The Trouble With Trouble

The Power of Getting Caught

In episode 4 of the Memoir Club Podcast, we’re going to talk about getting into trouble. We all got in trouble as kids—but what if those missteps are where our best stories live? In this episode, we explore the power of “getting caught,” why trouble is a rich source for memoir, and how to write about those rebellious or embarrassing moments without shame. Plus, we answer a listener’s question about writing scenes when you’re the “bad guy” of the story—and share a writing prompt that’s equal parts funny and revealing.

When you were a kid—what did getting in trouble look like?

Was it a slap on your backside, or worse? A raised voice? A timeout chair in the corner? Maybe it was a full-blown you’re “grounded for the rest of your life” situation… or one of those long, silent car rides where the punishment was waiting.

No matter how it happened, getting in trouble left a mark. Not just on your backside—but on your memory.

And oddly enough, those are often the stories we remember most clearly. The ones that taught us something. The ones we laugh about—years later. The ones that told us, “You’re growing up now… and here’s a line I don’t cross.”

So today, we’re diving into childhood mischief—not just for the humor, but for the meaning hiding inside it.

A Personal Story

So I’d like to begin by sharing a story about one of the times I got into trouble as a teenager. Nothing serious—no laws were broken, no one was hurt, there was no jail time involved. But I crossed the trust line with my parents, and it cost me.

I was fifteen the summer it happened—old enough to feel the pull between following my parent’s rules and having my friends think I was cool.

The family was down in Tall Timbers, Maryland. A little strip of river cottages tucked where the Potomac River meets the Chesapeake Bay. My dad had struck a deal with his boss (who owned the property): Dad would get the place ready for the season—prime the well, touch up the paint—and in exchange, the family would get a free week at the cottage.

It was a simple place. A couple of big rooms, an outdoor shower, and a wooden outhouse with two seats—luxury, if you squinted. I brought along my buddy Jimmy, who played bass in my little high school garage band. My sister Sherri, thirteen at the time, brought a friend too. On the first day, Jimmy and I met two girls our age hanging out along the beach. One of them—we’ll call her Trish—had a drum set. That’s all it took for us to become inseparable.

All week, we wandered up and down the shoreline, went to the corner store for RC Colas and Moon Pies, played music, and pretended to be older than we were. By the end of the week, Jimmy and Trish had a serious case of puppy love going on. They wanted one last night together before we packed up and left. So, the four of us cooked up a plan to sneak out and meet on the beach.

For some reason, on the beach, there was a huge hole dug into the sand—big enough to put a backyard swimming pool into. I don’t know why it was there, but we put it to good use. We climbed into it to stay hidden, because the beach closed at dusk and we didn’t want to get caught. We stayed there for hours—talking, whispering, sneaking cigarettes—each of us trying a little too hard to seem cool in front of the others.

Then came the flashlights. And voices. We froze and hunkered down. From inside that hole, we could see lights sweeping the shoreline and indistinct conversation. We stayed hidden. We didn’t want to be discovered.

Eventually, the searchers gave up.

And as dawn started to roll in, we crept back into the cottage, shoes in hand, hearts pounding. We were quiet as ninjas—until, in the dark, I bumped smack into my father, who had been waiting up for us.

He didn’t yell; he didn’t want to wake up my siblings. But he was clearly angry.

“Where the hell have you been?”

“We went down to the beach,” I mumbled.

“No, you didn’t,” he said. “We were down there with the police looking for you. And you weren’t there.”

I tried to explain. It didn’t go well.

So our last day of vacation ended. We packed up early. Jimmy was banned from our house. I was grounded for weeks. And worst of all? My drum set was impounded. For a whole month.

It took a while for my parents to trust me again. The initial anger eventually faded, replaced by a cool distance that was almost harder to bear. I knew I’d pushed too far, and I resented the extra scrutiny of my social life. But I kept pushing boundaries until I finally left home at 18.

Reflection & Writing Tips

Childhood mischief is fertile ground for memoir.

