2020-annual-review-workshop-goals-lessons-learned

2020 Annual Review

How have you been doing during the pandemic?

I’ve asked, and been asked that on countless meetings this past year. And I’ve always fallen back to this answer:

I’m just glad that all my friends and family are healthy and employed.

The coronavirus reminded me just how fragile life is. I’ve have a few friends who’ve gotten the ‘rona and survived, thank goodness. I’ve heard many more stories of third-degree connections who’ve died (rest in peace).

We all live in a connected system, and the health of that system depends on everybody else. Even if you’re an introvert. Even if you don’t believe in wearing masks. At an individual level, we all have a symbiotic relationship with public health and the economy.

So I start this annual review by just feeling immense gratitude for my health, and the health of the loved ones around me.


I’m trying a different review this time around, thanks to the Annual Review Course held by Tiago Forte and David Perell. Taking an online course to review the year with strangers might sound, well, strange.

Here’s why it turned out to be such a good experience, and why I’d gladly spend money to do this again:

  • Taking a workshop over the course of a weekend in itself establishes a container for reflection. It’s much harder to put off an annual review when you pre-commit with time and money
  • Being in a guided workshop with extremely sharp and accomplished people was not only motivating, but clarifying. It was helpful to see how others reviewed their year and worked through their goals
  • I got feedback on some of my sticking points

Doing annual reviews is typically a solo effort and can feel isolating. Whether you take a formal course or not, I can’t overstate how valuable it is to review and set goals with a group of people.

The structure of the annual review was simple: remember, connect, and create. Going through this process with other folks created the space for emergence. Allowing things to bubble up through reflection that I wouldn’t necessary get from normal “top down” goal setting. Speaking of which…

Emergence and Engagement

I often find myself asking: “Why write?” What emerged in this review process was that 80% of the joy of writing comes from engaging with people. It feels rewarding when people reply to my newsletter or to the questions I post on Facebook.

So why did I often forget to reply to people?

My story about scale got in the way. I first started UXBeginner.com so I could just send friends the same articles when they asked the same question: “How do I break into UX?” I loved how publishing enables me to scale from one to many.

I now appreciate Paul Graham’s message about doing things that don’t scale.

1:1 conversations are now the lifeblood of this blog and I’ll continue to carve out time for replies and conversations. I’m also excited to optimize my blog and email sequence to increase engagement.

Doubling Tripling down on writing

There’s no doubt that writing for 30 days straight was absolutely the most important thing I did to improve my writing practice. The challenge helped me regain my writing muscles, as well as identify my interest in the overlap of psychology and money. I’m interested in doing this writing challenge at least twice a year to practice publishing over perfection (say that 3x fast).

Yet, this challenge also exposed some big gaps in my writing process. It was taking me too long to write new articles and newsletters. I’ve identified some of these writing blocks of mine—maybe you can relate:

  • Anxiety about going in the right direction and carving out the right “niche”
  • Lack of confidence in my ideas: was anyone going to care about this article?
  • Unsure if an article is too long, should be cut into two, etc.

What better way to address these problems than to join a community of writers?

I recently joined On Deck Writer’s Fellowship. It’s an 8 week program full of writers who share the same goals: write consistently, improve writing quality and grow our audience.

Even from my short time in this program, I’ve discovered a couple things about my writing process:

  • I have the tendency to try to “cover it all” in my articles such that they start to feel bulky and lose the lead. I realize I don’t need an article to address every single thing under the sun about that topic, but rather that I can go deeper, and tell more interesting stories, about one aspect of that topic. Takeaway: write shorter, story-driven articles.
  • There’s so much more room to not only tell stories, but to also tell more colorful stories. Voice, tone, lens, perspective – these are the things that ultimately readers to come to me more, so they’re worth developing.
  • The more I read, the better my writing.
  • The more I give and ask for quality feedback, the better my writing

These takeaways lead to my 2021 Goals, which I’ll share at the end of this article.

Emotionally, my 2020 was divided into two halves.

The first half was with my ex, and the second half starting a new relationship.

I struggled a lot in my previous relationship. There was so much love there, and yet I don’t think we were ever truly prepared for the realities of a long distance relationship. One of the hidden cost of dating long distance is that it starts out immediately with a power imbalance: who’s going to move for who? This leaves room for resentment and unmet expectations.

I think long distance relationships may work if a couple has already established a long foundation of living together. Starting off on a long distance relationship is something I would never recommend to someone again. There’s just too little time to establish trust and real knowing of each other.

I also saw a lot of blind spots in my relationship. I could’ve been a better listener, and should’ve taken the Communication course from Landmark much earlier. My relationship ended soon after the coronavirus hit. I’m grateful for the memories, experiences, and lessons learned.

Two of my friends – you know who you are – were like the emotional safety net for me during and after the breakup. Thank you.

In the second half of 2020, I reconnected with a friend of mine. There was no long distance to worry about, and the quarantine incidentally gave us a lot of space and time to focus on each other.

The relationship is blossoming and I’m grateful for that.

