Each of us, the sages taught, is measured on how we have lived our lives in six ways:
"When a person is brought into heavenly judgment, he is asked: Were your business dealings fair and honest? Did you have set times for Torah study? Did you engage in procreation? Did you anticipate redemption? Did you discuss wisdom? Did you discern 
We should recognize that we are part of the nation, which in turn is part of all humanity.
new insights?" (Shabbat 31a)

We should recognize that we are part of the nation, which in turn is part of all humanity.
new insights?" (Shabbat 31a) Most of these questions indeed are the cornerstones of a life well lived. But what is so important about anticipating redemption? Don't we all hope for the best? What does this trait reveal about how one has lived his life?
Part of the Nation
It is important to understand that tzipiyah leyeshu'ah does not refer to looking for solutions to our personal problems. Rather, we are expected to anticipate the redemption of the Jewish people and all of humanity. As Rashi explains, one should look forward to the fulfillment of the words of the prophets.
This is not a trivial demand. As individuals, we are easily caught up in our personal problems and issues. In truth, we should feel that we are like a limb of a great organism. We should recognize that we are part of the nation, which in turn is part of all humanity. Every benefit of every individual contributes to the life of the klal, thus advancing the future national and universal redemption.
The question tzapita leyeshu'ah is a critical measure of one's life. It is the yardstick that determines whether one's life has acquired an overall, universal value. By anticipating the redemption of the klal, we demonstrate that we are able to raise ourselves above the narrow concerns of our private lives. We strive not just for our personal goals, but for the ultimate elevation of the nation and the entire world. We are part of the nation; its redemption is our redemption, and its joy is our joy.
The Lookout
Rabbi Avraham Yitzchak Kook noted that the heavenly tribunal does not ask kavita - "did you hope" for redemption - but tzapita - "did you anticipate" redemption. Tzipiyah indicates a constant watchfulness, like a soldier posted to the lookout, at his observation post for days and even years. The soldier may not abandon his watch, even though he sees no change.
We, too, are on the lookout. We should examine every incident that occurs in the world. With every new development, we should consider whether this is perhaps a means that 
Tzipiyah leyeshu'ah is not only passive observation.
will advance the redemption of Israel.

Tzipiyah leyeshu'ah is not only passive observation.
will advance the redemption of Israel. However, tzipiyah leyeshu'ah is not only passive observation. Woe to the army that the lookout perceives a threat, but does not take any action. The moment there is some development in the field, the soldier must respond swiftly, either to defend or retreat. So, too, our tzipiyah includes the readiness to act promptly. While these two traits - constant watchfulness and immediate action at the right time - may appear contradictory, they are both aspects of tzipiyah leyeshu'ah.
[Adapted from Olat Re'iyah vol. I pp. 279-280; Ein Ayah vol. III p. 182]