Episode 21:nickd Buys A House
Yes, the system is fundamentally stacked against you and there is nothing you can do about it. Yes, you are abetting a series of societal problems that are probably larger than you – and which you are probably too busy in your own life to address. No, there’s no way to know whether you’re doing the right thing. Yes, there will be a dog – eventually. No, the dinner parties won’t get any better. Nor will your friendships. But the house is something. Your stuff looks better in it. Block everyone who doesn’t understand.
Summary
Nick just bought a three-story house in Chicago’s Avondale neighborhood after eight months of searching, and the episode opens with 20-plus minutes of move-in disasters before pivoting to concrete steps independent consultants need to qualify for a mortgage. The closing third is Nick explaining why he bought at all: to lock into a community he has spent years building, not to flip a property.
Highlights
- Mortgage underwriters require two consecutive tax years of payroll records. Nick’s brokers told him a credit score in ‘scientific notation’ means nothing without that history, so getting on payroll is the first and non-negotiable step.
- Nick recommends Gusto (gusto.com) or Wagepoint for payroll, both around $30/month for a solo operator. He says skip ADP.
- For credit building: put utilities on a no-annual-fee credit card, pay it in full each month, and never carry a balance. Nick uses Amex and Capital One to track his score instead of Credit Karma or Mint, which he says harvest data for marketers. He rotates free credit report requests across the three agencies every four months via annualcreditreport.com.
- Nick’s first month of post-move-in expenses (tools, shelving, contractors, Amazon orders, Thompson’s Water Seal) came to roughly $13,000 run through Draft. The down payment was a separate, personal expense. The $13,000 month was the highest expense month in Draft’s history.
- Nick’s mortgage rate is 3.5%. The new house costs about $300/month more than their previous Chicago rent and is three times the square footage.
- Nick’s core argument for buying over renting: neighborhood gentrification (the ‘cocktail bar wave’) is beyond any individual’s control, and owning puts you on the side that benefits from rising property values instead of the side that gets priced out. He frames the purchase as a 20-year community commitment, not an investment to flip.
- Nick says the business you build can generate the life you want, and calls the Avondale house ‘the house that Draft built.’
Read the transcript
My life has been really interesting lately.
Maybe that could be the title of your autobiography.
I went to this this depot yesterday. It was horrible. Holy shit. Why do people go to Home Depot? It’s horrible. I went there. I got $500 of random crap for the house.
None of what you actually need. You always walk into Home Depot. With the best of intentions. I need duct tape, I need three light bulbs, and I need some bleach. And you walk out and you’re like, I’m building a shed? What? What the fuck happened? What color is the shed? We all have to have a conversation about what color the shed is. Oh, you need some primer for that shed, and then you’re $300 deep into primer.
Face coat and a top coat and a gloss coat, and then you need to weatherproof it. God help you in Chicago if you don’t weatherproof literally everything. They sold us the house and this happened. They sold us the house and they hadn’t weatherproofed the front or back decks of it. So I had to buy two gallons of Thompson’s water seal. And I tell you, on Thursday, you’re going to love this. I got on this like workshop call with a client for three and a half hours, immediately got off, ate lunch, filled my, I got this. Spray nozzle thing with filled that with Thompson’s water seal. We’re already $100 deep on, and I haven’t done anything yet, right? Go out there with an extension cord, and it’s the first like dry day that we’ve had because it’s spring in Chicago and it rains every other day. and I immediately turn it on, and the wind was so strong that it just blew Thomson’s water seal directly backwards into my face. Oh God. And Thompson’s water field seal dries quickly. So now I have some advice for you, dear listener. You are coming away with a lot of actionable advice on this episode, I assure you. To remove Thompson’s water seal from a pair of glasses. Soak them in warm water with some soap in it. I used Mrs. Meyer’s lemon verbana scent for about an hour and a half. They should be like just crank the hottest water you can get out of the water heater. Just let it sit there. And then brush it off and towel it off and then microcloth it off, and then you will have no more Thompson’s water seal that has been dried onto your glasses and their presumably non-stick oleophobic coating. I’m sure this will come in very handy and useful to you in the future. I spent all of yesterday building shelving. I spent, and to get that shelving cut, I had to go to two different Home Depots while my zip car time was ticking down. Because I’m a millennial and don’t own a car. And everybody’s like, you should own a car. I’m like, no.