Why?

Because those moments are charged—with emotion, consequence, and–as we get older—with perspective. And most of all, because they show us at our most human.

You don’t need to have set a building on fire or stolen a car at age ten. It can be small:

• You tossed firecrackers into the school bathroom.
  
• You lied about who you were with.
  
• You carved your initials into the basement paneling.

These stories matter not because of the transgression, but because of what they reveal about:

• How you saw the world
  
• How your family handled conflict
  
• How you handled being wrong

So here’s how to approach writing your own “got in trouble” story:

1. Set the scene clearly.
Where were you? Who was there? What rule did you break—or what line did you cross?

2. Build tension.
Did you think you’d get away with it? Did your heart race when you heard footsteps? Was someone about to find out?

3. Show the reaction.
What did the adults do? Did someone yell, sigh, laugh? Were you grounded? Was your punishment immediate—or lingering?

4. Include how it felt.
Fear? Guilt? Defiance? Shame? Pride? Sometimes we’re not even sorry—we’re just mad we got caught. Be honest.

5. Reflect.
What did you learn—or not learn? How do you see it now, with adult eyes?

Here’s a bonus tip:
If you’re still embarrassed, write it anyway.

Embarrassment is often a sign that the memory still holds emotional weight—and that makes for powerful storytelling.

Key Takeaway

Memoir isn’t about painting yourself as perfect—it’s about being real.

And sometimes, the best way to reveal your humanity is to tell the story of the time you blew it. The time you knew better—but didn’t do better. The time your kid logic ran up against adult consequences.

Those are the stories people relate to.
Because we’ve all been there.
Red-faced. Caught. Grounded. Humbled.

Trouble is where we meet ourselves.
And where your reader meets you, too.

Listener Mailbox

This week’s question comes from Danny in Ohio, who asks:

“How do I write about a memory where I’m clearly in the wrong? I don’t come out looking good, and I’m afraid it’ll make people judge me.”

Danny, you’re not alone.

We all have stories where we’re the villain, the fool, the hothead, the kid who said something we shouldn’t have.

And yes—it’s uncomfortable.

But here’s the thing: memoir is not a highlight reel; it’s a searchlight.
And a good memoirist doesn’t only show the shiny parts—they show the shadows too.

Here’s how to write those “less flattering” memories:

1. Be honest—but kind.
To yourself and others. Don’t sugarcoat, but don’t beat yourself up, either. Be truthful and fair.

2. Show your younger self with context.
You’re writing as you were, not as you are now. Let the reader see your age, your naivety, your logic at the time.

3. Use reflection to show growth.
That’s the payoff. You made the mistake, but now you see it differently. That’s why you’re writing.

4. Most of all, Own it.
Readers trust writers who are willing to say, “Yep. I messed up. And here’s what I learned.”

So Danny—tell the story. You’ll be glad you did..

Prompt of the Week

Here’s your writing prompt this week:

Write about a time you got in trouble as a child.
What did you do? Who caught you? What was the consequence? How did you feel—then and now?

If you need a little help getting started, try answering these:

• What were you trying to get away with?
  
• What was your reasoning at the time?
  
• How did the adults react?
  
• What did this moment teach you—or fail to teach you?

Bonus Prompt:
Try writing this scene twice—from your perspective as a kid, and again from the adult’s point of view. What changes?

Wrap-up

If today’s episode brought back a memory—don’t hide it. Write it.

Trouble might’ve been scary then, but it’s often gold now.

Because those are the moments that shaped you.
That revealed you.
That connected you to the messy, funny, human side of being alive.

And that’s what memoir is all about.

If you’d like a copy of this episode’s Scene Builder Worksheet to help you along, go to MemoirClub.net and sign up for the Story Sparks newsletter. You’ll find what you need there.

And if you liked this episode, share it with a friend—maybe someone who still owes you five bucks from seventh grade.

Until next time, remember:

Your story matters. Let’s write it together.