761 - I Tried AI’s ‘Roast Me’ Feature… And It Went for the Jugular

The Cliff Ravenscraft Show — Where Strategy Meets Soul

Curiosity got the best of me.

While testing out an AI tool on the X platform, I saw a suggested prompt that stopped me in my tracks:

"Roast Me."

I hesitated for a second, then clicked the button. And let’s just say... AI didn’t hold back.

The response it gave me was brutal. But here’s the thing—it didn’t actually impact me. Instead, it triggered something familiar: an old insecurity that, at one point in my life, I might have believed.

In this episode, I share the full story—how a few sentences on a screen stirred up echoes of an outdated belief, and how I immediately recognized that those thoughts no longer held any power over me.

We’ll talk about:

• The danger of well-placed criticism and why it feels real (even when it isn’t).
• How our words shape the meaning of what we experience.
• The shift in perspective that allows you to rewrite your narrative.
• The simple question that determines which story you’re living.

At the end of the day, the world is full of perspectives—some that shrink you, some that expand you.

The question isn’t which perspectives exist. The question is: which one will you allow to shape your future?

Listen in, and then let me know…

Did this message resonate with you? Have you ever caught yourself looking at your life through an old filter—one that no longer reflects who you are today?

Send an email to [email protected] and tell me your thoughts—I read every email.