You’re describing to me a very good spec for the worst video game ever, but the video game that the majority of people in the world go through at some point in their life.
It’s several different video games.
Grand Theft Auto, but for home ownership.
Yeah, it’s very open-ended, like Grand Theft Auto, right? Like, you can complete the missions in Grand Theft Auto. Or you can go off the grid and paint your house plaid, or do something da-da, or build a spite fence, or And it’s sometimes you get like 10 different games in a day where you, um, I have a to-do list right now that just says home fuckeries And HomeFuckeries contains install recessed door sensors for the security system put up the towel bar and toilet paper holder in the downstairs bathroom, install the bar shelving, install the laundry room shelving, finish the pantry shelving because I bonked out yesterday installing shelving. Because this house came with no shelving, no curtains, and almost no bathroom hardware. Oh, God. That was just those three things, 10 grand. Oh my. And you may be wondering, Nick D, 10 grand is a lot of money for that. You’re crazy and stupid and terrible. Excellent point. I didn’t have a drill. You know? And there were three bathrooms. So I had to get all of the hardware for three bathrooms. And it’s a three-floor house. I had to get curtains or not. Blinds for all of them. And blinds are expensive. You don’t think blinds are expensive. Blinds are expensive, and then you multiply it by 28 windows. Nick D, you didn’t need all 28 windows. I didn’t get all 28 windows. I only got 13 windows. You presumptuous asshole. Oh my god. So none of this has to do. I mean, this is. I’m going to bring this back to actually business stuff. No, no, this is good.
We’re live right now. We are on fire. We need to ride this demon horse to the grave.
Replace side gravel with soil and mulch. Well, in order to do that, I needed a wheelbarrow. When I went to Home Depot, I filled up the back of my truck and couldn’t buy a wheelbarrow because I couldn’t physically fit it there. So I’m getting a wheelbarrow Amazon primed to me. If you are deep cuts on Nick D podcasts, you know my resistance to signing up for Amazon Prime. You know that because I gave this huge half-hour thing with Kurt Elster about how I love waiting two months before I buy anything on Amazon. That was from a different life. I blew two grand on Amazon in one go the day I closed. Welcome to homeownership. Holy God. And I tell you, man, I you know, I was expecting the down payment to be expensive because that’s pretty well set up for you. Like. But, like, and this house is pretty move-in-ready. It’s not, you might be thinking like the house is falling apart. No, if you look in it, it’s a move-in-ready, beautiful, wholesale rehabbed house. It’s just not we haven’t rubbed our butts on it and claimed it as our own yet. And in order to do that, you need $13,000. This has been the number one expense month for draft in its history. And the down payment came out of Nick DeSabado, not Draft. Oh my. Oh my.
We’re not counting the down payment in this. Now I got some scary nit or a scary question. Like, we think it’s $13,000, but. I mean, you’re describing to me what sounds like a waterfall-based project, not an agile-based project. We don’t, there are dependencies here we have yet to uncover. You might go to install a piece of shelving, and you’re like, oh. There’s a door here. Oh, there’s spikes behind the door. How do I remove spikes? What’s going on? You have no clue what’s coming down the tunnel. Right, right. I mean, I have a plumber coming this afternoon, right?
And the I am, let me anticipatorily say I am so sorry. Right. So the plumber is coming, and I’m just bending over. Like, it’s horrible. Like, I’m he’s here to install a battery backup for my sump pump, and that’s it. And I’m fully expecting this to be four figures.
Oh, what will he discover? Wow, it looks like you don’t even have any pipes. We’ve got to install pipes. Got to install the house.
The whole house is fresh piping. That’s the great thing about it. I’m still probably going to end up spending like a staggering amount of money on this. And all of you are going to be like, oh, boohoo, Nick D, you knew what you were getting yourself into. I kind of didn’t. Even after everything everybody told me who was also a homeowner, I took, you have no idea how many people I took out to dinner about this. This has been eight months in the making. We started looking at houses in September. It’s May. Oh my.
So you knew you were given forewarning.
