Well, you should challenge what it means; both to you, and as general conventional term.
You should challenge that there is such a thing, and that anything at all possesses any inherent meaning. You should challenge this desire for certainty, this desire to make speculative assumptions about any and all phenomena, to attempt to isolate them, attribute definitive labels and meanings to them, categorize, and pin things down. You should challenge that there is anything at all to be gained or lost, to become or annihilate, etc.
What is love? Does it actually exist beyond these four letters which are aligned in a specific order and designated to a particular concept? If it does, then how? As a feeling? What is a feeling beyond the concept of it?
The point is to deconstruct our own preconceived notions, and challenge our certainties. Because the essence of things is not found through speculative assumptions mistaken as certainties, or imposed meanings mistaken as the essence.
If we expect meditation to be some sort of tool for 'gaining this' or 'losing that', we will inevitability be disappointed by these expectations.
So, if we engage in meditation with the expectation of 'attaining/gaining' some sort of understanding or certainty, or 'avoiding/losing' pain and discomfort, this is a mistake. Meditation is a tool for recognition only. Simply recognizing everything as it is, that is liberation.
Shunryu Suzuki Roshi said something like:
"When you see something, then you intellectualize it.
Then it is no longer what you saw."
To intellectualize things is to project a conceptual shadow over reality. We mistake these conceptualized forms, these shadows for being real. Then we chase them like kittens because we think that they can be captured and pinned down. And despite the futility of this, we continue to chase them every chance we get.
During meditation we just watch these shadows dance around without chasing them. And whenever we find ourselves being tempted to chase them, or if we have already begun to chase them, we simply return our attention to the breath.
So, it is this balance between "chasing"; deep contemplation, curiosity, challenging preconceived notions and biases, and "not chasing”; returning our attention to the breath, simple awareness as it is.
I hope that this is of some benefit and helps to encourage your practice :)