The Dark Cloud That Doesn’t Show Up on Paper

Playing to Win

September 30, 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

  • Success doesn’t make you immune to darkness, it just hides it better.
  • Depression doesn’t always feel like depression, until it hits you in the face.
  • Stigma keeps high-performers silent, but silence kills momentum.

The Dark Cloud That Doesn’t Show Up on Paper

 
On paper, my life is fucking awesome.

I’ve got the money. More than I ever thought I’d make. I’m surrounded by incredible people. I’ve got the cars. The team. The business is growing fast, almost on autopilot. I’ve got a great family. The kind of life people would kill for.

And yet… sometimes I wake up and there’s just this heavy, dark cloud.

I can’t explain it. There’s no “trigger.” It’s not some big event. Just this weight. This fog. And it doesn’t lift because I go run five miles, or slam caffeine, or pet my dog, or go hug a fucking tree. It doesn’t respond to the usual self-help band-aids.

That’s when I realized: I don’t even know I’m depressed until I feel fucking depressed.

There’s no slow slide. It’s just bam—you’re in it.

And for a long time, I didn’t talk about it. Because what do I have to complain about, right? I’ve got everything. But that’s the trap. The more “success” you stack, the harder it gets to admit that something’s not right.

You look at your life like a checklist, and everything’s checked. So why do you still feel like something’s off?

That’s what no one tells you. Success doesn’t immunize you from the dark days. It just makes you feel guiltier when they hit.

So I’m sharing this to say: if you’ve ever felt this, you’re not alone. If your outside life doesn’t match your inside experience, you’re not crazy. And if you’re high-functioning and still feel stuck some days, that doesn’t make you weak.

It makes you human.

I don’t have a magic fix. But I know this: ignoring it doesn’t help. Pretending it’s not there doesn’t help. You’ve got to call it what it is, stop hiding behind performance, and start having real conversations.

Dark clouds don’t go away just because you “should” be happy.

Talk about it. Face it. Keep moving.

If this hit home and you want to talk about what it’s like to win externally while struggling internally, reach out. You’re not alone.

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