How to Buy a House
My softest of soft skills
This post is an easter egg for one of my friends who is thinking of buying a house. He doesn’t know that I am writing this. ^_^
In this guide I will be focusing on the softer sides of buying a house that I haven’t heard people talk much about — and certainly nobody has told me any of these things when I was in the buying process once upon a time, in my past life among oceans and emeralds.
(This is a guide for people who are buying a house to live in, rent out modestly, or else have a net worth of less than approximately $5,000,000. I do not have much to say about buying properties for the purpose of having a mini or actual real estate empire. If someone fills me in, that would be cool. But this guide is for the kinds of buying a house in which the house remains a house, rather than transforming into a token of financial exchange.)
If you are thinking of buying a house, you should start off by looking at houses. Yes, you have to go in person. No, you can’t skip this step. Yes, you should go often and early, before the pressure to buy a house creeps up too high.
You want to just go to listings — many listings, well before your timeline for actually buying the house. You want it to feel pretty casual and not at all forced. You want to go when you are in a state that you don’t actually have to go and nothing rides on it, you are just being chill. If you find something you love you’ll think about getting it, otherwise you are in no rush to spend a couple hundred grand or more on a house.
Mostly you should go to the listings that spark your interest for some reason (and see how your interest aligns with what is shown you, to have a map of imagination versus reality), but also the mediocre listings, listings you are not sure about, and bad listings. Feel free to go to listings that are way above your preferred price, and below your preferred price, and see how they compare in terms of your own personal fondness for the place. Go to the crazy mansion for sale. Visit the abandoned school. Check out the penthouse. Drive to the extremely cute lake house really far away. Schedule a tour of the airfield and the airplane condo thing that doesn’t make any sense why it exists. Learn about why it exists.
I don’t have the house anymore, as it was never in my name — but I liked the house I found and helped buy a lot more than my friends’ houses, and it cost a lot less. Buying a house is not much less personalized than buying a car. There are objective measures, like safety and newness of engine, but there are many aspects that are highly personalized.
You will want to build a mental model of what kinds of things are out there. You want to notice how you feel in your body when you see a place: “Maybe — but” or “Yes — except” or “Beautiful, but for somebody very unlike me,” or “Absolutely not.”
This prepares you to know what an “Absolutely hell yes” feels like later.
In seeing what exists you create a much richer model of your own needs and preferences. The realtor will tell you a house is great. It will be much easier for you to make informed comparisons if you have seen other houses.
When you have only seen 3 houses, the way that a “maybe” feels is very different from when you have seen 30 houses. You know much more what to do with a maybe when you have seen 30. You know much more clearly what needs to happen to make a maybe a yes, and what is the dealbreaker that would make the maybe a no. It all becomes much less handwavey.
When you see a house on the market that you really want, the window to act on it (in a competitive market) tends to be very short. If it’s a nice house, other people will want it too, and your money is just as good as anybody else’s.
If you like the place, often you will want to show interest intensely and early with the owner or broker — within a week.
That week will not be the time for you to do all of your research on competing properties. You will not want to be wishy-washy in that week. You will want to be firm, and focus on the negotiation — not worry about if what you are looking at is actually what you want or not.
Tactics like paying cash, waiving an inspection, going above the asking price, or getting into a personal negotiation are common to win something as important as the house you want against other people who also want it and are willing to pay for it.
Being able to move fast when you know what you’re looking at and know its value to you is therefore important in real estate.
Not moving fast because you aren’t sure, or aren’t sure what you are looking at, is one way to not get high value properties.
If you aren’t sure, you will lose out to somebody who is sure. Somebody else’s money is as good as yours, which means that willingness to hand over the money in an uncomplicated way is one of the main measures of what is “better money.”
Learn what you can and cannot change about a house. This way your fantasies about your future stay in line with what is possible with the property you are thinking about purchasing. When your fantasy about a property is different from what the property can provide, you will know it is not the property for you and the “maybe” will turn into a no. You should keep looking at properties until you find one that is more suitable.
Paint is cheap. Painting is one of the cheapest, most fun, and easiest things you can do yourself. Changing the colors of rooms is pretty fun, and if you mess up, you will feel like a loser for a little bit, but if you care enough you can fix it or have a friend with a steady hand fix it, Tom Sawyer style.
Furniture is also easy to change. If there is a small den that’s painted grey, with an ugly office desk and a white board but a nice window, you can easily paint it white, add some plants and rugs, and transform it into your dream yoga nest within a week if you’re up for it.
