「How to Avoid AI Sycophancy: 6 Practical Ways to Get Honest, Unbiased Answers」

In the past two years, with the rise of AI, terms like “one-person company” and “digital nomad” have become increasingly common.

Some countries have even introduced digital nomad visas to support this new way of working.

One person, one laptop, and AI as an assistant—

that’s enough to work and live from almost anywhere in the world.

It sounds free. It sounds ideal.

But the lighter the structure, the more likely one problem appears:

👉 a lack of external feedback and constraints

Last week, I wrote about how to avoid AI’s tendency toward agreement：

「How to Avoid AI Sycophancy: 6 Practical Ways to Get Honest, Unbiased Answers」

When your question carries a clear opinion, AI often follows your lead. It gives you a sense of validation.

That can feel good—but it’s also a subtle trap.

One method I mentioned was simple:

👉 activate a “devil’s advocate” mode

Ask AI to take the opposite position.

Challenge your assumptions. Break your logic.

At the end of that piece, I wrote:

“You need a strong heart.”

 

This matters even more if you’re running a one-person business.

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Because people don’t like being criticized.

And in “devil’s advocate” mode, AI can be blunt—sometimes harsh.

It doesn’t protect your feelings. It highlights your weaknesses.

That kind of feedback takes emotional tolerance.

But that discomfort is exactly where the value is.

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This reminds me of my previous startup experience.

Years ago, there was a place called Garage Café for founders.

Every Friday, they held a regular event known informally as:

👉 “The Critique Session”

The format was simple:

pitch → criticism → constructive advice

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After founders presented their projects, the real session began.

People would ask questions from every angle:

• Does the market logic make sense?

• Is the product solving a real problem?

• Is the technical approach viable?

Criticism came fast and direct.

Sometimes founders were visibly under pressure.

But that was the point.

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In the final part, the tone shifted.

Instead of criticism, people offered:

• suggestions for improvement

• useful resources

• potential collaboration

This “sandwich structure” created dense feedback in a short time.

And it trained founders to handle pressure.

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Over time, you learn:

• how to face tough questions

• how to respond quickly

• how to stay clear under pressure

Later, public pitching feels much easier.

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My own project went through many of these sessions.

At first, it was uncomfortable—even frustrating.

But gradually, I realized something:

👉 every critique is a form of calibration

Some friends later told me I handle pressure well.

But I know that wasn’t natural.

It was trained—through repeated exposure to criticism.

In reality, I’m quite introverted.

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The “critique session” and AI’s “devil’s advocate” mode are similar. They both do one thing:

👉 create an external system of criticism

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In traditional companies, this system comes from:

• team discussions

• investor feedback

• market pressure

But in a one-person business, these are often missing.

AI can partially fill that gap—

as long as you allow it to challenge you.

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If you’re building a solo business, or planning to become a digital nomad,

you might try a simple habit:

👉 regularly switch on “devil’s advocate” mode

Let your ideas be tested, not confirmed.

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Criticism is uncomfortable.

But it makes you think more clearly.

And when you don’t have a team,

that clarity becomes your advantage.

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