Looking Back and Ahead: My 2021 Annual Review and Plan for 2022

Ramses Oudt 17 min read
Looking Back and Ahead: My 2021 Annual Review and Plan for 2022

How often do you reflect and look ahead? If you're like me and most of my readers, the answer is: not enough. We may daydream about what we want to accomplish, but we never say it out loud.

That's why I'm going to share what I did and didn't achieve in 2021. I'm also going to look ahead at this year—2022.

Writing an annual review in public feels strange. I like reading other people's annual reviews. And I also have a regular reflection practice. Yet, I've never bothered to sit down and reflect on an entire year.

I'm not sure why I haven't done such a long-term reflection before. Maybe it's because a year feels like too long for me. With an overly active ADHD brain like mine, time doesn't make much sense anyway. I'm in a perpetual now, so looking back to 365 days feels like an almost impossible task.

And yet here I am, writing an annual review. It's an exercise that I hope will make me more conscious of where I'm headed—and to consider if that's where I want to be.

The past year has been a rollercoaster ride of emotions. Working freelance for the first time ever was scary. Securing income is one aspect, but doubting my output really screwed with my head.

Doing creative knowledge work is always hard, but the added stress of having to find my clients was more of a burden than I had expected. It's also the reason I decided to go back and work for a company again. Not only does the financial security help, but I also need the satisfaction of working towards a vision with a team.

So, it's a good time to reflect and look ahead. While this site is about Tools for Thought, the acts of reflecting and planning are the most important tools we have.

Because most of my journaling practice is freewriting (à la Julia Cameron's morning pages practice), I will approach my annual review the same way. I know there are extensive templates that provide dozens of prompts, but I don't like those much. Instead, I like to stick to my three reflection questions:

  • What went well?
  • What didn't go well?
  • What will I focus on next?

After reviewing 2021 by answering those questions for each of my goals, I'll look ahead to the year 2022. I'll look at my aspirations, but also what potentially stands in my way. As I work with knowledge, that often means refining my stack of skills.

When people ask me how I pick the skills I acquire, it's often because of this review process. I look at situations and see what went well (so my knowledge was adequate), what didn't go well (where my knowledge or behavior was inadequate), and what I'll do when I find myself in a similar situation again (saying something about what I learned or need to learn).

Hopefully, reading this reflection and my plans will be as useful for you as it was for me writing them. I hope it'll give a glimpse into my thinking process in case you might want to try a similar approach to learning and growing as a person.

Review of 2021

Even though this is the first year that I do an annual review, that doesn't mean I don't set goals for myself every year. Still, goal-setting is always a difficult process for me.

As a practicing Stoic, I'm fully aware that very little is within my control. So even though I set quantifiable goals, I focus on my input for those goals. Or as Michael Ashcroft puts it: "clear intentions, held lightly."

As 2021 was my first year as a freelancer, my goals mostly revolved around earning enough money to keep a roof over my head. That doesn't mean that I didn't set goals to grow as a person. Working as a knowledge worker (especially as a solopreneur) means that you bring your mind to everything that you do. That's why my professional and personal growth goals go hand-in-hand.

For 2021 I set the following goals for myself:
- Gain enough clarity about my own learning process so I can teach it to others.
- Launch my first course on learning how to learn and help people apply my framework through a live cohort.
- Grow RoamStack membership levels to the point that I can pay all my bills from the membership fees.

While these goals may seem like external goals, I only cared about my own input. To some, they may seem fuzzy as I haven't provided exact numbers for those goals. I only care about intentions, though. Clear intentions, held lightly.

Still, these were important goals. Not earning enough money to keep your house and do groceries is an existential threat, hence I set them as my objectives.

Let me dive into each goal and see how well I did.

Goal: Gain enough clarity about my own learning process so I can teach it to others

For over four years I've walked around with the idea of teaching professionals how to become better at acquiring skills (by acquiring the skill of meta-learning).

