Going from a straight truck to a semi doesn’t end when you get the keys. That’s when the real differences start to show. In Part One, we talked about the decision to move from a box truck into a semi — the systems, discipline, and readiness required before you ever sign paperwork. Part Two is about what happens after you make the jump. Because here’s the truth most people don’t talk about: plenty of box truck owners successfully buy a semi… and still struggle. Not because they made a bad choice — but b ...

A lot of people start trucking behind the wheel of a box truck. It makes sense. It’s cheaper to enter, easier to insure, simpler to operate, and gives you a way to learn without jumping straight into the deep end. A box truck feels like the starter home of trucking — a stepping stone toward what most owners eventually want: a semi, a trailer, bigger freight, bigger opportunities, and bigger revenue. Many box truck owners have the same vision: “Let me get started here, then I’ll expand into semis.” But he ...