My Annual Review + Planning Loop

My Annual Review + Planning Loop

​Every December, I feel a familiar tension. Part of me wants to close the door on the previous year as fast as possible and start fresh with new goals, new energy, and a clean state. Another part of me knows that if I don’t slow down and actually look back at the year I just lived, I’ll end up repeating the same patterns, without much of the learning on the things that happened.

Over time, I’ve landed on a review and planning loop that’s intentionally simple, but deep enough to keep me honest. It helps me zoom out, reconnect with what I really care about, and translate that clarity into action.

This loop has three layers:

My Annual Review + Planning Loop
My Annual Review + Planning Loop
  • a 3-year dream that describes the life I want to build for myself
  • a yearly plan that defines my focus and themes
  • quarterly quests that turn intention into momentum

​And while this article is focused on the annual -> quarterly path, it doesn’t live in isolation. Throughout the year, I also do weekly reviews and daily planning to keep the system alive. I’ll mention where those fit, but I’ll save the details for a separate post.

The point isn’t a highlight reel

When people hear “annual review”, they often picture a highlight reel: wins, milestones, promotions, trips, a neat list of things accomplished.

That’s not necessarily a bad thing, but it’s also not the part that changes anything.

The dangerous thing about a highlight reel is that it can become a story you tell to yourself, it can make you feel productive without being aligned, it can keep you busy without being intentional. You can even “win” on paper while slowly drifting away from the kind of life you actually want.

So my goal isn’t to manufacture motivation or cherry-pick accomplishments so I can feel good for a day. My goal is to understand:

  • how I actually spent my time
  • what I cared about in practice, not just in theory
  • what I neglected
  • which patterns are quietly shaping my life

A year is long enough for my memory to lie, recent weeks crowd out early months. Work is busy, loud and measurable, so it tends to dominate my story unless I deliberately zoom out.

​And if I’m not careful, that’s exactly how burnout sneaks in: I’ll normalize long stretches of “just pushing through,” I’ll accept stress as the default, and I’ll only notice the cost when I’m already depleted. A real review forces me to see those trade-offs early, not as drama, but as data.

Step 1: Gather the evidence for the year

I don’t try to do an annual review from memory

Memory is selective. It overweights what happened recently, what was emotionally intense, and what I’ve already repeated to myself as a story. It isn’t a reliable source to make an analysis and have a comprehensive view of my year.

So the first step in the process is boring, but necessary. I collect sources that contain the real story of the year:

  • my calendar (work and personal)
  • my journal and notes
  • my ToDos
  • photos (surprisingly good at triggering forgotten seasons)
  • lightweight metrics I care about (training streaks, articles published on my blog, etc.)

At this stage I’m trying to answer one question only: What actually happened?

I’m not judging or analyzing it yet, I’m simply collecting data points about my reality.

​Step 2: Rebuild the narrative from the calendar

Next, I scan the year month by month and capture anchor moments.

Not every meeting, not every ToDo.

Anchor moments are things that shaped the year’s trajectory. Those moments that changed my energy, my focus, my relationships, or my priorities.

Examples:

  • trips
  • family moments that changed the rhythm of life
  • work inflection points (a new role, a big meeting, a hard quarter)
  • health events
  • relationship highs and lows
  • weekends that changed what I did next or how I felt

This step is quite hard to build, and I don’t use any specific tools for it, just a good Apple Calendar, but it helps a lot the system I have in place to collecting that information in the first place, but after the year starts feeling like a story again.

And if often surprises me. I’d notice, for example, that a “slow season” was actually packed, just not with the kind of output that fills my memory. Or I’d realize that I spent an entire month in reactive mode and forgot it wasn’t “normal”, it was just... the season I was in.

The output of this step is a rough timeline that gives the rest of my reflection something concrete to attach to.

Step 3: Enrich the timeline with notes

At this point, I have a rough yearly timeline: anchor moments, seasons, and the events that shaped the year.

But my calendar alone is not sufficient, it is still missing something important: context.

A calendar can tell me what happened, but it can’t tell me:

  • what I was worried about at the time
  • what decisions I made (or avoided)
  • what I was trying to prioritize
  • what felt heavy, exciting, uncertain, or meaningful
  • what ideas were forming in the back of my head

That’s where my notes and my second brain comes in.

After I’ve identified the anchor moments, I go back and “enrich” the timeline by pulling information that lives outside the calendar:

  • journal entries
  • project notes and planning docs
  • weekly review notes
  • random captures
  • any lists of worries, goals, or decisions from that year

All of which lives in my Apple Notes (yes I know, Apple ugh, but after trying many note taking tools including Obsidian, I keep coming back to Apple Notes).

I don’t read all my notes, that would be insane, as I have tons of them, but I do try to skim through them and reconnect with the state of mind I was in. In this step AI is proving to be quite helpful, though so far I’m just piloting it, as I still don’t fully trust its output, but this past year it has been super helpful to be able to “talk” to my notes (and yes, using Apple Notes is a disadvantage, as I need to make an export to feed my custom GPT).

After I curate the information I add a few lines under each anchor moment with information like:

  • what was really going on
  • what I learned
  • what I would do differently
  • what I was grateful for then, and now looking in retrospective

This is always a bit different depending on exactly what happened, but hopefully those examples get my point across.

Once all the information is beautifully laid out, we can move to the next step.

Step 4: Answer what matters the most

After reviewing the year, I try to answer a few questions general questions, and some questions that come up from the exercise. I typically look for signals like:

  • Am I happy? is my family happy?
  • Where did I feel most energized? Most drained?
  • What did I repeatedly postpone?
  • What did I say I valued but didn’t protect with time?
  • Where did I over‑index on work at the expense of health, relationships, or presence?
  • Which systems helped? Which ones quietly broke down?

