The quest for the perfect productivity system often feels like a search for the Holy Grail. Everyone claims to have discovered the ‘right’ way to manage tasks, each with their own revolutionary method. Yet, as I wade through the sea of list-making gurus and productivity ninjas, my skepticism remains unshaken.

I embarked on an experiment: to live listlessly, if you will. The result? As expected, chaotic.

The Digital Dilemma:

I once found myself sharing sushi drenched in mayonnaise (a peculiar Chilean delicacy) with the founder of Todoist, the world's premier to-do list manager. This encounter offered a glimpse into the transformative potential of to-do lists. Despite my ventures into the digital realms of Todoist, Evernote, Notion, Asana, and Trello — none resonated with me.

It appears there are two camps: the steadfast system loyalists and the restless experimenters like me, forever in pursuit of that elusive perfect method.

A staggering fact looms over us: the average mortal juggles 150 tasks, with nearly half doomed to remain unchecked. This reality alone stokes my anxiety. "If your to-do list contains everything, then it’s probably taking you everywhere but where you really want to go," muses Gary Keller, the author of The One Thing.

My attempt to abandon lists cold turkey faltered, not because lists are inherently flawed, but because I lacked clarity on what truly matters.

The Renowned Strategies:

• The 1-3-5 List: A straightforward approach for categorizing tasks. Learn more

• Warren Buffet's 2-List Strategy: A famed strategy by one of the world's most successful investors. Prioritize your top 5 goals out of 25, and voilà, you have your focus. Dig in here

• David Allen's GTD: A comprehensive method for task management that emphasizes specificity and regular reviews. Watch here

• Cal Newport's Task Management: After a decade of refinement, Newport shares his system. Discover his method

• Rad Reads: Khe Hy's exploration of productivity, from peak efficiency to questioning its very foundation. Read his insights

• Dan Pink's To-Done List: A refreshing twist on traditional to-do lists. Explore here

• Oliver Burkeman 2-list strategy: The author of Four Thousand Weeks recommends making one ‘open’ list that contains every task and a second ‘closed’ list that you cap at the 10 most critical tasks. Tuck In.

• The Hunter Method: Select a singular focus for your day and immortalize it on a sticky note. Whenever distractions beckon, let the determined gaze of your sticky note reel you back in, keeping you on the hunt for your day's most essential prey. Read more here

• Tiago Forte's PARA Method: A unique take on organizing tasks and life. Check it out

Here I am, compiling a list about making lists. I could keep going but I’d hate to spoil your week as you think about all of the things you aren’t getting done while you happily binge-watch Griselda.

Still, If you have other strategies you’ve tried and rejected, adapted to suit your personality, or are absolutely in love with, well then… I’d love to hear from you.

The Sticky Note King:

Once, my workspace was a kaleidoscope of bright 3M notes, each a testament to my quest for efficiency. Now, they serve more as markers of my anxiety than serenity. This journey from sticky note king to a skeptic of the list-making paradigm mirrors a deeper exploration into the essence of productivity.

We are hard-wired to make lists. Our brains more readily recall interrupted tasks than completed ones, otherwise known as the Zeigarnik effect. Your unconscious mind is nagging your conscious mind, “Yo!, let’s make a plan.” Once in place, a feeling of accomplishing comes regardless of whether we reach the goal or not. It’s why we return to list-making time and again.

Lists have become my mechanism for feeling accomplished, yet they often stem from a place of not-enoughness. This has prompted me to reevaluate my relentless pursuit of productivity. After years of practice, I’m still learning how to let go of always trying to get more sh*t done and instead learn how to embrace idleness.

The Yellow Slip Time System:

It's likely my contemplation on this topic is a response to my Dad’s remarkable organizational skills. He spent 46 years refining his professional systems, even trademarking one of his processes.

If you’re so inclined you can view a template of his 79 years of life on an Excel sheet - no joke! Beyond the efficiency and peace of mind that such systems provide, they also bring him joy.

While my Dad navigated his tasks without the marvels of modern technology, Mayram Bahrani fully embraced them. As a researcher at Andreessen Horowitz's crypto unit, she relies on the productivity App Notion to meticulously organize her work.

For Mayram, Notion is more than an app; it's an extension of her mind, a digital realm where tasks, ideas, and works-in-progress coalesce. She notes that her more neurotic colleagues prefer Obsidian, a system where every fifteen minutes of the day is meticulously accounted for. While the thought of such precision in scheduling, frankly, terrifies me — I know it would delight my father.

The Underlying Motivation:

It would seem that I’m not alone in this elusive ultimate task-management system hunt. Just as getting our 10,000 steps in can be an indicator of being fit, getting through the steps of our to-do lists has become a mark of our utility. But who decides the size of this measuring stick? And if we reach it, don’t we just tend to then make it longer?

In light of my system—or rather, the absence of one—I turned to my friend and maestro of list-making, Alison Coward, for illumination. Alison, with her impeccable lists and enviable penmanship, embodies a commitment to clarity and purpose that I've often admired. "From a professional standpoint, I see lists as a means of keeping promises to my clients. On a personal level, it's about keeping promises to myself."

For Alison, her lists serve as protection against the tide of decision fatigue. Her past self, in a moment of planning foresight, had already charted the course for her present self, sparing her the paralysis of choice that so often ensnares me. "At this point in my life, I can't imagine functioning without my lists," she confesses. "This could be to avoid the anxiety of forgetting something or simply the sheer volume of tasks—it's likely a mixture of both."

The Dance Between Structure and Flow:

Listifying life is representative of something larger. Perhaps, in the lingering effect of COVID four years on, we are still playing catch-up. This is really about the interplay between structure and spontaneity, of prickles and goo.

Most of us don’t find the system that works for us and then quit it. We continually improve upon it. We adapt and evolve our systems of organization to suit us as we, our work, and our lives change.

This dance of organizational and spontaneity isn't just about managing tasks; it's about navigating the promises we make—to others and, most importantly, to ourselves. Finding a system that serves you today, a balance that honors both your need for organization and your desire for freedom might be key to navigating the productivity maze.

Our fixation on productivity often masks a deeper yearning for validation through achievement. But true productivity is not about increasing our output, it’s about being fully present in what you choose to engage with.

In the end, the art of list-making—and perhaps life itself—is an ongoing experiment. It's about finding what works for you in the here and now, embracing the journey of self-discovery, and recognizing that a ‘perfect’ system is a myth.

Our lists, like us humanoids, are works in progress, ever-evolving with the rhythms of life.