A critical factor of success in achieving long term goals is to schedule corresponding daily todos on a calendar. Because if something isn't either obviously urgent or scheduled on a calendar, it never gets done.
For this reason, I sorely miss the Timeful app (bought and shut down by Google) which nailed the process perfectly, integrating one-off todos, habits (e.g. 3 runs/week) and calendar management in a single system. AI-based suggestions for scheduling todos was the icing on the cake.
To this day, sadly I still haven't found a decent replacement.
Google Calendar took the automatic habits scheduling engine from it but is otherwise inadequate for todos, and well-established todo managers like Things / Wunderlist stubbornly refuse to allow something as simple as drag+dropping todos onto a calendar at a specific time of the day (which is the critical bit), and they don't support habits ("tick this box n times a week")
Plan (getplan.co) seemed promising but is too alpha for daily use and development seems to have stalled. SkedPal nails it in theory but is over-engineered and bloated, its UI asks too many questions and cognitive load is high, it needs "Apple-ification".
Any other recommendations very welcome ! Even happy to beta test or collaborate on something new (I know the world already has too many productivity apps, but it lost the "right" one with Timeful IMHO)
I use org-mode for daily todo tracking (and more); I have it configured to auto-generate a TODOS.org file at every project root. I add these to my org-agenda and can easily capture todo items, schedule them (with a calendar view), view my daily/monthly/yearly agenda, and more (i.e. org-pomodoro) with a quick keyboard sequence.
I recently decided to start tracking my life todos in addition to the work projects, which was as simple as creating a life directory and running `git init`.
Org-mode does require using emacs, if it is too crufty for you or you don't like the learning curve, try spacemacs! Its org layer[0] is well configured, and it is also well suited for modal editing if that's your thing.
I do wish Wunderlist will add more calendar integration, it is more useful for repeated or short-term goals for me. Basecamp works well for team collaboration, but it is getting quite busy UX wise.
For long term goals and planning, I prefer to break things down into bullet points, and categories, and check them off as I go. https://taskade.com has been great for that (though no calendar integration), especially with their Chrome Extension that loads your most recent list on each new tab.
Todoist is replacing Wunderlist for me with their more frequent updates.
Sounds like you've already tried plenty of productivity apps, but in case you haven't tried it, I've found Todoist quite good.
The "Apple-ification" as you put it is done pretty well. In place of drag + drop to set a time of day, tasks can be created with inline date parsing. So tasks can be created with something like: "Meeting with Tim at Tues 3pm", and it'd pick that up. It's missing direct support for habits aside from having recurring todos.
If you'd like, I've got a 3-month premium code left over I can send your way. Not affiliated with them, just a happy user.
The difference is that those apps use time blocking (e.g., block out an hour for a task in the middle of actual calendar events) and are usually automatic in nature. The ideal system blocks out the time for a task -- it's not just setting a due date.
I too have tried most if not all of the tools in @renaudg's post and have come to the same conclusion: nothing really matches Timeful.
If you use Apple's Reminders and Calendar apps at all, I highly recommend Fantastical. It works really well. I love being able to see my one-off todos and chores and appointments all in the same view.
The one thing it might lack is guidance to organizing projects/subtasks/dependencies. But luckily I don't need those in my calendar.
Was Timeful rolled into Google Inbox, at least in spirit? Tasks/TODOs (single or repeating) can optionally show up in Google Calendar, though no AI-based suggestions, as far as I know.
For this reason, I sorely miss the Timeful app (bought and shut down by Google) which nailed the process perfectly, integrating one-off todos, habits (e.g. 3 runs/week) and calendar management in a single system. AI-based suggestions for scheduling todos was the icing on the cake.
To this day, sadly I still haven't found a decent replacement.
Google Calendar took the automatic habits scheduling engine from it but is otherwise inadequate for todos, and well-established todo managers like Things / Wunderlist stubbornly refuse to allow something as simple as drag+dropping todos onto a calendar at a specific time of the day (which is the critical bit), and they don't support habits ("tick this box n times a week")
Plan (getplan.co) seemed promising but is too alpha for daily use and development seems to have stalled. SkedPal nails it in theory but is over-engineered and bloated, its UI asks too many questions and cognitive load is high, it needs "Apple-ification".
Any other recommendations very welcome ! Even happy to beta test or collaborate on something new (I know the world already has too many productivity apps, but it lost the "right" one with Timeful IMHO)