Behind the Scenes of the Annual Review 2022
Last week, I wrote my first public Annual Review, read it here!
I did two exercises to prepare for my annual review and explore what might be fun for me to write and interesting for others to read. After sharing both of these with a few friends, they encouraged me to polish them up and share them.
Part 1 is The Annual Review: A One-Act Play. I had been struggling to write an annual review for a while because I had multiple competing motivations for writing one. I started writing one in mid-December and kept rehashing it. This is a one-act play that started as a joke dialogue riffing on my inability to finish my annual review. In the end found writing it more fun and interesting than writing my annual review.
Part 2 is Analysis of My Favorite Annual Reviews. I researched other people’s annual reviews and wrote down the things I like and the things I might borrow, stylistically and content-wise, for my own Annual Review next year. So below is a summary of some of my favorite annual reviews that I found from other people in the online creator-writer-entrepreneur network.
Part 3 is Looking to 2023, where I reflect a bit on all of the things that I enjoyed about all the different Annual Reviews, and how I might structure and approach my 2023 Annual Review as a Philosopher, Wordsmith, and Archivist.
Part 1: The Annual Review: A One-Act Play
This story has three characters, each of whom represents one possible motivation for writing an annual review. Think about them the same way you think of the characters in Inside Out or similar movies, where somewhere deep inside of a brain these three characters are trying to come up with the best possible annual review.
The ARCHIVIST wants to write a by-the-book annual review. He is most interested in making a comprehensive catalog of the year, covering all the dates and what happened. He is a dispassionate wonk. His guiding principles are accuracy and clarity.
The PHILOSOPHER wants to glean some new meaning or insight from this year’s annual review. This year felt different, and he is eager to extract something salient from all this navel-gazing. He is somewhat haughty and simultaneously a wide-eyed truth-seeker. His guiding principles are extrapolation and coherence.
The WORDSMITH, who is most beholden to the audience, and wants to write something that is equally entertaining and informative to both people who are already invested in his writing and people who may have just subscribed to the newsletter. He is a bit needy and sarcastic but also a talented writer. His guiding principles are entertainment and engagement.
This is the transcript of their meeting to plan and write the annual review.
(Scene: Three men sit in a room with a chalkboard and notebooks. They call to order the Annual Review meeting. The ARCHIVIST stands up and walks to the chalkboard to begin writing when he is interrupted—)
What are we really doing this for anyway?
We’re writing the annual review. Let’s get started: “January. On the 1st, I did nothing that I can remember.”
(The WORDSMITH jumps out of his seat and motions theatrically.)
We can’t start out that way. We need to hook people in.
I don’t agree, this is more important to us than anyone who will read it. But if you insist, let’s start with a quote: “‘Life is what happens when you’re busy making other plans.’ -John Lennon. OK, sounds good? Moving on. January 1st: I did nothing. January 2nd: I believe I exercised. January 3rd–”
That intro is no good. He got Covid at the beginning of the year. His wife had it too, remember? Very eye-opening experience. A little bit scary and cathartic. That is the truth of this year’s start and how the essay should start.
(ARCHIVIST hastily erases everything on the board and begins to write again.)
“January 1st - I did nothing. I had Covid. January 2nd. I still had Covid. January 3rd—”
No, wait–that’s still wrong. Plus, we can’t start with that quote. It’s too basic. We need something more powerful. Do you remember the opening scene of Rent?
We didn’t watch Rent this year.
I know, but the opening song–the big number that goes like, “Five hundred, twenty-five thousand, six hundred minutes, how do you measure a year?” We should do something like that, some creative riff on the nature of time, how it is ephemeral, sand slipping through our fingers no matter how we grasp, but it’s the effort to grasp and the way that it feels in our hand that makes it all worth it. Something like, “Our life is a library, full of books containing different characters, stories, and themes, and what is a year but all the books between bookends we placed at arbitrary distances along the shelf?”
What does that mean, though?
Yes, what does that mean?
It doesn’t matter–it’s got a vague prosaic quality while also saying something about life.
(The PHILOSOPHER stands up and walks to the only window with one hand stroking his beard, deep in thought.)
