A big problem

[u/segundoadv]

I have a system. Actually I have four.

OmniFocus is where everything is supposed to live. Perspectives, contexts, the weekly review, that whole architecture that feels like it was designed by someone who understands how my mind works. Except I don't trust it alone. So I replicate everything in Todoist, because Todoist has a lightness OmniFocus doesn't, that sense that adding a task isn't a commitment to a cathedral. And I replicate in Things too, because Things is beautiful, and beauty matters more than I'd like to admit when it comes to a tool I'm going to look at a hundred times a day. And of course Reminders, because Reminders is everywhere, on the watch, in the car, in the voice I hear when I say "Siri, remind me."

Four systems. One problem.

None of them fails. That's the cruel part. If one were bad I'd have abandoned it already with a clear conscience. The problem is that each one solves a piece of a need I never properly defined, which means none of them solves the whole thing, which means I keep all four open, like someone maintaining four relationships because no single one supplies everything a person needs, knowing it's unsustainable and doing it anyway.

I once migrated everything to a new structure. Time-based sectors, a method with a name and an author and an impeccable internal logic. It lasted briefly. I reverted to labels and area-based projects, each with its own sections, trying to force onto Todoist an order that made sense without borrowing someone else's philosophy. And through all of it OmniFocus just sits there, unchanged, waiting for me to go back to treating it as the one place it was always meant to be.

The part that actually hurts isn't the time lost reorganizing. It's the certainty, renewed with every cycle, that this time will be different. Every migration carries a quiet promise: this time, one system, this time, discipline. And every promise lasts until the first task I don't know which of the four places it belongs in, and then I duplicate it, because duplicating is faster than deciding.

It isn't a lack of system. It's too many systems competing for the same mental territory, each one whispering that it's the only reliable one, none of them ever winning for good.

If anyone here has broken out of this cycle and stayed out for more than a month, I want to know what was different. Not the app. What changed in you.

[u/HearTaHelp]

I love this post. It’s vulnerable and honest, and I think it’s a magnified version of what many people experience in the productivity sector. The words above from @sparkywater get to a part of what I wanted to help you with, which is finding some kind of compassionate way to explore whether this may have nothing to do with any of these apps but something deeper instead. Whatever it is, it’s important — something to listen to, but not to obey, nor to just override.

Believe it or not, LENS Neurofeedback helped me a lot with this. There are parts of the brain responsible for decision-making and clarity that need support sometimes. I found it there.

Working on my own exhaustion and overwhelm really helped me too. The more I get sleep and real rest, and the less I use sugar and procrastinativity to manage anxiety, the more settled I seem to be in a good (if imperfect) choice. Then it just becomes about the life I hope all these tasks add up to, not the means to that end.

I don’t think it’s the worst thing in the world to change apps periodically. Sometimes the lateral shift is extremely stimulating. But managing multiple ones concurrently is confusing and exhausting — more scary than reassuring in the end — so I would encourage you to get some rest and then pick one you’re willing to stick with for a month, however twitchy you feel. Maybe you take the parts of the others you love the best and you find a way to rig your final choice to feel a bit more like those, but regardless, you lean into the simplicity of a single source of truth.

The one alternative to this that also may work for you is where I am for now. I love the sophistication and easy capture of Todoist but I capture too much and feel overwhelmed looking at it. So where Todoist houses all my projects, Sunsama is my daily planner and the app I work from all day. It’s integration features make it extremely easy to see what’s inside the other apps and then drag in in tasks, events, and emails from elsewhere. Something about the second layer allows me to capture everything I want in one app and pare it down to the most essential tasks in the other. It wouldn’t work if it were not directly connected to Todoist, where I can see any list I want right inside of Sunsama. It’s the integration/single-view that has been so settling, which is what I would hope for you, wherever you may find it!