Most of our memories of letting go are painful. We recall agonizing losses where we missed someone/something terribly. We don't want that to happen again -- so we cling to things (and people we treat like our possessions). We also avoid feeling that bad again, so we are highly motivated to hang on to what we've got. We become hard wired to NOT let go. "Finding freedom via letting go" seems absurd and inconceivable.
Knowing how yucky it feels to let go, we implicitly understand when others desperately want to take us prisoner. We relate to their clinging, neediness and dependency on us that seems to necessary to feel good about themselves. We play the martyr -- making a noble sacrifice of our needs. We give buckets of attention and get droplets in return. We go without getting understood, asked about, and really related to -- in order to avoid those dreadful feelings of abandonment, loss and emptiness. We accept these prison terms of engagement even though it feels like being confined, trapped or taken hostage. Inside these entanglements, we cannot feel our true feelings or know what we really think. We're kidding ourselves to keep from breaking out of our consensual captivity. We keep things fake and superficial to not disrupt the dance of desperation. We don't admit to ourselves what we really want to: give to relationships, change from our present arrangements and get in return for our giving.
In the context of all this captivity, there's lots of freedom to be found by letting go. We find our deeper feelings and feel real for a change. We discover the truth of what we want and how free we've become to go for it. We realize the sacrifice we made and our new freedom to stop paying the price. We uncover hidden choices we did not know we had or ever considered before. We let go of "who we think we are" and "what happened to us". We even begin to see familiar situations with a new pair of eyes, vantage point and frame of reference.
After we let go, we're empty in a good way. It's not a hollow feeling of getting eviscerated or left behind. We're free of preconceptions that limit our possibilities. We are open to unexpected changes. We don't know what things mean at first. We watch life unfold with lots more fascination. We live more freely than we ever imagined was possible when clinging was our thing.