Column B Strategic Planning

Column B planning rejects the standard approach of looking at current constraints ("the bricks around you") and instead focuses on "the castle on the hill"—the magical, improbable future you want to exist. By anchoring in a 10-to-30-year vision, you avoid incrementalism and create a "ladder to the moon" that guides every microscopic daily task.

The Core Framework: Column A vs. Column B

• Column A (Incremental): Looking at current resources, stacking bricks as high as they can go, and iterating based on immediate constraints.
• Column B (Vision-Led): Dreaming of a perfect, "mythical" experience first, then working backward to determine what must be built today to make that future inevitable.

The "Chaos to Clarity" Workflow

Every idea begins in a state of "Chaos" (amorphous, embarrassing, and lacking mastery). Your job is to move it to "Clarity" through the following steps:

1. Imagine the 2050 Vision

Don't start with what is possible; start with what is desirable.

• Define Wild Success: What does the world look like in 10–30 years if you succeed perfectly? (e.g., "Everyone on the planet has their basic human needs met").
• Define Terrible Failure: What happens if the current "freight train" of industry continues without your intervention?
• Identify the Gap: Locate the specific "gap in the market" that only your vision can fill.

2. Draft the Vision Deck (The "Ugly Baby" Phase)

Create a pitch deck for every new project, even if it feels embarrassing.

• The Problem First: Dedicate the first few slides strictly to the problem. If the audience doesn't feel the pain, they won't value the solution.
• Visual Communication: Move the idea from your head onto a slide. Visuals clarify thinking more than text or speech alone.
• Iterate on Rejection: Treat every "No" from a stakeholder or investor as a prompt to add a new slide that pre-emptively answers that specific objection (e.g., a "Market Size" slide or a "Competitor Comparison" slide).

3. Build the "Ladder to the Moon"

Break the "Crazy Big Goal" into a sequence of rungs.

• Establish Mission Pillars: Categories of long-term investment (e.g., "Design anything," "In every language," "On every device").
• Set Crazy Big Goals: Define audacious annual milestones within those pillars that make the team feel "inadequate" but motivated.
• Determine the Microscopic First Step: Identify the smallest, most immediate action that starts the climb.

4. Close the Loop

Integrate community feedback into the vision-led roadmap to ensure the "castle" serves real people.

• Tally Requests: Systematically track user requests (Canva tracks 1M+ per year).
• User Testing: Watch 10 random people use the product. Look for hesitation or confusion; this provides more "astute" feedback than any internal brainstorming.
• Release and Celebrate: When a "Crazy Big Goal" rung is reached, hold a high-energy celebration (e.g., "smashing plates" or "releasing doves") to mark the transition from chaos to reality.

Examples

Example 1: Product Expansion

• Context: A design tool focused only on social media graphics.
• Column B Thinking: "In the future, design and productivity will be the same thing."
• Mission Pillars: Design Anything; Publish Anywhere.
• Ladder Rungs: Year 1: Presentations; Year 3: Video; Year 5: Websites; Year 10: AI-generated branding.
• Microscopic Step: Add a "Presentation" template to the existing social media editor.

Example 2: Overcoming Investor Rejection

• Context: Pitching a market that investors claim is "too small."
• Chaos Phase: Initial pitch is rejected 100 times.
• Application of Clarity: The founder adds a "Lay of the Land" slide and a "Market Growth Projection" slide based specifically on the feedback from the 10th and 20th rejections.
• Output: A 2012 pitch deck that remains valid and accurate a decade later because it was forged through the "Chaos to Clarity" refinement process.

Common Pitfalls

• Stacking Bricks (Column A Trap): Getting so bogged down in Slack messages and emails that you only plan for the next two weeks. Set aside "vision time" to step away from the "forest" of daily tasks.
• Setting "Realistic" Goals: Realistic goals are easily abandoned when roadblocks appear. Only "Crazy Big Goals" provide the motivation to persist through "dark tunnels" (like a 2-year code rewrite).
• Fear of the "Ugly Baby": Killing an idea too early because it looks "embarrassing" in its first draft. Accept that the first step of the ladder is always microscopic and imperfect.
• Obsessing Over Timelines: You will likely be wrong about when a goal is achieved (e.g., a 6-month project taking 2 years). Focus on the direction and the rungs, not the calendar.