The heart of Jesus' teaching was the Sermon on the Mount (Matthew 5-7), together with his parables, many of which are about losing and then finding (the lost son, the lost coin, the lost sheep). All of these teachings, and Jesus' lived example, call us to win by losing, which is so countercultural and so paradoxical that Jesus finally had to live it himself to show us it could be true.
The Sermon on the Mount begins with the so-called Eight Beatitudes (Matthew 5:3-12). Read them from the perspective of how they describe Jesus as the suffering servant:
How happy are the poor in spirit; theirs is the kingdom of heaven.
Meister Eckhart, OP, (1260-1328) said that to be poor in spirit is to "know nothing, want nothing, and have nothing." That sounds a lot like Buddhism! And this is Jesus' opening line.
Happy the gentle: they shall have the earth for their heritage.
This is so contrary to our love of power, certitude, and control. Who of us really believes this? Could you ever build an empire or even an institution with this kind of na�vet�?
Happy those who mourn: they shall be comforted.
We now know that grief is a privileged portal into soul work and transformation.
Happy those who hunger and thirst for what is right: they shall be satisfied.
Happy are the merciful: they shall have mercy shown them.
There is a perfect correlation between how we give and what we can receive. Consider this for the rest of your life.
Happy the pure in heart; they shall see God.
Happy the peacemakers; they shall be called children of God.
Happy those who are persecuted in the cause of right: theirs is the kingdom of heaven. (Matthew 5:3-10)
Each of these invitations, for that is what they are, are concerned about vulnerable and outpouring relationship, which is necessary for the second half of life, in the same way that the Ten Commandments serve for ego-identity in the first half of life. The Beatitudes are descriptions of a mature human person much more than prescriptions for other-worldly salvation. They offer something astoundingly new to human consciousness, which is a lifestyle based on vulnerability, mutuality, service--and thus a willingness to be usable for God, history, healing, and one another.