Stop Gambling with Your Pitch

My daughter doubles down – in the good way.

We’re not at the casino.

We’re in the car, driving home from her MRI scan, and I’m laughing so hard I’m squinting at the road through the tears streaming down my face.

She describes the medical fashion situation:

How the tighter the ties, the wider the slit in the front opens.
How the top functions like a backwards cape as she’s walking.
How she dutifully leaves her nose hairs in the locker room… but gets yelled at for not bringing the (metal?) key with her into the MRI.

Comedy gold.

She has that rare skill of describing everyday moments as if they’re wildly absurd.
Plus, she’s deeply self-aware and painfully attuned to how things fit together… or absolutely don’t.

So I suggest that one day she try writing comedy.

And then – and this is the important part – she doesn’t deflect or downplay it.

She doubles down.

She launches straight into another story.

This time it’s a grocery store run with a friend.
They’re buckling their Alani energy drinks into the cart like toddlers.

Of course, grocery carts are designed for human children, not sloshing cans of ambition.

The drinks spill.
Chaos ensues.
More stories.
More laughs.

She’s inspired by what she’s already good at.

And that gets me thinking about your Elevator Pitch.

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Stop Gambling. Start Playing to Your Strengths.

Most people treat their pitch like a roulette wheel.

They spin it every time they talk to someone.

A little of this.
A little of that.
“Let’s see what lands today.”

That’s gambling.

And the roulette wheel rarely lands where you want it to.

Instead, the strongest pitch doubles down on what already works.

The stories you tell best.
The problems you explain effortlessly.
The moments when people’s faces light up and want to keep talking to you.

That’s not luck.
That’s signal.
If you’re tuning your pitch based on how people react.

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There Are a Lot of Ways to Use Your Strengths

Will my daughter become a stand-up comic?
I have no idea.

But the skill of comedy writing shows up everywhere:

In storytelling.
In leadership.
In connection.
In making people feel seen.

Same goes for you.

Your strength doesn’t need a new title.
It needs to be recognized.
Then it needs repetition.

So stop gambling on new versions of your pitch.
Start investing in the one that grabs attention.

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Your Turn

Where could you double down on your pitch instead of rolling the dice?

Here’s how to Identify Your Strengths.