Jim talks with Kyle Jekelek about the part of building a career that doesn’t make for good storytelling: the slow accumulation of judgment.

They cover early misreads, the temptation to confuse motion with progress, and the quiet skill of knowing when to push and when to stop. Along the way, Kyle draws an analogy to selling on the New York City subway—learning quickly who’s actually listening, when to speak, and when to move on without wasting energy.

It’s a measured conversation about ambition without mythology—and why the long game rewards clarity, timing, and restraint more than noise.