But we already have a connection to the arbitrary nature of time. It was once something that excited us. Do you remember at five years old, the day when the teacher sat us down to look at eight index cards hung on the wall that said, “M A Y 5 1 9 9 3”? And then she explained that it was a date, and that each day has a name. And that every day that humans could remember also had a name. And it was all we thought about all day–our minds brimming with possibilities. Now that I think about it, that was our first introduction to psychological richness—the first time we can remember staring off into the distance at castles in the sky. This has been something like, “the year of psychological richness.” So maybe that’s how we start, with a theme?
Yes, I understand the last few issues of the newsletter mentioned psychological richness, but I fear that if we commit to this theme then the annual review next year will not be consistent.
Does it matter?
Does anything matter?
(They all pause, but the ARCHIVIST and WORDSMITH exchange worried glances, then the PHILOSOPHER turns from the window and joins them again near the chalkboard.)
Okay, a theme it is. But how to hook people in?
With a definition, obviously. “Psychological richness refers to the presence of novel, complex, and perspective-changing experiences in one's life. Alongside happiness and meaning, it is one of the three qualities that psychologists consider part of ‘the good life.’”
Respectfully, why would anyone care about an essay that starts that way? Let’s raise the stakes–if a character doesn’t change, nobody cares about the story. How about, “I had a good life before, but I was only living in two dimensions. This was the year of psychological richness.”
Let’s run this back. Clearly, this was the year of fatherhood. His daughter–his first child–was born in January. She dominated the year unlike anything else. Yes, other things happened, but fatherhood is the prism through which the rest of the year should be filtered.
Truthfully, I think you’re correct. If we really needed a coherent theme, we could integrate fatherhood into psychological richness.
A coherent theme is good. How would that work?
What is becoming a father if not one of the most complex, perspective-changing experiences available to a man? It certainly changed his perspective on a lot of things. Don’t you remember any of the essays he wrote this year?
It certainly changed how he thinks about self-care:
"I had to become a father to see myself through time, not as a snapshot of immediate needs, but as a long-term project. I am not just me today, in this moment, following up yesterday and preparing for tomorrow. I am me across my whole life, from helpless child to old man–son, brother, friend, student, teacher, husband, uncle, father, and who knows what else–and I am worthy of investing the effort and money that one would invest into a child in their care.”
It also allowed him to thread the needle between his dreams, his insecurities, and his childhood relationship to his Mom:
“It seems paradoxical that by diving in and “feeling every feeling,” I would gain insight on how they are inherently transitory, but that has been my experience. The things that stick with me the longest and bother me the most are the things I try to avoid or ignore, when what I really want the most is to just let them go. After all, you can’t let something go if you don’t know you have it. Maybe that’s what I’ll try to teach my daughter.”
Those are good excerpts, and he wrote them both this year. But let’s not get carried away with the theme. Let’s make sure and record what actually happened. We can start with the broad outline so we have a good idea of January:
(The ARCHIVIST walks to a new part of the chalkboard and starts writing.)
“The baby was born.”
I think the difficult part in this will be explaining how fundamentally a baby has changed his life and impacted him, while leaving space for other things to have an impact, and not making the entire review about being a Dad.
We can just call it out, something like: “2022 was the year I became a father. All the cliches are true. You never sleep. You’re always tired. It’s like your heart is living outside your body. It was both my biggest achievement of the year and, in another way, not really an achievement at all. I was there and supportive but my life did all the work. Plus, becoming a father isn’t an achievement in the same way as winning a race or reading a certain number of books or reaching an income threshold. It is more like there is a new layer to my life–one that pervades every aspect of my life and changes the way I think. Every time I make a decision or memory it’s now put through a new filter of ‘what about her?’ because I’m a Dad and that’s what my daughter means to me. So it’s not like one achievement or one thing that happened, but rather a separating line that adds a new layer of meaning to everything that comes afterward.”
(Bemused) That’ll do.
I agree. Question–should we include the fact that in the first four or five weeks she was alive, he binge-watched the Sopranos for the first time while feeding her early in the morning and late at night?
No, that’s not particularly meaningful.
Yes, and not really appealing.
