Jill yearned to sell everything and live full-time in a motorhome. For her, there existed no stronger pull than the allure of going right to the precipice of civilization and then continuing over without even slowing down. Falling into the unknown, knowing only that it’s the surest way to know you’re fucked. The sultry mix of gas fumes, septic aromas, and barely chilled vegetables rotting in an overworked traveling refrigerator combined to form an irresistible fragrance that marked a life on the move. To pack all of our belongings and hit the open road in search of deep, irreplaceable memories full of irreparable emotional traumas, that was a call she could not silence and her heart refused to ignore.

I fought the good fight and forced a ceasefire. It wasn’t easy. I wasn’t arguing against reason. Her desire for location independence was the very border separating passion from obsession. In the course of battle, past insults were revisited. Childhood scars were torn open anew. But eventually, we backed away. For a time, we were able to forsake the conflict. I wasn’t fooled into believing that it was the end of aggressions, but it was peace. And I was happy to move on and fight about other things, like beard shavings in the sink. For a time.

Until Ol’ Travellin’ Jill’s wanderin’ eyes happened upon an Internet discussion that exposed her brain to the wonderful world of housesitting. Her brain soaked in the information and cogs once stalled spun with renewed energy. Her brain spoke to her: This is the workaround we’ve been looking for! Jeff can’t argue against travel if it costs nothing to stay in someone else’s house! THIS is the crack in the dam! This will chip away at his stubborn resistance to the vagabond lifestyle! This will speed the steady erosion of his will to live!

 And Jill looked upon sites and discussions and determined that it was good—that it was right. And so it is writ.

Housesitting is an outgrowth of this goddamned “sharing economy” we’re in. The same economy that gave the world Uber assaults and AirBnB home-destroying parties. The sharing economy is full of great ideas on paper. Once those ideas go from paper to people, however, we get little annoyances like Craigslist murders.

As with everything in the sharing economy, the Internet is key. In the same way it connects cannibals with people who wish to be eaten, there’s a site that helps homeowners find complete strangers to stay in their homes and feed their beloved animals and try on all the clothes they didn’t pack while they are away living the life. There’s no screening process, so even “people” like me can participate in this game of disaster hot potato.

Jill pitched housesitting to me as a cost-effective travel plan—“We just have to buy the airfare (if the house is out of state), and take care of a few animals and then we can vacation for free!”

That’s fine as long as you ignore the fact that the entire point of going on vacation is so you don’t have any goddamned responsibilities. You can leave the hotel room a mess because there’s an exploited class of people who will come in and clean it after you leave. You can spend a day browsing overpriced Made in China junk at souvenir shops, not caring if you left the iron plugged in and face down on a stack of old newspapers.

So how does a housesit actually compare to a vacation? Let’s look at the facts:

Housesitting is a vacation in the same way that an unpaid internship is a job. You’re working for someone who pays you nothing and you’re supposed to feel lucky that you were chosen for the position. You end up doing a bunch of fetching and sorting and killing time until you get to go home.

Housesitting is a vacation in the same way a prison sentence is a vacation. The duration of the housesit is set by the terms of the homeowners. If you signed on for three weeks you can’t just say, “Fuck this noise!” and leave when you’ve had your fill after 5 days. You’re on a hook from the moment you say, “Yes, I’ll rub lotion on your naked mole rat for the privilege of running up an electric bill I won’t have to pay and farting into your family’s couch cushions.” You’re OBLIGATED to stay until the owners come home.

Housesitting is a vacation the same way indentured servitude is doing someone a favor. During a housesit, you’re on call. You can’t just spend a day at the nearby water park if the furry family members need to be walked or fed. You need to be there to put the garbage out and let housekeeping in. In a way, it’s different than indentured servitude because you volunteer for the housesit. So it’s even dumber.

What it really is, is a roadshow of horrors and anxiety.

Personally, I hate being in someone else’s home. Even if you invite me in and insist that you’re not offended by my face. Even if you’re not home to be offended by my face. I still won’t feel comfortable.

When I’m in someone else’s space I can’t be my clumsy, relaxed self. I have to take my shoes off and use coasters. I have to wear pants. If I make a mess, I feel bad. If I break something valuable, I feel responsible. When I scratch my bare back with kitchen forks and put them back in the drawer without washing them, I feel guilty. After I go through bedroom closets and find marital aids, I feel awkward because that thing was huge! And how . . . I mean, how did it, you know . . . HOW?!

