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TrajectoryEssay

Confidence is not a signal

September 14, 2026

My old self: "Someone gave me some really good advice. They were some confident about it."

My new self: I've had advisors tell me things with total certainty, and three months later I looked back and thought, what was that person thinking. When someone tells you what to do, or how to handle a situation, investigate if that's based on their lived experience or something they heard or seen.

Some of the worst advice I've received from "advisors" and "mentors" sounded exactly as confident as the advice I get from AI tools today. These tools, perhaps like what a human might do, are for engagement, not for your success. They'll tell you the thing that keeps you talking.

A good mentor does the opposite. They'll call you out, tell you your pivot is wishful thinking, push back even when you get defensive about it. They are willing to engage in a conversation and lead by example by changing their mind when you have a good point, and putting their foot down when you're being a child.

At the end of the day a mentor doesn't have all the information you have, so you still have to filter their advice against what you actually know. I stopped grading advice on confidence. I grade it on whether the person has actually lived through the consequences of being wrong, and whether they can be talked out of a bad call when the facts say so.

But at the end of the day, you are the only one responsible for the decisions you make. Not the mentor, not the AI. Advice is an input, not a verdict.

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