OK, he seemed to enjoy it quite a bit so just wanted to throw that out there. Anyway, February! Not a lot happened here. A lot of the family of three sitting around eating Doordash and Uber Eats. Perhaps a rant about delivery prices from the WORDSMITH? Or rumination on being stuck in the house from the PHILOSOPHER?
(The PHILOSOPHER and WORDSMITH both shake their heads and chuckle.)
Archie’s got jokes huh?
This isn’t my only job. Anyway, March. This one is easy: “Write of Passage. There are several ways to approach this. We can show before, during, and after. We can link out to the website. We can describe each of the classes. Perhaps include before and after writing samples?”
Hopefully, the annual review itself is enough of an “after” sample.
We certainly need to cover the impact of Write of Passage and how much it changed him, but I don’t know how. “I have always wanted to be a writer, but I never actually wrote anything because I was afraid of failing. I spent a lot of time learning about writing, but I never actually did any writing myself. I recently took a writing course called Write of Passage and learned that the only way to become a published writer is to actually write and then publish it. This realization was like a sports metaphor for me, where I realized that I can't just show up to a race and expect to win without training. I need to actually put in the work and practice writing consistently in order to improve and eventually become a published writer.”
Let’s leave the writing to me–it sounds like a robot wrote that1. We can just refer them out to the actual essay.
That should cover it.
Not much of significance happened in April, although May was big. It was when the Center was endowed. We’ll put in a short note about the writing group he formed after Write of Passage and how helpful that was. This might also be a good time to mention his involvement in the Soaring Twenties Social Club.
That’s easy–the landing page is a work of art, we don’t even need to explain that it’s a group of writers and artists or that he likes participating and getting feedback. Just let people discover it.
OK, done. Now, May is pretty big. There’s happy hour for his wife’s birthday.
Yes, that was pretty significant wasn’t it?
It’s hard to sell going to sushi happy hour as a particularly weighty experience.
The point isn’t that they went out to get sushi for happy hour at the same restaurant they ate at the day after they got married. The point is that the day after they got married, it was pure bliss, they sat there for four hours, he had a friend who worked there. On her birthday this year, they were in and out in an hour to get back to the babysitter, but even after all the stress of the baby, and having to rush out and squeeze in a date, and getting no special attention having to sit too close to people, he realized how happy he was, and she did too, and they realized how much they really loved one another–and how affirmed they felt together doing this thing called life.
It’s going to be really corny if we write all that out.
Yes, now that’s something juicy! We need to write something dramatic. Something like, “he received the text that the center was receiving an endowment and bawled like a baby on the couch. After all six years of hard work and the occasional self-doubt, his team had made it. The late nights, early morning, and wondering whether he was doing the right thing–all of it vindicated in one fell swoop. Their work would be permanent. No matter what happened from then on, he could look back at the center and know that his work had mattered. His wife walked in and read the text and fell to the couch, weeping with him.”
That is powerful. You know how meaningful that idea is to him–that someone should understand the full weight of their work and sacrifice in time to appreciate it. He wrote a whole essay about it.
Yes, it was a meaningful moment. However that is not going in the annual review. First of all, why is that written in third person? Isn’t he writing this as himself–unless I missed something and he wants to do some kind of derivative Inside Out type dialogue? Second, that’s not what happened. There was one–maybe two–lonely tears of joy. And his wife was cooking dinner when he told her.
We can compromise. We’ll find something in the middle.
Alright–in that case the summer was big. There were the two trips in June, the family reunion in July, the baby starting daycare, and then the expo and allergist appointment in August.
Frankly, the trips were great but I don’t think they need more than a sentence each. “With friends, he took a fun weekend trip to Austin to watch a UFC fight–his first time away from the baby. At work, he was selected to join a small delegation of educators who visited the Rio Grande Valley, on a private jet.” That pretty much covers it.
He’s right. That’s good enough.
There is an interesting juxtaposition in July though. On the one hand, he took the baby to spend a week getting to know her family for the first time at the family reunion. On the other hand, he had to entrust her to strangers for the first time, after enrolling her in the preschool. There’s so much to mine from there.
