Caleb Kapusinski graduated with the class of 2021 and now works in sales as an account manager for a general contractor. His episode is organized around two convictions he has carried into the workforce and has not stopped thinking about since.

The first is that a smaller school creates space for a fuller person. At Cambridge, Caleb played basketball, ran cross country, performed in theater, and served in house leadership, not because he was exceptional in all of those fields, but because the school was small enough to say yes to all of it. He believes that habit of saying yes is increasingly rare, and increasingly valuable.

The second is that Cambridge taught him to ask why. In his work, that translates to getting past a client's first answer to find the real problem underneath. In the classroom, it meant Socratic discussions oriented not toward the right answer but toward genuine understanding. The two convictions are, he argues, more related than they appear: a well-rounded person who knows how to ask good questions is, in his experience, exactly what the labor market is not producing and very much needs.