I was given a significant amount of forewarning. And even so. You know, I today is the first day in. Two weeks that I haven’t been either packing or unpacking or drilling or spraying a sallow gunk onto my own face. Are you waterproof now? Probably. I’m probably radioactive at this point. Aaron. Aaron, I didn’t even realize. Did you know that there are two different kinds of drill bits and they look the same? And one of them is a normal drill bit and the other is a masonry drill bit? I didn’t. I didn’t until it caught on fire. It melted. Oh, my God.
Oh, God. I hope somebody’s filming this. I hope this is a documentary in the making. It’s like this old house, but the house is on fire and there’s no driver at the wheel. I have so many questions. Where do we begin? We’re already 11 minutes deep in this episode, Kai.
How are you feeling? Um, I discovered parts of my body I wouldn’t care to discover. Um, There’s, I have a giant knot in my right shoulder. My left butt cheek is aching, and I don’t know why. There’s a giant bruise on my right shin. And my right hand. And parts of my left hand, but mostly my right hand, especially the palm of my right hand, is cut up because I handled the shelving that was very sharp after being cut by the second Home Depot yesterday. And the only way to like fix it would be to bandage it around the hand. I have lifted enough things for a lifetime at this point. Moving took eight and a half hours, and that was a week ago. Yeah, yeah, I don’t know. I feel like I’m running on fumes all the time. And but I’m actually like, in spite of all of these things, I’m kind of happy. I mean, I got the house. Again, it took eight months. There wasn’t, you know, the gory details personally about what was required to get this house.
Goat sacrifice. Which.
That’s basically what happened. Yeah, a lot of goats died horrible grisly deaths At my lovely hands and and I fe I feel nothing But yeah, you know, there’s light in here, and it’s comfortable, and it’s clean, and it’s a better place than I’ve lived in my entire life. Good. And yeah, yeah. Like, even though there’s a ton of work, like, probably most of it is done. There’s the plumber who’s gonna take all of my money, and then I have the oh, another thing: washer and dryer, didn’t have them. The washer and dryer people are coming tomorrow and dropping those off. And that’s actually it for a minute. There were a bunch of little things that required contractors to come out, but they’re pretty dumb. Like. I feel like I’m ready because I’m going to a music festival and then I’m speaking at a conference in three days. That was well-timed lol. I feel like the house is like secure and safe enough for me to abandon for a week without me like crying about my baby.
Which is good. 50% chance the house will not spontaneously catch on fire.
If it catches on fire, it will be a slow, careful, deliberate fire. Much like my business.
Okay, so so let’s let’s go up a level here. I want to ask: how did you prepare as an independent business owner to buy a house? And how should an independent business owner prepare to buy a house? What lessons can we draw from what you did, what you learned, what you tried, and what you experienced?
Yes, so if you’re an independent business owner, you probably think that the prospect of a $100,000 down payment on a house is a terrifying and Horrible consequence for you. And you’re right, it is, but it’s not impossible. So, the first thing that I can do, and if you live in the United States, you have to do this. There’s no whining. I don’t want any whining from you. And you’re not going to like it. You’re not going to like what I have to say. Are you ready for it? You have to get on payroll. You have to sign up for a payroll system and become compliant with your state and federal authorities on payroll. You have to begin paying Social Security and Medicare tax, and that’s going to cost you. You’re going to not just pay for the payroll system, of course, but you’re going to have to pay Social Security and Medicare taxes on a base salary that you’re giving yourself. My salary is the biggest expense that draft has after taxes. And you’re going to be paying taxes now. Congratulations. You are now part of society. There is no substitute for mortgage underwriters other than two contiguous tax years minimum of you being on payroll. If you are not listening to this and thinking, I need to pause this podcast and get on a payroll system today, you will not ever have a house. You will not ever have a condo. You might actually have a really difficult time getting a car without your parents’ help.
Yeah, I’ve been dry. I own a Honda and I’ve thought about buying a new car, and I’ve intentionally delayed that purchase. Until I have two years of payroll, because I know how challenging it is for anybody to be like, Yeah, we’re going to give you a loan aside from like a credit card when you don’t have that history to show, like, oh, look, I actually make money.