As well as we could put something together where we talk about the difficulty of entrusting a child to strangers, or the odd situation we find ourselves in where people live so far from their family, the thing is–and I can’t believe that I’m the one that’s going to say this–I think it’s a bit of thematic departure. It might be an interesting essay on its own but doesn’t flow well here.
That’s fair. We will put in a sentence each like the trips. Then after that, Fall flew by because it was his first semester fully back at work, plus he was teaching extra classes and writing on the side. We do want to make sure and include the trip to visit his sister.
People do love travel writing.
Yes, but that’s not what he got out of it.
Fair enough–it seems important.
Yes, it was a special trip because it was affirming that he enjoyed being a Dad, and that he is looking forward to watching his daughter get to play with her cousin. Not exactly a densely packed lesson but very meaningful.
We can make that work. Although at this point he might seem like kind of a sap. And people might be getting bored, feeling like he is just listing things off that he did.
Great point! There are two last things that I think we should include, and I think that they make a wonderful segue into the forward-looking part where he discusses goals for next year. The first is his trip to the allergist, setting up an appointment to get his allergies taken care of for the first time in his life. And the second are his trips to the speech language pathologist and later oral surgeon, to schedule the double jaw surgery he has needed for a long time. In a way, he was showing up for himself. Since the plan is to do that a lot more often, for him and others, I think the theme of 2023 should be “presence.”
Yes, we should include those memories. I will leave the theme of 2023 to be decided by you two.
I like the idea, but “Presence” seems so stuffy. Let’s just say the theme is “Showing Up.” It’s more fun, more to the point,
Close enough. But it doesn’t capture how ambitious he is being about the upcoming year.
Good point—shall we do a list of all the movies and books he’s read?
Until he has some specific angle to offer on that list, he is pretty certain nobody wants to read that.
OK, then. “Showing Up,” and what else?
How about, “Dream Big and Show up?”
Accurate—I love it.
Alright, “Dream Big and Show Up” it is!
In reality, a robot did write that, as in this was put together by ChatGPT.
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Part 2: Analyzing My Favorite Annual Reviews
I read or skimmed a few dozen annual reviews. I like most of them, because I enjoy reflection. When thinking about how to structure my own annual review, I went back through my favorites and came up with these fourteen annual reviews.
Below, I go through what I liked about each of the annual reviews. And, while I did not settle on a single format for this year’s Annual Review, I made a note of what elements I plan to think about or borrow for next year’s Annual Review.
I initially prepared this as a note to myself but a friend saw it and suggested I share it, so please forgive the fact that it’s a little “raw,” and if you see any typos or broken links shoot me an email.
Annual Review 2022 (from David Perell)
What I liked about it: David’s Annual Review was the first I read at the beginning of 2021. I knew very little about him or Write of Passage, but I was enthralled. I think of this as kind of a gold standard for Annual Reviews.
What to borrow or think about for next year: The temptation to just “do what David does” is so strong, that I’m actually not going to borrow or think about doing anything from David’s Annual Review for next year. Instead, I’m going to build mine from the ground up and compare when it’s finished, seeing if there’s anything else to throw in or reconsider.
Leo’s Lemonade (New Years Edition) (from Leo’s Lemonade)
What I liked about it: I think Leo does brevity particularly well. I admire and envy his current project where he is living in twelve countries over twelve months. I think that his newsletter (especially this edition) is a great way to pack a lot of interesting information into a short format. It helps that he has great photographs and graphics to use, and that he is doing something super interesting.
What to borrow or think about for next year: One interesting thing I noticed about Leo’s photos is that–in this issue–he’s not in any of them. I don’t normally think to take “action shot” or “still life” pictures when I’m out and about, and I hope to do that more this year so I can include them next year. I also hope to create or find some cool graphics to include in my own annual reviews for next year.
My 5 Favorite Books I Read in 2022 (from Better Than Food)
What I liked about it: I love Better Than Food book reviews. He has a dry sense of humor and is insightful. He is also stupid well-read, but almost all the reviews are self-contained: you don’t need to “bring a book to that book” to understand what he’s saying. He is so good at articulating what his favorite reviews are. (He also reminds me of one of my best friends from high school and college who referred to himself as a “gentleman dirtbag,” and I hope if Clifford ever sees this he knows that is one of the highest compliments I can give.)