Housesitting is just caretaking. I know Jill has seen The Shining. I don’t think she’s ever read the book and that really pisses me off but let’s put that aside for now. Jill is sitting right in front of me as I write this and I don’t even want to fact check that point for this post. Because if I confirm that she’s seen the movie without reading the book, I’ll be too angry to finish writing this post. The point is, even if she only saw the vastly inferior joke of a movie, she knows that the caretaking lifestyle leads to isolation, madness, and death by fire axe. Of course everything leads to death. Living leads to death. Death is inevitable. But I’d like to avoid madness as much as possible.

Madness is hard to avoid when the kids are restless. And the kids will get bored if the housesit is longer than 4 days and the house isn’t attached to a water park. The kids get bored before we even leave our driveway most trips.

Bored kids, massive discomfort, and madness. Yes, the homeschooling life grants us the flexibility to pursue these options but it doesn’t mean we should. Obviously shouldn’t doesn’t mean didn’t.

So far, we’ve taken on three housesitting assignments.

Our excursions into what I’d call “lifestyle tourism,” to see how the “norms” live, have provided me (and now you) with some fascinating learnings. Overall, we’ve discovered that:

Every home has exercise equipment. Treadmills. Weights. A fucking Soloflex. In a perverse twist, one home had the treadmill right next to the bed. When I’m in bed the last thing I want to think about is running. It’s a violation of the sanctity of the bed to have a piece of exercise equipment in a place of rest. I could just imagine sitting in bed watching The Walking Dead and finishing off a half-gal of cookie dough ice cream while the fucking treadmill stands next to the bed in powerful, silent judgment. I’d throw a blanket over it but then I’d get cold and scared because then I’d imagine it was Michael Myers from Halloween under the blanket instead of the hateful treadmill.

People who use housesitters either have hundreds of TVs or no TVs. I realize that three homes is a super small sampling, but I can say with absolute authority that America has a television problem. If you don’t resist this addiction, then your home will be overtaken with televisions in every room—sometimes two in a room. And once infiltration is complete, you will no longer be able to form an opinion, or sleep, or appreciate your life.

Every housesit follows a very particular pattern. Someone gets maimed within the first 24 hours and it’s usually Ben (he put his six-year-old fist through a pane of glass and nearly lost a finger, he also fell off a zip line right on his face). Something gets broken within 48 hours (the glass pane, some picture frames, a treadmill). We discover a fantastic place to eat. And the trip always ends with a vow by Jill to “NEVER do this AGAIN!”

Those were the overall lessons. But each experience was unique. And worth sharing. Though, I’m not going to name names here because that would be horrible. I’d also like to state for the record that we liked all the people we sat for. In two cases, these people became friends who we saw outside of the duration of our sit.

All of the sits were within 30 miles of Chicago.

This is what happens when you let the voyeurs in.

 House of Enlightenment. Our first sit was in a wealthy suburb. It belonged to a professor who travelled 13 months a year and his wife who tended her award-winning garden when she wasn’t in Israel, eyeball deep in an archaeological dig. These were accomplished folks.

The assignment seemed simple (on paper): keep two cats and a goddamned award-winning garden alive for three weeks. Maybe not simple.

Now, to demonstrate what was really at stake here requires a little bit of backstory, so humor me. Jill grew up as the Chief Operating Gardener for the Gazebo of Death, home of the Planter From Which Nothing Grows. As an adult, every plant she’s tried to keep alive in our home has died and ended up looking like something that would give Tim Burton the heebie jeebies. And here she was, in charge of an award-winning garden that was written up in the kinds of magazines that give Martha Stewart the tingles in the nethers. For three weeks. Three weeks is PLENTY of time to kill a garden.

(After Jill signed on to this assignment, I reached out to some of my more shadowy acquaintances to inquire about new identities for myself and the family.)

Worst of all, I’m highly allergic to cats, and I wasn’t able to take three weeks off of work to fully enjoy not breathing during this housesit. Which meant that I couldn’t be there in person to provide Jill with the scapegoating services I normally deliver. Thankfully, my very absence proved to cause every problem Jill experienced, so I was able to fulfill my duties remotely.

When I did arrive, I wasn’t properly prepared for the musty manor. The only conversations I had with Jill about the house were panicked retellings of how a furious Ben punched out a pane of glass in the door to the greenhouse and nearly severed his finger. She didn’t spend time describing the curios.

I was greeted with shelves and knick-knacks and itch everywhere. It was like browsing an antique shop. Where everything looks like junk unless you’re a historian. Roughly seventy-nine percent of the available living space was occupied by mementoes commemorating moments already lived. Obviously not lived in the house where they were displayed because there simply wasn’t room for it.

Thinking of my kids running around this house full of bric-a-brac, I began calculating the cost of the potential damage. I stopped when the liabilities surpassed the cost of five new identities.