Yeah, you can have a credit score that is measured in scientific notation and if you have not been on payroll for two contiguous tax years. Don’t blame me on this. I am channeling exactly what my mortgage brokers told me. And they know way better than I do, man. You have to do that. You have to get on payroll two years ago if you want to buy a house today. If you want to buy a house, and this is again, condo, investment properties, anything, you have to be on payroll. There is no substitute. Banks don’t give a shit about you. That’s so funny. You want to pay them $150,000 in mortgage interest and they will have none of it.
They will have none of it. It absolutely blows my mind how challenging it could be for somebody who is financially successful, who runs their own business, who is an independent consultant, but. Has not been on payroll, has just been like, okay, cool. Like, I’m going to take this money, I’m going to pay taxes on it, and the corporation money just passes through to me. Even if you’re like, I could literally buy this in cash, they won’t give you a mortgage. You are too high risk. It’s boggled my mind to see friends and colleagues go through that.
It is time to adult the fuck up about your business. You are running a business. A business is a corporation. A corporation is a business entity that is recognized with specific rights through the government. That government requests that you be on payroll after a certain size. You cannot just take distributions. You should be tax compliant. You should be able to get yourself on health insurance. You should show an employment record. That is what society expects of you. Don’t kill the messenger on this. This is something that I’m sorry to report is absolutely necessary for you to have a. like decent secure future for yourself that if you’re going to ever get like a business loan, you need to be on payroll. If you need a line of credit, probably you also need to be on payroll. Hopefully, you are sensing a trend here and going on payroll. Here is how you get on payroll. You go to either gusto. com, G-U-S-T-O. I’m going to leave my refer link in the show notes, or you go on wagepoint. com. They were an ex-client of mine. They’re wonderful people. Both of those people provide you with payroll solutions that cost about $30 a month for a solo business and about $4 or $5 a month per employee after that. That counts contractors. And you pay that, and they file all your paperwork for you. Don’t use ADP, fuck ADP. Don’t use anything that claims to do 10 million other things for you. Fuck them. They’re going to take up too much of your time. Unless you have an assistant, which case you probably listen to the Make Money Online episode about hiring an assistant.
I switched to Gusto about, I think it was just over a year ago, a year and a half ago. And At first, I was like, ah, 30 bucks a month. This is going to be a pain. But then I realized, like, this takes care of all the problems. I’m, again, tax compliant. I’m starting that paper trail. And I’m setting myself up for success if and when I decide to make a larger purchase. And a listener of the show, Glenn, wrote in and asked how we as independent consultants Handle making those larger purchases. And I think one thing that, as we are highlighting here, that is very important, is making sure you are compliant in that sense, making sure there is a paper trail, making sure you are on the grid.
Yes, absolutely. You need to be visible and present. The next step in that is what you thought was the first step. It is that you need to clean up your credit score and you need to gain a Decent sense of credit. A lot of my friends wouldn’t believe this. They don’t open credit cards. They only have debit cards. So you need to open a credit card. You need to have a good credit record, you know? You don’t have to use the credit card. You can just leave it there. Or what do what I do. or did for many years and just pay utilities on it. Like you have to pay the utilities and never carry a balance over a month. And you’re paying zero dollars for the credit card. Get a no annual fee credit card and do that. Amex and Capital One both allow you to track your credit scores. I would recommend using them instead of a service like Mint or Credit Karma because they harvest your data for marketers. And I’m a neckbeard and don’t like that. But if you absolutely must use something like Credit Karma, that will tell you your credit score. Every four months, if you go to annualcreditreport. com. You can request one of your credit reports from one of the three reporting agencies. I do it so that I get an agency in May, August and January. And so I rotate it every four months and I get only one report. Find any blemishes, call the hell out of all of those people and get them excised from your credit report. When I married Erin, I had her added to my Verizon account and They opened a phantom account under my name that I couldn’t access and started billing me from it. And then they sent me to collections, and it ended up on my credit report. That took Probably nine hours of phone calls to get removed from my credit report. And then it took like three months for it to finally like churn off of the credit report. You have to do that for every blemish that you have on your credit report. You need to come clean.
And just to be clear, that level of corporate fuck-uppery is not uncommon. Like, when you get your credit report, you’ll be like, 17 years ago? What the hell? This closed account? I was six then. And there will be something that.
Yes, yes, absolutely. And that bites you now. And that’s horrible, right? The system is horrible and stacked against you at every turn. And you are going to be fighting constantly to fix it.
But if you understand the system, it’s a winnable game.
