Don't Get an Assistant! (Nassim Nicholas Taleb)

One of the best pieces of advice I have ever received was the recommendation by a very successful (and happy) older entrepreneur, Yossi Vardi, to have no assistant.

The mere presence of an assistant suspends your natural filtering—and its absence forces you to do only things you enjoy, and progressively steer your life that way.

(By assistant here I exclude someone hired for a specific task, such as grading papers, helping with accounting, or watering plants; just some guardian angel overseeing all your activities).

This is a via negativa approach: you want maximal free time, not maximal activity, and you can assess your own “success” according to such metric.

Otherwise, you end up assisting your assistants, or being forced to “explain” how to do things, which requires more mental effort than doing the thing itself.

In fact, beyond my writing and research life, this has proved to be great financial advice as I am freer, more nimble, and have a very high benchmark for doing something, while my peers have their days filled with unnecessary “meetings” and unnecessary correspondence.

Having an assistant (except for the strictly necessary) removes your soul from the game.

Think of the effect of using a handheld translator on your next trip to Mexico in place of acquiring a robust vocabulary in Spanish by contact with locals.

Assistance moves you one step away from authenticity.

from 'Skin in the Game' by by Nassim Nicholas Taleb
https://www.amazon.com/dp/B077QY23RV