Holes
A hole refers to any part of you that has been lost, meaning
any part of you that you have lost consciousness of. What is left
is a hole, a deficiency in a certain sense. What we have lost
awareness of, is of course, our Essence. When we are not aware
of our Essence, it stops manifesting and is lost. Then we feel
a sense of deficiency. So a hole is nothing but the absence of
a certain part of our Essence. It could be the loss of love, loss
of value, loss of capacity for contact, loss of strength, the
loss of will, loss of clarity, loss of pleasure, and any of those
qualities of Essence. There are many of them. But when they are
lost, they are not gone forever; they are never gone forever.
You are simply cut off from them. (Diamond Heart Book 1, pg 17)

Content of holes
For instance, the loss of the will is generally related to fears
about castration, as we discussed earlier. The loss of strength
is related to repression of anger and also fear of separation
from mother. The loss of compassion is always due to suppression
of hurt. Each “hole” is filled generally by the same
thing, with variations depending on the childhood history, and
cultural and social circumstances of the person. Compassion, for
instance, might be replaced by sentimentality and belief that
one is a loving person; intuition might be replaced by excessive
ideation, and strength by a show of being tough. (Diamond Heart
Book 1, pg 50)

Defending of holes
When we stop defending against feeling a hole, the actual experience
is not painful. We simply experience empty space, a feeling that
there is nothing there – but not a threatening nothingness
– a spaciousness, an allowing. This spaciousness allows
Essence to emerge and it is Essence and only Essence that can
eliminate that hole, that deficiency from the inside. (Diamond
Heart Book 1, pg 22)

Holes and dissatisfaction
Most of our discontent, pain and discomfort is the result of
losing a part of ourselves. It's not because of the economy; it's
not because we are ugly or fat or this or that. These are not
the real reasons. So trying to get fulfillment by solving these
supposed problems doesn't work. The dissatisfaction comes from
not allowing ourselves to experience a part of us. We are full
of holes, and the only way we can be fulfilled and complete is
to stay with those holes so that part of us is allowed to manifest
and function. This cannot happen as long as we try to fill our
holes with something else. (Diamond Heart Book 2, pg 122)

Holes and society
Allowing ourselves to tolerate the holes and go through them
to the other side is more difficult now because everything in
society is against this. Society is against Essence. Everybody
around you, wherever you go, is trying to fill holes, and people
feel very threatened if you don’t try to fill yours in the
same way. When a person is not trying to fill his holes, it tends
to make other people feel their own holes. So, it’s becoming
more and more difficult to do the Work. And the Work is also becoming
more and more needed. (Diamond Heart Book 1, pg 23)

Filling holes with others
When we relate to someone else in a deep way – the deeper
it is, the more this happens – we fill those holes with
the other person. Some of our holes get filled with what we believe
or feel we’re getting from the other person. We feel valued
because this person appreciates us, and this fills our holes.
We don’t know consciously that we’re filling it with
their appreciation, we just feel full when we’re with them;
we feel valuable. So, when I am with that person, I really feel
I am valuable, but unconsciously I feel the other person has my
value. The other person not only makes me feel valuable, but whatever
the other person is giving me, is part of me, is part of that
fullness that I experience. (Diamond Heart Book 1, p18)

But the fullness of the Work is not the same thing as the fullness
that people experience by filling their holes. The experience
of filling a hole is not usually experienced as a fullness, really.
You don’t experience fullness when somebody is filling your
holes. It always feels shaky, and doesn’t feel really satisfying.
It feels like a temporary kind of relief. There is a sense of
grabbiness, of holding: you don’t want the other person
to leave. You don’t want them to change the way they behave
toward you. At a deeper level, it is actually a blockage, not
an openness. While the fullness of the Work is the absence of
blockage. (Diamond Heart Book 1, pg 27)

Holes, personality, memory
A hole is usually filled with part of our personality that has
the memory of what was lost, the memory of the situation that
brought about the loss, the memories of the hurts and conflicts.
We have to go through the hurt at the deepest level, get close
to the hole itself, and then we will see the memory of what was
lost. When we see the memory of what was lost, the Essence that
was lost will start flowing again. So, any deep loss is an opportunity
to grow, to understand more about yourself, to experience holes
you believe can only be filled by someone else. (Diamond Heart
Book 1, pg 21)