Discomfort Is the Doorway

Playing to Win

September 09, 2025

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Welcome to the Latest Newsletter
of Playing to Win!

My newsletter is designed specifically to help business owners like you grow your companies with tried & applied bits of business knowledge, all communicated in actionable, bite-sized chunks. I will share insights and advice aimed at enhancing your business operations, boosting your success, and allowing you to focus more on what truly matters. Let's work together to achieve your goals and make your endeavors a reality.

Key Points of the Newsletter

  • Discomfort isn’t danger, it’s direction.
  • Playing small to keep others comfortable is a form of self-betrayal.
  • The world doesn’t need safer language, it needs stronger leaders.

Discomfort Is the Doorway

 
Here’s a hard truth no one wants to hear: if it makes you uncomfortable, that’s probably where you need to go.

We’ve built a culture where discomfort is treated like danger. Where the second something stirs your emotions, you're told to back off, shut up, sit down. And worse, if you make someone else uncomfortable? You’re the villain.

Bullshit.

Discomfort is not a threat. It’s a signpost. It means you're brushing up against growth. Resistance. A worthy adversary. And instead of retreating, you should f*cking run toward it.

But that’s not what we’re taught.

We’re told to play it safe. Keep our voices small. Don’t offend. Don’t challenge. Be “sensitive.” Watch your language. Say nothing bold, and God forbid you curse, because someone might take offense.

Let me ask you: what has playing small ever built?

When did you ever hit your next level by tiptoeing through life making sure no one was triggered?

You didn’t.

You grow when you lean in to the discomfort. When you show up fully—even if it’s too loud, too bold, too “offensive.” That’s how impact happens. That’s how leadership is born.

The real world doesn’t work like the safe spaces we’ve created in our minds. The real world rewards those who step into the fire, not those who avoid the heat.

So yeah, I swear sometimes. Not to shock, but because I refuse to filter the truth. And if that pisses someone off? Good. Maybe they needed to be rattled. Maybe that discomfort is the exact doorway they’ve been avoiding.

Stop apologizing for showing up with intensity.

Stop toning it down to make others feel safe.

Stop thinking you’re wrong because you’re uncomfortable.

Discomfort is the path. Go toward it.

If you’re done playing small and ready to stop asking permission to be powerful, you’re in the right place. Let’s go.

Stay tuned for more insights in our next newsletter. Remember, it's the small adjustments that often make the biggest impact on your business's profitability. Here's to your continued success!

Stay driven to push your business forward,
Ryan Niddel