There are aspects of a house that are much more impossible to change.
I stayed in a house once, and every guest who came in thought the house was unusually elegant. It was a very charming house (and if I was renting it out, people would have liked it), but I would have gone crazy if I was living in it.
It felt like somebody could sneak up at any moment. You could always hear the noise outside, and the outside could always hear you. The house was built in such a way, with proximity to other houses, that it did not feel private the way most houses do.
Furthermore, it was not arranged in a way such that having a TV den, a drum set, an art room or a kids’ room made sense without the house feeling extremely cluttered, destroying the original elegance that was its chief quality.
These are not things that were going to be possible to change.
The structural build and location of the house were not sufficient for dimensions I care about. If I wanted less noise and an art room I was not going to get these without tearing down and redoing the whole house. Even putting a shed in the yard as an art studio would have ruined the yard, and ruined the views of the yard from inside the house.
I am sure it is somebody’s thoughtfully crafted dream house — it just is not mine.
When you visit many houses, you start to build models around what is possible to change, versus what you are buying mostly as-is.
Properties I considered buying, but said no to include a condo with a terrific view but was too dark, with terrible ventilation, and an old house that required $50k for fixing the foundation, right off the bat, before other repairs to its dainty and beautiful white Victorian historical components. Plus it was on a busy street, and so I wouldn’t have front porch privacy.
Kitchen and bathroom updates can cost tens of thousands of dollars, but they are doable. You can also repaint cabinets yourself, change the sink or toilet, and even upgrade to a bathtub pretty easily. Something like adding an entire upstairs bathroom, when there is none, can be possible, but more tricky. Landscaping the yard to be more beautiful can be relatively easy, but not having a yard because your property doesn’t come with a yard is not something you will be able to change.
You want to look at room shapes, room types, windows, entryways, how light moves through the house, how you would be moving through the house. Some houses will feel very wrong on these dimensions, and some will feel a lot more like they fit you.
Location is not something you will be able to change. If there is a river nearby and you are in a flood zone, you will have to live with that. If you are on a hill, you will have to live with that.
The materials that floors and walls are made out of can be hard to change. High versus low ceilings you might be able to adjust only by a foot or so, if at all. Adding carpeting can be straightforward. Adding mirrors and white boards is easy. Adding a hot tub is not too hard if there is space for it.
If you really like a house but it has a lot of “bare walls,” adding even very intricate shelving with wood and painting it the color of the wall, is pretty easy. Adding cool shelves and bookcases that are “built in” to the walls is actually an elementary woodworking project, and there are tons of YouTube videos about how to do it.
Actually, looking up how woodwork can change the look and feel of a place, and what bathroom, kitchen, and general renovations people are DIYing on Youtube, can give you a lot of knowledge about what parts can be changed about a house (aka added on materials you bought at Home Depot and painted to match the walls) versus what is structurally the house you are buying.
Understand your own capacity to supervise and perform renovations.
In the current economy, you will always be able to find a contractor who will say yes to whatever you want — it will just cost you a quarter of a million dollars and take 5 years.
It is safe to assume that you can hire someone to work on your house, but don’t expect to just contract it out and then not worry about it ever again.
Most likely, you will have to conceptualize and supervise the work you want, and hire a specialist for each job — that is, be the contractor you wish you could hire for an affordable price.
In the same way that you don’t just drop off your car at the mechanic, tell a hairdresser you’ve never met to “do whatever you want,” or walk into a clothing store and tell the clerk to ring you up some coats, you will need to have some vision and an idea of the scope of problem you are recruiting another person’s help to solve.
If you buy an abandoned old mansion hoping that you’d find somebody to just restore it back into its ornate tip top shape — good luck. You’ll have to hire a professional restorer, and that can get expensive very fast.
Meanwhile, something like knocking down part of a wall to turn two rooms an open-plan living room, or adding a new door to a useless small room to turn it into a walk-in closet for an adjacent bedroom, are comparatively easier and much more standard changes you can make by hiring most carpenters.
Stuff like “changing the electric,” “adding insulation,” “fixing a dangerous deck,” or “updating the water heater” can cost $4,000 - $12,000 dollars or so, but they end up being fairly standardized, doable operations, even though they can sound pretty hard.
You still may want to supervise. I had a new water heater put in once, and the man had left the water heater balanced on a very small rock the width of a cucumber he had found in the room. “Uhhh….are you sure you don’t want that to be more stable?” He went and found a few larger rocks and made a nicer seeming foundation.
