Generally speaking, your weaknesses and progress are far more complex to measure than even understanding your chakras would allow.
Your weaknesses are those aspects of yourself in which you find discontent.
Your progress is your learning, enlightenment, etc. in which you have taken steps to overcome those areas with which you are discontent.
If you wish to be magically aware, seek to understand the energies of the world around you. If you wish to learn a specific tradition of magic, explore those traditions. The chakras themselves are merely a visualization of the energetic flow through you - they explain, and help you work with, the various aspects of the self and how you interact with the world around you. Even without exploring the chakras you can come to improve them through seeking balance, enlightenment, and understanding.