Absolutely. Absolutely. And, you know. Having just been through the process and kind of fresh off of it, I can’t believe I’m actually mentioning this, but if you email the email address and the footer, Make Money Online, and you ask me any questions about the process, I’ve been down that process. If you live within the city limits of Chicago and want access to my mortgage broker and realtor and real estate lawyer, that team was instrumental. Another thing, when you’re in the middle of the process, trust your experts. The whole thing is a black box and you have no idea what you’re getting yourself into. Often they don’t, but it’s their job to figure it out. I think that now is a very good time to buy, especially in the neighborhood that I bought in. And those of you who are listening and from the city of Chicago. You should be putting together money to do this if you expect to stay in the city limits anytime within the next five years. I think that there’s going to be huge bloodbath between haves and have-nots on people who buy and people who rent. And that’s most of what motivated us to buy. So that’s a little bit of a personal thing, but it’s important to put down roots.
Dive into that for a second. So the next question I was going to ask you was, why did you make the decision to buy instead of continuing to rent?
Well, so our apartment was awesome. You’ve been over to our home, Kai. You knew. The yard, you could have fit another house there. It was amazing. It was a block away from the middle of the best neighborhood in the city. A large part was they wouldn’t allow us to have a dog, so now we can have a dog. We’ve called it the dog enclosure, so there you go. Another part is exactly what I just said. We’ve lived we had lived in Logan Square for eight and a half years, and we’ve seen it change a lot. And we’re not even in Logan Square technically anymore, but we know that the wave of progress in the city is coming out to us in Avondale. And we want to get ahead of that, and we want to get on the ground floor of that. And so it’s not just moving, but it’s moving to this place in this neighborhood at this time. We knew that prices will never be better. Rates will never be better. Our mortgage is 3. 5. It’s a round off error for us to buy at this point, which is amazing. The monthly expenses on this house, given how move-in ready it was, other than all the things I complained about earlier, it’s maybe $300 over our previous rent. Man, if you’re listening to this, after the property tax increase hits in Cook County in 2017 or 18, your rent is going to go up by that much because they can’t afford not to. Your landlord is going to feel very sad and then fuck you.
The landlord will feel no remorse about the rent increase because there’s somebody else standing in line who’s like, sure, I’ll rent that. And it’ll turn over immediately. Jumping on one point you said there, like you’ve highlighted, there’s a huge upfront cost to buying a house. You’ve got the down payment, you’ve got the mental and emotional upfront cost. And you’ve got the, oh, there’s 10,000 things I didn’t realize I needed to do to the house. And I’m now best friends with every clerk at Home Depot on front and cost. But beyond that, once you’re over that hump, I mean, you’re right. Like, you have exponentially increased the quality of the house you’re in, the quality of the place you’re living, and it’s only going to be costing you a tiny bit more each month in terms of that month-to-month cost.
We tripled the square footage of our residence. I mean, we owned a whole lot. And if you got a condo in this neighborhood, you could get a condo in Logan Square for about as much right now, which is great. or a duplex or something like that for about as much as we paid. There is a generational shift in favoring cities. Fewer people want to live in the suburbs. More and more talented people are moving to the city. And this is great, you know. I had a conversation with somebody the other day at a friend’s party, and she said, I love you know, I live around Armitage in California, which is like Not central Logan Square, but it’s got like a nice commercial district, and it’s definitely improving significantly. And it’s off of a major bike trail that just opened last year. And it’s full of these cocktail bars and restaurants and a really awesome boutique. And a few other really great things are a little bit down the road, and it’s off of two major bus lines. And she was telling me, like, you know, I love I love all the cocktails at Scofflaw and I like going to Sing Swim, but I can’t believe how much the neighborhood has changed and I’m scared that I’ll be priced out. And I thought I had closed that morning and I went to this party. And I thought, actually, you know, if I owned property at Armitage in California, I’d be like, every time a cocktail bar opens, my property value goes up. So you have this group of people dreading the cocktail bar even as they continue to drink the cocktails from the cocktail bar. And then you have other people cheering on the oncoming cocktail bar wave, right? And I just don’t want to be on that side. I think that, again, I talked a lot about this split between haves and have-nots. And if you look at it, if you believe, okay, well, there’s very little that’s going to happen to stanch the cocktail bar wave, right? I’m one cog in a system, and I know what I do to try and help that. I do a lot of like charitable giving and a lot of community outreach and all that sort of stuff. I help my friends get cheaper places. I try and build my own locally focused community around it. But to an extent, you are powerless to stanch the cocktail bar wave. Like, it’s going to happen. And if it doesn’t happen with this cocktail bar here, and you deny their permit, it’s going to happen someplace else. And you’re going to end up with this huge game of whack-a-mole. I mean, there are two answers, move or put down roots. And I’ve lived in Chicago for my whole life. You know, I’ve lived in the Northwest Side. For three quarters of my life. I went to college on the north side. Wow, what a commute.