I’m not really trying to prosecute myself. I’m trying to understand myself.

Often, the best insight is something small and specific, a recurring friction point, a habit that reliably improves my mood, a type of commitment that always takes more of me that it should have.

This isn’t about judgment.

It’s about seeing the truth clearly enough that it changes what I do next.

​Step 4: Update my 3‑year dream

Only after the review do I open the document that matters most: my 3‑year dream.

This isn’t a list of goals. It’s a description of a life I want to live, written in a way that’s specific enough to feel real.

How I structure my 3‑year dream (and my task manager)

I organize my dream into three buckets:

  • Self: my physical health, mental state, learning, and inner life
  • Work: my career, creative output, leadership, and impact
  • Relationships: my family, close relationships, friendships, and sense of belonging

This mirrors how I organize my task manager and planning system. Every project, habit, or commitment ultimately lands in one of these three areas.

That consistency matters. It turns the dream into something actionable, because it maps cleanly to how I already make decisions day to day.

Here’s an example of a 3 year dream:

# 2026 — My 3‑Year Dream

## **😊 Self**

* I’m in great physical shape: lean, strong, flexible, with a sustainable fitness routine  
* I practice martial arts  
* I spend regular time outdoors, in nature or the garden  
* I read books on physics, creativity, and anything that deepens my understanding of myself and the universe  
* I feel calm, content, and aligned with my values, even in moments of stress and uncertainty

## **🧠 Work**

* I’m an inspiring and respected engineering leader, known for helping people grow  
* My YouTube channel is growing steadily  
* I’m working on my book  
* I’m building my website and newsletter to help other developers level up  
* I feel deeply fulfilled by the quality of my work and its positive impact on people

## **💕 Relationships**

* I’m fully present and emotionally available to my kids  
* My relationship with Diana is stronger than ever  
* We spend regular time together as a family, traveling, laughing, and having tech‑free quality time  
* We host regular gatherings with friends  
* I feel a deep sense of belonging and gratitude for the people in my life

The example in question is based on my actual 3-year dream, but it’s not exactly it, as I consider it quite personal.

When I revisit this dream, I ask two questions:

  • What still feels true and alive?
  • What feels outdated, performative, or no longer mine?

The dream isn’t a contract. It’s a compass.

​Step 5: Turn the dream into a yearly plan

The 3‑year dream gives direction. The yearly plan gives focus.

I don’t try to plan every month of the year. That always breaks on contact with reality.

Instead, I define a small set of yearly themes, typically three to five, that represent the most important shifts for the year.

Then I translate each theme into something I can actually execute.

Here’s the simple template I use.

# 🗓️ Yearly Plan Template

Theme 1:
- Outcome: What does “a good year” look like here?
- System: What habits or routines make that outcome likely?
- Trade-offs: What am I willing to not do to protect this focus?

(Repeat for 3–5 themes)

Example themes for me might be:

  • Strength and calm
  • Create consistently and lead well
  • Presence and connection

The yearly plan isn’t meant to be perfect. It’s meant to give me a small number of stable priorities that can survive a messy year.

Step 6: Translate the year into quarterly quests

This is where intention turns into action.

I treat each quarter like a focused adventure rather than a mini‑year.

A few simple rules keep me from overplanning:

  • one main quest for Life
  • one main quest for Work
  • everything else is optional

The reason is simple: if everything is a main quest, nothing is.

Here’s the exact template I use.

# 🚀 Quarterly Quest Template

## Main Quests
* Life
    * 🎯 What: What goal are we working towards? What’s our desired outcome?
    * 🥰 Why: Why do we care about this? Why is it important to us?
* Work
    * 🎯 What: What goal are we working towards? What’s our desired outcome?
    * 🥰 Why: Why do we care about this? Why is it important to us?

## Side Quests
* Life
* Work

--- 

## Prompts

### 💼 Work Main Quest Prompts:
* What's the one thing that would move the needle the most?
* If you fast-forward 3 months, what accomplishment that would make you most proud?
* What’s the one thing that would make everything else easier or unnecessary?
* What’s the one thing that you’ve been postponing but would be transformative if you tackled it?
* "If I spent the first two hours of my workday purely focused on X, it would have an enormous impact on my work."

### 🍃Life Main Quest Prompts:
* What’s the one thing that, if accomplished, would bring the most joy, fulfilment, or peace to your personal life?
* If you fast-forward 3 months, what’s the one accomplishment that would make you most proud?
* What’s the one change that would positively impact every other area of your life?
* What’s the one thing you’ve been avoiding but know would have a transformative effect on your relationships/happiness?
* "If I dedicated an hour each day purely focused on X, it would have a profound impact on my life."

How I choose my Q1 main quests

I pressure‑test each quest against three criteria:

  • Does it align with my 3‑year dream?
  • Does it express this year’s themes?
  • Is it concrete enough to win in 90 days?

Then I tighten it further by making the “What” measurable. Not in a corporate way but in a “will I know if I actually did it?” way.

Final step: Put it on the accountability system (aka notes, calendar and ToDo list)

​A quarterly quest isn’t real until it has time.

This is the moment where plans either become real or quietly become wishful thinking.

After defining the quests, I:

  • write down the yearly review, the 3-year goal, the yearly themes and the Q1 quarterly quests into my notes for accountability
  • block recurring time in my calendar for the main quests
  • set up any important tasks and deadlines in my to-do app.

​Conclusion: A simple loop that keeps me aligned

The annual review is the reset.

It helps me zoom out, tell the truth about what actually happened, and reconnect with the life I’m trying to build.

From there, the process becomes a loop:

  • 3-year dream gives me direction
  • yearly plan gives me focus
  • quarterly quests give me momentum
  • the calendar makes it real

​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.

Thanks for reading!