7 reflection tools to help you complete your annual review + planning

for when year in review prompts feel too daunting and overwhelming.

it’s a wonderful life (1946) dir. frank capra

as with every other years, i spent the last week of 2023 reading other people’s year in review and coaching them through theirs instead of completing my own. i’m still surprised by how hectic last week had been compared to the year before—i was making plans with friends and family and trying to catch up with my holiday watchlist, which left very little to no time for me to sit down and complete my 2023 wrap up. took me a second to realize it wasn’t happening any time last week, so i decided not to force it and came up with this massive piece instead.

that’s the thing about annual review: it doesn’t happen overnight. you were never supposed to complete it in one sitting, because the more time you spend on it, the more gratifying it will be. and that becomes another whole thing: everyone around you is telling you to do your version of yearly recap but nobody is teaching you what materials to gather, which tools to utilize, and how to make the best out of it.

below is 7 reflection tools to help you complete your annual review and prepare you into planning for the new year. what this list tells you is basically what to look at when you’re doing your year in review. i’ve also included an example of my setup, how i turn them into valuable insights, and additional prompts that go with the reflection.

disclaimer:

• many of these techniques i learned from Notion Mastery (affiliate link), a membership program designed to help you level up with Notion¹. i’m a proud affiliate partner and alumnus, and what you’re seeing below is a direct outcome of having gone through the course and community experience as well as having been using the tool for 3+ years.

• i didn’t come up with the prompts; most are heavily curated from The Moon List, Unravel Your Year, and The Business of Community.

reading logs

BOOKS, ARTICLES, AND KNOWLEDGE OF VARIOUS FORMATS

last october i wrote quite a lengthy essay on why i think reading, amongst many things, serves as a time machine as powerful as writing and journaling. if you don’t keep a journal (nor you intend to rely on the practice of filling it out), keeping a log of your readings is the easiest way to help us collect valuable insights even if we don’t necessarily take notes out of them. the log itself already is a reflection of our curiosity and attention span at a certain time in our lives, and you’ll be surprised by how much your answer to the simple question of “why did i decide to read this?” will inform us about ourselves.

prompts to help you go through this reflection:

• what have you been loving recently because it feels tailor made for you?

• what deeply captured your full attention?

• contrarily, what did you halfway focus on?

• what questions and explorations are you taking with you into the new year?

brain vomits

RAW THOUGHTS & PONDERINGS

i don’t necessarily take elaborate notes out of the things i read, but if i was reading something and a relevant thought came across and grabbed my attention in a chokehold, i would want a place to capture that thought immediately for further inspection. there is a dedicated section in my journal that serves this purpose that i review regularly and towards the end of the year—some of which got repurposed into essay ideas while some others stayed unanswered. the point is to use these raw, unfiltered thoughts to guide you through your review and unravel what would otherwise have stayed hidden.

georgia o’keeffe on making your unknown known:

making your unknown known is the important thing—and keeping the unknown always beyond you—catching crystallizing your simpler clearer version of life—only to see it turn stale compared to what you vaguely feel ahead—that you must always keep working to grasp—the form must take care of itself if you can keep your vision clear.

prompts to help you go through this reflection:

• if your body and mind could talk, what have they been saying this year?

• what is one question that you found yourself asking over and over again this year? (and is there a version of an answer?)

• what patterns in your own behavior or thought process did you recognize (or continue) this year?

writings wrapped

+ OTHER CREATIVE OUTPUTS

personally, this is my favorite way to wrap up the year. looking back at everything i’ve written throughout the year, published or not, whoever the audience is, never fails to give me instant joy and allows me to celebrate how far i’ve came in my writing journey. depends on what type of creative journey you’re embarking on, this could be youtube videos published, newsletter streak, or podcast you’ve created. good news is that most platforms nowadays already have a “yearly wrap” feature do the heavy-lifting work for you (unless you have a specific metrics you’d like to dig more into).

to me, this is also what “running your own race” looks like.

Ava

did a fantastic job articulating this concept in her essay: you set certain standards for yourself, and you focus on meeting them. when you meet them, you’re proud of yourself. when you don’t, you urge yourself to try harder. you don’t question your standards based on what anyone else is doing. you don’t look over at someone else’s race and think, i’m doing a bad job because you’re going faster. you just focus on your own pace.

prompts to help you go through this reflection:

• how have your practice evolved over the last 12 months? what feels different now?

• how is your work a reflection of you?

• who are you becoming this year? does it excite or scare you?