During my 10 years in the world of corporations, I grew my career and income thanks to my learning efforts. Whenever I was faced with a new challenge—be it my role changing or getting caught in a reorganization—I would take matters into my own hands and learn the skills necessary to survive and even thrive.

While I've successfully taught myself skills like sales and data analytics, my approach has always been quite messy. When talking to friends and colleagues, I always had trouble telling them exactly how I approach learning a new skill. Many would just tell me I was "talented" or "highly intelligent," both of which are absolute bull crap. I don't agree with them and see myself as someone with average talent and intelligence.

So last year I finally set out to figure out my learning process and to capture it in some kind of framework. While I've gained a lot more clarity about my process, there's still enough to figure out.

What went well
I spent most of 2021 figuring out how to explain my process to others. Starting in one-on-one coaching calls, I slowly inched towards defining my learning framework. From selecting materials to taking notes to designing drills; everything got battle-tested with my clients.

While I was skeptical this approach would work, luckily it did. Not only did coaching fellow professionals help me stay afloat financially, I also figured out all the crucial parts of my learning process. So at the end of 2021, I delivered three sessions that helped dozens of people design skill-building projects.

In line with the Feynman Technique, I noticed that explaining my process to others helped me to distill the essence of what works. Like note-taking, the topic of meta-learning becomes abstract. By talking about the steps in the process, I gained a lot of clarity about what works and what is just fluff.

What didn't go well
While I did host a few sessions about learning how to learn, I could have easily done more. Perfectionism has a strong grip on me; instead of shipping I just kept chipping away at my written materials without publishing them.

Another bitter pill to swallow was the little interaction with the live audience in the sessions. It's a fine line between broadcasting and tricking people into participating with facilitation exercises. I don't want to make a session interactive for the sake of it being interactive. But I do need feedback, and I struggle to get it from the people attending live sessions.

I've also noticed that doing live sessions take a mental toll. I easily spend an entire day prepping for the call, setting up equipment, and making sure people actually attend. On the day of the call, my mind keeps wandering to the session, distracting me from doing much else. I'm not sure how to tackle this, but I suspect that pre-recording sessions could ease the stress of shipping.

What I'll focus on next
I still have a lot to explain about my meta-learning framework. But now that I have fewer financial worries, I can give away more of my knowledge for free. Not only will this help more people build the skill set they want or need, it'll also help me refine my learning framework even more.

To ship more and accelerate the rate of feedback I get, I'm going to lower the bar for myself and reduce the scope of what I aim to publish. That means that I'll provide less content and instead will organize groups of fellow learners. I'll still be sharing my process, but I don't have the bandwidth to write an extensive curriculum—nor do I want to.

So, I'll focus more on people getting into the daily habit of learning, starting by guiding them through the process of learning in general. Instead of me providing all of the content, participants will be sharing the resources they stumbled upon. I'll also assume the role of the curator. That way, we co-create a curriculum for any type of learner to become more effective.

Goal: launch a learning how to learn course (and organize the first live cohort)

I'll say it off the bat: I failed miserably at this goal. While I did organize a few live sessions at the end of last year, I did not create anything that looks remotely like a course. I blame my perfectionism for not shipping.

At the start of 2021, launching a learning how to learn course was one of my main priorities. As I wanted more ownership over how I could spend my time, launching a course seemed like the obvious answer to generate enough income.

Turns out, launching a course is hard and you need to be in it with your heart. If your main driver is to earn money from the course, you're setting the wrong aim. I stepped into that trap for sure. But making that mistake did teach me a few important lessons.

What went well
I spent a lot of time in 2021 writing course materials. Even though I published little and my ideas live in my note-taking tools, the act of writing them helped tremendously to clarify my overall learning framework.

Through the live sessions about my learning process, I was able to get a better sense of what I want a meta-learning curriculum to look like. It also helped to position myself in the Tools for Thought community as more of an expert on learning.

