The mouse makes a soft click. A sound with no physical weight, yet it feels like dragging a stone. The little digital card, the one that says, ‘Finalize Q4 report,’ slides from Friday’s column into the abyss of ‘Next Week.’ This is the fourth time it has made the journey. The task is now a seasoned traveler. It knows the route. The pixels don’t care, but I can feel their judgment radiating from the screen, a low-grade hum of disappointment.

The Wisdom of Hiroshi J.D.

I used to believe this was a personal failing. That the problem was my lack of grit, my inability to just do the thing. My list was a weapon I used against myself. Then I met Hiroshi J.D. He was a union negotiator, a man whose entire professional life was a to-do list of intractable human problems. He spent his days in rooms thick with tension, mediating disputes between dockworkers and shipping magnates that had been festering for years. His tasks didn’t have clear start or end points. You don’t just ‘Resolve generational mistrust’ in an afternoon.

“Lists are for groceries,” he said, adjusting his glasses. “My work is about stalemates. You can’t put a stalemate on a list. It will just sit there and rot.”

“

He explained that for years, he tried. He’d write things like ‘Draft new pension proposal’ or ‘Follow up with legal,’ and those items would become permanent fixtures, mocking him. They were too big, too dense. They were dragons.

There’s this thing about old maritime maps. In the unexplored corners of the world, where cartographers had no data, they wouldn’t leave it blank. An empty space is terrifying. So they drew sea monsters and wrote ‘Here be dragons.’ It was a way of giving a name to the fear of the unknown. That’s what we do on our to-do lists. ‘Renovate the kitchen’ or ‘Learn a new language’ aren’t tasks; they are vast, uncharted oceans where dragons swim. We put them on the list, and then we avoid them, because we’d rather face a list of 14 small, known things than one enormous, unknowable beast.

From Walls to Doors: The Power of Questions

Hiroshi’s solution was to stop listing outcomes. Instead, he started listing questions. His notepad wouldn’t say, ‘Convince management to accept Clause 14.’ It would say, ‘What is the real reason they are rejecting Clause 14?’ It’s a subtle shift, but it changes everything.

An outcome is a wall to be scaled; a question is a door to be opened. His job wasn’t to complete tasks, but to find the right questions that would eventually, slowly, lead to an agreement. It was a revelation. It reframed the entire purpose of the page.

I’ll admit something, a contradiction that feels necessary. After all this criticism, after calling these lists monuments to our procrastination, I still write one every single morning. It’s a ritual I can’t seem to shake. For a while this made me feel like a hypocrite. I was complaining about the very tool I relied on. But my approach changed after talking to Hiroshi. My list is no longer a document of expectation. It is a space for inquiry. I put a maximum of 4 items on it. One is always a question. One is always something I can do in under 4 minutes. One is the big, important thing. The fourth is a wildcard.

This new structure helped me face a monster that had been on my list for 244 days: ‘Go through grandpa’s old video tapes.’ It was a colossal task, emotionally and logistically. It sat there, judging me. Hiroshi’s method broke the stalemate. The task became a question: ‘What’s the first step to preserving those tapes?’ The answer was simple: ‘Find a digitization service.’ The next day, the task was just that, a small, concrete action. The dragon was still there, but now I had a tiny sword.

Automating the Friction Points

This is where the real friction lies-in those tedious, multi-step tasks we think we have to muscle through ourselves. Hiroshi spoke about the old days, reviewing negotiation footage. His list would have an item like ‘Transcribe the 44-minute meeting audio,’ and it would paralyze him for a week. He described the sheer dread of sitting down, pressing play, pausing, typing, rewinding. A 44-minute recording could take 244 minutes to get right. These days, a task like needing to gerar legenda em video for archives or for members who are hard of hearing is not a dreaded, multi-day project. It’s something that happens in the background. Automating the friction points is like slaying half the dragon before the fight even begins.

The List Is Not The Point

The most important realization is that the list itself is not the point.

We have been sold a fantasy: that if we could just find the right app, the right notebook, the right system, we would unlock a state of perfect, frictionless accomplishment. That we would become masters of our time, every minute accounted for, every task checked off with a satisfying swoosh. It’s a lie. A beautiful, seductive, and ultimately corrosive lie. It turns our lives into a series of tasks to be executed rather than a story to be lived. The anxiety doesn’t come from the tasks themselves, but from the constant, nagging feeling that we are failing to complete an imaginary syllabus for life.

My personal mistake, the one that truly taught me this lesson, was putting ‘Become a better person’ on my list a few years ago. I am not joking. It sat there for weeks. What does that even mean? How do you check that off? It was the ultimate dragon, an abstraction so vast it consumed all the other items on the page. It was a symptom of a mind poisoned by the idea that self-worth is something you achieve through task completion. I was trying to put my own soul on a checklist.

A System Built Around Forgiveness

So my system now, the one I use despite my deep mistrust of the form, is built around forgiveness. The list is written in pencil. It has a built-in ephemerality. At the end of the day, around 4 p.m., I take the piece of paper, look at what’s done and what isn’t, and then I crumple it up and throw it away. The act is the closure. It’s a physical release. It’s an acknowledgment that the day is over and my worth is not tied to the ink remaining on that page. Tomorrow, a new page awaits. It might have some of the same items, it might not. It doesn’t matter. The goal isn’t to achieve Inbox Zero for your life. The goal is to close the book at the end of the day and rest.