How to "discipline" someone who is hard on themselves?

Hi all,

I need some advice on how to help manage someone that reports to me. Long story short, they keep making the same mistakes, but they are so hard on themselves when they do it makes it hard to give feedback. They know it's wrong, but haven't been able to break the habit.

In general, the person has a hard time getting to work on time. They are salaried, so they don't have a 100% exact start time, but they have certain tasks they need to do in the morning. They are typically not getting here on time to get them done on time. They also routinely forget about meetings. When these issues occur, they are truly apologetic and know it was wrong, so I feel bad.

I'm not trying to toot my own horn, but in general, I am a very chill and open minded manager (mostly because I've only managed exception people that don't need a manager). I check in to make sure all is good at home, they have reliable transportation, what I can do to help, etc, but it comes down to that they are not a morning person and are working on being organized.

We talk about how they need to be here on time and I don't want to write them up or anything, but I can't be at their house to wake them up or remind them every time they have a meeting. So, how do I give more advice/help more when they keep having the same issues, know they're making mistakes, feel really bad, but then it happens again?