I came into the Chief of Staff role the same way many people do: excited by the promise of impact, but unsure what the job actually demanded day to day. I quickly realized that success as a CoS isn’t about having the title, but about judgment, trust, and knowing how to operate in ambiguity without burning out or overstepping. I’m currently a Chief of Staff at a digital health startup, partnering closely with the CEO on strategy, execution, and company management. Before that, I worked in a pseudo–Chief of Staff role at lululemon Studio (formerly MIRROR), supporting senior leaders across strategy and operations during a period of rapid change. Alongside my own roles, I was deliberate about learning the craft from others: I spoke with 20+ Chiefs of Staff to understand what actually makes the role work (and what quietly derails it), and interviewed 20+ founders before choosing my own CEO partnership. I also stay closely connected with a core group of Chiefs of Staff, regularly trading notes on what’s hard, what’s changing, and what really matters. I coach the way I wish I’d been coached early on: less mythology about the role, more clarity about how to show up well. My goal is to help Chiefs of Staff land the role with intention, ramp with confidence, and become trusted partners to their executives without losing themselves in the process.