What to borrow or think about for next year: If I plan to do a review of my favorite “media,” next year, one question is how much of myself should I put in it? Right now, everything I write about is inseparable from me, more or less. But Cliff (the reviewer) says very little about his personal life aside from how the book emotionally or intellectually affects him. One thing I do like that he does that I plan to borrow is to summarize and synthesize my own content as new content. He has already reviewed all of the books he is talking about in this video.
✨ Letter 139: Goodbye 2022 & Hello 2023 (from Letter from a learn-it-all)
What I liked about it: Jen is a really fun person to read. Her writing strikes an excellent balance between cozy and exploratory. The fact that those things shouldn’t go together is what I think makes her newsletter (Letter from a Learn-It-All) so magnetic.
What to borrow or think about for next year: I love that Jen actually discussed and listed six of the different annual review templates that are popular. She also has one of the most persistent “vibes” to her writing of any Substack essayist I follow.
Three Quasi Unrelated Thoughts to Start the Year from (The Semi-Serious View)
What I liked about it: Silvio is another great writer who does a fantastic job of combining things that shouldn’t go well together: the casual and the profound, the personal and the universal.
What to borrow or think about for next year: This post was exactly as advertised: three quasi-unrelated thoughts. There was no further looking back, cataloging stuff, etc. While I plan to have more in future annual reviews, I know from reading my own journal from the past how powerful it can be to ruminate on things I was just daydreaming about before. I think I will integrate more of this in future newsletters and annual reviews.
8 New Year's resolutions for The Intrinsic Perspective (and 1 for me) (from The Intrinsic Perspective)
What I liked about it: I’m a huge fan of Erik Hoel’s. I actually have a piece mostly written and coming out soon where I dive into some of his favorite essays.
What to borrow or think about for next year: What I liked about it most was how focused it was on his writing. I am not sure whether mine next year will expand from my writing, or be both writing and personal–similar to this year’s–but, I do want to devote more time in my next annual review to specifically what I plan to do for my writing in the coming year.
I'm studying all the utopian novels this year (from The Novelleist)
What I liked about it: I love that Elle Griffin is (1) a utopian and (2) a novelist.
What to borrow or think about for next year: It would be nice if I niche down enough over the course of this year to set a super ambitious and relevant reading goal in my 2023 Annual Review, so that I can invite people along with me.
Substack or Bust (from the Dean’s List)
What I liked about it: Encountering Michael Dean’s writing is a mashup of experiences: it’s like reading Hunter S. Thompson the gonzo journalist, and Neal Stephenson the cyberpunk novelist (circa Snow Crash), combined with stumbling upon one of those long forum posts you encounter deep on the internet that almost seems like an alien intelligence because it is able to thread so many needles at once. I have always been a fan of Michael’s but I really liked this essay about moving to Substack because it synthesized so many ideas I’ve had for a while—but also blew my mind with a few completely fresh perspectives.
What to borrow or think about for next year: Very envious of his “let’s riff” section at the bottom and the number of comments. I tried a “crowd work” section on my first 20 or so issues of Thought Bananas and almost never got any feedback—but I liked “let’s riff” so much I’m bringing crowd work back. I also like the way that he picked one big event that coincided with the end of the year, and turned it into a de facto annual review, which is something I might try. The pull of cataloging the year is strong, but doing it this way is putting your money where your mouth is: it’s not just reflection, it’s reflection coupled with action—a big action at that (like moving your whole website).
On Making It To Lunch (from the G Word)
What I liked about it: Grace is a fantastic writer. This was so good because it was so idiosyncratic and fun. Grace divided the year into four parts but I have no idea if they were the quarters of the year or just arbitrary divisions, and I think that’s great.
What to borrow or think about for next year: I like the idea of dividing my year up arbitrarily based on the landmarks of my year and what happened, as opposed to months, quarters, or something else.
chasing answers newsletter #34 (from chasing answers)
What I liked about it: Randy’s style is very different from mine but he has one of the most “readable” newsletters I’m subscribed to. What this means is that, when I get most newsletters in the email, I usually open the email, read a line or two, and then archive it or send it to a “read later” app. This is because I always know I can go back and read it in the Substack app later. However, whenever I open one of Randy’s emails, I just read it all the way through every time—it never needs to archived. A lot of people try to use colloquial language and “write like they talk,” and Randy is one of the only people I know who pulls this off really well. It just flows–I don’t know how better to put it.