As I didn't have the course ready yet but my fingers were itching to write more about learning how to learn, I pivoted Think Stack Club more towards the topic. Turns out, the majority of the members are interested in it. For many, the whole reason they're in the Tools for Thought space is that they want to become better at acquiring new knowledge and skills.

What didn't go well
Even though I have thousands of hours of teaching experience (north of 6,000), that doesn't mean I can effectively design an online course curriculum. Working in a school is way different from working alone, and delivering a course online is much harder than in person. Coupled with my perfectionism, I have tens of thousands of words written, but it's one big mess that lives in my note-taking tools.

I've also noticed that I tend to make things too complicated. While writing and talking out loud about the learning process did help to simplify many explanations, I do tend to include too much whenever I write or present. Instead of focusing on a single idea in an article or session, I jam in a couple. While I do get better at connecting the different parts of what I teach, I still get feedback that I can sometimes overwhelm people with information.

Overall, I have not been vocal enough about the core principles of what I have to tell. I tend to throw something out, but I need to heed my own advice and keep repeating what's useful. We all forget quickly, so I need to up my game when it comes to repeating my ideas and why I think they're useful. Self-promotion remains a skill that I find difficult to improve.

What I'll focus on next
I've decided to redefine this goal and make it a priority for 2022. As mentioned before, I will lower my bar. Instead of crafting an entire course, I'm going to co-create it in learning sprints.

Why? The curse of perfectionism stings more with big projects. So, I'm deliberately going to reduce the scope of this goal and iterate on it in smaller steps. You can read more about my next steps in the section where I look ahead to 2022.

Goal: Grow RoamStack Think Stack Club to the point it pays the bills

When I started RoamStack with Francis Miller in August 2020, our aim was to have a side-project that forced us to learn. We were both obsessed with Roam Research since early that year and spent a god-awful amount of hours understanding the tool. Hence we saw an opportunity to educate fellow Roam users.

As Roam didn't have any onboarding experience and most Roam courses were expensive, we set out to teach everything we knew about the tool. However, experimenting all day became too tedious for Francis and he decided to shift back his focus to his information design projects. That left me alone and granted me the opportunity to spend more hours on the project.

With the Roam team slowing down development and many power users leaving the community, I faced the fact that I had much less to write about. I shifted my focus to helping members (mostly knowledge workers) improve their workflows. Yet, I was still focused on Roam Research. Late last year I finally broke ties with Roam Research and decided to fully focus on building a stack of thinking tools. While the transition has been rocky, I look forward to what's in store.

Let's see what did and didn't go well this year, and what I'm going to do next.

What went well
As of writing this, the monthly recurring revenue of Think Stack Club is just above €2,100. That means that this website officially pays all of my bills. But living in Amsterdam is expensive, so it doesn't cover all of my monthly expenses.

That's why I've been coaching individuals and small teams to supplement my income. This has brought me in contact with more use cases for knowledge management, which in turn enabled me to better help members. While one-on-one coaching is taxing on my schedule and mental energy, I've learned a lot by coaching over 100 professionals.

Ultimately I got my current job as Community Manager at Logseq because of the work I've put into RoamStack/Think Stack. I had essentially built a portfolio of content and rituals that the Logseq community also needs, so I was hired to do something I have only recently learned through trial-and-error. This shows the power of producing useful content in public. While for the most part I worked one-on-one with people, having the community and releasing content has helped tremendously to position myself as an expert and land a new job.

What didn't go well
I raised the membership price by almost doubling it, and subsequently scared off a third of the members. That was painful—and that's an understatement.

Dozens of members had assured me what I was offering the community was worth more. Yet, I discovered that the majority was only interested in access to me and the content, not in the community itself. What I focused on after the price hike was not what most people were looking for. I missed the product-person fit by pivoting too many times while not hearing from enough paying members what they were looking for.

What had worked for a long time was organizing live events, but at some point, I noticed the participation rate was starting to drop. Most people would join sessions with their camera off, just consuming what I had to tell. While everybody's needs are different, it did teach me that the make-up of the membership had changed. There's less desire for a community, but there is a desire for knowledge about how to use Tools for Thought.