This was a home of academics so television was verboten. Mostly. They did have one, it was just tucked away in the basement and every channel was PBS or BBC. At least, I imagine those were the channels it allowed when it worked.

It really wasn’t a house for kids. Or at least, my kids. They were bored from the beginning. And Jill was harried—getting someone to fix the glass (for $80) and refilling the woodpecker feeder (costing us $60—I’m not even fucking joking) and planting new flowers in the garden that she was desperately trying to keep alive.

Everyone was happy to leave.

On the last day, a cleaning lady walked around the house and looked in every room and left. We didn’t see her do a goddamned thing. We guessed that maybe her services went beyond our middle-middle class understanding. Maybe she was just letting her aura fill the space with good vibes. Maybe she was just displacing the bad vibes of the poors who had got their poor thinking all over the knick-knacks.

We left. And Jill vowed “never again.”

Our next sit was at the Dog House. It was about as much of a 180 degree turn from the House of Enlightenment as you could get. Located in a much more blue-collar neighborhood, this house had a dog, two werewolves, two birds, and a pond full of wild frogs. We never saw the werewolves turn back into human beings but we talked to them like they were people just in case. When the owner told me they were Scottish deer hounds I thought he said Scottish beer hounds and I told him I knew those guys before they were bitten.

The Dog House also had televisions. Three huge, wired up, working televisions. They were so huge, it was insulting how big they were. And they had all the latest video game systems. And a pool. And bows, arrows, and a big ass target in the backyard. And a room full of guitars, a drum set, and a synth keyboard.

This house was designed for noise. For living. For barking dogs, chirping birds, and screaming kids. The backyard was huge. Elsa stalked the pond for frogs and Ian shot the bow and Ben demanded to swim around the clock.

Their downtown had some amazing restaurants. One was a New Orleans themed eatery called Moe Joe’s that had me looking up available local real estate.

I could breathe in that house. And the one dog was a cavapoo—which is like a stuffed animal possessed by a spirit made up of gum drops and rainbows. It begged to be loved. All it wanted was to be loved. There was no danger of the kids giving it too much attention. I think it began to glow with pure bliss the more the kids played with it. And the werewolves were super patient and tolerant with the kids too.

Though they were sneaky. When they were on all fours, they stood table height so with no effort at all they could grab and gobble down almost an entire bacon pizza that Jill left on the table.

And that was pretty much the worst thing that happened.

Well, that and me breaking their treadmill and the kids fighting with each other and Jill being harried again because she was there for 3 weeks by herself with the kids and that’s a hell of a thing. So of course, she vowed “never again.” And she meant it that time!

Our next housesit was at the House of Huge. By far, the largest, most impersonal home I’ve ever been in. This house was 16,000 square feet, occupied by a family of four. Four giants, I’m guessing. The assignment was to care for two adorable dogs and regret every life decision we’ve ever made. Because there was no legal way we were ever going to be in a house like this again.

This house had a 12-seat movie theatre.

This house had two three-car garages.

This house had an entire closet just for candles. Just for fucking candles!

This house had a kitchen as large as the first floor of my house—so big that they had to have a television on each side of the space. We don’t even have one TV in our kitchen. Though sometimes, if the counter is clear, we bring the iPad in there which kinda counts.

This was a house my home could live in.

I know there are people who have started out with less than me and have ended up with more. This isn’t a pity post. I’m aware of my failings and I’m taking all the blame for my poor decisions. I won’t even blame Jill which would be easy and also accurate. No. It’s my fault, and mine alone, that I didn’t leverage my white male cis privilege more.

But damn. All this time, I thought I lived in a house and it turns out I live in a room.

Not that a house that enormous doesn’t present its owners with certain challenges. Sixteen thousand square feet is a lot of space to fill. I’m not even sure Jill could clutter up that much space. It was interesting to see how these people handled it. They decorated in some unexpected ways.

There were two tables that were completely set for dinner. One table was large enough to seat twelve—with places set from silverware to wine glasses. I wondered how long they were like that. If they were like that for us or just always.

Every corner and nook seemed to have its own theme—the dog statues and portraits under the staircase, the horse motif with horseshoes by the piano, the various pineapples in the kitchen, the beach and seaside paraphernalia in the screened-in porch.

Jill counted two hundred throw pillows on the first floor alone. They were placed just so on the dozens of chairs and multiple couches that were facing each other in silent conversation. Some pillows had sassy little phrases on them. “Life is short, eat the cake.” Others had quotes from Coco Chanel. None had been sat upon.

