# Rolling with the Punches: Why Cybersecurity is Backgammon, Not Chess

DevFeed: [Rolling with the Punches: Why Cybersecurity is Backgammon, Not Chess](<https://devfeed.tech/articles/rolling-with-the-punches-why-cybersecurity-is-backgammon-not-chess-39493.md>)

Original publisher: [Read original article](<https://www.philvenables.com/post/rolling-with-the-punches-why-cybersecurity-is-backgammon-not-chess>)

Author: phil7672

Published: 2026-08-22T16:49:47Z

Content type: opinion

Language: en

Sources: [Risk and Cyber](<https://devfeed.tech/sources/risk-and-cyber.md>)

Topics: [Cybersecurity](<https://devfeed.tech/topics/cybersecurity.md>), [benchmarking](<https://devfeed.tech/topics/benchmarking.md>), [Vulnerabilities](<https://devfeed.tech/topics/vulnerabilities.md>), [Threat Research](<https://devfeed.tech/topics/threat-research.md>)

Tags: [benchmarking](<https://devfeed.tech/tags/benchmarking.md>), [cybersecurity](<https://devfeed.tech/tags/cybersecurity.md>), [leadership](<https://devfeed.tech/tags/leadership.md>), [risk](<https://devfeed.tech/tags/risk.md>), [vulnerabilities](<https://devfeed.tech/tags/vulnerabilities.md>), [zero-day](<https://devfeed.tech/tags/zero-day.md>)

## AI overview

The article argues that cybersecurity is better understood as backgammon than chess because organizations must prepare for many possible outcomes amid complex dependencies, supply chains, changing technology platforms, and unpredictable attackers. It also argues that cybersecurity benchmarking should focus on control effectiveness and outcomes rather than inputs such as budgets.

## Source excerpt

It is tempting to compare cybersecurity to a chess game. Two adversaries facing each other, plotting strategy and tactics. Move and counter move, anticipating actions and grinding out a win. In reality, in our complex world of dependencies, supply chains, constantly shifting technology platforms and unpredictable attackers, this is all way more haphazard. Indeed, a better analogy is backgammon, where you position yourself for many different possible outcomes to maximize your chance of...