So I mean, you knew this was the decision you were going to make. You knew this was the path you wanted to take.
I mean, drafts. Fortunes have improved with Logan Squares also. And I like taking advantage of that. I like that there’s three pour over coffee joints within walking distance of my house. I like that there’s a Michelin-starred whiskey bar five-minute bike ride away from me. And You know, you can wring your hands about rent increasing, or you can do something about it. And a lot of people, again, this is a multi-year investment in your eventual future. A lot of people don’t have the five-figure sum necessary to do a down payment. I feel for them, and it sucks. But I did. Draft did. And if you take anything away from this podcast episode, it’s that the business that you create can generate the life that you want. And there is no more Obvious and naked expression of that than the four walls I’m sitting in right now. Now you’re living in the house that Draft built. It is the house that Draft built. It is absolutely the house that Draft built. And I couldn’t feel happier about it. I mean, I’m nearby a lot of my friends, and they’re all doing great. You know, this was not a decision I took lightly, and it’s a decision that I’m willing to reckon with for the next 20 years. Like, I do not plan on moving for a very, very long time. And it’s why it took eight months. It’s why it it’s it’s why it was Something that we, you know, we had a lot of like serious conversations about, and then I spent years planning for it.
Yeah, this is the culmination of a multi-year, multi-step process for you and Erin.
Yes, yes. It’s recognizing where the tide is going to be and doing something about it. To improve your lot in life, so you’re getting ahead of it and not just, you don’t want to find yourself screwed in five years by something that was out of your control.
Mm-hmm.
The cocktail bars are out of your control unless you make it a full-time job to engage with City Council. Do you know how corrupt City Council is? Have fun with that. I prefer to negotiate with people who are nice to me. Like lawyers and mortgage brokers.
Fuck that. Like my clients. I love you, clients. But yeah, you’re right. There is this, this, there is a tide where The place you want to live and rent right now is the place where other people are going to want to live and rent. And that means the shops are going to say, Oh, there’s a lot of people who want to live and rent here. We should open up things there. And there’s this. Constant back and forth of, oh, there’s more cool things, let’s move there, and rent increases. And you don’t have any control over that. Just in the same way, we talked about this a bit in our episode on negotiation. When you’re an employee, your employer owes you nothing. Your employer will let you go with the drop of the hat. If you’re uh uh Renting, well, your landlord owes you nothing. If they’re suddenly like, oh, gee, I know that I could rent this place for 500 bucks more a month, guess whose lease is getting terminated? Yours because, well, you’re not, you’re not the cash cow you could be. And they know that, hey, they kick you out, and in a month, they’re going to be full again. So You’re right. It is almost strategically a better bet to own the house because you put yourself in full control of your fortune there. You put yourself in full control over where you are and How you could affect your surroundings.
