Manifest 9: Why is Monthly Planning So Hard?

Monthly planning and reflection can be effortless, and immensely powerful.

👋🏼 Welcome new humans!

Thanks so much for your time and attention; this newsletter shares links and resources to achieve more by doing less.


• Monthly planning is hard, here’s why it’s important
• Need a nudge to get you going? Check out the Minimalist Monthly Planner
• Watch “Building a Website w/ Notion & Super” recap video here

When it comes to planning and reflection, the month is often the most daunting, and the least sexy. Four-plus weeks seems too far to go backward to find anything useful, and it often feels hard to predict what our habits and projects will look like one month into the future.

There's a bigger danger at play when prospecting and retrospecting (we'll get into these later): living too much in the past or the future can prevent us from living in the present. Let's take a minimalist approach to monthly planning & reflection (p&r), and for those of you interested in getting started (it is the first of the month after all), I have a Minimalist Monthly Planner Notion template, exclusively for subscribers.

Why Reflect Monthly?

It's a tough sell. Daily reflection allows us to celebrate our wins and acknowledge our challenges, as a pencils-down moment. Weekly reflection feels actionable because you can take unfinished or delayed actions/projects and prioritize them going into the following week.

We rarely set personal or professional goals on a monthly cadence. One fact I find personally frustrating: months never align with starts or ends of weeks!

However, monthly p&r allows us to tap into moments that are out of our short-term memory, and re-surface questions, ideas or memories that can lead to a more mindfully productive month.

Retrospection and Prospection

Arthur Brooks, Professor at Harvard Business School and Contributor at The Atlantic, dives into p&r in his latest episode of How to Build a Happy Life: How to Know That You Know Nothing. He and Dr. Ellen Langer dive into what it means to live in the present, by first highlighting how much time and energy we exert on living in the past and future.

"(there's a) unique nature of the human mind, compared to any other species that's ever existed. The human brain makes it possible for us to be in other time periods in the current moment."

Arthur Brooks, How to Know That You Know Nothing

For Brooks, prospection is thinking through the most probable future scenarios, and choosing the most suitable option. Retrospection is the act of reliving or thinking about past events. Although he outlines some benefits to both practices, he concludes the conversation with this:

“…thinking about the past, enjoying your memories, for example, are looking forward to the future, especially if these things are positive, they're great, they can aid happiness. The problem is, if you're excessively prospective and or retrospective, it can crowd out your ability to be alive. Right now.”

Arthur Brooks, How to Know That You Know Nothing

If you're active in Notion or productivity circles, you've likely seen complex, elaborate, formula-driven productivity systems that people often tout as remedies for our increasingly-complex world. I have no doubt that for some people, tracking days, projects, actions, and learning at microscopic levels feels the most natural, but I personally get overwhelmed if I feel like systems I've set up are too time-consuming or mentally taxing to maintain.

From the moment I started seriously using Notion to organize my life, it’s been a nonstop path toward less information, not more. The goal of creating a powerful system that only shows the information you need at any particular moment is a goal I’m fascinated by, and drives my thought-process when creating systems for creators and small teams.

Systems must be manageable, ordered, and above all, enlightening.

Making the Case for Reflection: The Forgetting Curve

In The forgetting curve: the science of how we forget, Anne Laure Le Cunff references German psychologist Hermann Ebbinghaus' Forgetting Curve, which arose from a self-study he conducted on the functions of memory.

Some key takeaways from the study:

"just 20 minutes after learning, we can only recall 60% of what we have learned. After one hour, only 45% of what has been learned is still in our memory, and after one day only 34%. Six days after learning, the memory has already shrunk to 23%; only 15% of what has been learned is permanently stored."

Although the (loosely-scientific) data focused on learning and retention, this has direct impacts on not only memory, but also productivity and personal development.

Looking a month into the past allows us to recall wins, challenges, journal entries, and habits, much of which we'd likely forget otherwise (if you explore the Notion template, I use wins and challenges quite a bit). Even if you use a Bullet-Journal styled system, it still requires you to manually go back in time to resurface past notes, rather than redisplay them automatically at pre-set moments, ie. at the start of each month.

Planning without Reflection sets us up to repeat the same mistakes

“Often all it takes to live intentionally is to pause before you proceed.”