• what memorable responses have you had to your work?

favorite moments

BIG WINS, SMALL JOYS

this one may seem like a no-brainer, but there is actually a vast difference between revisiting your favorite moments out of thin air vs. having a year worth of journaling habit to back you up. without any reflection tools to dig into, our brain will most likely zoom in to the most festive, eventful memories that we can remember where we *think* we felt the happiest. this doesn’t mean they aren’t worth celebrating—they are, and should probably go into our review! but happiness comes in different forms other than what feels like “cloud nine moments”, and we often overlook the simple pleasures that bring us joy without even trying that are also important to be grateful for.

i like having a visual diary of my favorite moments of the year, and my journal database does that for me. i have a view called “favorite moments” that holds all my journal entries with happiness score equals to more than 7, and it’s always very interesting to see which days are self-proclaimed “the happiest”. predictably, happiness means seeing the corrs live in my city for the first time, exploring bangkok with a close friend i haven’t seen in 2 years, and reuniting with friends over weddings and movie premieres. but it’s also nice to see happiness turns out to be as simple as watching kevin costner still win the golden globes over bob odenkirk (which of course got recorded in the journal).

prompts to help you go through this reflection:

• what are you most proud of accomplishing?

• what are all the things you’re grateful for from this year?

• which connections have you cherished the most this year?

• what’s changing this year in ways that delight you?

lowest moments

WHAT WENT WRONG

making room for grief is the complete half of celebration, if not the key of reflection itself. so in addition to having a “favorite moments” view, i also keep another one that serves the opposite: to display journal entries that mark the days i felt the lowest and challenged (happiness score equal to lower than 4).

as with everything else, life roadblocks come in varying sizes. i’ve experienced losses this year that seemed nearly impossible to recover from, but sitting where i am right now and going through this reflection always managed to knock some sense into my head that things did get better at the end, however hard it had been at the time. it also goes to say how dramatic i can be when things go wrong and the comedy that follows when they didn’t end up being permanent situation.

prompts to help you go through this reflection:

• what are the things that didn’t go as planned this year in your work, in your life, and in the world?

• what parts of yourself and your life have ended this year?

• if you could forgive yourself for something from this year, what would it be?

• what are the hard questions this year brought up that you’re still wrestling with?

• what will you miss about this year?

themed practices

WHAT GETS LOGGED, GETS REVIEWED

back when i was still working on my english i would read books out loud for an hour and force myself to hold a conversation in every live event that i attended, logged the action into my journal entry and marked it as “practice day”, and kept it up for a long time. it was an ideal tracking system that requires absolutely nothing else other than showing up at the practice without any bare minimum—the complete opposite of my previous attempts where i over-complicated everything by fussing with metrics to track and milestones to achieve. i decided to throw all that away and focused on the only important thing: showing up.

a year and a half later, my speaking noticeably improved and i could manage conversations just fine without relying on the tracker, but the habit of logging my practices stuck and proved to be the only thing that works for me. so i started doing the same thing for other things i want to be better at:

• drinking water

• eating vegetables

• working out

• keeping a running habit

• connecting with friends

unlike SMART goals that you can pre-plan and set an ETA for completion, identity-based goals rely on you showing up and do the thing that will bring you closer to said identity. for example: there is never gonna be any prestigious roadmap that will get me to eat vegetables more, but i could, however, add some greens in my noodles for lunch today, and count that practice towards the goal.

prompts to help you go through this reflection:

• what new priorities have you uncovered this year?

• what’s supported you most this year? what’s really helped?

• what do you wish you’d made more time for?

places

WHERE TO GO (AND NOT TO)

ever since

Regina

and i unspokenly committed to trying out coffee shops around the city as many as we could this year, i started logging our discoveries into my places database and turned it into a heatmap. this ended up being a pretty cool catalogue of places to go back to for when we were burned out from trying out new places and just wanted a quick no-brainer to hang out, and was what kept us from going back to places that are clearly overhyped and not worth the visit.

prompts to help you go through this reflection:

• what are the places in your city, town or neighbourhood you’d like to explore?

• who are the people you’d like to connect with more?

• when did a field trip make a difference this year, and how?

on why humans need annual reviews to make sense of things:

terrible years really make you understand the point of a new year. i know nothing much will have changed between dec 31 and jan 1, but we need to be able to partition off everything that’s happened to us, we need a moment to say, ‘that’s done, we’re done with it, it’s over’ and have a little hope that the future will be different. we need to be able to stop and take a breath and sing, in the middle of winter, and prepare ourselves for spring.

i know it’s probably too late to wish you all a happy holidays, nonetheless, i hope you had a good one, and thank you for sticking with me and doc day afternoon.

here’s to 2024!

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