Triangulate your position. What do your mind, emotions and intuition tell you about where you are with your question/choice/relation? The time to go forward is when you get the inner yes from all your centers. Until you do, learn to endure ambiguity and ambivalence rather than making a premature decision.
From the I Ching point of view, the time to go forward with any major choice is when a deep inner knowing tells you it is time. It is the Self (the totality of all psychic structures) and global intuition that are best qualified to make such choices. The mind and ego can be involved, but should not be the rulers of the process because it is above their level of competence. When the mind-ego alliance is in charge of decisions, you tend to get that ping-pong game sort of dialog in your head: "But what about this? But what about that? But what if this happens?" etc. In the hierarchy of psychic structures, the Self
is the ruler and the mind and ego are like the ministers, the cabinet members or facilitators. When the big decision has been made, they are very necessary to figure out how to implement it. If you are still in doubt about a decision, the I Ching advice is to hold back — don't go until you know, in most cases you are better off maintaining the present position until you are sure.
A classic illustration of these principles involves romantic relationships. A mind-and-ego-dominated person tells himself, "Well, I have to be going out with someone — what about this person? What about that person?" A merchant mind kicks in, like someone anxiously scanning personal ads or evaluating merchandise: "Well, this one likes candlelit dinners, but this one is taller. But this one seems more reliable. But this one…" From my point of view, the default position for the conscious person is solitude, often the most powerful place to be, but with a willingness to come forward into relationship, ready to give it all the incredible energy and attention it is going to take when called to do so from the depths of one's being. You wait for the soul mates and spiritual allies, and recognize that even these depth relationships are likely to have problematic phases and will take a lot of care and resources. You don't go forward into a random relationship out of the lonely restlessness of the social ego, which is addicted to social matrix noise and anxious to fill space with some sort of body or chatter or whatever. By endlessly distracting yourself with superficial relationships, you may miss out on the soulful ones. It is the same with career choices, major relocations, and big plans. The ego loves decisive action, hates to wait in ambiguity and ambivalence and wants some sweeping change that will supposedly resolve everything. One of the greatest assets of a mature person is the ability to be at rest with ambiguity and ambivalence. A little mind can't stay open to uncertainty and reaches for premature closure, becomes a true believer in something, a religion or secular fundamentalism.
Consider this a propitious time to triangulate your present position