Freedom is that which is boundless and limitless with no path and no destination; that is the Tao.
Taoist meditation seeks various goals, among them strengthening the mind; relieving stress; and developing the capacity for spiritual insight. Beginner meditation is called "practicing stillness". If you have never meditated before, consider it mental and physical discipline for the purpose of strengthening and settling the mind. When you become comfortable with sitting, you then begin to cultivate the yielding, receptive nature of awareness. Next, you will train your attention in various ways to open different layers of the psyche. When the mind is at ease and not distracted, in harmony with the body and poised within itself, then yielding begins.
The spiritual Taoist is concerned with uniting seemingly opposing energies deep within the psyche, also called the "mystical marriage". Taoist mysticism holds that the human soul is fractured. The mystical marriage heals the psyche of its conflicts and obsessive self-centeredness, repairing the fracture and returning the soul to its whole state. It is from this wholeness that one gains the independence necessary for transcending the self. This is what the Taoist calls freedom: the Taoist mystical path.
How to Meditate: The Basics
Meditation is natural. Just as you are born with the knowledge of how to breathe and think and digest, you are born with the innate knowledge of how to meditate. A teacher is someone who reminds you of this. Teachers themselves do nothing special. There is no passing of energy or any such thing; those who say so are manipulating your imagination. An observant teacher, however, may teach some imagination exercises to help develop attention. There can be synergy in the form of support when people practice together; however, ultimately, it's all up to you.
Religions and doctrines can confuse and over-complicate the practice, so don't get caught up, but by all means study them if you feel such study helps you. Just like training for a marathon, you must practice proactively; you're not "just sitting there". In physical training, you are doing through action; in meditation training, you are undoing through stillness. You are emptying yourself so as not to be full of your self, so that you may experience a deeper layer of the mind's nature.