Ryder Carroll, The Bullet Journal Method

The number one reason people fail to develop new habits is underestimating the difficulty in the action. When we consider the cadence of monthly planning – every 30 days or so – this also makes it harder to build the habit, as its harder to incorporate habits into your routine.

It can also feel like a better use of time to jump straight into planning the upcoming month. By doing so, it's impossible to make strategic changes to how and where you apply time, energy, and attention, if you can't see what succeeded and what failed in the past.

In Ryder Carroll’s The Bullet Journal Method, the Monthly Migration (the "monthly process of filtering out meaningless content from your notebook"), allows for a purging of projects that are no longer worth pursuing. Migration here is focused on cleaning up open-items, but there's so much more potential for the monthly review, when we start to incorporate tagged journal entries, habit-tracking, and project management.

If you use Notion, there's a magical way to get all this data: Rollups.

One magical feature of Notion is Rollups, or the surfacing of properties from a different database.

Rollups can seem convoluted at first, but they work like this:

  1. I have an entry in a Months database title, November.

  2. I have a week entry in a Weeks database titled, Week 44

  3. I have a day entry in a Days database titled, Nov 01

If I'm tracking a habit of meditation daily, ie. in the Nov 01 page (with a simple checkbox), I can rollup that data into both Week and Month views, giving a snapshot of how I'm progressing, without having to do any real work during the reflection period itself.

If you track the most important aspects of your days, you’d get something like this at the end of the month:

All of these entries are occurring on a daily basis, but when viewed as a whole, there's two key effects:

  1. All of your accomplishments over the past month are clear and in one place

  2. You have a visual representation of anything from reading, to workouts, to journal entries, to feelings throughout the month

  3. All important data points are displayed, reducing chances you’re forgetting/overlooking key areas

If we circle back to The Forgetting Curve, using a tool like Rollups can allow us to visualize anything and everything we track daily.

How to Move from Reflection to Planning Mode

“A project is sufficiently planned for implementation when every next-action step has been decided on every front that can actually be moved on without some other component’s having to be completed first.”

David Allen, Getting Things Done

I love this quote from Getting Things Done (blog post), because we can easily swap out 'project' with 'month.' Setting up the upcoming month through the lens of identifying all the actions that need to take place can apply to projects, goals, or habits.

Once we have a system to visualize all the most important data from the previous month, we can know bring this knowledge into planning the future 30 days. There are 5 key areas to consider when planning the upcoming month:

  1. What events, meetings or engagements do I have scheduled?

  2. What projects are to be completed within the month?

  3. What habits am I trying to build or continue to build?

  4. What other actions can I take to work toward my quarterly or yearly goals?

  5. What systems, projects, or actions can I archive?

This list could be a lot longer – clearing out your Getting Things Done Inbox for example – but i've found these to be the most consequential factors to setting up a successful and fulfilling month.

The Minimalist Monthly Planner template

If you're like me and often download tons of templates just to explore them and question your own methods, this one may look a little different.

The Minimalist Monthly Planner is a pared-down variation of Manifest OS, mainly to provide some context as to how you can track certain things daily, and have those items roll-up into the monthly view. Habits are limited to checkboxes (though I love to use relational databases for things like exercise or books), and journal entries are limited to Intentions, Wins, Challenges.

Here are some things to keep in mind if you explore the MMP:

  1. Do I already utilize some of these tactics?

  2. What aspects can I incorporate into my own system?

  3. How can I add or remove components to meet my goals?

If you have current systems in place when it comes to journaling, project management, or habit-tracking, you should 100% continue to use them. Perhaps, this template may stir some ideas on how you can plan on reflect monthly, using the systems you already have in place. Click below to sign up and I’ll send you the template, for free.

Get the Monthly Planner Template

Do you currently have a system in place for monthly planning and reflection? I’d love to hear about it! Drop a comment in this page, or if you’re on Twitter, send me a tweet or DM at @davefromhialeah.


Brooks, Arthur. “How to Know That You Know Nothing.” How to Build a Happy Life
Le Cunff, Anne-Laure. “The forgetting curve: the science of how fast we forget".” Ness Labs
Carroll, Ryder. The Bullet Journal Method
Allen, David. Getting Things Done

Other News

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Building a Website with Notion & Super

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