Seeking Task Management Utopia

The 80s were a weird time. Individualism and consumerism weren’t just growing; they were growing like a cancer—completely unchecked. If you wanted to keep up, you needed to have your act together. There was one sure-fire tool to help you do that: The Franklin Planner.

That’s what they wanted you to believe, at least.

There were entire sections of office supply stores that had different sizes of Franklin Planners, as well as a myriad of inserts to use in them. The plastic, shrink-wrapped inserts spread out before me are an indelible memory, etched deep in my mind.

My mother had a large Franklin Planner. It was flowery, colorful, and filled with colorful writing and highlighting. It embodied my mom. My father’s was a different story: professional, sleek, immaculately organized.

And I wanted one so badly.

I was always a precocious child.

My interests rarely made sense for my age. I was more interested in books, calculators, and early computers than my peers.

I was fascinated by the idea of a perfect planner and task management system. When my father handed down one of his leather Franklin Planner folios? I was ecstatic. I just needed to get a new filler and start planning my life.

Like the old man that my soul apparently was.

And while Franklin Planners still exist, they aren’t the ubiquitous productivity virtue signals they once were. In fact, I wouldn’t be surprised if some people reading this aren’t even familiar with them.

With our smartphones, who needs a bulky, ungainly paper planner?

But the drive behind the planners is stronger than ever.

Before the smartphone took over the world, there were only really a small handful of personal planner systems, with the Franklin being the most popular. Each system offered an opinionated take on task management and goal setting. Once you chose a system, you really had to adopt that system's opinions, or just not use it.

Fast forward to 2025. Our current reality couldn’t be further from that past.

This is just a rough estimate, but there are likely somewhere around 10,000 different apps on the iOS App Store that have some element of task management to them. Many are simple list apps. Others are full-fledged productivity systems, built on the principles of David Allen’s “Getting Things Done” system.

With so many choices, it seems like it should be relatively easy to find a task management system that clicks.

For me? I wish it were so.

I started with the Franklin Planner. The philosophy behind it never clicked for me to the point that I was willing to go all in. I played with a Palm Pilot, a Dell Pocket PC, and have tried more task managers on the iPhone than I care to admit, but here is just a sample: Wunderlist, Anylist, Microsoft To Do (after they bought Wunderlist), Things, Todoist, and, most recently, OmniFocus.

Each app had its strengths.

At the time, Wunderlist was the best-looking. But I didn’t need any of the collaborative aspects, and I couldn’t bring myself to stick with it once Microsoft bought them. I tried Any.do, Remember The Milk, and Toodledoo. I bounced off all of them.

When I bought my first MacBook Pro, I decided to go all in on Things. Things 3 was hailed as the most aesthetically pleasing task manager and an ideal example of what an excellent “Mac App” should be. I purchased it across all my Apple devices. I tried to make it work.

Maybe it's just me, but I was never overjoyed with how it looked. Nothing about it stood out to me from the others. I didn't ever really gel with its project management either. And there was one thing that finally got me to stop using it: I couldn't mark repeating, future tasks as complete until the day they were due.

There is a philosophy behind this, according to the internet (and we all know that means it must be true, right?). I don't care. If I have an upcoming, repeating task that I complete before the planned date, let me mark it as done, damn it!

When a system's opinions get in the way, it's time for a new system.

I'd long heard of OmniFocus.

It wouldn't be far off calling it the Franklin Planner of modern task management apps. It is complex, built for people with busy lives, with projects spread across a multitude of domains. Initially, this complexity intimidated me. But I decided it was time to go all in. I needed a change.

With the release of version 4 of OmniFocus at the end of 2023, it seemed like a good time to try it. Things was still on (and still is on) version 3, and has been since 2017.

I needed a different approach to task management.

I signed up at LearnOmniFocus.com and started going through the courses. Yes, there is a paid site to learn how to use OmniFocus better. Having this degree of buy-in helped motivate me to stick with it.

Still, I struggled. Folders, versus projects, versus tags, all added a layer of complexity that felt like more than I needed.

I’d read Getting Things Done by David Allen. I understood the principles and could see how OmniFocus was designed to complement those principles. But there was one major problem: my life simply doesn’t feel complex enough to warrant all of that.

At work, most of my duties are simple: see patients, do surgeries. At home, I didn’t have large, multistep projects that needed to be done and organized. The tool’s capabilities felt wasted.

The truth is, I don’t know exactly what I’m looking for in a task manager. I like the Kanban view of Todoist (OmniFocus says something similar is coming, but it isn’t here yet). I love the Forecast and customizable perspectives of OmniFocus. On Apple devices, nothing works better with voice input and quick capture than the built-in Reminders app.

I’ve been trying to find the best task management system for myself since I was a child. I’m still looking, still struggling. I can’t help but think that there is the best system for me. I just haven’t stumbled across it yet.

Some days, I feel all I really need is a slip of paper.

Others? I want so much more.

Maybe I'm the problem.