Yeah. I mean, the eviction scenario that you’re talking about sucks. I want to be abundantly clear. I’m not Nelson ha-haing you for getting priced out of a neighborhood. That is horrible. And I’m sad it happened. It shouldn’t have to be that way. I wish that the system was different. I wish that things went better for you. But it’s another factor of something that’s out of your hands. And again, knowing what the rules are, how do you do the best thing that you possibly can with that? Not just for yourself, but for your community, for your friends, for your colleagues. And when you talk about desirability, everybody I’ve talked to in the past five weeks that knows I’m doing this, they’re all like, wow, like everybody I know, or I, or whomever, they all want to live in Logan or Avondale. Or I want to live in Logan, but Logan got priced out, so now I’m moving to Avondale, or whatever have you. And it’s right north of Logan. It’s five blocks away from my old place. So it’s you know Again, these are very subjective pronouncements, right? It’s all the people that I know wanting to move to Logan and Avondale. But frankly, that’s enough. That’s enough for what amounts to an extraordinarily personal decision. If you, dear listener, also live in Chicago and all of your friends want to live in Lincoln Square, great Move to Lincoln Square. Move to Ravenswood, which surrounds Lincoln Square. You know, like move someplace where you feel like you’re invested in your community. Because I’m not just doing this to like, again, it’s a 20-year decision. It’s not like I care about the long-term price of my house. Lord knows I wouldn’t if I didn’t just drill several dozen holes in it. I’m not here to flip it, man. I’m here to stay here and put down roots and be at the nexus of an amazing fucking community. It’s one that’s been demonstrated to me for almost a decade.
Whenever I think about homeownership, I’ve been a serial renter since I was 18. I frame home ownership in a different way, but you’re framing it in a very intentional, community-based way where you’re saying, I’m not buying the house because, like, It’s, you know, I’m going to flip it. I’m going to double my investment here. You’re saying I’m putting down roots. I don’t have to worry about the community changing because of rent increases, because of these other variables. I’m picking this place and buying this house so I have the community I want. Yes. And I think that’s the best reason to buy a house.
Yes. I think so too. I mean, I, your relationships and the people you surround yourself with define who you are and define whether or not you feel fulfilled with your life. And in many ways, this house in this neighborhood, built in this way, is a long-term bid for that. I haven’t seen a whole lot of my friends lately because I’ve been drilling holes and things. But rest assured that when I come back from this trip at the end of May and come back from my other conference at the end of June. I will be seeing a lot more of my friends and working in a more intentional way to build this community. Because what else? What else is there in life?
No, there’s nothing. I mean, when you cut down to brass attacks, all that there is is community and the people you surround yourself with. Everything else, income you make. The projects you’re working on, the things you put out there, they are reflections of the community that you surround yourself with. And If you don’t recognize that, if you aren’t building yourself in the right way or building your community in the right way, it’s going to poison the well. So, yeah, I think, I think. Choosing the community as sort of the touch point that you make these big decisions from, that’s the right way to approach it. Are you either moving towards or moving away from a community? Are you moving towards a community you want to be with, or are you moving away from a community you do not want to be with? That’s a very fundamental question that’s valuable to ask yourself periodically. Yeah, absolutely.
I mean, I spent seven years getting people to move to Logan Square, right? Like, and and Photographing photos of four rent signs and mass texting them to people. I’m serious. I’ve gotten like friends to move next door to me as a result of that. I’ve like Talked to landlords and made sure that, like, they get referred out. I mean, my old apartment is going to a friend of mine. Like, we’re on that level about it, right? If you go to my website right now, nickd. org, I list six things that I’m working on right now. And two of them involve writing. One of them involves a mastermind that Kai and I co-run. One of them involves recording this podcast. And the last one, and I’m going to read this wholesale: creating a private, intentional community within the city limits of Chicago. When draft is closed, I spend most of my energy on helping other awesome Chicagoans make awesome work and grow as people in a deliberate face-to-face context. Slack, iMessage, and email are insufficient. You must put your body in the room. You must do it often. You must do it no matter what season it is, and you must not take the practice of doing so for granted. And that’s it. I mean, if you’re going to drop as much money as you have to live in a city versus a rural area, embrace your community. It’s not just enough to go to the cocktail bars. It’s the people that fill the cocktail bars. It’s the people that you get to hang out with every day.
It’s the people who show up for dinner. It’s the people who show up for lunch. It’s the people who could show up and There’s a plate for them at the table, no matter whether they were invited or not, or whether they are expected or not. It’s the people that you’re able to call that extended family that are part of your community.
Yeah, yeah, it is extended family, and it’s a lifelong commitment, and I’m willing to make that.
Notes:
- Cara Smulevitz, who will be helping us get a dog.
- This depot. No. Just no.
- Amazon Prime, which nickd uses now.
- nickd’s realty team: Frank Mitrick (realtor), Ed Collins (broker), Dorothy Culhane (lawyer). Reach out to all 3 and say nickd sent you.
- Gusto. Get on payroll or don’t get property ever, full stop.