I’m sure the small rock was doing just fine, from a mechanics standpoint, but it made me nervous enough and seemed like an easy enough thing to ask about while the strong man was in my house.
When it comes to manual labor, sometimes people aren’t trying to screw you over — sometimes they are just tired, and having just solved a problem by working all day, they’d rather check it off as adequately done, versus noticing it could be done better and redoing something they just did.
I tend to have waters and soda on-hand for whoever is at my house, including whoever is coming to my house to do work. It is something I stock anyway, so it costs me basically no money. The workers often forget to bring these even if they want them, are always pleasantly grateful, and if they are a bit more cheerful and energized when doing the work, this is better for me. Plus I am traditional enough that having someone over, even to do work for me, without offering them anything feels bad to me.
Many houses need some amount of renovations, though there are people who are happy to pay a premium price for a brand new house that needs absolutely no work. In this case, you may consider what future work the house may need, and if you are game for it.
Does the house come with a hot tub? Hot tub chemicals are now in your life. Is there a beautiful lawn and garden? Ask who the gardener was and if you can hire this person to keep up the garden, or teach you what they did.
Is there a bespoke saltwater infinity pool? There might be one company in the city that does maintenance, and “bespoke saltwater infinity pool maintenance” is a problem in your life. Are you up for this problem? Is someone in the household up to this problem? Or will the special pool remain sad and empty forever because everyone is too tired to even call the pool guy and set up a recurring maintenance schedule?
You want to size up your own capacity and enthusiasm for doing these things. “Not paying rent, and paying a mortgage instead” is nice in theory, but when you have an $8,000 bill hitting you every few months and a lot of manual labor, you want to know your own capacity for rolling with the punches, or if you will start to really hate your life.
When I was renovating my not-really-mine house, it was during Covid and so it was a nice set of isolation projects, but it was still physically demanding in ways that threw me off my game a bit.
Understand your own game plan
Some people buy a house because they expect to stay with the same company, in the same city, for many years. Software engineers in Seattle, San Francisco, or Los Angeles can be like this. There is a company which is the employer; it has a headquarters, the headquarters will not move.
Buying a house, versus paying rent, dealing with a landlord, and potentially moving often rather than building a nest seems like the better thing to be doing.
Some people buy a house because they had a dream house they had in mind. Beautiful sunrises and sunsets, a place for the children to play, a library, a location within driving distance near friends and family.
Some people buy a house because their income allows it, the housing market is booming, and they have run the numbers around renting versus buying. Even with the risk and repairs, buying a house squares out.
There are many opportunities here to be secretly sad. Let me outline them for you.
Let’s say you bought a house as an investment instrument, but low-key didn’t expect to buy a house until you found your dream house. You imagined running around, painting it different colors, setting up a bar and a hookah room, having a meditation room full of pillows, but now none of this is happening because you have to keep everything “standard” and “normal” for the tenants / roommates who are living there with you that make it financially feasible for you to have bought the house in the first place.
Or suppose you moved into a house with a partner because it made financial sense, but you two aren’t married and aren’t having kids, and the upgrade in housing without the upgrade in relationship commitment unnerves you. “It’s just saving money and having a bigger place” can be the point, but this might not be comforting if you had quiet, private, and robust ideas around “what having a house means to you.” Now add to the mood — the place is a bit too small and there is a roommate so you can’t do sexytimes whenever you want to, which is confusing to feeling out progress in your relationship.
Whenever you do something that is meant to hit multiple birds with one stone, you run the risk of improving your position, but still not being quite happy because the birds you hit weren’t quite the right birds. Or maybe they were the right birds but you didn’t hit them, you just mildly harassed them.
It is important for you to consider which parts of which goals you want to make sure to hit. If you don’t want to do certain repairs, consider adding expected repair costs to your purchase budget, knowing you won’t have to pay those later, and buy a more expensive house up front. Maybe you want a house that works well as a group house. Maybe you want the opposite — the lowest down payment and lowest mortgage payment in the most popular area, so that it keeps you feeling light. If a special person enters your life, you know for a fact you will have to upgrade later if you start a family, and that certainty makes you feel safe and sane.
For me, I both didn’t want infinite repairs, and also didn’t want a brand new house (I would be self-conscious if every scratch I made as my fault). I wanted something obviously worn in, but still modern, and in a central area because I was living without a car. Future rentability was important, as the pricing calculations for renting versus buying were based on staying in the same city for a minimum of three years, but then potentially moving and renting the entire house out.
