Q. My teenage daughter is a very creative soul who loves creative expression like art and writing. But she is also a real slob. Her room is always a mess. No matter how much I ask her to clean up after herself, the room stays messy. There are papers all over the floors from the many projects she's always in the middle of, and her clothes cover every surface. My husband suggests we take a stronger hand and thinks that she has a real problem, but every time he speaks to her it seems like she gets deflated. How can we help her with her problem while still not destroying her self-esteem?

A. There are some children who are naturally neat and organized and there are others who have to acquire these skills. By gently guiding your daughter in a way that she will be ready to listen and comply, you will be providing her with some valuable tools for life.

As we watch our offspring growing up, it's natural that their actions evoke within us a tangle of emotions and leave us feeling incompetent (What kind of mother am I? Is this how I've raised my daughter?), frustrated (How many times do I have to tell her to clean up after herself?) and even fearful (How will she ever succeed if she can't even hang up her own clothes?).

Talking to your daughter at a time when these emotions are fizzing just beneath the surface will communicate these feelings to her and may indeed leave her feeling deflated. By neutralizing such feelings, you can convey a genuine desire to work together with her on this issue, and you'll be on the path towards remedying the situation; our attitude to the problem is the most important first step in dealing with it.

How do you neutralize such thoughts? Since children have their own free will, we cannot control them or their behavior. It's important to remember that our job as a parent is to teach them lovingly and patiently – but their choice of actions does not necessarily reflect our competence as a parent (even if it may call for a different method of teaching).

If you've come to the conclusion that your daughter is a "slob" and that's what you feel in your heart, your daughter will feel that, too. In Ethics of our Fathers we are taught, "Hevei dan et kol ha'adam lechaf zechut"–judge everyone favorably. The word kol ha'adam (every person) can also imply the whole person, so that we can understand the meaning of the verse as judge the whole person favorably. In other words, rather than allowing her flaws to obscure your vision, view the person as a whole person, her weaknesses and her strengths, and you will perceive a more favorable picture.

If you can externalize the issue at hand and view your daughter as the whole person that she is – a wonderful creative young woman – who happens to have a hard time with orderliness, you will lower the frustration a great deal, maybe even eliminate it altogether. You will then be able to approach your daughter with an understanding and empathetic heart. She in turn will feel your genuine desire to help her with her struggle and may readily accept your guidance.

And finally, acquiring concrete methods to help your daughter will allow you to focus on the present and stop your imagination from predicting the worst. You may have noticed that nagging, criticizing and blaming has not brought you very far, but you may be surprised to see how much your daughter will appreciate some practical advice, not to mention what it can do for her self-esteem.

Incidentally, it may be a good idea to allow her to have one space where she can throw all her stuff in a big heap. Perhaps her bed, or a chair – think of a spot where it will least likely disturb you. This way she can have the freedom she craves and you can have the orderly room you would like. Besides, it will be easier for her to put things away if they are all gathered up in one area.

Good luck!