Which prompt to choose
Three different problems, three prompts. Planning a new project is one thing; keeping one going alongside your job is another; getting back on track after you've dropped it is the third, and the most underrated. Choose the one you need today.
- New project with a deadline: first prompt, which splits it into stages with dates working backward from the deadline.
- Side project you carry on in spare moments: second prompt, which cuts everything into 20-minute micro-steps.
- A project that's stalled, to pick back up: third prompt, which gets you back in the saddle in five minutes.
How to do it
- Open the AI assistant.
- Copy the right prompt and describe the project in three lines: what it is, when it's due, how much time you have per week.
- Send. Take the plan and put it where you'll see it: the dates in the calendar, the steps in a to-do app.
- Every week go again: "here's what I did and what I didn't, update the plan."
The operational syntax for planning a project with a deadline:
Help me plan this project: "organizing my sister's wedding."
Deadline: in 5 months. Time available: 4 hours a week.
Work backward from the final date.
Give me:
1. The 5-6 main phases in order, each with a suggested deadline.
2. Week 1: the 3 concrete steps to start with right away.
3. The typical delay risks for this kind of project and how to prevent them.
Keep the plan realistic for 4 hours a week, not for a full-time organizer.
The operational syntax for a side project in spare moments:
I carry this side project on in spare moments: "writing a small family cookbook."
I only have blocks of 20-30 minutes, a few times a week.
Break it into micro-steps that close in a single session.
For each: what I do, what I'll have produced by the end of the session.
Order them so that even doing just one I've really moved forward, not just "got ready."
The operational syntax for picking a stalled project back up:
I had a project and I've left it stalled for weeks: "[describe what it was and where you were]."
Help me get back in without getting discouraged.
Give me:
1. A summary of where I'd probably left off, for you to confirm.
2. The single smallest step I can do today in 15 minutes to get moving again.
3. What to ignore for now, so I don't get stuck reorganizing everything.
After the plan, copy the dates into the calendar right away. A plan that stays in the AI chat is a plan you'll forget: the calendar is the thing that alerts you, the AI doesn't.
A real example
Davide wanted to launch a small podcast but had been putting it off for months. He used the side-projects prompt, saying he had half-hour blocks two evenings a week. The AI gave him micro-steps that closed by themselves: "session 1: choose the name and record 60 seconds of a test with your phone." Not "prepare the podcast," which is a wall.
By the third session he had three episodes recorded. When he skipped two weeks, he used the third prompt to get back in: the AI reminded him where he was and gave him a single 15-minute step. No guilt, no endless reorganizing. Just the next step.
When it does NOT work (and how to fix it)
If the plan is too optimistic and then you feel guilty
The AI tends to overestimate how much you get done in an hour. Say it in the prompt: "be pessimistic about times, double the estimates and leave slack for the unexpected." A plan you can hold to is better than a perfect plan you abandon in the second week.
If the AI gives you a thousand steps and you freeze
Too many items all at once block you instead of helping. Ask "show me only this week's steps, hide the rest until I've done them." Seeing only the next three steps is what gets you started.
If the deadline is fixed and the plan doesn't fit
Here the AI has to tell you the truth, not reassure you. Add: "if it doesn't fit in 4 hours a week, tell me and suggest what to cut or who to delegate to." An honest plan that cuts something is worth more than one that pretends it all fits.
A tip from someone who actually uses it
Keep a single project-status document, written by you, that you update at the end of each session with two lines: what I did, what comes next. It's your real memory between one session and the next. When you come back to the AI, you paste that document and start again in thirty seconds, instead of re-explaining everything. The continuity is on you, not the AI.
Frequently asked questions
Can the AI remind me of deadlines automatically?
No, and it's worth knowing right away: the AI isn't an alarm clock and doesn't send you notifications. It generates the plan and the dates, but the alerts come from the calendar or reminder app where you copy those dates. Keep them separate: the AI thinks, the calendar rings.
Can I connect the AI to my calendar?
In some cases yes, through dedicated integrations, but it's a more advanced step we cover separately. To start, copy-pasting the dates works perfectly well and doesn't depend on configurations that can break.
Does planning with AI make me more productive, or is it just a game?
The trap to avoid is mistaking planning for the work. Making a beautiful plan gives the feeling of having produced something, but the project only moves forward when you execute the steps. The AI shortens the time to plan precisely so you spend it doing, not reorganizing endlessly. If you find yourself re-planning more than executing, stop and do the smallest step you have.