🦾 The Girl Who Smiled at Fear

Hey Insider,

Splash. Sink. Struggle. Swim. Smile.

I watched her do it again.

And again.

Six years old, pigtails dripping, she'd climb out of the pool and jump right back into the deep end. While other kids clung to the edge, she was turning failure into a game.

I glanced down at my phone - another "pipeline review urgent" email. Another day of safe leads and predictable closes.

The Safety Trap

My pipeline looked like the shallow end:

• Familiar water

• Feet always touching

• No waves

• No risk

• No growth

I'd built a perfect record of small splashes. I was really good in my end of the pool.

The Diving Board Moment

Monday morning. Conference room. Coffee cooling. Sales team meeting.

"Enterprise territory needs an owner. Any takers?"

What my manager didn’t say was, that the territory had 2 sales reps in it previously both were no longer with the company, both had sold very little.

20 seasoned reps. 20 silent stares. 20 versions of 'play it safe.'

Then I remembered her smile right before she sank.

"I'll take it."

My manager's eyebrows shot up. My colleagues' heads turned. My heart raced.

Time to leave the shallow end.

The First Plunge

Enterprise Call #1-3: Wrong pitch. Tangled words. Total sink.

But I smiled.

Enterprise Call #4-6: Better questions. Clearer vision. Found the wall.

Started swimming.

Enterprise Call #7-9: First real conversation. Actual interest. Different water entirely.

The Deep End Math

My manager's whiteboard told the story:

Shallow End:

• 65% close rate

• $50K deals

• Zero fear

• Zero growth

Deep End:

• 35% close rate

• $250K deals

• Daily fear

• Daily growth

"Notice something?" he asked.

The math of fear meant more than the math of safety.

Your Courage Map

This week, channel your inner six-year-old:

□ Find your deep end

• Which accounts scare you?

• Which calls make you nervous?

• Where do you feel out of depth?

□ Plan your plunges

• One scary call daily

• One big pitch weekly

• One impossible ask

□ Track your sinks

• What worked?

• What didn't?

• Where's the wall?

Remember:

• Every splash teaches

• Every sink strengthens

• Every struggle skills you up

Your Turn: The Deep End Challenge

Tonight:

□ Write down your safe zones

□ Map your scary waters

□ Plan tomorrow's plunge

Tomorrow:

Jump smile-first into fear.

Because here's what that six-year-old knew:

The fun isn't in floating. It's in the falling, fighting, and figuring it out.

Hit reply and tell me: What's your deep end looking like?