The Situation

You’re smack dab in the middle of strategic planning for next year when you hit a wall of anxiety and doubt. Ghosts of strategic plans past are looming, and they’re reminding you of all the ways your previous plans have gone wrong – whether that means failing outright or succeeding in ways you didn’t anticipate. The communications plan that looked good on paper but didn’t end up converting customers. The hire that didn’t work out in the role they were recruited for but found a home in a different department. The succession plan that fell apart because of illness. The product rollout that never was in the aftermath of supply chain breakdowns. The capital reinvestments that relied on growth projections that were, in hindsight, delusional. In the face of this spotty track record, you start to see two roads ahead of you: Double down and try to break the plan down into ever more granular, measurable, controllable detail, or abandon it entirely. Surely there’s a third way?

The Play

In an uncertain world, you’ve got to plan for the only certain thing: that things won’t go according to plan. It sounds a little circular, but the point is to focus on the process of planning, rather than relying on the plan. The process lets you center humility, intellectual honesty, optimism, and a growth mindset.

• Recognize and work to counteract the biases that skew planning and decision-making.

• Train yourself to respond to the unanticipated.

• Keep your Bayesian updating muscles strong.

• Remain flexible and agile in the face of plans that go sideways.

→ Cultivate a posture that values learning, adaptation, and iteration to harness the power of choice and focus while remaining flexible.

Go Long

New Essay: Why Plans Don't Work Out

“For us, planning with uncertainty is figuring out how to build the only sure thing – that things won’t go according to plan – into the plan. We think the best way to do this is to approach each situation with high intellectual honesty, high humility, high optimism, and a growth mindset. It’s a posture, over a plan, that embraces learning, adaptation, and iteration while understanding that plans don’t have finish lines.”

New Interview: Jason Harp on Using Chaos for Good

“When you get punched in the face, instead of stumbling backwards, stumble forwards. Instead of forcing things to change, adapt to the fact that things are changing and make them change in your favor. Use the chaos for good rather than planning for good times or forcing the next thing to occur.”

Permanent Podcast

Throwback: A Small Business CEO's Guide to Uncertainty

A flashback to 2020 uncertainty, with advice on building a durable offense and proactive resourcefulness.

Go Deep

Curiosity sparked? We've put together a list of resources on building uncertainty into the plan.

OODA Loop (Wikipedia)

+The Observe–Orient–Decide–Act cycle developed by military strategist and USAF Colonel John Boyd. Originally developed for combat operations and military campaigns, the OODA Loop helps you take uncertain and rapidly changing circumstances to generate quick and agile decisions – before using feedback from those decisions and new information to re-run the loop. “Decision makers gather information (observe), form hypotheses about customer activity and the intentions of competitors (orient), make decisions, and act on them. The cycle is repeated continuously. The aggressive and conscious application of the process gives a business advantage over a competitor who is merely reacting to conditions as they occur or has poor awareness of the situation.”

Deep Survival: Who Lives, Who Dies, and Why (Laurence Gonzales)

+Where planning meets risk, life and death situations, and fear. “After reading hundreds of accident reports and writing scores of articles, I began to wonder if there wasn’t some mysterious force hidden within us that produces such mad behavior. Most people find it hard to believe that reason doesn’t control our actions. We believe in free will and rational behavior. The difficulty with those assumptions comes when we see rational people doing irrational things.”

Using Bayesian Updating to Improve Decisions under Uncertainty (Brian T. McCann)

+How Bayesian updating improves decision-making through a few simple steps: 1. Think probabilistically; 2. Assign exact estimates to your degrees of belief; 3. Combine prior probabilities and evidence strength estimates using Bayes’s rule. You’re probably already updating, so why not do it intentionally – and better? “But, perhaps the most valuable aspect of thinking in Bayesian terms is its wide applicability—it applies to just about any sort of managerial issue that involves the formation and updating of beliefs. The more accurate these beliefs are, the better your managerial decisions will be.”

Good Strategy/Bad Strategy (Richard Rumelt)

+Taking the “strategy” out of “strategic planning” and bringing it into the light. The logic of a good strategy is less about vision and more about identifying critical issues and opportunities to guide coherent action. “A good strategy includes a set of coherent actions. They are not 'implementation' details; they are the punch in the strategy. A strategy that fails to define a variety of plausible and feasible immediate actions is missing a critical component.”

Wrestling’s Greatest Shoots: Bruiser Brody vs. Lex Luger (Grantland)

+Please don’t pretend you don’t want to know more about this shoot match. “The two wrestlers go at each other and they tie up — it’s the way every wrestling match starts, or at least how they used to begin. Brody starts clubbing Luger with forearms. Luger is stunned, but he looks more confused than hurt. Maybe it’s his overmuscled posture, maybe it’s his inability to look hurt, maybe he’s just confused.”

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