Why your productivity system keeps failing

Stop optimizing for task completion. Start solving problems that matter.

After fifteen hours of work, I would watch an hour of TV before going to bed feeling like I’d wasted the entire day.

Something had to be wrong with me, right? Normal people didn’t feel guilty about an hour of Netflix after so much work. So I tried to find a fix.

First came the todo apps: Things, Todoist, anything that promised to help me “get things done.” Then automatic schedulers. Then elaborate note-taking systems where I’d link tasks to projects to areas of life. I even built a custom app to mathematically calculate which tasks were most valuable based on impact and urgency.¹

Each system worked for a few weeks. Then the old feeling would creep back: busy but not productive, working hard but going nowhere.

The breakthrough came when I realized I wasn’t asking the right question. The question wasn’t “How do I get more done?” The question was “What problems am I actually trying to resolve?”

Until I answered that, no system could help me.

Wanderer in the Storm by Julius von Leypold

The Problem With Task-Based Thinking

There’s a hidden assumption in my old ways: that the tasks themselves are the right things to be doing. That if you just execute well enough, you’ll be productive.

This assumption is wrong.

I’d complete twenty tasks in a day and still feel unproductive. Not because I was being irrational, but because most of those tasks weren’t actually serving any problems I cared about. I was optimizing for task completion when I should have been optimizing for problem resolution.

Here's what my task list used to look like on a typical day:

1. Do all the readings for philosophy seminar

2. Respond to group project messages

3. Go to gym

4. Attend club meeting

5. Work on problem set

6. Review notes from yesterday

7. Research for next paper

I’d get through maybe fifteen of twenty tasks and feel behind. But here’s what I couldn’t see: most of these tasks existed for the wrong reasons.

“Go to gym” was on the list because “working out is something people do” and “I should probably stay fit.” But it was disconnected from anything real. Just a floating obligation that generated guilt when I skipped it.

“Do all the readings for Philosophy seminar” was there because they were assigned. I never asked if reading every page would actually help me understand the concepts or if I could learn more effectively another way.

“Attend club meeting” was there because I’d joined the club. I never asked if being there served any purpose beyond avoiding the guilt of not showing up.

I was doing things because they felt like obligations, not because they served any actual purpose. And when I did try to justify them, it was always backward: “I’m doing this problem set because it’s assigned, which affects my grade, which affects my GPA, which helps me get a job, which helps me... survive? Be successful? I guess?”

The chain of justification could stretch back far enough, but it was always after the fact. I was never asking the critical question upfront: Is this the best way to resolve the problems I actually care about?

Landscape With Mountain Lake, Morning by Caspar David Friedrich

The Shift: Start With Problems, Not Tasks

When I reframed my thinking this way, everything changed.

I want to stay healthy and capable. That’s a problem—an aspiration I’m working toward. It requires ongoing work. It never fully “resolves” but it can be actively worked on or neglected.

I want to understand ideas deeply enough to use them. That’s a problem. It shapes what I do in my classes and how I spend my time.

I want to build things people find meaningful. Another problem. It determines what projects I take on.

Exercise stopped being a floating task. It became a direct step toward resolving a problem I actually cared about—staying healthy and capable. When I miss a workout now, I don’t see a character flaw. I see a practical question: What got in the way? How do I structure things better?

That Philosophy seminar reading? I started asking: Does reading every page serve the problem of understanding these ideas deeply?

• Sometimes yes: the reading is dense and I need to work through it carefully.

• Sometimes no: I can skim for the main argument and spend my time thinking through the implications instead.

The club meeting? Does attending this serve any problem I care about?

• Sometimes yes: I’m building relationships or working on projects that matter to me.

• Sometimes no: I’m there out of obligation, and I can leave the club or just skip meetings that don’t serve my goals.

The difference is subtle but everything downstream changes.

• Before: I’d look at a task and ask: “Should I do this?” Then I’d try to build a justification chain backward to something meaningful. Since I can justify anything, I end up doing it or feeling guilty.

• Now: I look at a problem I care about and ask: “What’s the best way to resolve this?” Then I create tasks that serve that purpose. Sometimes the answer is “none of the tasks I had in mind.” Sometimes I realize I’m working on things that actively detract from my real problems.

This is top-down thinking versus bottom-up thinking. Bottom-up: start with tasks, justify them afterward. Top-down: start with problems, create tasks to serve them.

Bottom-up gives you a fragmented picture. You can connect individual tasks to immediate goals, but you can’t see the whole. You don’t know if you’re working on the right things. You can’t tell if there’s a better path.

