The Page of Cups is about cautiously exploring your own emotions (about the course ahead).
Now is the time to carefully show your emotions to those around you, but don't go overboard straight away. Only show as much of your emotions as you need to get good advice.
You've been rational about your choices for a long time. Now is the time to consider your emotions, and to cautiously discuss those emotions with those whose advice you value.
You're too cautious at the moment, it might be wise to discuss your emotions with others just a bit more.