How waypoints get their dates.

A waypoint without a date floats. It sits on the list, always next and never pressing, and a month later it’s still sitting there.

A waypoint with the wrong kind of date has the opposite problem. Pick an exact day for something you can’t predict, miss it by a week, and the waypoint looks late when it was only guessed too tightly.

A date is a guess

When you date a waypoint, you’re guessing how long something will take before you’ve started it. Some guesses deserve a day. “Book the venue” can happen by Friday. Others only deserve a month. “Finish the first draft” might land in October or might not, and naming a day doesn’t make it land sooner.

A loose date still does what a date is for. It puts the waypoint in order against the others, it tells you when to start paying attention, and it gives you something to move when plans change.

To choose, ask what you can name. If you can name the week, pick a day. If you can only name the month, pick the month. If you can’t name either, the waypoint is probably too big, and splitting it in two usually gives you one half you can date.

Day or month

In YearCraft, every waypoint on a goal can carry a date, and that date can be a day or a month. A day reads “By Oct 3”. A month on its own reads “By end of Oct”, and it counts as the last day of that month, so it sorts in line with everything else.

Four buttons let you choose a date quickly:

• Today
• Tomorrow
• Next week, which sets a date a week from today
• End of month

To choose another date, select a month. You can stop there or choose a day in that month. The goal’s own end date is marked with a small flag, so you can see how much time you have before you plan to finish the goal. Dates outside the current year show the year too.

A month can become a day later, once you know more. Open the waypoint, pick the day inside the same month, and the label changes from “By end of Oct” to the date.

What the colors mean

The date label changes color as the date gets closer or passes:

• Orange: the date has passed
• Yellow: it’s today
• Dark text: tomorrow, or later this week
• Lighter text: anything further out
• Light orange: a month-only date whose month has gone by

The label also tells you when the waypoint is planned. A passed date says “Past Sep 25”, this week’s dates say “By tomorrow” or “By Thu”, and later ones show the date.

Where the dates show up

Today’s “Up next” takes each goal’s next open waypoint, the first one still open on its trail, and lists them soonest first, with undated ones last. A later waypoint never jumps ahead of an earlier one on the same goal, even when its date comes sooner. The order on the trail is the order you meant.

Right after hello, Juniper’s journal check-in names your soonest dated waypoint when there is one: “You’re aiming to finish ‘Outline all chapters’ in 18 days.” For a month-only date it says “by end of Oct” instead.

Two days before a waypoint’s day, Juniper sends a note that links to the goal, where you can mark the waypoint reached or move the date. Month-only waypoints skip that note, since there’s no day to count back from. If a date keeps slipping, Why most goals stall by February covers moving it without dropping the goal.

Where the first dates come from

When you join YearCraft, Juniper asks for one goal and suggests a trail for it. That’s three waypoints with rough dates, from about three weeks out to about four months out. You can keep what fits, swap a waypoint for another of her ideas, or add your own. The trail gives the goal a shape on day one, and every date on it can change later.

After that, “Ask Juniper for ideas” on a goal suggests three to five waypoints, each a title with a one-sentence description. She doesn’t suggest dates for these. You know your calendar better than she does, so you choose a date as you add each waypoint.