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The risk that wasn’t supposed to work

May 20, 2026

The risk that wasn't supposed to work

In 2016, I said yes to a puppy I wasn’t sure I actually wanted.

 

I had three kids. Two dogs already. My youngest was 1.5 and finally walking. My husband had been asking for two years. I’d been saying no.

 

Then one day I thought,  maybe I have a little more space now.

 

So I said yes.

 

Enter Karly.

 

She chewed the kids’ toys.

 

Tried to run onto the school bus.

 

Stole the neighbor’s shoes.

 

The first year was pure chaos.

 

Nine years later, she’s our sweetheart.

 

Here’s what I notice when I tell this story now:

 

When people hear it, they decide pretty quickly whether the risk was a good one or a bad one. The chaos was bad.

 

The fact that she became a sweetheart was good. The “risk paid off”, net positive.

 

That’s how most of us evaluate risk in our leadership too.

 

We take the risk. We watch the outcome. We label it.

 

That stretch role was a good move.

 

That difficult conversation was a mistake.

 

 

That idea I pitched flopped.

 

But that’s not actually what risk does for a leader.

 

A risk you take in your leadership isn’t measured by whether the outcome looked clean. It’s measured by:

 

  • What it built in you

 

  • What it revealed about the system around you

 

  • What it made possible that wouldn’t have existed if you hadn’t moved.

“Only those who will risk going too far can possibly find out how far one can go.”

The chaotic puppy year is the year my kids learned what patience looks like.

 

It’s the year I learned what I could absorb and work through.

 

It’s the year our family got the dog we now can’t imagine life without.

 

(Karly is in the picture above)

 

The “bad” part of the risk wasn’t a cost. It was part of the build.

 

A few questions worth sitting with:

 

  • What “risky” leadership moment am I currently labeling as a failure that may actually still be building something?

 

  • What did the messy part of my last big risk reveal that I couldn’t have seen any other way?

 

  • Am I evaluating risk by outcome, or by what it makes possible?

 

The real question of leadership risk isn’t did it work.

 

It’s what did it build.

 

“Only those who will risk going too far can possibly find out how far one can go.”

T.S. Elliot

American-British poet, playwright, and literary critic