Douglas Hubbard's The Failure of Risk Management: Why It's Broken and How to Fix It (2009) is a fast, fun, opinionated, helpful book about how to think better in circumstances of uncertainty when important decisions need to be made. From the Preface:

... This is more like a first book in astronomy for recovering astrologers—we have to debunk the old and introduce the new.

Hubbard entertainingly critiques Nassim Taleb's excesses while praising what he gets right. In Chapter 8 ("Black Swans, Red Herrings"), making the case for data-driven thinking:

If I point out the usefulness of conducting some aspects of risk management more like an actuary might conduct them, I may hear the objection, "But the insurance industry has a lot of data—we have none." Here, I'll reiterate a few more points from my first book, How to Measure Anything:

• Whatever your measurement problem is, it's been done before.
• You have more data than you think.
• You need less data than you think.
• Getting more data (by direct observation) is more economical than you think.
• (An addition to the original list): You probably need completely different data than you think.

Above all, Hubbard recommends thinking quantitatively, testing methods against real-world experience, keeping score of results, and paying attention to one's own biases. Good advice throughout life!

^z - 2023-01-02

cf Black Swan Swindle (2010-04-29), The Words of Risk Analysis (2022-12-22), Foundational Issues in Risk Assessment (2022-12-22), ...