Planning: When to Think, When to Act

how igor ticks , book-notes

The plan trains the planner. Planning isn’t about predicting the future—it’s about preparing your mind to meet it. It clarifies goals, surfaces unknowns, and builds the pattern recognition you’ll need when reality punches your plan in the face. But the goal of planning is action, not the plan. The moment you’re polishing instead of testing, you’ve crossed from preparation into procrastination.

The Value of Planning

All things are created twice - once in the design phase, and then again in the implementation phase. If you don’t perform the first creation, someone else will.

Loading (/end-in-mind)

The plan trains the planner. Planning isn’t about predicting the future—it’s about preparing your mind to meet it:

  • Clarifies the goal - Forces you to articulate what success actually looks like
  • Surfaces unknowns - Planning walks you toward the edges where risks hide; without it, you wander randomly and may never find them until they find you
  • Prepares pattern recognition - When reality diverges, you notice faster because you thought through scenarios
  • Builds alignment - Gets others on the same page before chaos hits
  • Lowers activation energy - Sometimes you need enough plan to feel ready to start

The Danger of Over-Planning

“Everyone has a plan until they get punched in the face.” — Mike Tyson

“No plan survives first contact with the enemy.” — Helmuth von Moltke

“Plans are worthless, but planning is everything.” — Eisenhower

But here’s the counter: if you have no plan at all, there’s nothing to adapt. The plan gives you a starting point—a hypothesis to test against reality. Without it, you’re just reacting randomly.

Planning as Security Theater

_Based on this tweet_

If there’s something you want to do, some goal you have, it’s easy to dip a toe in the water, test the temperature, and plan. A lot.

Planning makes us feel good if we’re afraid. It provides the illusion of security. Never mind that we don’t know which scenarios are actually going to happen, never mind that we’re planning for the wrong thing—planning makes us feel safe. And if we’re nervous, we can plan forever.

Feedback Loops Beat Forecasting

The difference between the expert and the novice isn’t theory or intelligence or plans. It’s relevant domain knowledge—gathered from empirical observation and experience.

The trick is to get into that feedback loop as soon as possible, and run it as fast as possible. Give yourself the most possible opportunities to learn, per unit time.

We only learn while we are moving. Momentum is emotional gravity—forward motion creates its own fuel. See also Activation Energy.

The SpaceX Way vs. The NASA Way

NASA gold-plated everything: plan and test and plan and test, generating mountains of paper detailing every contingency.

SpaceX just shrugs, says “it’s unmanned,” and sends it. Half the time it blows up. That’s the whole point.

One rocket blowing up in an actual end-to-end test beats many man-years of planning and plotting.

Knowledge Only Comes From Empirical Observation

Everything else is speculative. The sooner you get into a feedback loop, and the faster you run it, the more iterations you can do in less time. While others are planning and speculating, you actually learn something.

Relevant data is the most precious thing in the universe. Worth blowing up any number of rockets to get it.

Rockets are just stuff. You can always get more stuff. You can never get more time.

Cowboy Style

Expect things to go wrong. Anticipate it. Accept it when it happens. Doesn’t mean the dream is dead.

It just means we’re doing it cowboy style.

The Missing Third: Review

We talk about “planning vs. doing” as if there are only two modes. But there’s a critical third part: Review.

Plan → Do → Review

Without review, you’re just spinning. You do things, but you don’t learn from them. You make the same mistakes. You can’t tell what’s working. The feedback loop that makes “just ship it” powerful? Review is what closes that loop.

Review is where learning happens:

  • What actually happened? Not what you hoped or feared—what occurred?
  • What worked? Double down on this.
  • What didn’t? Why? What would you do differently?
  • What did you learn? This is the gold. This is why you did the thing.

This is why coaching is so powerful—it’s structured review. A coach helps you see what you can’t see yourself, asks the questions you’re avoiding, and holds up a mirror to your patterns.

Without review:

  • Planning becomes guessing (you never learn if your predictions were right)
  • Doing becomes busywork (activity without progress)
  • Mistakes repeat (because you never extracted the lesson)

The SpaceX rockets blow up—but then engineers pore over telemetry, find the failure mode, and fix it. The explosion is “Do.” The analysis is “Review.” Without review, you just have expensive fireworks.

Why People Skip Review

If review is so valuable, why do most people avoid it?

Review is threatening. Not because someone else will judge you—but because you will judge you. And you’re the harshest critic. You know exactly where you cut corners, where you made excuses, where you told yourself a story instead of facing the truth.

Review forces you to check your excuses. That comfortable narrative about why things didn’t work? Review makes you hold it up to the light. Was it really bad luck? Really someone else’s fault? Really impossible given the constraints? Or did you just… not do the thing?

  • It’s ego-threatening. Planning feels optimistic; review feels like judgment.
  • No one makes you. Planning has deadlines. Doing has deadlines. Review? Optional. Easy to skip “just this once” forever.
  • You have to confront yourself. You can’t review effectively while protecting your ego. You have to admit what you actually did, not the story you tell yourself.

This is why external structures help: coaches, retrospectives, weekly reviews, journaling. They create forcing functions for the thing you’d otherwise skip. A coach won’t let you get away with your excuses—and that’s the point.

How to Make Review Actually Happen

Since you’ll avoid it, you need to trick yourself into doing it:

  • Schedule it. Put it on the calendar. Weekly review, project post-mortem, whatever. If it’s not scheduled, it won’t happen.
  • Make it social. Review with someone else—a coach, a partner, a team. Harder to skip when someone’s waiting for you. Harder to lie when someone’s watching.
  • Lower the bar. A 5-minute “what worked, what didn’t” beats a 2-hour retrospective you’ll never do. Start small. Something beats nothing.
  • Attach it to existing rituals. End of week, end of project, end of quarter. Piggyback on transitions you’re already marking.
  • Write it down. Journaling forces articulation. You can’t just vaguely feel like it went okay—you have to say what actually happened.
  • Separate review from judgment. Review is data collection. What happened? The judgment comes later. When you conflate them, you avoid both.

The goal isn’t perfect review. It’s some review. Consistency beats depth.

When things go really wrong, you need structured review. In engineering we call this a Correction of Errors—a blameless post-mortem that asks “what happened?” and “how do we prevent it next time?” The key word is blameless. COEs work because they separate the person from the failure. You can be honest about what went wrong because you’re not on trial. The same principle applies to personal review: you’re not judging yourself as a person, you’re examining what happened so you can do better.

The ratio matters. Most people over-plan, under-do, and skip review entirely. If you’re going to skimp on something, skimp on planning. But never skip review.

Finding the Balance

The goal of planning is to get you into action and make progress. It’s not to have a plan.

The plan is a means, not an end. The moment it stops propelling you forward—the moment you’re polishing the plan instead of testing it—you’ve crossed from preparation into procrastination.

  • Plan enough to have direction, not so much that you’re avoiding action
  • Use planning to clarify the goal, then get into a feedback loop
  • When nervous, notice if planning is productive or procrastination
  • Ship early, learn fast, iterate
  • A “good enough” plan executed today beats a perfect plan next month

See also