The walls were covered with prints and photos and quotes. For every family photo, there were four other frames that contained a word collage or a large quote or some random thought about life. The walls screamed “LOOK HOW MUCH LIFE WE HAVE HERE!” And by screaming, they disproved their point.

I began noticing books in trays everywhere. Books stacked in serving trays. Like the books were meant to be eaten. I’m not sure that people who put books in trays know what books are for. I took pictures in case what I was seeing was just a shining-like hallucination. There were at least 25 trays with books in them throughout this house. I stopped taking photos of books in trays because taking photos of books in trays is the only thing weirder than stacking books in trays more than 25 times and leaving them that way for everyone to see. We own trays and books and so far we’ve never thought to combine them. It never would have occurred to me. It makes me wonder—what else are we missing out on?! What else should we be mixing together? Beer steins on chairs? Silverware in flower vases? DVDs on ceiling fans? Ostrich eggs in Baseball mitts?

Obviously the books in trays, and the themed spaces, and the pillows with sassy phrases, and the nearly countless framed things on the walls were meant to be seen. But the books weren’t meant to be read. The pillows weren’t meant to be cushions. The stove, with all the pineapples and stuff placed on top of it, wasn’t meant to be fired up. This was a house where life was staged. Where the dining places were set, forever waiting for an event.

I never thought I could pity someone with so much. But I did. Not knowing them, personally, and being in their space for 6 days, I pitied them. The house was beautiful but I didn’t envy any of it.

Though I will say that I took some pleasure when I discovered that our only refrigerator is better than their third refrigerator.

This was a long post and I’m happy to put it behind me. If you made it this far, I’m sure you are too. I just wanted to capture it all, to share my scars as vibrantly as possible before they fade to white.

And hey, I’m not saying that housesitting is a bad idea for everyone. If you’re a writer and want to travel the world while working on a novel—empty houses in new environments can be exactly the quiet inspiration you need. If you’re unemployed and looking to stay one assignment ahead of homelessness, these are your cold-weather gigs. If you’re a fugitive cannibal on the lam, running from the authorities and vengeance-seeking families, the world can be your hideout.


But for me, there’s no place like home.







  1. Terrific post! I’ve always wondered how people travel the world with no income and no marketable skills, and yet seem to have the best times. Jill’s way would seem to be great, but how do you obtain references? At least for your first time? And of course, once the kids grow up and move out, the possibilities are limitless!

    • jeffandjill

      03/14/2017 at 11:41 am

      Yeah it’s important to begin getting references. That’s why we started local. Every sit was 30 miles from our house so we were able to meet the homeowners before the sit and go over things. Then we watched their stuff. And after, they’re supposed to leave reviews telling others “Hey this traveling band of scallywags is legit. And even though they’re offensive to behold, they didn’t steal anything! Recommend!” We were trying to build a reputation. Until this post came out.

      Thanks for reading!

  2. I’ve thought about housesitting – but I’d be terrified of accidentally letting a prized pooch outside, never to be seen again. Someone told me that they were going to Paris for a couple of weeks and would be house SWAPPING. Apparently, it’s a thing. You get their house and they get yours. Why anyone from Paris would want to spend two weeks in Albuquerque, I can’t figure out. This gal is also car swapping with them – there is just no way in hell I’d let someone from another country drive around in MY car. The liability issues freak me out (not to mention the fact that I’d have to clean the car — and that would take a week in itself).

    • jeffandjill

      03/15/2017 at 7:20 am

      AH YES Houseswapping. No way. I live in a craphole but it’s full of my crap. And I’m as protective of my crap as a dung beetle. There’s no way I’m letting anyone in my house unsupervised. The first thing they’d do is get their oily fingers all over my limited edition books. Then they’d judge us the same way I judged the peoplein this post. And who wants that??

  3. You have to send this somewhere. It was brilliant. And I’m with Jill, more house-sitting, just so you have to write about it. Ah, the humanity. Too many TVs depresses me too. Living in an apartment I had to get a small TV. I just can’t do those large flat-screen ones because I’d feel like it was too large for the apartment and just so depressing like we’d be living in a dystopia. I’m only half kidding about that!

    • jeffandjill

      04/04/2017 at 2:52 pm

      Wow. That’s high praise from a super talented writer. Thank you. It almost makes all that hell worth it.

  4. I loved this post!
    For many years, I worked as a personal assistant and chauffeur for a few wealthy families in L.A., so I can totally relate to your descriptions of these houses. It’s like you house sat for the people I worked for!

    To mish~mash some famous quote: “The rich are not like us.”

    But they are fascinating. Just like your stories. Keep on writing!!

  5. Thanks so much for posting. What a hell of a story!

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