Mom’s Prison Planner: A Hilarious Family Disaster!
Every family has its quirks, but ours has one that will go down in history as both the most embarrassing and the most hilarious: the saga of Mom’s “prison planner.” Yes, you read that right. A planner. For prison.
It all started when Mom decided she needed to “get organized.” She’d recently gotten into planners—the fancy kind with stickers, color-coded tabs, and inspirational quotes. To her, planning was therapy. Grocery lists, workout goals, reminders to water the plants—if it could be written down, it went in the planner. She loved it so much that she joined an online planner group. That’s where she found a free printable called “Prison Planner.”
Now, in Mom’s defense, the creator meant “prison” as a metaphor—for breaking free of habits, conquering obstacles, and basically not letting life box you in. But Mom didn’t read the fine print. She just saw the cute layout and thought, Perfect! I’ll use this one for the family.
The first red flag came at Sunday dinner. She whipped out her shiny new planner and announced, “Okay, family meeting! We’re going to use the prison planner from now on.” Dad dropped his fork mid-bite. My brother nearly spit out his iced tea. “Uh… Mom?” I asked cautiously. “Why are we planning for prison?”
“Not for prison,” she corrected cheerfully. “It’s just a planner called prison. See?” She held it up. And there, on the front, in bold block letters, was the phrase: PRISON PLANNER.
We lost it. Tears-streaming-down-our-faces kind of laughter. Mom, however, doubled down. “Don’t laugh! It’s practical. Look—this section is for meal plans, this is for goals, and here’s where we track progress. Doesn’t matter what it’s called.”
Things only got funnier when she brought it to church. During a women’s group, she laid her planner on the table, and the cover caught everyone’s eye. “Uh, Susan,” one of her friends whispered, “is there… something you want to share with us?” Mom had no idea why the women looked so concerned until someone finally asked, “So, when exactly are you going to prison?”
Word spread fast. By the end of the week, my brother was telling everyone at school that Mom was preparing for jail time, Dad joked about baking her a cake with a file in it, and I may or may not have posted a photo of the planner on social media. The caption? “Our mom’s got a five-year plan… in prison!” The post went viral among our friends.
Mom eventually realized the mix-up but instead of being embarrassed, she embraced it. She started writing “Cell Block A: Laundry Duty” and “Warden’s Notes: Grocery Run” in the planner. She even bought herself striped socks to wear while updating it, declaring them her “prison uniform.”
What could have been a simple mistake turned into one of our family’s funniest running jokes. To this day, if anyone’s having a rough week, someone inevitably says, “Better put it in the prison planner!”
So no, Mom’s not serving hard time. But thanks to one hilariously mislabeled organizer, our family got a lifetime of laughs—and a reminder that sometimes, the best plans are the ones that go hilariously wrong.
