The 2024 Annual Review: A December Ritual

Inside the proven system for turning reflection into results.

Colors of Trinidad, Cuba. I often visit the Caribbean during my Annual Review trips. 📷

Every December since 2005, I've taken time away to conduct what I call my Annual Review. It's a practice that has helped me achieve different goals, stay focused on what matters most, and create positive change in my life—and I'm not alone! Thousands of readers have adopted this framework for their own process, often sharing that it's helped them accomplish things they never thought possible.

The core principle behind the Annual Review is simple but powerful: we tend to overestimate what we can accomplish in a day, but drastically underestimate what we can achieve in a year. This exercise helps bridge that gap.

The Review consists of two main parts:

1. Looking Back

A honest assessment of the year that's ending, focusing on two key questions:

• What went well this year?

• What didn't go well this year?

I ask these questions first, before any future planning, and aim for at least 6-8 answers to each.

The key is to focus on things within your control—outcomes you influenced rather than random events that happened to you.

Here’s a cool thing: even in challenging years, this exercise often reveals more positives than you might expect. Several years in the past two decades I’ve been very depressed, but I’ve still been able to identify some achievements or “wins” that I’d totally forgotten about.

It's also crucial to acknowledge what didn't work, as these insights help shape better plans for the year ahead.

2. Looking Forward

Creating a thoughtful roadmap for the year ahead by setting specific, measurable goals across different life categories like Work, Relationships, Wellness, Learning, Travel, and Fun. Each goal gets paired with concrete action steps to help make it reality.

The goals must be measurable—avoid vague aspirations like "be happier" or "make more money." Instead, think "read 52 books" or "save $X per month for a down payment on a home." This specificity makes the difference between dreaming and doing.

I also choose a theme or short phrase for the year (like "Reinvention" or "Forward Motion") to help focus my energy and decisions. This becomes a north star for the months ahead.

The Annual Review isn't about making New Year's resolutions that will be forgotten by February. Instead, it's about creating an intentional framework for progress—one that's both structured enough to drive real progress and flexible enough to adapt as circumstances change.

Over the next few posts, I'll walk you through my exact process and share how I'm approaching my own Review this year. I'll also share the tools and templates I use, so that you can conduct your own Review.

Whether this is your first time hearing about the Annual Review or you're a longtime reader, I invite you to join me this year in developing your own practice. There's something powerful about taking time to consciously shape the year ahead instead of just letting it happen to us.

Stay tuned for more detailed posts about each part of the process. And if you're eager to get started, you can always check out the original post that started it all, any of the archival posts on my main site (just search “Annual Review” and you’ll find several dozen of them), or download the simple spreadsheet template I use for some of the planning.

Here's to making next year our best one yet! Or at least, you know, a good one.