Take ‘Chief of Staff’ off the pedestal

Courtenay Hallwood on generalist superpowers, learning through discomfort, and self-belief.

📚What You'll Learn

1. How to build self-belief through proving capability to yourself, not through external validation

2. Why generalists are uniquely positioned to navigate early-stage startups and organisational scaling

3. How AI cannot yet orchestrate the brain of an organisation, making human judgment still essential

✍️ Some Takeaways

• Throw yourself into things to learn they're learnable.

• You can do anything, but not everything at the same time.

• AI solves for speed and output, not orchestration.

• Chief of staff isn't a pedestal role, it's a skill-set match for generalists.

Where to find Courtenay Hallwood

https://www.linkedin.com/in/courtenay-hallwood/

Where to find Milly

https://www.linkedin.com/in/milly-tamati/

Generalist World Resources:

Podcast: https://open.spotify.com/show/0qbGzMU...

The Generalist Quiz: https://www.generalistquiz.com/

Essays: https://www.generalistcareer.com/

Upcoming events: https://lu.ma/generalist.events

Positioning Guidebook: https://www.generalist.world/positioning