How A Syllabus Could Change The Way You Plan

Here are a few (I think) obvious truths stated dramatically:

• We live in a world of constant change and uncertainty.

• Ambiguous anxiety is a chronic (and nearly universal) condition.

• There are no sure bets.

• No checklists for success.

• No blueprints for building a life or career you find fulfilling and satisfying.

You already know all that.

And yet, how many times have we searched aimlessly for a set of instructions that doesn't (and can't) exist? How many times have we let a project fall by the wayside because it didn't go according to plan? How many times have we declined an opportunity or challenge because we didn't know how to do it?

When I asked you about the topics you'd like me to cover in the future, navigating and planning for uncertainty was a big theme. Here's an example of what I mean:

I'd love some down-to-earth "not advice" on how to set goals and make plans when life (and work) keeps throwing curveballs. How do I juggle my dreams and the day-to-day grind without getting burned out? How can I map out a future that's true to who I am while still getting me where I want to be, especially when I'm pulled in a million different directions?

Look, I struggle with this, too. I don't know anyone who doesn't. But I also have thought long and hard about these very questions, and I have ideas.

Goal-setting and planning are difficult for many reasons.

But a critical reason, perhaps the one that leads to the most frustration and trepidation, is the expectation that we have to get it right. Getting it right, we seem to assume, makes it a sure thing. We just need to figure out how to string together the right steps. In the right order. To achieve a particular outcome.

Literally no plan works this way. But that doesn't stop many of us from trying.

We yearn for order in a chaotic world—and the planners, calendars, and bullet journals we use promise to create that order. They are linear. They're chronological. They're full of lines and boxes that stack neatly on top of one another. They ask us to name the tasks we need to complete, assign them due dates, and check them off one by one. They take each project, break it down into steps, and again, and again, until a project is a set of interchangeable parts—rather than a whole.

There's a short passage from Jeannette Winterson's 12 Bytes that I think about often. "Reality is not made of parts but formed of patterns," she writes. "There is nothing solid. There are no binaries. There is energy, change, movement, interplay, connection, relationship." And here's the bit that often comes up for me when I'm trying to wrestle some web of ideas into a more or less solid text:

I would like to start in 2 places simultaneously. Unfortunately. I have to write in series, whereas the great strength of the brain is parallel processing.

Our planners, project management apps, to-do lists, and, by extension, our plans steer us back to the linear, the sequential, and the mechanistic—even though we think and feel in multilayered, interlocking patterns.

So how might our plans change if we gave them a different form? How might we think differently about projects and goals if we put them into a medium other than a calendar or list?

The medium I have in mind is the syllabus.

I've made syllabi for different programs I've taught for years. One of my always-on-the-back-burner projects is making syllabi to share with you about topics like labor theory or feminist economics—just for funsies. I even have an idea for a satirical creative nonfiction project in the form of a curriculum for a "neoliberal" arts degree.

But a couple of years ago, Sean told me that he had made himself a syllabus to follow. He had a syllabus for learning to quilt. He had another one for exploring color theory.

When I mentioned this in a workshop in early 2023, I got tons of requests for his personal syllabus, as well as plenty of requests for him to teach his own workshop. He wasn't ready to share then. But he's since opened up about his process.

Before we get into specifics, let me back up for a minute.

What is a syllabus?

A syllabus is essentially an outline for a class.1 A syllabus typically gives a description of the class, its learning outcome, and the weekly topics and assignments. There's usually information on expectations for class, how classwork will be graded, and what to expect from the teacher or professor.

A syllabus is a compelling medium for a plan because it has both chronological elements and systematic elements. It defines completion in terms of learning rather than any particular achievement. And it connects varied resources to the subject at hand.

Sean's syllabus probably isn't as detailed as one you'd receive before a college course—but the form gives him some space to play with his plans. In the rest of this article, I'll first share how Sean creates his own syllabus. Then, we'll get nerdy with a bit of learning and goal-setting psychology. And then, I'll break down the process with an example to follow along with.

