CoThinking — by Jotham

I am obsessed with productivity systems. From Ali Abdaal to James Clear, Keep Productive to Cal Newport… task apps, calendars, daily planners, and personal knowledge management—if it exists in the Apple ecosystem, chances are I’ve tried it before.

Have I become more productive after this exercise? Yes! I can’t imagine going back to the life of drifting aimlessly, living life by default and not by design. However, I went past the point of diminishing returns a long time ago.

Fiddling around with productivity tools has become its own form of procrastination. It’s a more dangerous sort because it tricks you into believing that you are much more productive than you actually are.

There are plenty of courses teaching you how to implement GTD, Zettelkasten, and PARA methods. Many are free; others are unjustifiably expensive. I found myself unable to stick to a fixed system, but it pays to understand the underlying core principles.

Even now, I encourage my peers and juniors to dive into the world of productivity systems and tools. But to avoid the same pitfalls, here’s a summary of what I’ve learned thus far:

Picking Out an Ecosystem

I think it’s OK to keep up to date with the latest trends in the productivity space. However, it’s essential to be mindful of the migration cost of constantly switching between different ecosystems.

Every day, I receive a new email highlighting new A.I. capabilities or a feature that makes the app perfect for specific use cases, but it’s generally not worth the jump.

I fell down the productivity rabbit hole because I want to enjoy my day job, but there is a clear distinction between enjoying using an app and doing the actual work. Most new features are unlikely to make you productive, even with “GPT” in the headline.

Here are things to consider if you’re looking to commit to an ecosystem:

1. Create a List of Requirements and priorities

This is the most challenging step, and I recommend taking time to think this through. Even the most obscure app has a dedicated fanbase because it does one niche thing and does it well.

Every app has strengths and weaknesses, and ranking your requirements is critical to stopping yourself from succumbing to the shiny object syndrome. The parameters to consider include cost, supported platforms, UI/UX, quick capture capabilities, dedicated features, collaboration, and file storage.

2. Decide if You Want an Integrated System or a best-of-breed

A single app that does everything, from task management to notes, is unlikely to be powerful or customisable (Noteplan 3, TickTick). On the other hand, using highly specialised dedicated apps can be expensive and complicated to keep track of (Things 3, Cron, Obsidian).

Deciding this early on will help you narrow down your options a lot. In most cases, you will adopt a hybrid approach—but deciding how to segment it is a decision by itself. Most people I found online prefer bundling tasks and calendars into a daily planner while having a separate PKMS / note-taking system.

3. Abuse the Free trials

Productivity tools can be expensive, but most have a comfortable trial period to test them out, ranging from 7 days to a whole month. Some tips include:

• Cancelling your subscription immediately after signing up to prevent unexpected charges

• Having multiple email accounts to extend the testing period,

• Taking advantage of rewards (limited-time discounts, referral bonuses, cancellation discounts).

Only pay for apps that you are sure you will stick to for months at least.

Workflow Matters More Than Technology

Not only is it free to learn a workflow from YouTube videos and Reddit threads, but systems and processes significantly impact productivity more than the technology itself.

Productivity apps exist to facilitate processes, not dictate them on your behalf. Many apps are designed to suit a specific workflow (Omnifocus with GTD), and you can’t use the app to its fullest extent without understanding the principles it is built upon in the first place.

Adopting a new app sometimes only involve a slight tweak to your workflow, but others demand an entire overhaul, and it took me some time to learn where to draw the line—especially when I haven’t figured out a default workflow yet.

Most apps come with help documentation, and it is worth taking 30 minutes to review the app’s core features quickly. Some apps do not have a straightforward user onboarding journey (cough Obsidian), which makes them very non-beginner-friendly. However, most apps I’ve encountered have YouTube tutorials and reviews highlighting how to use the app as intended.

When creating a personalised workflow, my advice is to keep it simple and stupid. For instance, systems like Zettelkasten are effective but require constant maintenance to upkeep. They’re great for academics or journalists but are called digital gardens for a reason. It is only beneficial when you have thousands of notes and spend most of your day managing textual data.

But for most people, it takes effort to upkeep the system daily. Capturing and using atomic notes is more troublesome than Googling or understanding the subject matter outright.

Currently, I’m using a dumbed-down version of GTD for task management and time-blocking. I also have a single folder to dump all my notes, navigating them solely using tags and smart searches. It’s fast and gets the job done.

The Role of Fun and Readiness in Productivity

A big hurdle for me when choosing productivity apps or workflows was deciding between user experience and everything else, such as cost, A.I. capabilities, data privacy, etc.

Affordable apps with great UX tend to lack features. An app that does everything like Sunsama and Akiflow is expensive.

Obsidian is an excellent example of this—it’s fast, quick, highly customisable and a beast of a PKMS tool. But I hardly used backlinks, and I spent more time tinkering with the system than actually processing and producing content. Scrolling through my list of installed community plugins gives me anxiety. I disliked having to wait for notes to sync every time I switched devices and how it’s not designed for the Apple Pencil.

On the other hand, apps like Things 3 are dead simple to use. The UX/UI is wonderful, and you can tell that the developers have spent years finicking over the tiniest of details. But it lacks basic functionality compared to many other apps, like natural language input, streamlined time-blocking abilities and more.

From personal experience, especially for someone new in the productivity space, it’s worth prioritising the “fun” -ness of the app over its features.

Adopting a powerful tool and workflow for future-proofing is tempting. You may want to find the “best” ever app or workflow and stick to it. But very rarely is there the “best” app—the only one that is right for you now. Switching methodologies as time passes is common, but the problem lies in how we change.

Hence, for new practitioners, having a fun system to dedicate towards is more important. It’s not worth setting up a more convoluted system for a 2% increase in productivity.

It’s not that these advanced systems suck or are over-engineered. It’s that we are not ready to take advantage of these advanced systems just yet—which leads to the following:

Output Is the Only Thing That Matters

I was inspired to write this article because of a recent note migration exercise involving 550~ notes collected throughout a year, which, granted, is a small amount within the PKMS space.

Because of formatting issues, I had to import them manually one by one—which allowed me to review my notes and purge many irrelevant ones.

I ended up with only 75 notes afterwards—most of it is my published content and essential details on my friends and family. Most of my Zettelkasten notes and Readwise highlights didn’t make it.

This made me reflect on my approach towards note-taking:

• Is building a second brain overrated?

• Why bother with digital productivity when the great minds in the past could do well with pen and paper?

• How important is note organisation in relation to note creation?

• Why am I outsourcing my remembering process instead of adequately understanding, contemplating, and digesting the content I’ve read?

After sitting on these questions, I concluded that digital productivity and PKMS tools are still very much relevant. The fact that I am delivering results at work more consistently than before and still have 75 important notes in the first place is attributed to the systems I have built, and is worth celebrating.

But it’s also a stark reminder that our productivity systems only exist to help us do important work better and faster. The system is rarely the bottleneck—we are.

Right now, I’m trying to stick to the “whatever works” principle. I’m using Apple native tools for now—Notes, Reminders and Calendarall of which compelled me to switch to the Apple ecosystem 18 months ago.

Of course, I will still try out new tools for fun. I’ll probably write a few reviews on them down the road—as long as I recognise it for what it truly is, a hobby and curious pursuit instead of an attempt to be more productive.