Robert Heaton

Software Engineer /
One-track lover / Down a two-way lane

Tales from a San Francisco housing search

25 Oct 2014

This essay began life as “How to find a house in San Francisco”, but this angle died when it became clear that I had no actual justification for any of the “advice” it contained. Despite this, much of what I had written still made for what felt like a good story, and so I’ve collected 9 of the thoughts and experiences that had the biggest impact on me whilst looking for somewhere to live in San Francisco. Reading them may not improve your life in any tangible way, but I hope that you may still be at least a little amused.

Some context

I recently got a new job and moved from London to San Francisco, where there are a lot of people and not enough places for them to live. The places that there are are jaw-droppingly expensive, thanks in large part to the recent and torrential influx of douchebag software engineers. There are some incredibly important and far-reaching questions to be asked about why this is happening, whether it is OK and what should be done about it. I will be addressing none of these issues, focussing instead on one douchebag, his ego, and some things that crossed their mind whilst gentrified apartment-searching.

Note again that this is in no way a guide for how to look for a place to live. In many ways it’s barely even about looking for a place to live at all.

Magical thinking

Like most people, I find it very comforting to imagine that I have agency over the important things in my life. I develop elaborate, carefully reasoned strategies for them, and cling tenaciously to the belief that they have any influence at all over the outcome. How could the guy with the conditionally formatted spreadsheet, carefully crafted intro email and pre-prepared list of charming affectations possibly fail? And how could he have the slightest chance of success if all he did was “go with the flow” and “talk to people like they are actual humans”?

It may be that all of my calculation and analysis of my housing search was completely pointless and had no effect on anything. It may also be that the primary predictors of success are your “actual personality”, willingness to pay ridiculous quantities of money in rent, and blind chance. For the sake of my ego and self-image, I will ignore these possibilities.

My perfect Craiglist ad

“Apartment hunting” in SF is essentially synonymous with “trawling through Craigslist”. For my own future reference, this is a list of what I found attractive in an ad, in case I ever need to find an exact replica of myself to live with (when I completely lose what little ability I have left to relate to anyone apart from myself).

  • 2-3 lines about each of the people who currently live in the apartment. I don’t really care what the lines say (apart from “hobbies include ritual goat sacrifice and pretending my roommates are goats” or “very, VERY strongly prejudiced against the Chinese”), but it shows that the people writing the ad expect you to.
  • Some jokes. Like 2 or 3. Good jokes preferred, but amidst the paginated sea of drudgery that is Craigslist almost any attempt at levity is a big plus
  • On the other hand, keep the wackiness under control. There’s a very fine line between endearing, tractable zaniness and Totalbananastown, and Craigslist is not the place to try and walk this line.
  • Try not to use the word “awesome”
  • “Looking for a roommate” is a little better than “House available” is much better than “Roommate needed ASAP” sounds a lot like “Some kind of life form to help pay my rent required, zero craps given about who”
  • The ad should be written by the people who the respondent will be living with, not by the person moving out. Respondents care a lot about the former and exactly zero about the latter.
  • Hopefully the person moving out is either skipping town, moving in with their significant other, or leaving for some other can’t-be-helped reason that doesn’t arouse suspicion. If not then consider lying.
  • It’s fine to have house rules regarding pets/parties/partners/acceptable levels of onanism, but don’t start the ad with them

Some trends and numbers

I sent 41 application emails in 10 days. I received 17 replies, arranged 15 viewings, received 4 offers and accepted 1. I now live with some excellent people who wrote a terrible ad in a delightful, well-appointed apartment in a highly sought-after location near several…

I asked one girl out for a drink (ignored) (see below), was asked out by one (different) girl (agreed), and made one new friend (total badass).

From talking to ad-placers, it seems that your typical Craigslist ad gets something of the order of 50-200 responses. The Tragedy-of-the-Commons-be-damned solution is of course to up your game and spam out as many applications to as many plausible-looking ads as you can. A spreadsheet is a must.

If you don’t get a response on the day or day after you send your application, you’re almost definitely never getting one. I quickly began marking leads as LIKELY DEAD 2 days after sending them.

What people on Craigslist care about

  • Whether you bring the party home
  • Whether you are friendly towards the number 420 (??!?! more research required)
  • That your boyfriend/girlfriend/multi-membered hareem doesn’t stay over too often
  • That you have lived with other people before
  • That you have social media profiles you can send them
  • That you don’t have your own pets but like their cat

Whenever anyone asked “On a scale of 1-10, blah blah blah blah blah?” I always answered 7.

Application email


  • Create a high density web of hooks for the reader to snag themselves on
  • Suggest that I might be exactly the kind of interesting person the reader wants to tell people they live with
  • Plenty of implied social proof that suggests I am not a sociopath and have actual friends who would attest to this
  • Make it easy to arrange a viewing
  • Imply that I have, earn and would be willing to trade actual real-person $$ in exchange for a room

“Say Steve, who are we seeing next?” “That British guy with the sweatshirts who plays poker and works at Stripe.” “Oh cool, I remember him, he sounded like a swell dude.”

