Having a system that can show progress visually is like having a reward system to satisfy both upper and lower intelligences. The Upper is satisfied by seeing long term marks toward accomplishing the habit to be formed, or to the goal itself.
The Lower is satisfied by accomplishing an immediate task and having the reward of marking it off. This may get old to the lower, so it may become uninterested after a while. What you may need to do is incrementally put a different or bigger reward to have it work towards.
For Example:
After a week of marking off the calendar, the lower may not feel that this is a reward any longer. If you add in that there is a weekly reward along with the daily, then it may be more enthusiastic about getting things done.
Some apps offer badges for accomplishments to show on social media, some people may take a picture, get ice cream, do a giveaway, whatever entices the lower to do better and stay on track.
The thing is, this is a part of the planning process to your success. It is hard to do things successfully making stuff up as you go. It very hard to hit a target you cannot see.