What to borrow or think about for next year: Beyond just the annual review, I hope to cultivate a stronger “voice” in my regular newsletters this year.
Sunday Candy #20 (from Sunday Candy)
What I liked about it: Like all Sunday Candy posts, Sandra is vulnerable, has great writing, and creates a sublime vibe.
What to borrow or think about for next year: When Sandra writes, I feel like I am an old friend of hers. But reading over her essay about her newsletter being consistent, I realize that there’s not much insider info. Meaning, she does a great job making her writing feel familiar, without making it feel like you need to, “be a part of the club” to get it. I want to be able to cultivate that kind of familiarity that also stands alone as good writing to a first-time reader.
Whose Mountain #7 (from whose mountain)
What I liked about it: I really enjoy Latham’s newsletter, because he is clearly someone who is practical and lives in the real world, but there’s a touch of mysticism and romanticism in everything he writes (even when he’s not actually writing about mysticism, which he does a lot of).
What to borrow or think about for next year: The way this was a reflection on the whole year of growth as illustrated in small vignettes was really well done. I think that I might incorporate that next year. It makes you really think about what mattered, instead of listing a bunch of dates.
My Annual Review: Leaning into Ambition and Not Destroying Myself (from Boundless by Paul Millerd)
What I liked about it: Generally, Paul’s success even with a long newsletter is super inspiring to me. A lot of people tell you to cut your newsletter and make it easier or shorter, but a lot of people also tell you to be yourself and write what comes naturally to you. Well, length comes naturally to me, so seeing Paul’s success with a long newsletter really does a lot for me and encourages me to iteratively improve, rather than simply try and cut down.
What to borrow or think about for next year: Paul does a fantastic job with sharing comprehensive news on both his professional and personal life. I have been pretty shy about putting too much about my actual personal life in my newsletters, but I am going to reconsider that and consider what it might look like to give better updates. I also like that I don’t think Paul uses someone else’s format. It seems like he literally just asks himself, “what are the best things to include in this newsletter/annual review” and then does that–which I love. It can be very tempting to follow a more popular format that someone else has laid out for you.
Review of My 2022 Creative and Business Goals with Joanna Penn and My 2023 Creative and Business Goals with Joanna Penn
What I liked about it: What I think Joanna Penn does masterfully is weave together her personal and professional resolutions–but she keeps her personal resolutions to the ones that inform her writing and work.
What to borrow or think about for next year: I think it’s super interesting that Joanna Penn does a full Review episode for the last episode and a full Goals episode for the following year. I think that I might also consider how I can broaden the scope of my annual review from just my writing to my personal life, but keep only the explorations of my personal life that are relevant to my writing.
Part 3: Looking to 2023
Here are the things I will try to do in next year’s Annual Review, based on all this reflection:
Include more pictures, not just of me but of cool scenes from my year.
Do a meta-review, where I synthesize my best newsletters and essays from the past year.
Consider using some of the questions other people have generated for brainstorming.
Keep a consistent vibe through the Annual Review.
In addition to cataloging the year, make my Annual Review very relevant to what is happening when I write it.
Make sure and treat Thought Bananas (or what it becomes) as an independent entity of me, the writer, and break down what happened in 2023 for it and the goals for it—as this is largely what people will want to see.
Make a strong decision about whether to include my personal life alongside my writing, based on how people respond to newsletters over the year.
Generate a reading list or—if that’s impossible—preview some writing and set some goals.
Divide the year up based on the 'seasons’ of what happened that year, so it flows better as a story, rather than using months or quarters.
Related to the above point, explore the highlights of the year through vignettes, not just a long list of “and then this happened.”
Do a separate year-end wrap-up and next year’s goals.
In my wildest dreams, 2023 is an unfathomably successful writing year. At the end of it, I do an Annual Review that people are clawing for, and that really helps and inspires a lot of people. Until then, I plan to do as I say in this year’s Annual Review, “Dream big and show up.”