Welcome to another Thought of the Day and Question of the Day post, where we reflect, laugh, and sometimes cringe at our own persistence. Today’s wisdom from Cicero reminds us that making mistakes is human—but doubling down on them? That’s where the trouble starts. And our question digs into those moments we’ve already failed at twice and still think, “Surely this time it’ll work.” Let’s talk about why we repeat ourselves and what we learn (if anything) in the process.
Thought of the Day:
“Any man can make mistakes, but only an idiot persists in his error.” – Marcus Tullius Cicero
Oof. Thanks, Cicero. Nothing like being called out by a Roman statesman who’s been dead for over 2,000 years.
Everyone makes mistakes. We misjudge, we misstep, we think, “I can totally fix this by doing exactly what didn’t work last time, but with more enthusiasm.” It’s not the mistake that’s the problem. It’s the repetition. It’s the stubborn refusal to admit, “Maybe I’m the common denominator here.”
I make this mistake often on the golf course. The ball just sitting there 15 yards from the water hazard and I know if the water wasn’t there, 10 out of 10 times, I smoke the shot clean. But the water gets in my head and plop. I know the smart this is to take the drop on the other side, but 5 more balls in the water and the next thing you know, my Par for the hole turns into an 11.
This isn’t about perfection. It’s about pattern recognition. And if we’re brave enough to admit our patterns, especially the self-sabotaging ones, we give ourselves a chance to choose differently next time.
If this hits home, you might enjoy this reflection on self-sabotage and the comfort of old habits or this reminder that sometimes we need to pause before we keep pulling people out of the river.
Question of the Day:
What’s something you tried once, failed at, and then thought, “Maybe the third time’s the charm”?
I’m going to go back to the golf course with this. I know the smart thing to do is take to penalty and hit the next shot past the hazard but deep down I know I can make the shot. So I try, and try again. Before you know it, I’m like Roy McAvoy in Tin Cup asking for another ball.
There’s something wildly optimistic—and maybe a little unhinged—about thinking, “One more try.” Especially when all signs point to no. But that’s the hope in us, isn’t it? The stubborn spark that says, “I can still do this.” Whether it’s sourdough baking, trying to love group fitness classes, or trying to love baked beans, we try again.
Sometimes the third time is the charm. Other times, it’s the comedic finale in a very short-lived trilogy. Either way, we walk away with a story and maybe a little humility.
Let’s Hear from You
What’s the mistake you kept repeating because this time felt different? Share it in the comments—bonus points for humor and humility. Or better yet, join our free daily email and get a Thought of the Day and Question of the Day delivered right to your inbox to keep the conversation (and reflection) going.