Annual Review 2021: The Year of Pruning
In gardening, there’s this idea of pruning — when a gardener prunes a plant’s branches to strengthen the main stems and to bring it into a certain shape.
2021 was the year of pruning for me. By the end of the year, I worked in an entirely different industry. My close friends were a different set of people. And I spent my spare time in a totally different way. I’m happier in every way, but this year was hard, harder than 2020.
The first half of 2021 was terrible work-wise, and it culminated in me getting laid off in July. Let’s call this The Great Inflection. I won’t rehash that story here — you can read it in this essay and in the 55th edition of my newsletter — but know that this was a monumental shift that affected my entire life. I’ll be referring back to it throughout this essay.
As is often the case, the most painful parts were also the biggest points of growth. In 2021, I mended and burned bridges and figured out the kind of work I want to do. Going into 2022, for the first time in a long time, I feel like my heart and my brain are finally in line to produce the best work I can do.
In this essay, I reflect on the 4 main areas of my life:
Personal
Professional
Writing
Creativity
For each area, I’ll answer 4 questions:
What went well?
What didn’t go well?
What did I learn?
What am I working towards?
Buckle up, friends. This is a detailed essay, and one of the longest ones I’ve ever written.
Personal
I always like getting the worst news first. So here goes.
What didn’t go so well?
Emotional health. I called them Emotional Upheavals.
Every 2 weeks, something at work, with a friend, or with family would happen, and it would knock me off my feet. Often for days on end. I would struggle to work or muster up the motivation to get out of bed. Depending on the gravity and the emotional energy I spent, the recovery period could range from a couple of days to, in the case of The Great Inflection, months. These Emotional Upheavals were the biggest source of growth and frustration for me.
Most of them happened in the first half of the year, leading up to The Great Inflection. There were smaller aftershocks all the way until the end of the year.
I'm proud of how I handled it all. But it was so frustrating how this volatile environment killed any creative momentum I had up to that point.
Spiritual health. I spent a few months reading Psalms. I regularly met with my church small group on video each Friday. I also finished reading Dietrich Bonhoeffer’s book Life Together with my group. But I struggled to maintain my daily devotional practice and read my Bible regularly. When I did read it, I struggled to remind myself of the lessons throughout the day.
What went well?
Habits. As my heart took beating after beating from situations outside my control, I dug my heels into what I could control: my habits. During the worst weeks of my year, I doubled down on my meditation and journaling practices. Even when all I wanted to do was lie in bed and listen to sad songs, I met my friends in the evenings for workouts and frisbee games. Forgetting my issues, even for a few hours, reminded me that while pain is necessary, suffering is optional.
I’m proud of how I reacted to everything and how I kept myself on track as much as I could.
Mental health. I measure my mental health by my curiosity and enthusiasm for learning.
In 2021, I worked on inducing flow and strengthening my focus muscles with time blocking. I started out the year hardly being able to focus for more than 40 minutes before needing a social media break. By the end, I could read for hours again, could grok white papers, and write for hours on end.
My big brain took a while to get back to itself, but it’s back, baby.
Physical health. All 4 markers I measure for my physical health improved this year:
According to my WHOOP, my heart rate variability or HRV in December has improved from my January number (Why not an Oura ring? It’s not built for sports, and I can’t play ultimate with it on.)
My body composition, specifically my body fat %, muscle mass and overall physique rating (based on % of fat vs muscle), are the best they’ve ever been. I don’t have any set goals, but my current numbers rival the ones from when I was an elite swimmer. (Ex. My current metabolism is still the same from when I was 19 and training 10-20 hours a week.)
(For the health nuts out there: I’ve used the same Tanita body composition scale for 10 years now. It’s probably not as precise as newer scales. But my priority isn’t precision. Instead, I just want a baseline by which to measure my progress and 10 years’ worth of numbers gives me that.)My mobility. My goal over the pandemic was to get my stability and mobility back while ultimate frisbee was on pause (I had ACL surgery in 2018). In 2021, I started doing 5-10 minutes of mobility work every morning, based on Kelly Starrett’s book Ready to Run and virtual mobility coach, The Ready State.
I’m a lot bouncier now and can land fine on both legs. I can also cut without my knee tweaking (a recurring post-surgery issue).How I feel before and after ultimate. One of my goals last year was simple: to not be sore after a tournament. My mechanics and mobility still need work, and I haven’t gotten to zero soreness. But I’m on the right track because (1) I feel less sore the day after tournaments or multiple games and (2) the soreness is even on both legs or sides of my body. This means that my dominant right side isn’t overcompensating for my weaker left side and that I’m also stronger over all.