Hey guys!

I liked your post - it felt like there were some cool people and a great apartment on the other end of it [0]. I’m a 26 yo British guy and have just moved over from London. I’ve already spent a lot of time in SF over the past few years, and have so far managed to find my way around without cycling into any oncoming traffic [1]. It’s taken a while, but I’ve finally convinced your stupid government to let me stay so that I can be a software engineer at [2]. Here’s a poorly edited list of things about me I think are moderately interesting [3]:

  • Me and a friend started, we recently sold our 10,000th sweatshirt! [4]
  • I really like writing - if you have a few minutes you don’t mind never getting back then you might want to check out this post [5]
  • I play jazz piano and sax and dabble in electronic music production
  • I’ve found a great tai chi class on Saturday mornings [6]
  • I paid for university playing poker [7]
  • More keywords: cycling, Arrested Development [8], The Last Psychiatrist [9], rollerblading, hanging out [10]
  • Me on the internet - Facebook, Twitter and LinkedIn

Recent polls have mostly indicated that I’m friendly, fun, and able to move in whenever. I lived with 3 friends for 3 wonderful years in London [11], and I’m looking to keep living with cool people who are fun to spend time with [12]. It sounds like that’s what you’ve got going on here. It would be great to come by and say hi - I’m free on Monday after 7pm and Wednesday after 9pm if any of those work and my cell is 123-456-7890 [13].



[0] Earlier versions went “It felt like it was written by some actual humans who I could imagine relating to, rather than robots who only care about how much you tolerate cats”, but this felt too difficult to parse for an opening sentence. It’s also not classy to lead off by badmouthing hundreds of people behind hundreds of other Craigslist ads, even if it is an implicit complement to the people I was writing to

[1] “I’ve been here before and already have some friends”

[2] “Stripe” if I thought the recipients would have heard of Stripe, “” if I thought they wouldn’t

[3] This is a total lie - it’s a very very edited list of things about me that I think are extremely interesting

[4] How zany! How interesting!

[5] A technique I used when writing job applications as well - link to something I’ve written and multiply the amount of information they have about me by like a hundred. At least 5 people said they clicked through and read this and other posts

[6] Deleted if I felt they wouldn’t appreciate Tai Chi. There’s plenty of time to convince them that they’re wrong when we’re living together

[7] Everyone likes poker, right?

[8] Most people in my target demographic have seen Arrested Development, but we all like to think that it’s still rather niche and that we discovered it first. We feel a strong bond with anyone who understands how important it is to be a Mr Manager.

[9] A genuinely niche-ish blogger who seems to evoke similar bonds between those who follow him

[10] Whilst “I like hanging out with friends” is obviously true, it seemed prudent to say so anyway. This continues to re-enforce the suggestion that I do in fact have friends and that hanging out with them is important to me and that I am not a sociopath

[11] 1. I have friends 2. I was able to live with them without anyone needing to resort to violence apart from that one time

[12] Some ads were looking for a new and embedded part of their household, others for warmish bodies to pay rent. I wanted to appeal to the former

[13] Ending with specific times and a phone number makes it trivially easy to either hit reply or send a text and meet the fellow behind this masterpiece

Of course, in reality I imagine that what most people saw was:

Hey guys!…Cool people…London…poorly edited…Tai Chi…hanging out…Wednesday…Rob

and then randomly decided whether or not to reply based on how well the Giants were doing. Delusions of agency.

Rejection, part 1

The very first viewing I arranged was at a delightful looking apartment in Hayes Valley occupied by two 26 year-old female women. Being extremely predictable and unimaginative, I was already very interested based on demographic data alone. I arrived full of hope in my best and most yellow Dangermouse t-shirt and was met at the door by an alarmingly attractive girl (pseudonym “Barry”). I reflexively turned on both barrels of quintessential British charm, and was surprised and relieved to discover that I appeared to have brought my A-game. As Barry showed me round it emerged that she was possessed of an appealingly acerbic charm of her own, and by the time we came to sit down to trade hobbies and vital statistics I had already been encouraged to go and fuck myself several times. I felt that things were going well (yes I am single why do you ask).

I remembered from the ad that she had spent a few years in London (+3 points), and it turned out that she had even lived about 5 miles from where I used to live (+2 points). I recognised several album covers from the shelves (+2 points) and offered several pompous and unrequested opinions about their relative merits (-10 points). Barry’s roommate was by now also free to talk, and she remembered and appeared very interested in several of the more interesting facts that I had planted in my email intro (+4 points). She noticed that I had drawn a map of how to get to their place on my hand, and for some reason both she and Barry appeared to find this hilarious and “creative” and “very visual” (+??! points). As I felt myself starting to run out of both quips and questions I excused myself, saying that I had to go and have dinner with some friends (+2 points for having friends). My true love walked me out and we hugged goodbye (+15 points).

