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Tom Sawyer and the Art of Not Painting

AJ Oberlender • February 4, 2021

Why Painting Will Never Be My Thing: A Story of Fence Manipulation and Family Rescue


I absolutely hate painting. Period. End of story. No elaborate explanation is needed, but since you’re here, let me tell you why my disdain runs deep.


The “Tom Sawyer” Childhood Drama


Back when I was a kid—long before Mazi and I were debating what color to paint our baby’s room—I got into some trouble. My mom, in all her genius glory, decided my punishment would be painting our wooden fence. Now, here’s where things get interesting. At the time, I was reading The Adventures of Tom Sawyer, and I swear she must’ve planned this to mess with my head. She was basically playing mind games with my literary education.


So there I was, paintbrush in hand, pretending to be farther along in the book than I actually was. My friends, like good neighborhood kids, came over to hang out. I played it cool, hyping up how much “fun” I was having painting this fantastic fence. And just like that, my friends were begging for brushes. Did I step back and let them take over? Of course, I did. That’s what a master manipulator—I mean, good friend—does.


Unfortunately, there’s no photographic evidence of that fence, but trust me, it was the Picasso of punishment projects. Or so I told myself.


Fast Forward to Today: Still Hating Painting


Now, fast forward to adult AJ, where painting isn’t just a punishment—it’s a nightmare. Mazi (my amazing wife and partner-in-all-things-home-projects) had been asking me to paint our baby’s room for months. Months. But I kept dodging it. My excuse? A furniture set we couldn’t sell. Because clearly, you can’t paint until the room is empty, right? Well, we finally sold the furniture last week, so I was out of excuses. Begrudgingly, I started priming the walls with her, and somewhere along the way, I told her my childhood fence story.


Her response? “So that’s why you’ve been avoiding painting?” Busted.


Enter My Sister, the Hero


Lucky for me, my sister, Gabby, stepped in like a superhero with a paintbrush. Honestly, she saved the day—and probably my marriage—by volunteering to help. Thanks to her, the painting is done, and I don’t have to pretend to enjoy it. I can focus on what I truly love: building furniture. (By the way, you can call me Harrison Ford. Or don’t. I’m good either way.)


Why This Post Matters


This isn’t just a thank-you post to Gabby (though she totally deserves it). It’s also a reminder that sometimes, the people around us step up when we need them most—even if it’s for something as mundane as painting. So, here’s to teamwork, sibling heroics, and my eternal hatred of painting.

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