The issues have now moved higher up my body to my lower back and thoracic spine — a different set of less acute problems. I guess that’s good? 😂
Friends. This year, I developed two important friend groups that gave me the distractions and emotional support I needed.
The first one is with my friends Ryan and Dennis (hi guys!). They were my capstone project group in university, and we’ve seen each other through jobs, relationships, and life changes. This year, we started a book club to keep in touch during the pandemic and finished Quiet, Tiger Woods, and Flow. It’s always a good few hours of fruitful discussion whenever we see each other.
The second friend group is my frisbee-turned-life friends. We started out in March with a handful of ladies training together to get ready for the ultimate season as COVID-19 restrictions loosened. Eventually, we invited more friends to come out, and the group started to include guy friends and boyfriends, too.
Now we have a big group, with around 12 people in the group chat. We celebrated Christmas and friendsgiving together, went on hikes, scheduled “lunch n learns” in each other's work calendars 😏, had barbecues, hung out at tournaments, and celebrated each other's birthdays.
Ever since I learned about the concept of a “10 Club” (tweet and essay), I’d wanted friends for the long haul. And now I do, and I’m immensely thankful.
Family. My parents, sisters, and I got used to being under the same roof after spending most of 2020 trying to adjust. My parents and I finished watching all the Pirates of the Caribbean movies and shortly after, tore through all the Marvel movies in timeline order.
In August, all 6 of us flew to Whitehorse in the Yukon to go on a 2-week road trip. We saw the northern lights, came pretty close to the Arctic Circle, and met some adorable Alaskan Huskies. We almost got persuaded to move to the Yukon — there’s a tight Filipino community there. (Honestly, being Filipino-Chinese means that we’ll always find people like us anywhere we go.)
What did I learn?
I’ve always struggled to make and keep friends. I used to be terrified of being alone that I stuck around long after the mutual investment had withered away.
This year, I learned how to respect myself and my work, to give myself what I need, and to enforce my boundaries — so that other people learned to respect me, too. I realized I hated having other people’s expectations placed on me, especially if I didn’t feel like I had the choice to comply — much more than I hate the possibility of a life alone.
Along with this process of creative recovery and self-respect, I started to enjoy being alone! I became less afraid of hard conversations. I gained the courage and the freedom to reevaluate the people around me, get to the root of my Emotional Upheavals, and do what needed to be done. I proactively mended relationships that had been broken, and cut off ones that had started taxing me beyond what they gave me.
What am I working toward?
Single leg squats and getting stronger. Ultimate demands a lot of single leg work, from jumping to cutting to changing directions. Now that the soreness isn’t a bad pain, the next step is to rebuild the strength in my legs and core.
Online 10 Club. I neglected all of my online frens in 2021 because I didn’t have the emotional bandwidth. But now that I’m a lot better and have an IRL 10 Club, I’d like to build one for my online life, too.
Twitter, Write of Passage, CabinDAO, and my newsletter — I’m excited to meet and rekindle friendships with y’all who share the same intellectual interests and with whom I can grow and (eventually!) hang out IRL.
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And with that, I’ll let you get back to reading!
Professional
What went well?
Work (eventually). The Great Inflection is “great” for two reasons: it was a titanic wrecking ball that shattered plans for my future. But it was also a good disruption to my life: I didn’t realize how emotionally and mentally depleted I was from the grind.
In fact, amidst the pain of loss, I was relieved to be let off the hook. This gave me the space and the excuse to focus on my writing and creative recovery. A few months into it, my blog snagged me a spot in cohort 3 of the Creator Cabins residency. The residency eventually led me to a core contributor role at Cabins — and the flexibility to work on my blog and in web3.
And that brings to the next item on what went well:
My entry into web3. If you’d told me last January that I’d be writing about web3 and DAOs in my annual review, I wouldn’t even know what you were talking about.
After I built some initial credibility within CabinDAO as a writer — I worked with the cofounder to put this report together on DAO knowledge management in under a week — I continued giving feedback, helping DAO leaders turn their expertise into articles.
Eventually, new members started messaging me, started asking me about how to get involved in Cabin’s writer’s guild.