Planning with a syllabus

Sean makes one syllabus per quarter, and right now, he's working on his first-quarter learning goals. His syllabus contains both some high-level habits he wants to keep in focus (e.g., movement and breathwork) and the specific learning projects he wants to work on. Sean has, as he put it, an "infinitely deep bucket" of interests. Realizing that is why he approaches his interests in this way.

"If I don't do that," Sean told me, "I tend to get really scattered and all over the place." Without some structure and focus, he's only able to skim the surface of an interest before he gets distracted by another. Working with a quarterly syllabus allows him to relax a bit—he can focus on a few things for a few months and know that other interests can get scheduled for the next quarter.

For Q1 2024, Sean told me he's focusing on a few learning projects: linocut printing, lo-fi music production, and singing. This seems like a good time to mention that we're not full-time parents—your mileage may vary.

Once he knows what he wants to learn, he starts to round up the courses, books, videos, etc., that he'll learn from and adds them to his syllabus. For each of these learning projects, he also gives himself an assignment—a way "to close the loop" on what he's learned. He tries to show some restraint when it comes to these projects but isn't always successful. Case in point, his linocut assignment is to create a deck of tarot cards from scratch. Oh, and he has to learn tarot to do that... so I guess add that to the list, too!

While Sean primarily uses a syllabus for personal growth and skill development, I use this style of planning for work, too. It probably won’t replace your to-do list or calendar, but planning to learn is a viable way to approach marketing campaigns, product development, professional growth, management projects, and more.

The basic structure planning to learn with a syllabus is:

• Choose a topic to learn about

• Then, do some preliminary research into the learning resources

• Then, create an assignment that will demonstrate learning progress

Each of these three pieces is important. And I'll come back to each one in just a bit—but first, why take this kind of approach to personal growth and exploration?

Learning goals have serious benefits

Psychologists studying learning and education have found that self-directed learning goals lead to greater growth than normative or imposed performance goals. In other words, we're much more likely to challenge ourselves, overcome obstacles, and achieve higher levels of mastery when we choose to learn of our own accord rather than when we need to prove ourselves to others.

Carol Dweck, famous for the idea of the "growth mindset," also described how two motivational patterns shape our learning behavior. Adaptive motivational patterns are "those that promote the establishment, maintenance, and attainment of personally challenging and personally valued achievement goals." An adaptive motivational pattern will lead to setting personally meaningful and challenging goals with confidence. While maladaptive motivational patterns lead to behaviors like playing it safe, assuming a lack of ability, and giving up too soon.

Learning goals, Dweck and others have found, cultivate adaptive motivation patterns. Performance goals, on the other hand, sometimes lead to adaptive motivation patterns (particularly among already high-performers and well-resourced students) but also lead to maladaptive motivation patterns and feelings of helplessness in the face of challenge.

Choosing to learn rather than choosing to perform is likely to lead to selecting more challenging projects, persisting even when things get hard, and establishing higher self-confidence and self-efficacy. That sounds pretty good to me!

So let's get back to the three components of Sean's personal syllabi.

First, topic selection

Choosing a topic gives us that first layer of structure in the form of some degree of specificity. Too often, especially for goals or projects that we don't see as "work-related," we gesture toward what we want rather than actually stating it. I might say, "I want to work on my writing," but that doesn't actually say much about what I want to work on. But if I say, "I want to learn about logic and argumentation to support my writing," then I have some structure to use.

If I further mold my topic into a question, I can get even clearer on how I will structure my learning. So I might say, "How do different forms of argumentation lead to more persuasive writing?" Now I know that my learning is 1) focused on how arguments are structured and 2) working toward the goal of more persuasive writing. And yes, this is my first learning project for 2024.

At the beginning of 2023, I embarked on learning to make video essays. I wanted to figure out whether what I've learned about making audio essays could help me make compelling videos. This learning project had two components: What makes for a compelling and shareable video essay? And can I grow my audience by incorporating that kind of video?

Of course, choosing a topic is easier said than done. Sean told me that he chooses his topics based on a "gut feeling." He asks himself, "What's most interesting to me right now?" Because he's learned that choosing what he thinks he "should" do means he won't do it or he'll resent the project while he does.