Politics and Privilege

I managed to ignore politics until 2020. The year of social unrest and elections.

During Trump’s administration, I saw facts become alternative facts, news become fake news, and the right become alt-right. Ultra liberal outrage were no better.

In the wake of George Floyd’s death and the ensuing protests, I finally saw a more well-rounded view about racism. My Black roommate told me about his lived experience. I, like almost any liberal at the time, picked up How to be Antiracist and So You Wanna Talk about Race. Most importantly, Credit Karma held space for deep discussion about racism. That was huge for me, that I had coworkers who cared so much about racial inequality and were willing to teach others about it.

I realized just how fucking hard it was to have measured conversations with people. I found one conversation particularly illuminating. In the midst of a long thread, I asked a Blue Lives Matter proponent “Let’s set aside race for a second. What kind of police reform would you like to see?” Lo and behold—the points he made had 90% overlap with what the Black Lives Matter movement wants. Tribalism is a hell of a drug.

When Biden won, my gut feeling was validated. Americans were tired of being at each other’s throats. The polarization, the outrage, how politics became a perverted form of entertainment. In my opinion, Biden-Harris won because centrism won. As much as a barbell strategy makes sense in many domains of life, the boring middle is undervalued in politics. I personally won’t take that for granted.

Playing the infinite game

Until reading Finite vs Infinite Games, I didn’t realize that my view of work was short-sighted. I had the thought: “Once I have a few million dollars in the bank, then I’ll feel safe enough to stop working and spend all my time writing.”

I know, not the most thoughtful early retirement plan.

The idea of playing an infinite game gave me a few subtle shifts in my life:

  • Writing and publishing is just about the most infinite game I could play. I could always get better at writing; I don’t think there’s a stopping point of my writing ever becoming perfect.
  • Being an investor and capital allocator is a life long game and I shouldn’t feel rushed when making investment decisions.
  • Experience in an industry compounds. UX Design and UX Writing (my fields) are still relatively nascent. How can I set continue to allow my expertise to compound?

This gives me a different view of how hard I should work and to challenge myself to adopt even longer-term views of myself, my career and the work I want to do.

“You don’t rise to the occasion, you fall to the level of your training”

Covid revealed the quality of my habits, good and bad.

Previously in MeatSpace, I walked or biked to work a mile from the metro station each way. Once at work, there were plenty of different nooks and crannies and oh how I miss them – meeting rooms – that I could take advantage of to break up the day.

Once I started working from home, I didn’t take enough breaks. I’m in front of the computer a lot more now and it slowly chips away at my well being. If it wasn’t for self-management tools like TimeOut that forced me to take breaks, I might have gone crazy.

Now I prioritize simple things like taking a midday walk or going for a morning jog. I used to poo-poo cardio because lifting weights is more efficient, but I heavily discounted the psychological benefits of cardio. A quick run does wonders for my energy level (serotonin?) and makes me feel human again.

Two habits that served me well is a consistent diet and workout. When I have a bad day, at least I could fall back on these habits, whether it’s fasting for a day or literally lifting the stress way.

Some smaller but notable changes: I finally upgraded my home office scenario with a standing desk, 2nd monitor and noise cancellation headphones. Oh my gosh, why did I not do this sooner? Game-changer.

Other creative projects and distractions

UXBeginner is still very near and dear to my heart. My gut is telling me to double down on personal finance for at least the first 2 quarters of 2021, but there’s still a desire in my heart to create a new UX course. I’ll need to decide if this is going to be a distraction or a delight.

House-hunting was another distraction I had, especially at the height of the coronavirus in the summertime. I have roommates and started to realize I wanted a separate space for comfort and safety. Mortgages were at historic lows.

So I started looking at multi family units, thinking I’d live in one and rent the other out. I passed on a lot of opportunities, some of them good ones in retrospect. What did I end up doing?

I realized that my motivations to own an investment property were not in the right place. The opportunity cost of property investing was the focus it would take away from other things that matter to me: my writing. I also realized that if I really wanted to live in a different place, I could always rent. What I landed on is that the most I’ll do in 2021 is build an ADU, and deprioritize the housing search.

2021: The Year of Engagement

Engagement is the word that contains everything I want 2021 to be. Engaged with my work, in my relationships, and with my wider community. One of the great things about blogging about personal finance is that almost everybody has an opinion on the topic. I’ll use this as a jumping point to engage with my family, friends and wider circles.

To cap off this post, here are my goals for 2021, split into input goals vs output goals:

Input goalsOutput goals
Get to at least 1 week ahead in my publishing scheduleIncrease engagement with my audience (replies, comments, signups)
At least 30 minutes of focused reading a day, 5 days a week1000 email subscribers by the end of 2021
Practice Zouk once a week with my girlfriendTry relationship therapy / couple’s counseling at least once
Monthly poker nights with friendsStart drawing illustrations to accompany blog posts (Q2)

Thanks for reading. If you want to hear more about my annual review process, or have questions about the Annual Review Course I took with Fortelabs, hit me up.

Note to self: I am complete with everything that happened in 2020 and how I handled it.

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