This was when the Cabin boys — Jon and Zakk — dangled an irresistible opportunity in front of me: the chance to build a media publication in the cutting edge of tech. This led me to my current role of consigliere, which revolves around two main tasks:
Directing new writer’s guild members to the Cabin projects that best fit their skills and interests
Building systems, writing documentation, and training contributors to scale our content without sacrificing quality
Since I started, we made significant strides towards organizing the chaos of a DAO. We…
Launched an internal weekly newsletter and formed a squad to execute it
Grew from 1-2 regular writers and 1-2 concurrent writing projects to at least 3-4 active projects at any given time with 4-6 active writers
Launched a feedback and editing squad with an initial group of 7 editors plus 1 squad facilitator to boost the quality of our writing projects and help our contributors become better writers
Went from an informal process to a documented, squad-based approach where topic experts, writers, designers, and editors collaborate on articles
Figured out a web3-native, initial version of how to reward all of our amazing contributors
Hit our stride with a weekly publishing cadence of posts
I went from being an independent contributor at my previous web2 role to a people organizer and coordinator role at Cabin — a new professional challenge I’m enjoying.
Ironically, the success of my job hinges on how well the guild functions without me, so I can’t even take credit for this. I only put 8 hours a week into Cabin. Fortunately, the DAO attracts top-notch people. Aside from a couple of hiccups, the team continued to publish and work when I took time off in December.
Compounding career capital. Working at Cabin, the pearly gates of a career in web3 flew open for me. Thanks to Jon’s referral, I was invited to attend tech investor Balaji Srinivasan’s VR lecture series on network states. My Twitter audience hit its stride when I started sharing my work in the writer’s guild. I meet so many new people each week that I need my Notion CRM to keep track of them all. It’s so fun to see my personal interests and professional career intertwining in ways I never could’ve imagined.
What didn’t go so well?
The Great Inflection. Yeah, it sucked. But I had to put it in here. Let’s move on.
What did I learn?
Leverage. I used to feel anxious if I wasn’t the one doing the writing myself. It was the only thing I thought I was good at. This was the big blocker I faced in my previous role as a content marketer.
But big missions require me to get better at building leverage, particularly in organizing people.
It’s not just about figuring out what I’ll do with my 8 hours at Cabin each week. Leverage means I’m constantly reflecting and calibrating so that the hundreds of collective hours the team puts in is the most effective allocation of their effort and time towards our goals.
Fortunately, I find more ease and fulfillment building systems and helping others do their best work than I do writing content.
What am I working toward?
“The best way to predict the future is to invent it.” — Alan Kay
Building CabinDAO’s media guild to drive the DAO ecosystem forward. For the first time in my career, my professional success doesn’t depend on my ability to produce words on a page. Instead, it depends on my ability to help others produce outstanding work that move the needle.
Initially, the Cabin call to adventure was the possibility of turning my dream of building a publication within a tech company into reality. (You can read more about this in my CabinDAO profile.) Now that I’ve been a core contributor at Cabin for 2 months, I realized that I can actually see 3 complementary personal dreams I can fulfill:
A writer-first media publication to accelerate Cabin’s vision of decentralized cities and creator economies and grow the DAO and web3 ecosystems. As a former freelance writer myself, I know how crappy writers, journalists, and other media folks have it in terms of working conditions and pay. Our guild will compensate writers and editors for their articles and for the long-term impact of their work (ex. long tail views, conversions, reach, etc.).
An online writing apprenticeship where someone can join the guild with zero writing experience, work on progressively challenging projects with seasoned writers and editors, and eventually take on a top tier, white paper-esque article themselves (like this one). More experienced online writers will also find mentorship, community, and further education beneath our decentralized roof. We’re not just looking for the best writers — we’re producing the best web3 writers, thinkers, and philosophers, too.
An influencer machine where our writers build their audiences and become influencers on Twitter and other platforms. We want to build a distribution machine where Cabin’s network and influence grows as an exponential product of its contributors’ networks.
Along with this vision, I’m thinking about the best way to measure our progress towards our goals, including contributor engagement, audience growth, and time to first bounty.
But of course, true to the web3 way of shared ownership, this isn’t up to me. I’m currently working on a governance proposal to see if the community would like to set this as the media guild’s mission moving forward. It’s up to the members of the guild to say whether this is a direction we want to undertake.
More web3. COVID-allowing, I’d like to fly back out to Austin in 2022 for Build Weeks or to help out with DAO retreats. I also want to attend more web3 events, meet more cool people in the industry, and make more frens.
Writing
What went well?
Writing output. In 2021, I published 38 blog posts and essays. That’s more than what I published in 2020 and 2019 combined. My two favourite ones are “CabinDAO: LARPing as a City State” and “Becoming Autotelic: The Part About the Flow State that No One Talks About”. I wanted to rev my engines to go hard on my writing in 2022 — and I did that.
Distribution. For years, I had been honing my content marketing skills. I was happy to continue learning and build blogs for others while I figured out what I wanted to build my audience around. Then, when I stumbled upon DAOs, web3, and the metaverse, I knew that this was it. I went all in.