Sean believes that following what's most interesting and compelling to him when it comes to choosing what he wants to focus on will ultimately lead him to try a variety of satisfying and fulfilling activities. This echoes the psychology research I mentioned earlier. Sean is cultivating adaptive motivation patterns, leading to challenge-seeking and ultimately feeling more fulfilled.

Second, preliminary research and sourcing

Given what I already know and the vast resources of the modern age, I start to identify resources I can learn from.

For example, my interest in logic and argumentation, while inspired by my desire to write more persuasively, is actually informed a pretty big gap in my philosophical education. I'm much more familiar with the philosophy of religion and continental philosophy, and much less familiar with analytic philosophy. So that leads me to searching for "how to learn logic" and scoping out the resources that are philosophy-related.

Luckily, there is almost no question that hasn't already been asked by someone else on the internet. So I quickly find a philosophy message board and learn that I want to learn propositional logic and predicate logic. Now I know what to look for in my go-to learning library, Perlego. Like Sean, I'll also seek out YouTube videos and online courses. To get meta with this, I might even seek out philosophy course syllabi for introduction to logic or analytic philosophy.

When it came to my video essay project, I watched some of the top video essayists on YouTube and read fans' breakdowns of their styles. From there, I spent time in the help docs of Descript and Canva to figure out how I could recreate certain elements without learning a whole new piece of software.

Third, formulation of an assignment

This can be really straightforward, as when Sean sets a goal to read a certain number or set of works of classic literature for the year. My example is a little trickier. The reason I want to learn about logic and argumentation is to make my writing more persuasive. I want to be able to use what I learn. So I might give myself an assignment to use what I learn about logic and argumentation to outline an article or series and then write with that outline.

Being able to do that doesn't mean I'm done learning—but it does signal that I've made significant progress. And having a clear way to acknowledge that progress helps my brain take stock of what I've done. If I leave the learning project open-ended, I risk feeling unsatisfied or unaccomplished.

For my video essay project, my assignment was to work on replacing my existing Instagram strategy (detailed slide decks) with a video strategy for Instagram. That gave me a frequency to aim for, a focus for the content of the videos, and a constraint on how long they could be.

Once I have an assignment in mind, I can start to flesh out what I'm actually going to do to learn what I want to learn and complete my assignment.

Finally, getting to work

Sean told me that his goal is to be much more intentional about how he plans his learning in 2024. To do that, he's been working on developing a routine around a set of paper planners. His work world revolves around digital planning—ClickUp, Google reminders, alarms on his phone, etc. But he's found he prefers to manage his learning projects with a pencil.

"I write it all in pencil," he explained, "because I like to hold plans loosely. I'm currently doing two weeks at a time—so every week I'm looking two weeks out of what it is that I would like to be doing." He said, a bit sheepishly, that he doesn't know what he's going to be doing five or eight weeks from now.

I want to mention that, in my observation and experience, there is absolutely no need to get to the point of knowing what's going to be on the plan eight (or 12, or 24) weeks from now. As I like to say, planning is a learning process. Trying to achieve that makes it harder to learn from what we're doing. And, it makes it harder to quit.

Or not

And by "quit," I mean learning that something isn't as important to us as we once thought it was. For example, I quit my video essay project. I was having fun, learning a lot, and seeing some results in terms of reaching new people. But ultimately, I realized that it wasn't how I wanted to spend my time. I'm very glad for the skills that I learned during that short time, and I've applied them to other projects. But in the end, there were other, more important things to focus on.

"I personally have no problem abandoning ship," Sean told me. "If I feel like bailing or abandoning one of these projects, I will ... I have no commitment to anyone other than myself to do these things."

It's that commitment—that buy-in to our own goals, desires, and experiments—that can make all the difference when it comes to growth, personal or professional.

Whether or not you take a crack at creating your own personal (or professional) growth syllabus or not, I hope you'll consider how you want to challenge yourself and what you want to learn as you create your plans.