The Overcoached Entrepreneur: Why Playing Like the Pros Might Be Holding You Back

This past week, I went to an “elite” minor hockey league game.

What I saw really astonished me.

As someone who grew up playing the game, I’ve always loved hockey for its raw energy: the skill, the creativity, the absolute chaos that makes it beautiful. But this? This wasn’t the hockey I knew.

Instead of kids experimenting, pushing boundaries, and making magic on the ice, I saw overcoached robots, terrified of stepping out of line. Every pass, every movement, every decision felt like it had been drilled into them a thousand times. 

It was predictable, calculated, like watching a professional soccer match where the strategy is airtight but the magic is missing.

We’ve started coaching young players like they’re elite professionals. And it’s killing the game.

Hockey was built on spontaneity. On moments of brilliance that happen when instinct takes over. But when you coach creativity out of the game, you don’t develop the next generation of stars, you develop a generation of players who are too afraid to try something new.

And guess what? The same thing is happening in entrepreneurship.

I see it all the time, brilliant, passionate entrepreneurs trying to deploy the same tactics as seasoned professionals who are years (if not decades) ahead of them. They’ve been told, "Find someone who’s where you want to be and do what they do."

There’s some truth to that. But a beginner hockey player shouldn’t be trying to execute the same plays as Connor McDavid. They’ll get crushed, they’ll get discouraged, and worst of all, they’ll lose the love of the game.

Entrepreneurship is the same.

Trying to run a business like a seasoned pro when you’re just starting out is like a kid trying to dangle through the entire team when they can barely skate backwards. It’s a recipe for frustration.

The best players, the best entrepreneurs, develop their skills by playing the game, not by memorizing plays. They take risks, they experiment, they embrace the chaos. And over time, they build the instincts and skill set that allow them to play at a higher level.

So if you’re in the early stages of your business and you feel like you’re struggling, ask yourself: Are you playing your game? Or are you trying to play someone else’s?

You don’t need a perfect system. You need time on the ice.

Trust yourself. Take the shot. And for the love of all things holy, don’t let anyone coach the creativity out of you.

This week in the Dare2Grow Collective?

It’s here: The D2G collective is starting to grow. Filling up with entrepreneurs just like you.

This month we have 3 new cohorts starting ( all included in your membership)

The Newsletter Growth Accelerator: Feb 12th at 9:00am PST

The Pitch and Offer Accelerator: Feb 12 at 10:30 am PST

The Linkedin Impact Accelerator: Feb 19th at 12:00 pm PST

I suggest you join early so you can get to know the community, introduce yourself, and sign up for the programs you would like to start. Remember you have the entire year to access them all.

On top of that you will have access to our monthly Growth Club call for group coaching and access to live coaching hours every month.

Guarantee: I want everyone in this community to feel they’re getting real value. If you join and realize it’s not the right fit, no problem! You have 7 days to request a full refund—no questions asked, no hard feelings. 😊