Just from niching down and publishing, I doubled my Twitter audience. As of January 2022, I crossed 1,000 Twitter followers.
Niching down to web3 and growing my Twitter audience has been the biggest source of newsletter growth for me. Without much direct promotion, more people subscribed to my newsletter, as well!
What didn’t go so well?
The 100 in 100 blogging challenge. In Q4, I launched my 100 blog posts in 100 days challenge with this tweet thread. I was supposed to publish 100 posts in 100 days by February 26, 2022. I’m writing this on January 14th, and I’ve only published 30.
So technically, it’s a failure. But I’m not disappointed at all.
I had set a moonshot goal (at least for me) in public and fell far short, but still achieved the private goals I had set for myself:
To help me get consistent with my writing practice
To build in distribution into my writing routine (another reason my Twitter audience grew)
To get the buildup of ideas and half-finished essays out of my inbox and into the world
To help me hone in on my personal monopoly and find the topics I want to commit to (I started out thinking I wanted to write about creativity, the creator economy, and maybe web3. I ended up just writing about web3, DAOs, and Cabin.)
Thanks to this epic failure (lol), I now have a solid path forward for 2022.
What did I learn?
Figure out my highest-leverage activity and stick to it. In 2021, I learned that my highest leverage activity each day is writing (no surprise there). My best ideas pop out when I’m typing in Drafts to clear up my thoughts. The solutions to my problems come to me when I’m scribbling in my journal. My co-contributors at Cabin benefit when I document, write down, and share my thoughts and observations (a.k.a. “Roxine’s Memos”). My accountability, specific knowledge, and leverage compound each time I hit publish on an essay, a newsletter, or a blog post. This insight informs my goals for 2022.
What am I working toward?
10k on Twitter. On January 10th 2022, my Twitter audience crossed the 1k threshold. By the end of the year, I want it to cross the 10k one.
These are arbitrary numbers — 10k is when my follower count becomes too big that Twitter abbreviates it and it just so happens that it’s 10x the number I started the year with. Ny private goal for this is to continue practicing learning and building in public.
Sponsorship revenue. This is a goal that I’ve had for years but never really felt like I could achieve. Until I realized that it’s all just numbers.
In 2021, I dabbled in affiliate partnerships with Readwise, Hypefury, and Convertkit. Combined, they make ~$100 a month on average. Not life-changing money, but they took me from zero to one on the passive income scale.
I enjoy curated, tasteful recommendations, the way Tim Ferriss does on his podcast, so I’ve decided that sponsorships is the way for me to go.
If I hit 10k on Twitter, I can comfortably expect my email list audience to sit at 1,000 without much optimization. It’s not a big list, but that’s big enough for me to experiment with ad spots in my essays and my newsletter.
My entire business plan aligns all of our incentives (yes, including you!):
Write more, better essays (You/Reader happy)
Audience grows (Roxine n sponsors happy)
Impressions grow (Sponsors happy)
More revenue (Roxine happy)
Write even more, even better essays (You/Reader happy, Roxine happiest)
(Yes, I did just refer to myself in the third person.)
A note on memberships vs sponsorships: I’m not a fan of content paywalls and monthly subscriptions for content because they hamper growth. If none of my stuff’s behind a paywall, every piece works hard for me to build my audience.
Commitment to writing quality and consistency. In his underrated book Great by Choice, Jim Collins has this concept called a 20-Mile March — sustainable performance inputs you work to meet, through hell or high water.
To hit the goals above, I have a simple 20-Mile March for 2022:
Daily: 90 minutes of writing, aiming for 750 words initially, building up to 1,000 words
Every weekday: share 1 idea from industry articles I read. Build up to sharing 10-15 tweets per day.
Friday newsletter: Alternate between an essay and a curated newsletter every other week. Once I feel ready, build the cadence up to a weekly essay _and_ a curated newsletter.
Finally, I’m going to put this quote here as a reminder to myself:
“Freely chosen, discipline is absolute freedom.” — Ron Serino
Creativity
The Great Inflection gave me the space, time, and excuse to focus on my creative recovery and my writing. To be at my creative best, my emotional and mental states must be in sync.
What went well?
The road to creative recovery. Julia Cameron’s The Artist’s Way — a book that guides the reader through a 12-week course to creative recovery — was the most impactful book I read/course I took in 2021.
I religiously wrote my morning pages and planned and went on weekly artists’ dates. Through the exercises, essays, and practices and reconnected with Little Me. I haven’t finished the course yet, but I’ve already made significant progress: I’m reading fiction again, writing short stories, and treat myself with more gentleness and respect.