At dinner I boasted that “if I don’t get the apartment then I’ve still definitely got a date”.

The next day Barry emailed a generic “thanks but no thanks”. I was completely devastated for over 20 minutes. An appropriate length of time later I replied “Thanks for letting me know. The only reason I can imagine you went that way is that now it’s not A Bad Idea for me to suggest we go for a drink.” (yes I already told you I’m single why do you keep asking me that)

And she never replied.

"So tell us about yourself"

The interview-esque section of most viewings began with some variant on “so tell us about yourself”. This is surprisingly hard to answer without prior thought. I typically responded along the lines of:

I’m a software engineer. Here’s my complete work and education history
Wait this is extremely boring. Also I should try and show how incredibly interesting I am outside of work.

I used to play a lot of poker
Should I mention chess? Would these people appreciate chess?

I also used to play a lot of chess
Wait no these are all things I used to do, I still have hobbies don’t I?

I like cycling a lot
Good, a bit generic though. Also I don’t like cycling that much

I really like writing, I’ve got my blog at where I narcistically believe people care about what I have to say
Wait this sounds really lame, I need to make it clearer that a lot of people actually do care about what I have to say

Some posts do really well, my one about my last job search has over 100,000 views now
That was both arrogant and a known exaggeration

But sometimes I write total nonsense that no one has any interest in reading
OK let’s just shut this down

Also I like hanging out with friends

So yeah that’s me
I’ll show myself out

I find it hard to remember that “tell us about yourself” does not mean “try and convince us that you’re really smart and knowledgable and have lots of marketable skills.” For the most part, no one directly cares how intelligent or high-achieving or whatever you are, and people mostly only like talking to people who seem clever because it makes them feel clever themselves. “I’m totally understanding and holding the attention of this seemingly intelligent person, transitively I must also be really intelligent.” On the other hand, it’s no fun talking to someone smart if they make you feel stupid or even just bored.

If you happen to be bright or fun or extroverted or eloquent then well done, but these aren’t intrinsically desirable qualities. They only make you pleasant to be around to the extent that they make other people feel good about themselves, not the extent that they make you feel good about yourself.

I find it hard to remember this.

Confident sellers

There were 2 ways a viewing could end:

“We’re interviewing a few more people today and tomorrow and then we’re going to make a decision tomorrow evening. We’ll let you know.” Subtext - we know we’ve got a good thing going here, and if we deign to choose you then we know full well you probably don’t have many other options right now.

“So if you’re still interested then let us know in the next few days, then we’ll see who replies and go from there. It doesn’t matter if you didn’t like us or thought we were weird HAHAHAHAHA but it would be nice if you could let us know either way.” Subtext - the exact opposite of the above.

Predictably and depressingly, the first ending always made a place much more desirable. This probably isn’t a fair test, since the more confident sellers are presumably more confident for a reason, but I still wish I wasn’t so susceptible to this kind of (probably inadvertent) Sales 101.

Rejection, part 2

It’s galling when you give an interaction everything you have, pull out what you believe to be an incredible display of your talents, sensitivity and ability to relate to other human beings, and still get nowhere. There are no easy lessons to be learned, and no rational reason to believe that anything will be different next time.

We could potentially look into why you spend so much time worrying about and evaluating the image you’re projecting, and so little time genuinely focussed on the person you are talking to. We could talk about whether this is restricting your ability to truly connect with people, and whether this is even having an actively negative effect on that image you’re trying so hard to manage.

Or we could blame it on the highly competitive San Francisco property market.


I keep coming back to how comforting the belief that you are in control of your life is, and how the most frustrating things that happen to you are often those that shatter these delusions of agency. This essay was a detailed explanation of many, many deliberate thoughts and choices, but with absolutely no evidence behind them beyond unsubstantiated generalisations about human nature. Perhaps it’s a good advert for using your intuition and then just gettin on with your life.

When doing something as privileged as trying to work out exactly which neighbourhood and people to live with in one of the most expensive cities in the world, it seems prudent to be watching yourself for an overconcern with #firstworldproblems. But I do think that the stress and doubt a person feels about their relationships and place in the world are valid, universal and almost always real, whatever their circumstance. The appropriate response is therefore almost always patience and understanding, in the first, second and third persons.

To emphasise the obvious again, this was in no way a guide for how to look for a place to live in whatever city/town/remote forest dwelling you call your own. In many ways it was barely even about looking for a place to live at all.

(if you enjoyed this then you’ll probably also want to read the 3 deleted scenes that I cut out for various reasons, but are very similar to the above bits. If you didn’t enjoy this then for god’s sake don’t read them.)

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