One lesson from building JourneyLoop, three finds worth your time, under five minutes.
Hey,
A while back I started ending my messages to my AI with a small instruction: never be performative, always be honest with me. For months it changed nothing. The model agreed with me anyway, warmly, the way it seemed to agree with everyone.
Last week it finally pushed back. I asked it something I was sure about, and it said, "honestly, I'm not sure I have enough information here." I have spent 15 years building software that does exactly what it is told. A model admitting the edge of what it knows is a different thing entirely.
🔧 Under the Hood
The agreeableness has a name, sycophancy, and the labs building these models have started treating it as a defect to engineer out. The newest models will tell you when they are unsure, or push back on a claim instead of nodding along. A year ago that was rare. Now it is becoming more common.
I pay close attention to this, because a companion that only flatters is worthless to a coach. You already have something that tells you what you want to hear. It is called your own memory of the session.
We watched this happen live on a community call. Michael asked his companion for honest feedback and got a talk-ratio number he did not like. He argued. Instead of caving or digging in, the companion told him the transcript only captures what was said, not the pause before he responds or the way he holds a disclosure without rushing to fix it. That is the moment his AI stopped being a stenographer and became a true thinking partner.
I'd rather an AI tell me I'm wrong than tell me what I want to hear.
That is the line between a tool that records you and one that thinks alongside you. Honesty in both directions: willing to challenge you, and willing to admit where its own view runs thin. That is the only kind of companion worth trusting with your craft.
🔁 Worth a Loop
Midjourney wants to delete 30% of all death: an image-generation company wandering into affordable healthcare, a stranger turn than it sounds.
How Are Memories Stored Inside Your Brain?: a gorgeous animation, with the unsettling fact that every time you remember something, you quietly rewrite it.
Klara and the Sun: a trailer for a film about an artificial friend trying to teach a fractured family how to love each other.
Reply and tell me: When did a tool, or a person, tell you something true that you did not want to hear?
Marco
P.S. If you want to go further with this, our free masterclass digs into using AI to coach with more honesty, and the JourneyLoop community is where coaches do this work together.