There is a popular Zen story where a man is working in the fields when out of the corner of his eye he sees his good friend galloping down the road on his horse. He shouts out “Where are you going?” The friend, holding tight to the bridle, yells back “I don’t know! Ask the horse!”
The horse can be our thoughts, desires, passions, or obsessions. The horse is our attachments. It might be your need for recognition, or your desire to make increasing amounts of money, or your fear of losing your beautiful girlfriend.
I like this little story because it simply shows us how difficult it can be from the outside to discern whether actions are motivated from authentic, internal freedom or compelled from external sources. On the surface these actions might look identical. But they create very different internal states for the person in question.
Psychological thought and Zen align nicely with the idea that you can never be really happy when your life course is decided by external sources. One of the reasons why is that you are always at risk of losing these sources, at which point your life will apparently lack meaning and even worse you will cease to be yourself. This is anxiety provoking and symbolizes death, so you spend your time, consciously or unconsciously, attempting to make these external sources safe and unassailable. Meanwhile all that life has to offer passes you by.
It takes a great deal of courage to look inwards and honestly consider which structures you rely on to give you your identity. They are different for every person but what they all have in common is that they ultimately create suffering because they are by their very nature impermanent and on some level you know this.
The way out of the quagmire is to reflect on who and what you want to be in the world and to spend your time self-actualizing from the inside out rather than chasing after attachments to define you. When you fully define yourself by internal characteristics you are at no risk of losing them. Ironically, in this state you are in a much better position to connect authentically and lovingly with the people around you because fears, anxieties, and compulsions are not blocking your way. By eliminating attachments you actually end up with many more healthy and fulfilling attachments than you had before.
This style of living makes no moral judgments against having money, pursuing a career, or any other attachments you can think of. It simply places them as secondary and sees them as outcomes of the infinitely more important and rewarding task of growing into your true Self. At this point you are in control of the horse, and you can direct it wherever you want to go.