What I'll focus on next
Whereas 2021 was the year of live events, I do notice burnout in myself and Think Stack members. Paradoxically, I'll be organizing many live events for Logseq, where I do notice a desire to gather synchronously.

So my focus for 2022 will be on asynchronous content. I'll still be making videos, but these will be recorded without a live audience. I also want to increase the value of the tutorials that I produce by adding written walkthroughs—including screenshots and gifs.

Last but not least, I will rethink pricing once again later this year. As membership levels increase and my income is more secure now that I run Logseq's community, I might be able to reduce the ThinkStack membership fees. However, I'm not entirely sure if and when I'd do such a reduction.

Looking ahead to 2022

Now on to looking ahead to where I want to grow this year. Because of more financial security, I feel that I have a clearer mind. While there's still a lot on my plate, I'm lucky that it's all stuff that I enjoy doing.

As I said in the intro of this piece, I tend to look ahead at what I'll need to learn to meet the challenges ahead. To leverage my time and mental energy the best way possible, I look at my life as a whole and see where improving in one area means improving in other areas as well.

One example is data analytics. When I first started my career in sales, I was basically a telemarketer; I had no need to analyze data. But the further I grew in sales, the more I had to create business cases. And the more complex the business cases, the more complex the contracts and calculations in them. Before long, I was more of an Excel jockey than a salesperson. This ultimately enabled me to transition my career into system analytics, something I was much more interested in than account management.

By regularly reflecting on my work, I've been able to spot the holes in my skillset. Equally, I reflect on personal relationships and where I can improve. To what end? To have a "smoothly flowing life" as the Stoic philosopher Zeno once put it.

For 2022 I want to focus on the following goals:

  • Reach conversational fluency in Italian (B2)
  • Help 1,000 people grok networked thinking
  • Launch three first learning sprints about learning how to learn

Because I want to focus on what's within my control, I'll now share how I want to reach each goal. The emphasis will be on what I can do to reach it, like what skill(s) I'll need to acquire or what habits I need to develop.

Goal: Reach conversational fluency in Italian (B2)

Let's start with the skill I look forward to mastering the most: Italian. It's a common saying that the best way to learn another language is by falling in love with someone who speaks it. And I'm a sucker for clichés, because it's also true in my case.

I already learned Spanish to near-native fluency (C1), so I'm familiar with the process. I'll be writing a lot more on the topic of acquiring languages, but I'll make a short start here.

How do I go from not knowing Italian to being conversationally fluent in a year? For some, that may look impossible, while other people may think that's easy to do within 12 months.

A year will most likely be enough as I'm not aiming for perfection—yet. All I want is to be able to properly communicate with my in-laws while having a solid foundation to grow from. Being able to fully enjoy Christmas dinner and the conversations in Italy is my aim.

I've been investing about 2 hours per day on Italian so far for the past 2 months. That's about 60 hours so far. Not bad, but I can do better.

For those unfamiliar with my language acquisition approach: those 60 hours were not spent studying textbooks. My method is centered around two main drivers: a shit ton of television and flashcards with whole sentences plus audio. And I'm not forcing output, either. That means I shut up and just listen.

Does it work? Oh, it does. While a counterintuitive approach, I've learned both English and Spanish to fluency with it. I can also understand 95% of German because I binge-watched my favorite shows in German for some years. My girlfriend learned 7(!) languages with this exact approach (but she swapped the flashcards for extensive reading sessions). It works, but it takes time.

My aim is to keep getting 2 hours of input every day, which amounts to over 700 hours one year from now. That is the same amount of hours of input that the Automatic Language Growth method prescribes before one should start talking. That may sound like an insane amount of hours before I start to speak, but I know it works.

Apart from watching a lot of television, I want to follow my girlfriend's example and do extensive reading. It's what the linguist Stephen Krashen recommends to boost comprehension in a language, but I've never taken that advice seriously. But looking at my girlfriend, I think I should listen to that advice and apply it.

