Why doing everything right still feels so wrong

What to do if your strategy is fuzzy, your pricing is off, and your growth is stuck.

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Dear Friend, Subscriber, and Category Pirate,

Context is the quiet destroyer of even the smartest Category Designers.

You’re doing everything right—building your Good-Better-Best offers, posting Non-Obvious thought leadership content, and talking to your Superconsumers. But something’s still not clicking. And the more you push, the more stuck you feel.

This isn’t a marketing problem.

It’s the Existing Market Trap.

The Existing Market Trap is when you accidentally position yourself inside someone else’s category.

It’s when:

• You describe your product the same way everyone else does.

• You use pricing models borrowed from your competitors.

• You attract the wrong customers (the ones who ask for discounts, not transformation).

• You’re known, but not wanted.

• You try to grow, but you're growing sideways.

You’re not just competing in a crowded market.

You’ve unknowingly adopted its language, logic, and limitations.

The Existing Market Trap doesn’t feel like a trap. It feels like business as usual.

This is what happened to Qualtrics.

They started out positioned as survey software—a commoditized space, crowded with low-leverage, low-margin players.

The product was good. Customers were loyal. But the market treated them like a tool.

Why?

Because they were stuck in someone else’s category.

Everything from their website to their messaging to their pitch deck screamed “survey tool.”

But that wasn’t the real problem they solved.

Once they reframed the conversation, everything changed.

They named the villain: the Experience Gap—the space between what companies think is happening and what customers are actually experiencing.

They named the real problem: experience blindness.

And they claimed a new category: Experience Management.

That simple shift repositioned them as a strategic operating system for the enterprise—not just a survey widget.

And it led to SAP acquiring them for $8 billion.

They didn’t fix the trap by working harder.

They fixed it by seeing it and designing their way out.

You might be in The Existing Market Trap if…

Most signs don’t show up as big red flags. They show up as micro frustrations.

Here’s your trap-check. Score yourself before the market does:

Give yourself 1 point for each ‘yes’:

• Do people say, “This is interesting!” but never buy?

• Do leads compare you to cheaper alternatives or ask for discounts?

• Do you spend more time explaining your value than delivering it?

• Do your sales calls feel like mini TED Talks that don’t convert?

• Does the Languaging on your website, emails, and offer sound like what others in your space are saying?

Your Score:

• 0–1: You’re probably playing your own game. Keep going.

• 2–3: You’re in dangerous territory. Time to reframe before you flatline.

• 4–5: You’re deep in the Existing Market Trap. But good news—now you can design your way out.

This isn’t about shame.

It’s about signal.

The Existing Market Trap doesn’t mean your business is broken. It means your context is off. And context is something you can fix.

How to escape The Existing Market Trap:

Escaping the trap means redefining the game you’re playing.

That starts with three steps: