New year planning feels exciting in theory. In practice, it often turns into a list of too many goals with no path forward.
This is where AI tools like Claude and ChatGPT can shine.
Use Your AI Chatbot of Choice to Stress-Test and Simplify Your Plans:
Choose What Deserves Your Attention
Prompt:
“Here are the goals I’m considering for 2027: [paste list]. My available time, budget, team support, and existing commitments are: [add details]. Help me compare the goals by likely impact, effort, urgency, and whether one needs to happen before another. Don’t invent numbers or pretend you know which will succeed. Recommend up to three priorities for the first quarter, explain the tradeoffs, and put the rest in a “later or let go” list.”
Spot the risks
Prompt:
“For these priorities, what assumptions am I making? Identify the three risks most likely to disrupt the plan, explain what signs I should watch for, and suggest one practical response to each. Ask me about any missing information that would change your assessment.
Translate into a roadmap
Prompt:
“Turn the priorities into a first-quarter plan. For each one, give me a small first action, monthly milestones, who needs to be involved, and a way to tell whether we’re making progress. Fit the plan within the capacity I gave you. Flag any month that looks overloaded.”
Then, it is your turn to take it through the human pass. Move things around. Cut what doesn’t fit. For instance, if January looks like it requires three versions of you and one unusually organized capybara, the plan probably needs another edit or three.
Breaking big ideas into small, structured pieces makes them doable.
We can help
And if this exercise uncovers a project or workflow you want help untangling, tell us what’s on your plate. We’ll help you find a sensible place to start.
New to all this?
Try our free email course that gives you practical examples of multi-step prompts in action.

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