Confessions of a Professional Painter in a Family Business (Spoiler: It’s Not All Brushes and Glitter)

Being a professional painter in a family business sounds like a dream, right? Picture this: You’re a master of your craft, creating beautiful spaces, while your family cheers you on, offering moral support (and maybe some free lunch) every step of the way. What could possibly go wrong?

Well, let me tell you—everything and nothing all at the same time.

Welcome to the world of family-run businesses, where the line between professional and personal is blurrier than the paint on your brush. Here are some of the funniest, most frustrating, and most family drama-filled moments you’ll experience as a professional painter working in a family business.

1. The “Family Meetings” that Are Actually Just “Free Advice” Sessions

Ah, the family meeting. It starts innocently enough. “Let’s sit down and discuss how we’re going to improve the business!” they say. Sure, sounds productive. But what it really means is, “Let’s talk about how we think you could do your job better even though none of us have ever touched a paintbrush.”

You can’t escape it. Mom insists you need a new color scheme, even though you’ve been using the same classic tones for years and, surprise surprise, they sell. “I think you should paint this place all pink,” she says, as though that’s the magic solution to every problem.

Dad, on the other hand, thinks you should always use a roller and never a brush. “Rollers are faster, son!” he insists, without realizing you’re painting a delicate piece of trim.

And then, of course, there’s Aunt Karen, who decides now is the perfect time to tell you about that one time she almost painted a room in her old house. She didn’t, but she almost did, so she’s practically an expert. You nod, take notes, and maybe later you’ll consider that pink paint… but probably not.

2. The Unsolicited “Tips” During Your Workday

You’re in the zone. You’re feeling it. The paint is going on smoothly, the walls are looking crisp, and you’re one stroke away from a masterpiece. Then, from the corner of your eye, you see it. The Family Member.

They’ve appeared like some kind of ghost, silently hovering over your work, their judgmental eyes analyzing every move you make. They don’t even have to say anything. You know it’s coming. It always comes.

“Hey, don’t forget to cut in around the edges,” says your cousin Jeff, even though you’ve been painting professionally for over a decade. Of course you know to cut in around the edges, Jeff. You’re not painting a house for the first time.

But Jeff has a point. You know, maybe you could have been a little more precise in that corner, and maybe the little paint drip on the floor is totally your fault. You give him a polite nod and just keep painting—despite the fact that in your head, you’re saying, “Thanks for the free advice I never asked for.”

3. When They Want You to Paint Their House (Again)

Ah, family. They love you, right? So much so that they want you to come over and paint their house. Again. The thing is, there’s a delicate balance between doing family favors and never getting paid for them.

You get the call: “Hey, we were wondering if you could help us out and do a little painting this weekend?”

You don’t even have to ask what they need done, because you know. You’re painting their entire house, top to bottom, while they sip iced tea in the yard and pretend they’re helping by holding the ladder every now and then. You’ll end up doing the entire job, and if you’re lucky, they’ll feed you lunch.

But, oh, the worst part? They’ll ask for “just a tiny touch-up” in the bathroom, which will somehow turn into painting three walls, the ceiling, and the baseboards before you can even blink. And when it’s all said and done, you’ll get a pat on the back, a “Thanks, buddy!” and—let’s not forget—the world’s most awkward family reunion BBQ, where you silently wonder if this will be the last time you agree to paint their house for free.

4. The “We Have to Keep It in the Family” Mentality

You know you’ve crossed into truly uncharted waters when a family member “suggests” you help them out on a project that has nothing to do with painting. Somehow, this always involves you being “volunteered” to do something that technically falls outside of your job description.

“Oh, we need to build a fence around the backyard,” says your brother. “You’ve done some carpentry work, right?”

Suddenly, you find yourself trying to install a fence with no prior knowledge of fence installation and no actual idea how to operate a power drill. It’s like one minute you’re holding a paintbrush, and the next, you’re holding a hammer trying to keep your family from turning a simple project into a DIY disaster.

And don’t even get me started on the praise you get afterward. “Well, it’s not perfect,” says your cousin Tony. “But it’ll work. Good job, man!”

Great. Thanks for that.

5. The “We’ll Handle the Marketing” Delusion

You’d think family would be the most supportive when it comes to your business, right? Well, that’s true… to a point. Until they start pitching in with their “marketing strategies.”

Enter: your Aunt Sue, the social media expert who, according to her, has singlehandedly transformed her Facebook page into a personal brand. She insists on running a campaign for your painting business, even though you never asked for it.

“What if we just make your business page a tribute to you, showcasing all your work? I’ll post pictures of the rooms you’ve painted, and maybe a video of you working? We’ll get you so many likes.”

The only problem? Aunt Sue’s “marketing” strategy involves you taking a selfie with the paint roller in one hand, a brush in the other, and the paint-splattered shirt you’ve worn for five days straight. It’s... well, it’s something.

Bonus: She also insists on tagging your uncle Bob, who, as it turns out, is not a big fan of painting. At all.

Conclusion: Family Paint Business—Love, Laughter, and Paint Everywhere

In the end, working in a family-run business is like being in a circus—there’s a lot of moving parts, a little bit of chaos, and a lot of love (and a lot of paint). You might not always get the appreciation you deserve, and sometimes, you’ll end up doing way more than you were originally signed up for (and not getting paid for it, either).

But at the end of the day, family is family, and somehow, despite the madness, you wouldn’t have it any other way. After all, who else can you count on to show up uninvited and “help” with the job, then sit back and call it “teamwork” while you clean the paintbrushes for the fifteenth time that week?