When Luca Dellanna speaks, I listen.

Unlike many of the other management, productivity and behavioral gurus out there, Luca is ruthlessly committed to providing actionable, tangible advice that is rooted in the messy, chaotic reality of daily life.

This conversation, my second with Luca, revolves around his excellent new book, Winning Long-Term Games: Reproducible Success Strategies to Achieve Your Life Goals.

Why should you care? Because long-term strategies consistently deliver better results. In other words, being able to identify, play, and win long-term games is, quite literally, the secret to success.

With examples ranging from NASA janitors to Stonehenge spray painters, we discuss how to successfully identify reproducible long-term strategies and how to persuade others to get on board with them.

We also explore how hypotheticals can be an insanely powerful tool for ensuring our short-term actions remain consistent with our long-term goals (and yes, before you ask, my beloved premeditation makes an appearance).

I hope you enjoy our conversation as much as I did! For more thoughts on the episode, the full transcript, and bucketloads of other stuff designed to make you go; “Hmm, that’s interesting!” check out our Substack.

Important Links:

Show Notes:

The Tale of the Three Bricklayers
Tighten Up Those Feedback Loops
The Perils of Short-Term Thinking
How to Signal Long-Term Intentions
Reproducibility is King
The Mighty Power of the Humble Hypothetical
Concretizing the Abstract
Goldilocks Solutions
Extracting Tangible Benefits From Stratospheric Objectives
Intuition & Luck in Long-Term Games
Risk of Tactic vs Risk of Strategy; Flexible North Stars
Build Your Own Long-Term Company
Tesla’s Risky Success
Luca as Emperor of the World
MORE!

Books Mentioned:

Winning Long-Term Games: Reproducible Success Strategies to Achieve Your Life Goals; by Luca Dellanna
The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous; by Joseph Henrich
The Hitchhiker’s Guide to the Galaxy; by Douglas Adams
Antifragile: Things that Gain from Disorder; by Nassim Nicholas Taleb
The Infinite Game: How Great Businesses Achieve Long-Lasting Success; by Simon Sinek

The Plumb Line | #65 | 06/28/2025