Courtenay Hallwood is a Business Operations Lead at an early-stage women's health startup who thrives in ambiguity and early-stage operations. She spent five years in management consulting before taking a full year out to mobilise with the Army Reserve, serving on NATO's enhanced forward presence operation. Her career has been intentionally squiggly: management consultant to product manager to ops director to chief of staff at multiple startups. She's drawn to challenges, goal-driven, and believes generalists will eventually take over the world.

Throw yourself into things to learn they're learnable. Courtenay hated running two years ago but pushed through because it was the only way to get better. Now she runs half marathons. When you do hard things repeatedly, you learn that almost anything is learnable.

You can do anything, but not everything at the same time. Choose one challenge to focus on outside of work. Courtenay had running as her goal for years; now she's deciding what's next. The generalist temptation to do everything is real, but focus requires choice.

AI solves for speed and output, not orchestration. Even with AI, organisations still need someone asking "how do these pieces talk to each other?" and "are we moving toward our goals?" That's where humans stay essential. Token costs also make full AI automation less practical than keeping humans doing certain work.

Chief of staff isn't a pedestal role, it's a skill-set match for generalists. If you can navigate ambiguity, translate between teams, think cross-functionally, and lead without authority, you can do it. Courtenay had imposter syndrome about it, but landed it twice. The role plays directly to generalist strengths.