I had a lot of fun with this house, but in hindsight I wish I had learned more about the repairs that were happening, and been less shy about chatting up each repair guy. Don’t get me wrong — I leaned pretty heavily into these — but it just goes to show how “doing something a lot” can still be “not enough” if you have a certain thing you want an enormous amount of and a deep relationship with.
I wish I had stenciled in the tiny fish on the kitchen cabinets, to complete my “submarine windows and copper” kitchen to go along with the purple dining room. It might have been hard and failed, but the kitchen was painted white anyway for the rental later. I still have no idea how to do my fish project, but there was an opportunity there that would have allowed me to learn. I did complete my fantasy of painting many rooms different bright colors — a fantasy I’d had since my childhood.
And these things — “the non-standard things that make your soul and life feel complete” — are things that another person would have a hard time advising you on. There are people who have lived in a house, with boxes still packed, while major renovations are happening for 600 days, and they feel bliss. There are also people who would start to go completely mad.
And so understanding your own game plan is a way to keep you on track for being happy, even as you negotiate with yourself about what is acceptable for you, enough to push the “Let’s go” button and happily buying versus continuing on with your search. Grand Designs is a wonderful free show to watch about how this goes right, and how this goes wrong.
Don’t buy a house just because somebody else wants you to, on the timeline somebody else sets. It is a lot of money, and then you are stuck dealing with the house.
Often a family member or a spouse has an idea of what should be happening house-wise, either given your life stage or their life stage.
Perhaps an aging parent is worried about their health and your imminent abandonment right when they need you most, and you buying a place nearby seems like a nice solution to their anxiety. You would see mothers and fathers insist that their children buy a large condo so that they can stay in the mother-in-law suite and hang out with their sometimes existent and sometimes not-yet-existent grandchildren.
This can be a lot of pressure.
Remember that money you spend on a house is technically “undoable” if you sell it for an equal or greater value — but this ends up being a big transaction with many moving parts, and unless you are in the business of doing real estate transactions or somehow find it wildly fun, it would be a pain to “undo.” And there are transaction costs.
You wouldn’t buy a car that you’re uncomfortable driving, just because somebody else says it has “good resale value” or “is a good investment” or “think of your nephews.”
Everybody is going to give their two cents. In fact, because it is such a big decision, a lot of people will make sure to give their two cents because they are anxious and know that if you are talking to a lot of other people about this, they need to throw their opinion into the pot as well lest somebody less wise influences you too much.
This does not actually mean that they themselves belief they should be listened to, at the end of the day. They are likely saying something smart. They are also likely doing what people often do: they think through the advice that they heard from a friend, or remember the complaint from that one friend who messed up, or make sure to tell you the one thing that they wish they did differently in their own lives, or lecture you on the thing they are an expert in, or push on the one thing they have a high stake in, or the one thing they worry you specifically will mess up on.
They want to be helpful — and they are probably saying helpful things — but they are not holding your entire strategy, life, belief systems, or risk preferences in their mind all at once.
They are assuming you will do whatever synthesis makes sense for you to be doing, even if that means rejecting their advice.
Again, people often make the assumption that they will not be listened to, at all, and use that as a permission structure to say all kinds of things. Repeatedly and aggressively. Ultimately, if their plan fails, you’re on the hook for it, and none of you will be happy. If your plan succeeds, they will stop complaining about whatever they were complaining about, and conveniently forget they ever discouraged you. They may even congratulate themselves on the wonderful support they gave you and expect a thank you gift.
Whether your plan is good enough to succeed is on you to check. This could involve checking the components that are likely to go wrong, with both people who have had it go wrong and also people who have done the hard component thing enough times to have both done it wrong and done it right in a way that they know the difference.
If everybody else has to wait while you check your math and your plans — they can wait or they can help.
Learn about how other people do it.
Brokers, agents, doing it on your own by looking at the internet — it can get confusing.
Every city has different systems in place. In San Francisco, there are lots of startup services that help you buy a house because there is a startup culture.
In a smaller town, there may be the one person who does 80% of the town’s business, and knows about properties before they become publicly available.
And then there is the system of foreclosed homes that go to auction.
One reason people can get rich “in real estate” is because being a dealmaker in a confusing and high-stakes environment is often a way people can get rich, if they are good at it.
I have not bought enough houses, in enough different cities, to have much advice here. My one piece of advice is that asking around and having real conversations with people in the place you are trying to buy in, rather than just depending on the internet, can end up being very helpful.
I hope this is useful. If you have anything I should add, let me know — I will credit you and expand on this post so that it is maximally useful to people.
***Photos from iStock and Unsplash