2023 is officially coming to a close.

At the end of every year, I like to (1) reflect on the prior year and (2) plan for the year ahead.

I provided my simple seven question reflection process in my ​Personal Annual Review​ (you can download the template ​here​).

Today, I'll provide my ​Annual Planning Guide​, which will arm you with what you need to make 2024 your best year yet.

The guide covers the three components of my process:

1. Goal-Setting Framework
2. Four System Building Mental Models
3. Strategy for Tracking & Adjusting

I hope that it will spark you to conduct your own annual planning process for 2024, as I'm highly confident you will get incredible value from the exercise.

You can download the beautiful (and free!) printable PDF of the template ​here​.

The Goal-Setting Framework

There are two primary categories to consider as you plan for the year ahead:

1. Professional
2. Personal

Note: Some of you may prefer to break this up further, in which case you might split the Personal category into Health, Relationships, and Personal.

For each primary category, my goal-setting framework has four connected components:

1. Big Goals
2. Checkpoint Goals
3. Daily Systems
4. Anti-Goals

Here's how it works...

1. Big Goals

These are your big, year-long, audacious goals. These should be large and ambitious—but stop short of ridiculous.

The Big Goals are the summit of the mountain—motivating on a macro scale, but perhaps too far off and intimidating to be motivating on a micro daily basis.

2. Checkpoint Goals

You work backwards from your Big Goals to formulate a set of Checkpoint Goals.

If the Big Goals are the summit of the mountain, the Checkpoint Goals are the mid-climb campsite. You can't reach the summit without reaching this point, as all paths lead directly through it.

3. Daily Systems

"You do not rise to the level of your goals. You fall to the level of your systems." - James Clear, Atomic Habits

These are the 2-3 daily actions that you need to take to create tangible, compounding forward progress—the simplest daily actions to generate progress in a given arena.

If the Big Goals and Checkpoint Goals are your compass, setting your direction, the Daily Systems are your feet, moving you forward on your climb.

4. Anti-Goals

"All I want to know is where I’m going to die, so I’ll never go there." - Charlie Munger

Anti-Goals are the things we DON'T want to happen on our journey to achieve our Big Goals.

Anti-Goals are about avoiding the ​Pyrrhic victory​—a victory that takes such a terrible toll on the victor that it might as well have been a defeat.

If the Big Goals are your summit, Anti-Goals are the things you don't want to sacrifice while executing the climb—like your life, your toes, or your sanity. You want to reach the summit, but not at the expense of these things.

Putting It Into Action

To put the goal-setting framework into action:

1. Big Goals: Select 1-3 specific, measurable Big Goals within each primary category (Professional and Personal). Crystallize these Big Goals. Write them down.
2. Checkpoint Goals: Select 1 specific, measurable Checkpoint Goal for each Big Goal. Write it down below the associated Big Goal.
3. Daily Systems: Think about the simplest daily actions that would create forward progress toward your Big and Checkpoint Goals. Select 1-3 specific Daily Systems for each Checkpoint Goal. Write them down below the associated Checkpoint Goal.
4. Anti-Goals: To define your Anti-Goals, invert the problem: What are the worst outcomes that could occur from your pursuit of these Big Goals? What could lead to that worst outcome? What would you view as winning the battle but losing the war? Using your answers, select 1-3 Anti-Goals for each Big Goal. Write them down below the associated Big Goal.

To bring this to life, here's an illustrative example with one of my professional goals for 2024:

Big Goal: Reach 1 million subscribers with the Curiosity Chronicle newsletter. Currently at ~640,000

Checkpoint Goal: Reach 800,000 subscribers by June 2024. In order to reasonably reach 1 million by year-end, I'll need to hit 800,000 by the middle of the year.

Daily Systems: Content consumption, ideation, and creation are at the core of the newsletter's growth. 60 minutes of daily reading, 60 minutes of daily thinking (usually on walks!), and 30 minutes of daily writing will keep everything moving forward.

