To go further, the Author also suggests an alternate technique along the lines of Annie Duke's Thinking in Bets and Superforecasting where probabilities are assigned to estimates. I had previously encountered such practice in Scott Alexander's blog and thought it clever: have skin in the game and keeping track of wins and losses.
This whole section of the author's blog is very interesting. It goes into the US Intelligence Community's interest in superforecasters and the Good Judgement Project, a kind of elite tournament of forecasters. It talks about how superforecasters estimate by overcoming cognitive biases and questioning assumptions. And then it ultimately points out though that there are limits to forecasting and low probability events do occur all the time.
This whole section of the author's blog is very interesting. It goes into the US Intelligence Community's interest in superforecasters and the Good Judgement Project, a kind of elite tournament of forecasters. It talks about how superforecasters estimate by overcoming cognitive biases and questioning assumptions. And then it ultimately points out though that there are limits to forecasting and low probability events do occur all the time.
https://commoncog.com/blog/the-forecasting-series/