904. To Do Something You've Never Done, You Have to Do Something You've Never Done

No Days Off with Brian Gubernick · Sep 16, 2026 · 8m

Brian discusses a line he keeps coming back to: when you are trying to do something you have never done before, you may need to do something you have never done before. It sounds like a tautology until you separate the two halves, and Brian argues that almost everyone wants the first half without paying for the second. He explains why doing more of what you are already good at does not count as doing something new, and why that distinction is where most growth quietly stalls. He then applies the idea to two very different situations, the early stage startup and the established business that…