Anti-Goals: My Anti-Goals associated with my newsletter subscriber growth Big Goal are: (1) Never "sell out" with low quality, growth-hacky content and (2) Never let the scale of the reach impact my ability to connect deeply with any individual subscriber.

Four System Building Mental Models

Harsh Truth: Ideas are cheap, execution is expensive.

Even with our Big Goals to motivate us and our Daily Systems all planned out, we may fail to execute.

To guide your execution against your Daily Systems, here are four system-building mental models to support you in your journey.

Two-Day Rule

With whatever habit you're trying to build, never allow yourself to skip more than one day in a row.

Quoting a study in the European Journal of Social Psychology: "Missing one opportunity to perform the behaviour did not materially affect the habit formation process."

Skipping one day won't hurt your habit building, as long as you don't skip the next one.

30-for-30 Approach

Do the thing you're trying to improve at for 30 minutes per day for 30 straight days.

30 days of effort is a real commitment. If you are half-in, you won’t want to take it on and commit to the 30 days.

30 minutes per day is short enough that you can mentally take it on. Pre- start self-intimidation is one of the biggest drivers of stagnation.

30 days of 30 minutes per day is 900 total minutes of accumulated effort. This will yield surprisingly significant results.

Habit Stacking

James Clear famously pointed out that we execute on Daily Systems most effectively when they are fixed to a time or action that makes them easy to structure and regiment.

He calls this Habit Stacking:

• "I'll journal 30 minutes before bed."
• "I’ll do 25 pushups when I get out of bed."
• "I'll read 30 minutes of my favorite novel while doing cardio."

It's a simple, effective behavioral trick to execute against Daily Systems.

Minimum Viable Progress

Never skip a day, but anything above zero counts.

Have a goal in mind to do 30 minutes of the action every single day—but if you can’t hit that, just do any tiny amount above zero.

Remember: Anything above zero compounds!

Strategy for Tracking & Adjusting

There's an aviation concept called the 1-in-60 Rule. It says that a 1 degree error in heading will cause a plane to miss its target by 1 mile for every 60 miles flown.

The concept applies directly to your annual planning:

Tiny deviations from the optimal course are amplified by distance and time. A small miss now creates a very large miss later.

This highlights the importance of real-time course corrections and adjustments.

Conduct a three question monthly check-in on the last Friday of each month:

1. What really matters right now in my life and are my Big Goals still aligned with this? This is a simple way to pressure test your Big Goals and ensure they are still the right ones.
2. Are my current Daily Systems aligned with my Big and Checkpoint Goals? Assess the quality of your Daily Systems and whether they are creating the appropriate momentum. If not, make adjustments accordingly.
3. What do I need to cut from my life to progress more efficiently? Assess the quality of your environment and evaluate whether there are any toxic habits or relationships that are a drag on your growth. Make necessary changes.

Write the answers down.

The ritual takes ~30 minutes each month and creates an opportunity for monthly reflection and course correction on your journey.

Your Annual Planning Guide

To summarize my ​Annual Planning Guide​:

1. Establish Big Goals within each primary category.
2. Establish Checkpoint Goals for each Big Goal.
3. Establish Daily Systems associated with each Checkpoint Goal.
4. Establish Anti-Goals for each Big Goal.
5. Execute against Daily Systems using the Two-Day Rule, 30-for-30 Approach, Habit Stacking, or Minimum Viable Progress models.
6. Track and adjust using the 1-in-60 Rule Monthly Review.

The annual planning process is a life-changing exercise. I cannot recommend it highly enough.

To get even more out of it, consider conducting it in a small group format. Go through it individually, but then get together with a small group of your intellectual sparring partners and walk through it. Pressure test, question assumptions, and provide feedback. This is a great way to prepare yourself for 2024 to be the best year of your life.

As a reminder, you can download a beautiful (and free!) printable PDF of the template ​here​. Please share the link with anyone who you think will benefit from it.