Top-down lets you actually choose. You’re not just justifying what you’re already doing. You’re asking what you should be doing in the first place.

Neubrandenburg by Caspar David Friedrich

What My Days Look Like Now

Here’s what changed practically:

I stopped doing a lot of things. Things I thought I “should” be doing but that weren’t serving my actual problems. The guilt disappeared because I could see clearly: these weren’t helping.

I started doing things I’d been avoiding, like exercise, because I could see clearly: these directly resolve problems I care about.

I started skipping readings that didn’t serve my learning. Some professors assign readings to have students get the scope. The effort and time spent reading every single text doesn’t serve my real aim of getting insight, it’s just a time sink. Instead I read through summaries and discuss with friends.

I stopped trying to complete every assignment perfectly. Some assignments serve the problem of understanding concepts deeply. Others are just boxes to check for a grade. I can tell the difference now, and I allocate my effort accordingly.

My task list got shorter. On a typical day now:

• Work through problem set for Fluid Mechanics (serves: understand fluid engineering physics sufficiently)

• Run (serves: stay healthy and capable)

• Discussion with professor about a reading (serves: resolve confusion about arguments from last week)

• Revise the draft for my next essay (serves: build things people find meaningful)

Four tasks instead of twenty. But I can tell you exactly why each one is there and what problem it serves.

Most importantly, I can now tell if I’m being productive. Before, it was a vague feeling, easily destroyed by an hour of TV. Now it’s concrete: Did I work on resolving the problems that matter to me? Then the day was productive. Doesn’t matter if I worked three hours instead of fifteen.

Those fifteen-hour days that felt empty? They were full of tasks that weren’t serving my problems. I was busy. I wasn’t productive.

Morning mist in the mountains by Caspar David Friedrich

The Hard Part No System Can Solve

I need to address the obvious objection: “But I DO know what I care about, and I still can’t get things done.”

If that’s you, I’d ask: Do you know what problems you’re trying to resolve in concrete terms, or in vague ones?

“Do well in school” is vague. “Understand statistical thinking well enough to read research papers critically” is concrete.

“Stay healthy” is vague. “Maintain enough strength and energy to do the activities I enjoy without pain or limitation” is concrete.

“Be successful” is vague. “Build skills in X domain so I can work on Y type of problem” is concrete.

The vague version can’t guide your tasks because it doesn’t tell you what success looks like. The concrete version can.

This is the work no simple productivity system can do for you². You have to ask: What problems am I actually trying to resolve? What does resolution look like in specific terms?

These questions don’t have packaged answers. You have to think them through yourself. And it’s uncomfortable because you might realize you’ve been working toward problems you don’t actually care about—problems you inherited from parents, or peers, or some vague sense of what you’re “supposed” to want.

What This Means For You

If you’ve tried multiple productivity systems and they keep failing, the problem probably isn’t execution. You don’t need a better app or more discipline.

The problem is conceptual. You’re trying to optimize task completion when what you need is clarity on what problems you’re trying to resolve.

I’ll detail how to build a system around this in a followup essay, but the conceptual shift has to come at some point. No system will make you productive until you’re clear on what problems you’re actually trying to resolve.

For now, try this: Look at your task list. For each task, ask: “What problem does this resolve?” If you can’t answer clearly, or if the answer is “I’m supposed to do this” or “it would feel bad not to,” that’s a sign the task might not belong there.

Then flip it: Look at the problems you actually care about. Ask: “What tasks would best resolve this problem this week?” You might find that the tasks you generate are completely different from what’s on your list.

The tools are simple—just a calendar and a notes doc. The real work is conceptual: getting clear on what problems matter and building everything else around that.

Your version will look different because what matters to you is particular to you. But the core shift is the same: stop starting with tasks. Start with problems.

Philosophy sucks, but it’s too useful to give up

Productivity isn’t about completing tasks efficiently. It’s about resolving the problems you actually care about.

Once you understand that, the systems finally work. And those fifteen-hour days that felt empty? They become three-hour days that feel productive—because you can finally see that the work you’re doing actually matters.

The Port of Greifswald by Caspar David Friedrich

Written with the help of AI.

1. I haven’t given this project up! I am slowly working on it. What I referenced here was a local plugin for Obsidian, and it was not mathematically correct.

2. Some systems, however, can get the ball rolling. Well designed systems can make top-down thinking natural. I will describe how to get such systems in a followup essay.