Planning a new year can feel overwhelming.

Prepping for a New Year can feel daunting. On one hand, you want a plan so you have a roadmap to follow and you know what you’re doing from week to week.

On the other hand, if you’re like me, you want flexibility and spaciousness to let the plan unfold as the year does, knowing that things will change along the way.

So what’s the best way to plan your year? The key is having a plan that allows for that flexibility and spaciousness, yet still considers the major goals and milestones you want to accomplish for the year.

One of the best ways to accomplish this type of annual planning is by using LLM prompts. In this post, I’ll show you how you can use ChatGPT to plan your year ahead with a few simple, easy prompts. 

How to plan your year using ChatGPT

Before diving straight into ChatGPT, you want to do some introspection. (I know, this part often takes more time, but it’s important!)

To plan effectively, you want to clarify the “big rocks” as I like to call them: the things that matter most in the upcoming year. You do this by considering your values and what’s most important to you. So take some time to do that FIRST.

Next, define those big goals in concrete terms and break them down into tangible steps and milestones you can accomplish monthly. Be sure to consider your own constraints, whether it’s time, energy, other priorities, or anything else. (For this, you can use ChatGPT as detailed below.)

To go even further, you can break your plan down into a weekly checklist for yourself to stay on track, building in time for rest and flexibility along the way. (ChatGPT is great for this!) 

To help you plan, I’m sharing 8 copy-and-paste ChatGPT prompts below that you can use to plan your year in a way that’s structured but flexible, intentional but not overwhelming.

The goal isn’t a perfect plan. It’s an adjustable plan that’s aligned with who you are and what you want.

8 ChatGPT prompts to plan the year ahead

Simply copy and paste these prompts into ChatGPT, starting with the first one. Be sure to give feedback and edit along the way to get the plan exactly the way you want it. It’s YOUR plan, after all!

ChatGPT planning prompt #1

Copy and paste this into ChatGPT

I want help clarifying my big goals for 2026.

Please act as a strategic but supportive planner. Ask me reflective questions to help me identify 3 meaningful business or life goals for the year. 

Constraints:

– I want goals that are realistic and humane, not hustle-based.

– I value sustainability, flexibility, and aligned income.

– Please do not jump into planning yet. Ask clarifying questions first.

ChatGPT should then follow with some questions to help you identify your big goals for the year. (Again, if you have time to do this on your own first, you can skip this step and go straight to Prompt #2.)

ChatGPT planning prompt #2

Next, copy and paste this into ChatGPT

Here are the goals I’m considering for 2026:

[PASTE GOALS 1, 2, and 3]

For each goal:

– Help me define what meaningful progress looks like by the end of 2026.

– Help me clarify how much time or energy I realistically want to devote.

– Flag any goals that may be trying to do too much at once.

Chatgpt will then reply with more questions for you to answer. 

ChatGPT planning prompt #3

After you’ve answered those questions, copy and paste this prompt into ChatGPT:

Based on my 3 goals, create a quarterly roadmap for 2026 (Q1–Q4).

Goals:

[PASTE GOALS HERE]

Constraints:

– I want to work a flexible schedule and want to work X hours per week. (Define X)

– Assume I want the following rest periods built into the year. (Include any time off you’re taking)

– (Add any other constraints you may have, including the times you need to pick up your kids from school, any other required time off, or any limits in hours and days you want to work.)

Based on your answers to the above, ChatGPT will create a quarterly roadmap for your year.

ChatGPT planning prompt #4

Next, copy and paste this into ChatGPT

Using the quarterly roadmap you just created, turn this into a month-by-month action plan.

Requirements:

– Each month should have a theme.

– Include only a few clear actions per goal.

– Avoid overloading any single month.

ChatGPT will use this to break down your quarterly roadmap into a monthly action plan to make it easier to follow.

ChatGPT planning prompt #5

Next, copy and paste this into ChatGPT

Help me design a weekly rhythm for working toward my 2026 goals. 

Parameters:

– I want time blocks by category, not daily schedules.

– Include rest.

– Keep it flexible and realistic. 

This prompt tells ChatGPT to break down your monthly roadmap into a weekly action plan that you can follow every week.

ChatGPT planning prompt #6

Next, copy and paste this into ChatGPT

Create a repeatable weekly checklist I can use to track progress toward my 2026 goals.

Format:

– Categories

– Tasks

– Simple and not overwhelming

This should support consistency without pressure.

Now, your weekly plan is getting more specific and detailed, and looking more like a to-do list.

ChatGPT planning prompt #7

Next, you’ll want to tell ChatGPT what to help you AVOID in the new year, so you don’t get off track with your plan.

So copy and paste this into ChatGPT

Based on everything above, help me identify:

– What I should explicitly NOT focus on in 2026

– Where I can go slower than I think

– Signals that tell me it’s time to adjust the plan

The goal is for your plan to feel supportive, not rigid.

ChatGPT planning prompt #8

Now it’s gut-check time. For your last prompt, copy and paste this into ChatGPT.

If I trusted myself to evolve this plan as I go, what mindset or guiding principles would help me stay aligned throughout 2026?

Those guiding principles are what you want to remember — and follow — to make the most of your plan. Consider writing those keywords down somewhere or keeping them as a screensaver to remind you of your big goals.

Planning your year can be simple and easy

Planning your year ahead doesn’t have to take hours or days. It can be simple, easy, and even fun!

By using these ChatGPT prompts to help plan your year, you can clarify your big goals, break them down into a manageable plan, and define what actions you need to take on a regular basis.

The best thing is, it’s flexible, considers your own time and energy, and you can change it at any time. Happy planning!