The Two Questions Killing Your Progress

Playing to Win

September 16, 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

  • The worst questions to ask when chasing a meaningful goal are “How much does it cost?” and “How long will it take?”
  • True transformation requires obsession, not calculation.
  • If your North Star is strong enough, cost and time become irrelevant.

The Two Questions Killing Your Progress

 
Let me give it to you straight: the two worst questions you can ask when you set a meaningful goal are:

“How much does it cost?”

and

“How long is it going to take?”

Those questions aren’t about progress. They’re about permission. They’re disguised hesitations dressed up like strategy.

Let’s say you set a bold, compelling, high-impact goal. Something that means something to you. Something tied to your North Star. The worst thing you can do next is hesitate and go, “Well, before I move, let me calculate the price tag and timeline.”

Why?

Because you’re asking those questions to protect yourself from commitment. From discomfort. From jumping all the way in.

But if the goal really matters, if it’s truly non-negotiable, why would it matter what it costs or how long it takes?

If this North Star of yours is so compelling, like we’ve talked about on previous calls, then why are you trying to negotiate with it?

If it means everything… what would the price matter?

If it’s your future, your impact, your freedom on the line… what would the time matter?

When you delay progress to ask how much and how long, you’re stalling under the illusion of logic. But it’s fear. It’s friction. And it’s killing your momentum.

Don’t ask what it costs. Ask if it’s worth it.

Don’t ask how long it’ll take. Ask who you’ll become on the other side.

When the North Star is strong enough, the excuses evaporate. And the only question left is: “When do we start?”

So if you’ve been sitting on a goal, weighing the price and measuring the timeline, here’s your sign:

Stop counting.

Start moving.

Want help realigning your business to a North Star that makes excuses irrelevant? Let’s talk. That’s the work I do.

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