The Biggest Lie We Tell Ourselves: Homeownership Is the Dream

Homeownership. Is there anything better?

Yes. Lots of things. Vacations. Wine. Good food. A nice massage or pedicure.  Having “two nickels to rub together” and the freedom to actually rub them without worrying that I need one to pay another contractor.

Since launching The Virginia May, my charming little bed and breakfast, everything about my life has shifted. Scratch that—my entire identity has taken a sharp left turn off the highway of modern middle-class consumerism. Gone are the days of every six-week haircut cycles, salon acrylic nails, and racks of stylish, dry-clean-only clothes. These days, I’m a proud minimalist: the proud owner of the 3-pack of Amazon Essentials shorts for $19.99, rotating colors, tank tops from Costco, and wine so cheap the label just says "Red."

A special occasion? I throw on a sundress purchased from Kroger, ideally picked up while snagging a carton of eggs. That’s what I call efficiency.

I barely recognize the woman I used to be—and don’t even get me started on the woman who once thought owning a home meant "security." Because here’s the truth they don’t tell you: homeownership is the biggest hustle going.

Welcome to the Contractor Games- May the Odds Forever Be in Your Favor

Once you enter the realm of homeownership, especially as a solo woman running a business, you enter an unspoken pact with the underworld: the secret society of contractors.

Somewhere out there is a dimly lit, underground contractor speakeasy where they all meet quarterly. They swap war stories, compare boots, slap each other on the back, and collaborate like Bond villains. They control not a world-dominating laser beam—but something even more powerful: the fate of your foundation, your AC unit, your roofline, and your sanity. They huddle up like the rugby scrum, and shout the marine Ooh-rah!”

“Gerald,” one says, “make sure that patio door is juuust slightly off-center. Install a wooden threshold and—this is key—absolutely no caulk. Let water creep in slowly, like a well-trained spy. Four years from now, boom! Rotted subfloor. She’ll be knee-deep in a 5 foot floor replacement  before she knows what hit her. Of course the vinyl plank installed won’t be in stock anymore. She will figure it out.”

“Tim,” another one grins, “kink that AC line right at the bend. Nobody’ll notice. HVAC guys will make a few hundred bucks trying to diagnose it, and in the end, she’ll be so grateful just to be cool again, she won’t even ask questions the third time we show up.”

“Tell her 9 a.m. on Tuesday. Roll on Thursday night. Or not. You’re mysterious. She loves that.”

“And the quote? Don’t bother. Just smile and say, ‘By the job. She loves surprises.”

These men are practically pirates—missing fingers, missing teeth, and yet full of confidence. They operate with a curious blend of swagger and sawdust, shifty meth eyes and promising: “We’ll knock this out in a day.” With a lisp of spit into the imaginary spitoon….

A day? Try forty days and forty nights. I half expected Noah to show up in my driveway, asking if he could park the ark next to my trash bins. Even the animals  walked away two-by-two at the end of 40 days and 40 nights.  But not the contractor.  He is still here.

Text messages are the new cryptic crossword—like trying to decode a sentence written by a first grader with a broken crayon. If you can string together two coherent words, it’s a miracle.  “Ok so you was wantin to no what yesterday come to the grande total of do'nt tell anybody but I am going to cut you half on it shes like 130 unit you spend the money and teh library if u bye the parts and getting everyting taken care of well be looking at 7:50. ( yes this is an actual part of the contractor text) 

 I learned later that “library” is actually “labor,” and “7:50” was the cost, not the time.  I am still stumped as to how I could misunderstand so much given my background as an English teacher…..

Homeownership: The Endless Money Pit

When people say “owning a home is an investment,” what they really mean is: you are now a glorified facilities manager with a part-time job as a hostage negotiator.

Every time you get a little ahead—maybe you think about treating yourself to a weekend away—one of the units in the cottage starts to leak. The foundation sighs heavily and shifts three inches to the left and the vinyl plank starts to peek out the concrete underneath, and now the big beautiful windows need more caulking. Or the new AC unit from last year’s install doesn’t quite fit the amps you had from the previous 1902 model, so breakers trip. “ Ya you need two 60’s not a 60 and a 30. It’s a day job.” 

Retirement? Not quite. It's more like a full-time job managing unexpected disasters and doing YouTube DIY research at midnight with a bottle of cheap cabernet and a can-do attitude.

So, Is It All Worth It?

Yes, there are days I fantasize about trading it all in for a beach cabana, a sarong (an XL, unfortunately), and a life where my only responsibility is reapplying sunscreen and deciding between a nap or my beer margaritas.

But then someone stays at The Virginia May and tells me they finally slept through the night, that it’s the first time they’ve felt truly rested in months. They linger over breakfast, an oo an ah over how good it tastes- and I remember—this is why I do it.

I built something real. Tangible. A place that wraps people in peace, even if behind the scenes it takes constant patching, painting, plunging, and occasionally pleading with the toothless contractor who may or may not show up depending on the weather—or the moon phase.

And somehow, in all the chaos, it's still worth it.

So yes, the dream of homeownership is a lie. But maybe the real dream is carving out your corner of the world, even if it comes with continuous surprises, contractors, and a sundress from Kroger.

As for Happy Hour? It used to be at 4:00 p.m. Now, it’s more of a floating concept.

Noon? 8:30 a.m.? Who’s asking?