My Annual Review Process

Last updated: December 2025 9 min read

Every December, I do an annual review over the course of the entire month. I’m not trying to generate a highlight reel, and I’m not trying to manufacture motivation for January. I’m trying to understand the year I actually lived, including the parts that don’t show up cleanly in a work recap. When I do this well, I end the process with a clearer narrative of how I spent my time, who I spent it with, what I cared about, and what I neglected. That narrative becomes the foundation for choosing themes and goals for the next year.

Ever since I became a dad, the stakes have been meaningfully higher. I still care about building a strong career and providing for my family, but I also care about something that is easier to lose in the noise, which is whether I’m actually present with them. I care about whether I’m building the financial foundation that gives my family options in the future, but I also care about whether the day-to-day experience of our life is good while I’m doing it. This review is one of the ways I keep myself honest about that balance.

I started doing this in a more structured way around 2021. The structure matters more than I expected, because a year is long enough for your memory to lie to you. Recent weeks crowd out earlier months. Work artifacts tend to dominate because they’re visible and measurable. Quiet improvements or slow declines in health, relationships, or stress often fail to register until they become problems. This annual review is how I step back far enough to see trends that are hard to notice when I’m living in the week-to-week.

Let’s look at each step of the process.

Step 1: Gather the sources for the year

I first pull inputs from a small set of tools that collectively contain the story of my year. I treat this process like an investigation and find it best to not rely solely on memory.

My primary sources are:

Google Calendar, reviewed across four separate calendars:
- Work
- Personal
- Family (shared with my wife)
- Business (creative projects, consulting, and anything that’s “me but not my job”)
A paper journal, which includes day-to-day notes and also weekly and monthly plans and reviews that become source material for the annual pass
Obsidian, which holds both my annual review document and my broader “second brain” that I can link back into across topics and areas
Analog note cards, used occasionally when I want a more granular pass on what I was thinking at a particular time

Over the last year or two, I’ve also started treating a couple of AI tools as part of my “memory infrastructure.” I’ve had mixed success (okay, mostly failures) with AI wearables, and I don’t think they are a requirement for this process. I’ve had much better success with AI note takers like Granola, which I use regularly and which has meaningfully improved my ability to remember what happened and why it mattered. I’ve also had good results with dictation tools like Superwhisper, especially when I want to capture thoughts quickly and turn them into usable writing later. I don’t use AI to tell me what my year meant, but I do use it to reduce the chance that I forget the raw material.

Step 2: Rebuild the narrative from the calendar

Calendar review is the closest thing I have to log analysis for my life. I use it to reconstruct the narrative of the year without relying on recall, and I focus on anchor points rather than exhaustive detail. Anchor points are moments that made a difference in some way. They’re trips, major family moments, work inflection points, health events, relationship shifts, and weekends that stand out because they changed what I did next or how I felt. The goal isn’t to capture everything, but to recover the shape of the year so that the rest of the reflection has something real to attach to.

Step 3: Review the supporting material from the journal and notes

After I go through the calendar, I move into the supporting material. This is where my paper journal becomes especially valuable, because it contains weekly and monthly plans and reviews that capture context I might not remember from calendar entries alone. The calendar tells me what happened and when it happened, and the journal often tells me how I experienced it and what I was trying to do at the time.

This is also where Obsidian starts to do more than store the annual review. Obsidian is where my second brain lives, and I have notes across many different subjects and areas. Keeping the annual review in the same system means I can link directly from the annual narrative into the underlying material, whether that is a project note, a health note, a travel plan, a relationship-related reflection, or a system I was experimenting with. Those links matter because they let me preserve details without stuffing everything into the annual review itself.

I care about recovering the whole year because a work-only review can be deeply misleading. In 2021 and 2022 there were stretches where, on paper, I looked extremely productive. I shipped a lot, and I did work that I mostly enjoyed. If someone had asked for a summary of accomplishments, I could have produced one that sounded like a big success.

At the same time, I was stressed and burning out, and I was dealing with RSI issues in my hands and wrists. Those issues were signals that parts of my life were running too hot. A review that only measured output would’ve rewarded exactly the behavior that was pushing me toward a worse situation.

Step 4: Answer the annual questions first

After I’ve reviewed the year, I go through a set of questions that are broad enough to capture what matters and plain enough that I can’t hide behind clever phrasing. I keep them mostly consistent across years because consistency makes comparisons possible.

These are the questions I come back to:

Am I happy? Is my family happy?
How did I take care of my family?
Where have I contributed?
Did I deepen relationships with my core relationships?
How did my physical health improve or decline?
How is my emotional and mental health?
How did our financial situation improve or decline?
How did my career evolve?
Where did I grow intellectually?
Where did I grow creatively?
Which systems worked or didn’t work?

Step 5: Scan the whole system, not just one area

After the guiding questions, I work through the categories that fill out the rest of the year. I use the same sources throughout, but the category structure helps me avoid leaving big areas unexamined.

My core categories are:

Major events (family and career moments that had a meaningful impact)
Relationships (family, friends, and the quality of the time I spent with them)
Physical and mental health (patterns, not just isolated moments)
Travel (what it reveals about priorities, transitions, and stress)
Home, legal, financial, and car-related developments (the adult-life operations that are easy to ignore until they explode)
Work, career, and creative efforts (a deeper dive that I keep separate)
Fun (games, music, TV and movies, activities, and what actually felt restorative)

I separate work, career, and creative efforts into their own deep dive because work tends to generate artifacts and metrics, and it can easily take over the narrative of the year if I let it. The separate review gives work the space it deserves without allowing it to crowd out everything else. The separation also makes it easier to be honest, because I can look at work in its own context rather than treating it as a proxy for whether the year was good.

The way I move through these sections isn’t strictly linear, and I don’t force it to be. The categories are connected, and memory behaves associatively. Something about health will remind me of a system I was using, or not using. Something about relationships will remind me how I actually spent my weekends. Something about travel will surface a work stressor that was shaping my mood. I let the connections happen, and I capture them as they surface, because those links are often where the real insights live.

Timing is a major part of why this works for me. I spend basically all of December on the personal, family, and home retrospective because those areas are the most important and because they’re the easiest to neglect when work gets loud. Several of the jobs I’ve had used a fiscal year calendar where the new year starts in February, and that has been convenient because it lets me use January and into February for the work, career, and creative retrospective. Even when the fiscal calendar doesn’t align perfectly, I still try to give myself weeks rather than hours, because a year contains more than you think and it doesn’t resurface all at once.

Step 6: Turn the review into next-year themes and experiments

After I’ve reconstructed the year and captured the major patterns, I use the output to decide themes and goals for the next year. I don’t try to convert the review into a massive plan, because that usually fails immediately. I look for big-picture themes that explain what worked, what didn’t work, and what needs to change. Then I translate those themes into my 90-day Tiny Experiments approach, and I choose a small number of concrete experiments, usually one or two per area, that are small enough to be real and clear enough to track. This flows right into my Q1 planning.

Focus on the process

I keep doing this each year because it improves my ability to live intentionally, and it reduces the chance that I’ll sleepwalk through a year and only notice the trade-offs after the damage is done. The structure isn’t the point, and the tools aren’t the point. The point is to see the year honestly, including the parts that are inconvenient to admit, and to use that honesty to make the next year more aligned with the life I actually want.