🦾 The $2.4M Deal I Almost Ran From

Hey Insider, the barbell felt different that morning.

Heavier, yes – but it was more than that. As I stood there staring at 475 pounds for the first time, every fiber of my being screamed to strip some plates off, to stay safe, to stick with what I knew I could lift.

My hands were sweating, heart racing, and that little voice in my head had a lot to say about my chances of success.

It felt exactly like that moment 7 years ago when I sat in my chair preparing to meet with Uber.

The proposal was for $2.4 million – nearly four times larger than any deal I'd ever closed.

My hands were sweating then too, and that same voice had plenty of opinions about my chances.

The Hard Truth About That Voice

That morning at the gym, I almost listened.

Almost. But then I remembered what happened with Uber. I'd sat in that chair for 22 minutes, crafting perfectly logical reasons to wait, to do more research, to "better prepare."

The truth? I was terrified. Not of the presentation – I knew our solution cold. I was terrified of playing in a bigger league.

I finally opened my computer when I realized something that changes everything: Comfort zones aren't protective shelters – they're holding cells.

And that voice telling you to wait? It's not wisdom. It's fear wearing a suit and tie, masquerading as prudence.

The Weight of Decision

Back at the gym, staring at that barbell, I thought about how that Uber deal changed everything.

Not just because we won it (we did), but because it revealed the lie we tell ourselves about being "ready."

You're never ready. You're never fully prepared.

There's always more you could do, more you could know, more you could plan for.

I got under that barbell the same way I went into that Uber meeting – not because I was ready, but because I decided to be ready.

The weight didn't feel any lighter. The fear didn't magically disappear.

But something else happened, something I've now seen hundreds of times with sales professionals I coach: The moment you commit, everything changes.

The Transformation

That Uber deal taught me something I now see proven every day:

The gap between where you are and where you want to be isn't nearly as wide as your fear makes it seem.

The jump from $600K deals to $2.4M deals didn't require four times more skill. The jump from 405 pounds to 475 doesn't require superhuman strength.

What both require is the willingness to feel uncomfortable and move forward anyway.

Sales Fit Challenge

This week, I want you to find your 315. Maybe it's that enterprise account you've been circling for months.

Maybe it's the C-suite conversation you've been avoiding. Maybe it's finally asking for the deal size that makes your stomach turn.

Whatever it is, I want you to identify it. Write it down.

Then, tomorrow morning, before your brain can manufacture excuses, take the first step. Make the call. Send the email. Book the meeting.

The weight never feels lighter until you get under it.

The deal never feels smaller until you're in the room.

Your comfort zone isn't protecting you – it's limiting you. And the only way past that limit is through it.

Remember: That voice in your head telling you to wait until you're ready?

It's the same voice that nearly kept me in my chair that morning.

The same voice that almost kept me from the best deal of my career.

The same voice that nearly kept 475 pounds on the rack.

Don't let it keep you from yours.