By this time next year, I want to be speaking Italian. From then on out, I'll try to get as many practice opportunities as I can get. But that's in a year. Until then, I'll focus on input. And yes, I'll be boring you on this blog about my approach and results.

Goal: Help 1,000 people grok networked thinking

When I discovered Roam Research in February 2020, it felt like my prayers to the God of Knowledge were finally answered. Once that way of note-taking clicked for me, I was hooked on graph databases.

While I feel like I'm still only scratching the surface of what I can do with a graph-based note-taking tool, it has improved my life immensely. I feel that I can think much more clearly as I'm writing more. And because I mostly write in outlines that are super easy to connect, I see more patterns and relationships between the things in my life.

When working high-paced corporate jobs, I was always scrambling to dig up some information or share what I knew with others. My tools were lacking. No wonder I developed an obsession with Tools for Thought once I stumbled upon ones that worked for me.

That's why I preach the gospel of Tools for Thought. It's also why it's my goal to help as many people as possible deeply understand networked thinking.

We can talk about writing better notes all day, but in the end, it only matters if those notes will help your future self. Unfortunately, it often stays with just the talk as people move from tool to tool. I feel guilty about that as well, so I want to better follow the footsteps of Nick Milo and show off what's possible with Tools for Thought.

For too long have I run live sessions alone in the hopes of getting group interaction. But I've noticed that many people just listen in with their camera off, effectively lurking and not wanting to contribute to the discussion. That doesn't give me energy, so I'm changing up things.

I'll get back to writing guides as much as possible. But not having a format and process for writing walkthroughs makes that each article takes a massive effort. It would be easier if I'd just do screencasts, were it not that my video editing skills suck.

So, I have my work cut out for this goal: come up with a standard process for writing tutorials, supported by videos. For the videos, I'll need to improve my video editing skills, but I can start with short videos as long as I combine them with a written piece. Still, this is where a large chunk of my learning time will go into.

Luckily I have enough opportunity to practice my interviewing, writing, and video editing skills. Not only will I need to improve those skills to provide more value via Think Stack Club, I also need them for my job at Logseq.

For Logseq I also want to organize live sessions and produce better educational materials. So, I'll need to lean on the exact same skills. It's all coming together.

Goal: Run three learning sprints about learning how to learn (meta-learning)

In January of 2021, I did a month-long experiment to improve my writing. Through the Ship 30 for 30 program, I forced myself to write a short (~300-word) essay every day while getting support from a group of like-minded smart people.

While we had weekly check-ins, the program wasn't fancy. No curriculum, just accountability to write for 30 days straight. It's the perfect program for over-thinkers who want to develop a writing habit.

I want to create something similar, but for people who want a strategy to learn new skills rapidly. In Ship 30 for 30 I saw that the program worked if you wanted to ship work, but rarely did it lead to work worth reading. Some more strategy and deliberate practice are needed, which is precisely what I want to help people with for the skill of meta-learning.

My aim is to help people get into the habit of learning a new skill by spending some time on it every day. And we'll start by learning the skill of learning.

I'm an autodidact, so I want to draw from different sources and not just blindly follow a course. The idea of creating a course myself never sat well with me, as if I feel like I don't own the truth. So writing a curriculum and presenting it as the way to do things... nah. But presenting ideas and openly discussing them? I like that idea much more.

That's why I'm framing my first cohorts on learning how to learn as a learning sprint. It will be a course in the sense that I will present some ideas every day, but the program is focused on taking action and sharing what you know. It's like a book club, but instead we're tackling a skill and not a particular piece of work. All materials are fair game.

Conclusion: reflection is key

While I do weekly reviews, I tend to struggle with taking a longer view. But writing this review helped me a lot to gain clarity about where I'm headed and where I need to course correct.

So my last aim for this year is to review this review every quarter. I don't want December 2022 creep up to me and not having made much progress. Hopefully, a quarterly review will help me to take a long view while it still being a manageable timeframe.


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