Morning pages. I wrote these every weekday, went through 2.5 notebooks, and filled up my 12th journal this year. I used them to celebrate wins, work through problems, and heal from (a lot of) pain. I honestly don’t know how I could’ve endured 2021 without this practice.
What didn’t go so well?
The entire first half of the year. In a range from -10 to +10 with zero being the baseline, I was a -5 emotionally for most of the year. My mental recovered a lot quicker, but my creativity suffered from the emotional pains. Mentally, there were fits and bursts of inspiration, but generally, I hated writing and didn’t want to be near my computer.
(Looking back after writing this, I’m surprised and impressed that I was even able to output the work I did, in the state I was in. Makes me excited what 2022 will be like now that I’m firing at near-peak capacity.)
What did I learn?
Creativity is a product of emotional and mental health. Both my emotional and mental wellbeing affect my creativity and motivation for work. I have to keep them both healthy to be at my creative best.
Mentally, this means reading challenging and interesting books, learning meaningful skills, and working on creative projects that build leverage.
Emotionally, this means encouraging myself to do “frivolous” things I enjoy and letting me experience things I’ve always wanted as a kid: reading magazines, watching anime and dramas, singing in the shower, playing team sports with friends, and getting engrossed in a new video game.
These may seem frivolous, even childish. But the more I allow myself to do these things, the more I realize that they fill me with fresh visuals and novel ideas. They are the inputs that make my work remarkable.
Weekly artist’s dates. These could take anywhere from 2 hours to an entire day. The only “rule” for these dates is that they have to be activities the Kid in me wants to do. Occasionally I blew off my morning routine to read a fantasy novel on a Saturday. Other times I went to the movies and treated myself to kalguksu for dinner. Once, I spent a weekday afternoon trying different coffeeshops in downtown Toronto.
Those dates felt like skipping school, especially if I did them on a weekday. But I’ve worked hard for a career that gives me this kind of freedom. And these dates keep me creative. So why the hell not?
What am I working toward?
Rekindling my love for fiction. I finished 5 young adult fantasy novels this year! Staying up to finish a chapter or a book, trying to get my work done as quickly as possible, so I can go back to reading, and reaching for the book as soon as I woke up… I’d forgotten how it feels to be totally engrossed in a series.
Last year, I also started writing short stories to help me cope with all the duress I was under. I even posted one of them to a fan fiction website under a pseudonym. I felt so validated when people actually liked what I wrote. (No, I’m not telling you what it’s about, or what the pseudonym is.)
Before 2021, I had ignored the kid inside me as I obsessed about honing the intellectual aspect of creativity. In 2022, I’ll rely both on my intellectual curiosity and my childlike enthusiasm to guide my personal and professional projects.
(Side note: I’m fortunate to have access to ebooks and audiobooks from both the Toronto and the Markham public library systems. Double the books! Thanks to Readwise’s new integration with Libby, all my notes from ebooks I borrow from the library get saved to Evernote, as if I had bought the books from Amazon. 🙌)
A more enjoyable work environment. Part of respecting my creativity and my chose career path is (finally) giving myself the workspace I want. After 3 years of working in our cold, dark basement on a rickety table and a $75 IKEA chair, the first version of my new setup is almost done. I just need to fix my cables and then l’ll share a pic with y’all soon!
2022: The year of commitment & focus
“When you find the right thing to do, when you find the right people to work with, invest deeply. Sticking with it for decades is really how you make the big returns in your relationships and in your money. When you find the 1% of your discipline which will not be wasted, which you’ll be able to invest in for the rest of your life and has meaning to you—go all-in and forget about the rest.” — Naval
I’d been in an intellectual and professional wilderness for a long time. But it’s always because I’ve prioritized my “to learn” list over my “to do” list. In hindsight, my career and my creativity projects are all the results of my curiosity and desire to learn a certain skill.
I went into a career in content marketing because I wanted to learn how to write online. I worked in SaaS companies because I enjoyed being at the cutting edge of tech. Fortunately, as I continue to take on roles to learn, my personal interests and professional directions have started converging, culminating in web3.
My web3 frens are becoming IRL friends. My online writing is about what I work on during the day. My fun, “frivolous” activities nurture the creativity I need to produce essays that build leverage for me. My essays push me to understand and build specific knowledge in domains and to write about them in ways only I can.
2022 will be different — no one else will have a career like mine — but it’s more in line with who I am than ever before. And it’s because I’m fully leaning into my love for learning. Amidst all the goals, the overarching mission for me is to go as deep as I can with my curiosities, trusting that a rewarding career will follow.
If you’d like to do your own annual review, Khe Hy, James Clear, Chris Guillebeau, and Anthony Gustin all have frameworks you can follow.