about how bad of a decision this was.

Crunching the Numbers

In case you wanted some visual evidence of how terrible of a decision this was from a financial perspective, here's a graph:

The larger the gap between the red and blue lines, the more money I'm hypothetically losing. With the set of arbitrary and made-up numbers I chose here, it's about ~$125,000 over the lifetime of the mortgage.

When I was trying to make sense of the finances involved, it made sense to compare buying a house with continuing to invest the money, like I've been doing. To get a sense of how the house would work as an investment, I modeled it after a hypothetical future where I could rent it out for a reasonable market rate. Here's what you're seeing:

The red line shows investment returns from what I'd have to take out to cover the down payment and closing costs, plus investing all of the money I would be spending on the mortgage every month. In terms of Excel/Google Sheets, the formula I came up with:

  Investment Return Rate / 12,
  Months Since Starting,
  -Monthly Mortgage Cost,
  -(Down Payment + Closing Costs),
) - (Down Payment + Closing Costs)

where =FV is a function for calculating the value of an investment with fixed monthly contributions (in this case, investing the money I'd otherwise be spending on the mortgage).

The blue line shows investment returns from investing a hypothetical rent ($1,800/month) minus all of the non-mortgage expenses (tax, insurance, repairs, etc), plus the non-interest portion of each mortgage payment to account for equity in the house. In terms of Excel/Google Sheets, this looks like:

  Investment Return Rate / 12,
  Months Since Starting,
  -(Hypothetical Rent - Monthly Non-Principal Home Costs),
) + Months Since Starting * (Loan Principal / (Length Of Mortgage In Years * 12))

While this is a good ballpark estimate, there are some glaring omissions here. For example, both lines assume a constant "Investment Return Rate" of 4%, which is probably too low, but also doesn't account for any sort of capital gains taxes. Changing this to something higher, like 8%, widens the gap between the two lines. The blue line isn't accounting for depreciation/appreciation in the value of the house (which is especially hard to predict), or any of the potential tax incentives for owning a home.

In any case, the graph is moot because it assumes I'm collecting any rent, which isn't even an option since my loan is for a "second home" instead of an "investment property". That's because I decided the better interest rate was worth more than any subsidized rent would be. If I'm getting anything from the home now, it's coming from my family fixing it up, and hopefully a bit of appreciation in home value. Plus, it's hard to put a value on diversification, but I imagine it's probably good that I no longer have like 95% of my investments in stocks.

Looking Forward

An important question to ask at this point: how does all of this factor into my plans for financial independence/early retirement?

In short, it takes my plans, pulls their underwear clear over and around their head, kicks them to the ground, beats them to a pulp, sets them on fire, and snorts the ashes.

Before buying the house, my estimates for reaching financial independence were anywhere from 4-8 years. Now, I'm not really sure. A few months ago, this would have been a big deal for me, but post-quarter-life crisis, I'm less concerned with racing towards "retirement" and more focused on just living well.

If I did want to do the financial independence math, it gets a lot more fuzzy and hand-wavy now. On one hand, I took a big chunk (~25%) out of my nest egg and gave myself a fun, somewhat large, new recurring expense. On the other hand, it sets me up to have a consistent source of semi-passive income in the future.

I'm still maxing out all my tax-advantaged retirement accounts, but I'll conceivably be putting much less into my brokerage account. Having the mortgage might also inspire me to reign in some of my rampant "fun budget" spending, but who knows?

Anyway, this post is getting criminally long, so I'll just leave you with a fun fact: There are two words (not counting variations) in the English language that contain the letters m-e-o-w next to each other. One, naturally, is "meow". The other, perhaps less obviously, is "homeowner".


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