Habit formation is really difficult. The way I like to think about goal lists and daily schedules is as productivity supporting habits rather than directly productive habits.

It's not unusual to have some productive habits. Going to the gym before work, doing X hours of uninterrupted work each weekday, cleaning your home once a week, etc, can be hard habits to build, but it can and is done. The problem is that you need to do the habit formation work every time you have a new goal.

Other habits can help support productivity even if they aren't directly productive themselves. Being in the habit of creating schedules and sticking to them (or effectively using a to-do list) can help support other productive activities, but isn't directly productive itself. These type of habits are nice because you only need to build them once. If you always follow your schedule, you can engage in a variety of productive activities without building each habit individually; that habit can serve as an action trigger.

Obviously it's not always this simple. I think building up the habit of actually completing the work listed in your calendar can be very challenging, perhaps more so than building up individually productive tasks. I wasn't able to do it, even after scheduling in leisure time. I settled on a to-do list workflow (styled off of GTD) that works nicely for me. I now use calendars only for hard times (events, deadlines, birthdays, etc), otherwise I start to feel like everything on the calendar is as flexible as the daily work that I schedule in.

Doing some of the meta work described in the Anna Salamon piece would likely improve my goal management. I'll try to work some of those heuristics into my existing goal list, which is likely too vague. I wonder if there is a way to work some of those heuristics into a calendar or to-do list habit to improve their efficacy.