Stage 5: Intentional Living | Monthly Planner

A month is long enough to make real progress on something and short enough to course-correct when it's not working. Monthly planning gives you a structure for deciding what those somethings are, tracking the experiments you're running from Stage 4, and reflecting honestly at the end of each month on what happened.

Use it at the start of every month. Spend 30 to 45 minutes filling it out. The best practices below will help you plan well (there's real research on why most people plan badly and what to do instead). The template section is the planner itself. Print it, copy it into your notebook, or fill it in digitally. Whatever keeps you using it.

How to plan a month well

Monthly planning sounds simple. Pick some goals, write them down, and then just do them. But the research on planning tells a different story. Most people are quite terrible at it! Here's what the evidence says, and what to do about it.

We underestimate how long things take

Daniel Kahneman and Amos Tversky identified what they called the planning fallacy in 1979. They found that people consistently underestimate the time, cost, and risk of future actions while overestimating the benefits. This isn't occasional optimism, but a deep cognitive bias that persists even when we know about it.

Kahneman's later work with Dan Lovallo showed that the fix is what they call the "outside view." Instead of imagining how our specific project will go, we should look at how similar projects have gone in the past. If our last 3 months each had a goal we didn't finish, for examples, we can expect that our next month probably will too, no matter how motivated we feel right now.

So when you estimate how long something will take each month, multiply your gut estimate by 1.5. If you think you can finish a project in 2 weeks, plan for 3. You'll be right more often.

The 3-objective rule

Research on goal-setting consistently shows that fewer goals produce better results. Edwin Locke and Gary Latham's goal-setting theory (developed across decades of research, synthesised in their 2002 paper "Building a Practically Useful Theory of Goal Setting and Task Motivation" in American Psychologist) found that specific, challenging goals lead to higher performance, but only when people can focus. Too many goals split attention and reduce performance on all of them.

So pick 3 priorities per month, maximum. Not 3 categories with sub-goals each. Three things. If you finish them early, wonderful. Add more then. But starting the month with 7 priorities means finishing the month with 7 half-done things.

This is hard if you're ambitious. It feels like you're leaving things on the table. And you are, but that's the point. The things on the table will still be there next month, and you'll get to them faster by not splitting your focus now.

Buffer time is not laziness

Klaus Oberauer and Stephan Lewandowsky's research on cognitive load (published across multiple papers, including their 2011 work in the Journal of Experimental Psychology) shows that working memory has hard limits. When you schedule every hour of every day, you leave no room for the unexpected. And the unexpected always shows up.

A good monthly plan leaves about 25% of your time unscheduled. That's roughly one week out of four. Some of that time absorbs surprises (the dentist appointment, the friend who needs help, the project that takes longer than expected). Some of it becomes creative space where good ideas surface because you're not grinding through a checklist.

If a full month with no buffer makes you anxious, try scheduling your 3 priorities into 3 of the 4 weeks. Keep the 4th week open and see what happens.

Connect monthly goals to your bigger direction

Peter Gollwitzer's research on implementation intentions found that people who specify when, where, and how they'll pursue a goal are 2 to 3 times more likely to follow through compared to people who just set the goal. A later meta-analysis by Gollwitzer and Sheeran confirmed this across 94 studies.

For monthly planning, this means two things. First, each monthly priority should connect to something bigger (your focus areas from Stage 4, for example, or your vision from Stage 3). If you can't explain why a priority matters to your broader direction, it probably doesn't belong on the list. Second, be specific about when and how you'll work on each priority. "Work on the business" is a wish. "Spend Tuesday and Thursday mornings on client outreach" is a plan.

The review is where the learning happens

Chris Argyris, the organisational theorist, introduced the concept of double-loop learning in his 1977 Harvard Business Review article. Single-loop learning asks: "Did I hit my goal?" Double-loop learning asks: "Was it the right goal? Are my assumptions still correct?" Most people only do single-loop reviews, if they review at all.

At the end of each month, spend 20 to 30 minutes on the reflection prompts in this planner. The prompts are designed for double-loop thinking. They ask you to examine not just what happened, but whether your approach, priorities, and assumptions were right. This is where real course-correction happens.

If you skip the review, you're flying blind. You'll repeat the same mistakes and wonder why things aren't changing. The planning only works if you close the loop.

Monthly planner template

Access your Notion workbook here.

Fill this out at the start of each month. Return to it at the end for the reflection section.

Month overview

• Month:

• Theme or intention: One phrase that captures what this month is about for you

• How I want to feel:

Top 3 priorities this month

These should connect to your focus areas from Stage 4.
Remember: 3 maximum. If you can't choose, ask which ones you'd regret not doing.

Experiments running this month

From your Little Bets in Stage 4. What are you actively testing, and how will you know if they were successful?

Habits to maintain or build

Keep this short. 3 to 5 habits maximum. More than that and you won't track any of them.
Note the exact habits, frequency and anchor/triggers.

Commitments and deadlines

Things with hard dates. Appointments, deliverables, and events. Get them out of your head.

What you're letting go of this month

Equally important as what you're adding. What are you deliberately not doing, not worrying about, or putting down for now?

End-of-month reflection

What worked

Which of your 3 priorities did you actually complete? What helped you follow through?

What didn't work

Where did you stall or avoid? What got in the way, and was it external or something inside you?

What surprised me

What happened this month that you didn't expect? Did any of your assumptions turn out to be wrong?

What I want to carry forward

Based on this month, what should you keep doing, stop doing, or try differently next month?

AI companion (optional)

How to use: Run this prompt after you've filled out the monthly planner template. It works best when you paste in your actual answers rather than summarising them. The AI can spot overcommitment, vague goals, and blind spots you'll miss on your own.

Copy and paste the prompt below into Claude, ChatGPT, or any AI assistant:
I just finished filling out my monthly planner for [month].
Here are my 3 priorities: [list them].
Here are the experiments I'm running: [list them].
Here's what I'm letting go of: [list those].
I want you to do 3 things:
(1) Check whether my priorities are specific enough to actually act on, or whether they're still vague wishes. Push me to make them concrete.
(2) Look for conflicts or overload. Am I trying to do too much given a realistic month?
(3) Ask me one question I haven't asked myself about this month's plan.