Poking the Bear

February 10, 2026

What is your funniest “poke the bear” story?

Most of us know exactly what that phrase means without needing it explained. It is the moment when you do something you absolutely know you should not do, usually while fully aware of the likely outcome, and you do it anyway.

Not out of cruelty. Not even always out of recklessness.

Sometimes you do it because the temptation is sitting right there, grinning at you, daring you to see what happens next.

Poking the bear is rarely about the bear. It is about the part of us that wants to test the edge.

As kids, this shows up early. You say the word you were told not to say. You touch the thing that is clearly labeled hot. You ask the question that makes the room go quiet. You are not trying to burn the house down. You are trying to understand where the walls are.

As adults, we just get more creative about it.

We poke bears with sarcasm in meetings. With jokes that are a half step past appropriate. With texts we probably should not send. With decisions that feel like they might explode but also might make a great story later.

Sometimes they do both.

There is usually a split second before the poke. A pause where you know you could stop. You could choose the safer option. You could leave well enough alone.

And then you lean in anyway.

What makes those moments funny in hindsight is not the fallout. It is the clarity. For a brief instant, everything sharpens. You are fully present. You know exactly what you are doing. You accept the risk and press send, open the door, say the line.

That clarity is part of the appeal.

I have written before about how we are drawn to uncertainty, even when it makes no practical sense. In The Magic in the Distance: Why We Love the Great Unknown, I explored how the unknown pulls us forward because it promises aliveness, not safety. Poking the bear is a smaller, messier version of that same impulse.

We want to know.

Sometimes the bear turns out to be sleepy. Sometimes it growls. Sometimes it chases you halfway down the mountain and you spend the rest of the day laughing because you are still alive.

And sometimes you learn a very clear lesson about consequences.

That is the part we tend to edit out when we tell the story. We focus on the punchline, not the cleanup. But both matter. The humor only works because something was at stake.

Without stakes, it is not poking the bear. It is just tapping on glass.

These moments also reveal something about boundaries. Every bear you poke teaches you where the line actually is, not where you assumed it might be. Some lines are firmer than you expected. Others are surprisingly flexible.

You do not learn that by standing far away and behaving perfectly.

Of course, there is a difference between playful curiosity and chronic self sabotage. If every day is a bear poking exercise, something else is going on. But an occasional nudge at the edge is part of how we calibrate ourselves.

It is how we find out what we can handle.

It is also how we learn who we are around risk. Do you freeze? Do you laugh? Do you double down? Do you immediately regret everything and swear you will never do it again, right up until the next time?

Your funniest poke the bear story probably did not happen when everything was calm and predictable. It happened when you were tired, bored, curious, or feeling just safe enough to get yourself into trouble.

That is human.

We are not built to live entirely inside the lines. We are built to test them, occasionally misjudge them, and then tell stories about it later.

So think about yours.

Not the most reckless thing you have ever done. Just the one that still makes you laugh, even if you shake your head while you are telling it.

What did you learn?

Where was the line, really?

And did you poke the bear again after that, or did you give it a wide berth for a while?

There is no moral here. Just curiosity.

Sometimes the story is the point.