Iterations and shipping

Iterations are where Pencil expects you to spend most of your time. They're the layer between "we have a feature in mind" and "we have a list of tasks for tomorrow." Get the iteration right and the tasks pick themselves; get it wrong and you'll spend a week shipping something that didn't matter.

Picking iteration scope

A good iteration has three properties:

1. You can ship it in days, not weeks. If it's longer than a working week, it's two iterations.
2. A user (real or internal) can use it. Not a feature flag tucked behind a flag — actually use it.
3. You'd be proud to put it in a changelog. If the changelog line would be embarrassing, the iteration is too small to bother with.

The hardest version of this is the first iteration of a new feature. The temptation is to ship everything at once. Don't. Pick the thinnest slice that's still a real thing. "Billing — Stripe Checkout for solo plan, USD only, no proration, no team plan" is a good first iteration. "Billing" is not.

Iterations vs sprints vs goals

Pencil distinguishes these on purpose, and the difference matters:

• An iteration is a slice of one feature. It's scoped by what's being built.
• A sprint is a time-box, usually two weeks, that may contain many iterations across features. It's scoped by calendar.
• A goal is an outcome the org cares about ("100 paying customers," "p95 under 200ms"). It's scoped by what you'd celebrate.

A sprint contains iterations contains tasks. A goal is orthogonal — multiple sprints might contribute to one goal. Use iterations to plan work, sprints to coordinate, goals to remember why.

If you only adopt one of these, adopt iterations. Sprints and goals are useful but optional.

When to call something done

"Done" in Pencil means: the iteration is shipped, the requirements are met, and a user has touched it. Not deployed-to-staging-done. Not merged-to-main-done. Actually-in-the-world-done.

This is strict on purpose. The cost of marking something done too early is that next month you can't tell what's actually shipped vs. half-shipped, and the changelog lies to you. When in doubt, leave it open one more day and verify.

What to try next

Read Shortcuts and patterns to pick up the small set of moves that make day-to-day Pencil feel fast.