Why Growing Businesses Require a Different Way of Thinking

March 03, 20262 min read

Most of us grew up playing checkers…

Simple. Straightforward. All the pieces moved the same way. You acted, reacted, and hustled to get to the other side, to get “crowned”.

That’s how early business worked, too.

One move at a time… Fix the problem in front of you. Do the next thing. More effort usually meant more progress.

And then… somewhere along the way… that stopped working.

You didn’t realize it at first. The board still looked the same. Still squares. Still pieces. Still working to get clients and problems to solve...

But without warning, the game changed.

You were no longer playing checkers.

You were playing chess.

And no one told you.

In chess, the board looks the same, but the rules are different.

Not every piece moves the same. Some move in straight lines. Some move in L-shapes. Some move across the board with power. Others protect, sacrifice, or set up.

One move doesn’t just shift a single piece, it opens a pattern. It creates a consequence. It changes what’s available next.

Business at this stage is the same.

You’re still making moves. Still solving problems. Still doing the work.

But now every decision touches something else.

• Hiring one person changes the role of another.

• Buying equipment shifts cashflow.

• Taking on a new client creates delivery pressure.

• Solving a short-term problem might limit a long-term opportunity.

It’s not just about what you move.

It’s about when, how, and what it opens or blocks.

That’s the difference between checkers and chess.

And that’s the difference between early growth and what you’re navigating now.

You didn’t do anything wrong.

But if you’re still playing checkers… still thinking one move at a time… this stage will feel harder than it should.

Because you’re no longer just trying to win today.

You’re shaping the next few turns.

You’re making trade-offs.

You’re choosing what to carry and what to let go.

That’s strategy.

And it starts with seeing the board.

Not perfectly. Not all at once.

But clearly enough to know:

• What game you’re in

• What pieces you have

• What your next move might cost

You’re not stuck. You’re just in a different kind of game.

One that rewards perspective, not just motion.

And clarity, not just speed.

No need to become a chess master overnight.

But it might be time to stop playing checkers and learn to play chess in your business.

Annette Blankenship helps service-based business owners gain financial confidence, business freedom, and clear direction as they grow.

With over 30 years leading complex operational and financial systems in multi-billion-dollar organizations, she now works with owners to clarify their numbers, structure their operations, and sequence the decisions that move the business forward.

Her focus is simple: stabilize what growth has exposed so scale becomes sustainable.

Annette Blankenship, CSPF, PMP, CSM

Annette Blankenship helps service-based business owners gain financial confidence, business freedom, and clear direction as they grow. With over 30 years leading complex operational and financial systems in multi-billion-dollar organizations, she now works with owners to clarify their numbers, structure their operations, and sequence the decisions that move the business forward. Her focus is simple: stabilize what growth has exposed so scale becomes sustainable.

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