Questions for you:
- In what situations am I accepting unfavourable odds because I’m following predictable strategies?
- When facing likely defeat or stagnation, what would happen if I deliberately introduced more uncertainty into my approach? How would I do that?
- Am I too attached to “playing properly” by unwritten or implied rules when unconventional tactics might serve me better?
Organisational applications:
- Market entry strategy for disadvantaged competitors:
When entering markets dominated by established players with superior resources, deliberately increase variance rather than competing directly. Launch unconventional products, use unpredictable pricing strategies, or enter adjacent markets that shift competitive dimensions. Established competitors optimise for current game rules; changing the rules through high-variance approaches transforms a low probability of success into more viable odds. - Negotiation tactics for weaker bargaining positions:
When negotiating from positions of clear disadvantage (limited alternatives, urgent timelines, smaller scale), introduce calculated unpredictability. Walk away from “final offers,” make proposals outside expected ranges, or change negotiation dynamics by involving unexpected stakeholders. Predictable concession patterns guarantee poor outcomes for weaker parties; strategic unpredictability forces stronger parties to recalibrate assumptions and potentially accept terms they’d otherwise reject. - Sales approaches against dominant incumbents:
When competing for business against established suppliers with proven track records, avoid head-to-head comparison battles on conventional criteria. Instead, introduce high-variance elements: offer radically different contract structures, propose phased trials with asymmetric risk-sharing, or bundle services in unexpected combinations. Procurement processes optimised for the incumbent’s advantages, and in the worst cases written by the incumbent, struggle with truly novel approaches that elude the standard criteria, creating an opening for disadvantaged competitors. - Innovation portfolio for resource-constrained organisations:
Smaller organisations cannot match larger competitors’ R&D spending in conventional innovation races. Instead, concentrate resources on high-variance, unconventional approaches that established players systematically avoid. Pursue technologies or markets where success is uncertain but payoff is asymmetric. Large organisations are drawn to optimise portfolios for predictable returns; underdogs improve their odds by embracing projects that could produce disproportionate success.
Further reading
The video that inspired this story: “Ever Seen a Scrabble Game With No Words?”: https://www.youtube.com/watch?v=AJIAlRSs214
On underdog strategies and variance:
David and Goliath: Underdogs, Misfits, and the Art of Battling Giants by Malcolm Gladwell (Little, Brown, 2013). Examines how apparent disadvantages can become advantages when underdogs change the rules of engagement, with examples from military history, business, and sport.
The Underdog Advantage: Using the Power of Insurgent Strategy to Put Your Business on Top by David Morey and Scott Miller (McGraw-Hill, 2004). Business strategy specifically focused on competitive approaches for weaker market positions, emphasising unconventional tactics.
On embracing disorder as competitive advantage:
Messy: The Power of Disorder to Transform Our Lives by Tim Harford (Riverhead Books, 2016). Explores how disorder, improvisation, and unpredictability create advantages across domains. Particularly relevant chapters on how messiness disrupts stronger opponents’ optimisation strategies and why tidiness favours incumbents.
A Perfect Mess: The Hidden Benefits of Disorder by Eric Abrahamson and David H. Freedman (Little, Brown, 2007). Examines how moderate chaos and disorder provide competitive advantages, particularly for organisations challenging established competitors who have optimised for current conditions.
On competitive strategy and asymmetric warfare:
The Strategy of Conflict by Thomas C. Schelling (Harvard University Press, 1960). Classic game theory text including analysis of how weaker parties can improve outcomes through commitment, unpredictability, and changing game structures.
The Halo Effect: …and the Eight Other Business Delusions That Deceive Managers by Phil Rosenzweig (Free Press, 2007). Challenges conventional wisdom about competitive advantage, particularly relevant for understanding why successful strategies from strong positions don’t work for underdogs.
On variance and risk-taking:
The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing by Michael J. Mauboussin (Harvard Business Review Press, 2012). Analytical framework for understanding skill-luck balance and when increasing variance improves outcomes for disadvantaged competitors.
Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke (Portfolio, 2018). Poker champion on strategic risk-taking when facing superior opponents, emphasising how weaker players can improve odds through calculated unpredictability.
On game theory and mixed strategies:
The Art of Strategy: A Game Theorist’s Guide to Success in Business and Life by Avinash K. Dixit and Barry J. Nalebuff (W.W. Norton, 2008). Accessible game theory including when and why randomised strategies benefit weaker players facing stronger opponents.
Game Theory: A Very Short Introduction by Ken Binmore (Oxford University Press, 2007). Concise explanation of mixed strategies and why introducing randomness can be optimal when facing superior opponents.
On disruptive innovation:
The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail by Clayton M. Christensen (Harvard Business Review Press, 1997). Classic analysis of how established companies’ strengths become weaknesses when facing unconventional competitors pursuing different value propositions.
Blue Ocean Strategy: How to Create Uncontested Market Space and Make the Competition Irrelevant by W. Chan Kim and Renée Mauborgne (Harvard Business Review Press, 2005). Framework for competing by changing competitive dimensions rather than fighting on established terms—essentially increasing variance in competitive space.
On military strategy for weaker forces:
Strategy: A History by Lawrence Freedman (Oxford University Press, 2013). Comprehensive history including extensive analysis of asymmetric warfare and how weaker forces use unpredictability against stronger opponents.
Invisible Armies: An Epic History of Guerrilla Warfare from Ancient Times to the Present by Max Boot (Liveright, 2013). Historical examination of how militarily weaker forces use unconventional tactics and increased operational variance against superior opponents.
On sports and competitive psychology:
The Numbers Game: Why Everything You Know About Football Is Wrong by Chris Anderson and David Sally (Penguin, 2013). Data analysis of when taking higher-risk approaches improves outcomes for weaker football teams, with broader applications to competitive strategy.
Scorecasting: The Hidden Influences Behind How Sports Are Played and Games Are Won by Tobias J. Moskowitz and L. Jon Wertheim (Crown Archetype, 2011). Analysis of when conventional wisdom fails and when unconventional high-variance strategies prove superior for underdogs.
About the image
Probably the most abstract image in the book, if you haven’t worked it out yet, the stripes are the colours of the Scrabble board.
Illustration Matt Ballantine 2026
Random the Book 