Reader,

In 2019 I created a short email minicourse built around the need for us to learn from the past, deal with the present, and intercept the future. And it’s now 2026. What’s changed about learning from the past?

I wrote then that the intended and unintended consequences of past decisions play out in the present. That remains true. What has changed is the speed at which those consequences now arrive.

Artificial intelligence, automation, interconnected supply chains, social media, and relentless competitive pressure allow decisions to ripple through an organization almost instantly. We can now repeat old mistakes faster, automate them, and scale them before we fully understand what is happening.

That makes learning from the past more important than ever.

Learning from the past is not an exercise in memorizing facts. Nor is it an invitation to become nostalgic about “the way we used to do things.” It is the disciplined practice of asking:

• What happened?
• Why did it happen?
• What patterns were at work?
• What did we fail to notice?
• What should we do differently now?

The details change, but many underlying patterns do not. These underlying patterns are called archetypes. Here are five to examine.

Consider fixes that fail. A company uses AI to reduce costs and speed up customer service. The short-term numbers improve, but customers become frustrated, employees lose opportunities to develop judgment, and unusual problems go unresolved. The fix produces consequences that eventually undermine the original gain.

Or consider shifting the burden. Instead of developing employees’ ability to think critically, an organization gives them increasingly sophisticated AI tools. The technology produces acceptable answers until the situation falls outside the data, assumptions, or rules built into the system. The organization has treated the symptom, insufficient capacity, without addressing the deeper problem, insufficient capability.

The tragedy of the commons also has a modern form. Every meeting, message, dashboard, alert, and “urgent” request consumes a small portion of employees’ attention. Each demand appears reasonable by itself. Collectively, they destroy the time required for reflection, imagination, and good judgment.

We should also remember limits to success. The expertise, products, relationships, and operating practices that produced yesterday’s success may become tomorrow’s constraints. In a world of rapid technological and value migration, maturity can quietly become stagnation.

And then there is escalation. Competitors introduce AI, so we introduce more AI. They accelerate, so we accelerate. Soon, everyone is moving faster but no one has stopped to ask whether they are moving in the right direction.

The lesson of history is not that it repeats itself exactly. It is that human behavior, organizational pressures, and system dynamics create recognizable patterns. The names, technologies, and circumstances change. The patterns endure.

A prepared leader does more than conduct an occasional after-action review. She builds learning into the organization’s operating rhythm. She examines assumptions, searches for delayed consequences, compares outcomes with intentions, and distinguishes a temporary fix from genuine progress.

In 2026, the past should not become an anchor that prevents change. It should become a source of pattern recognition that improves our response to change.

The future will not resemble the past. But leaders who refuse to learn from the past may reach the future only to discover that they have brought their old mistakes with them and at greater speed and scale.

Before making your next consequential decision, ask: What have we seen before, and what did we fail to learn the first time?

Next week I’ll update the material about dealing with the present.

Cheers,

Bill