Andrew Fink left a stable career in management consulting to build a solo writing practice helping founders turn their ideas into newsletters, LinkedIn content, and now even books. His business is working. He makes a good living, has freedom to travel, train for races, and design his days. But lately, he’s been wrestling with a big question: should he grow this into an agency for more financial upside, and if so, what does that cost him?

In this conversation, we uncover the tension beneath that question: the pull toward growth and challenge on one side, and the desire to protect freedom, flexibility, and a life he actually enjoys on the other. Together, we explore how to move beyond rigid either/or thinking and into reversible experiments that generate real information instead of endless planning.

Because whether you’re a founder, consultant, or creator, most big business decisions don’t get solved by more thinking. They get solved by taking the next small step, seeing how it feels, and letting that experience guide what comes next.