We have near analogies that are close enough for us to have an idea. Anesthesia, being knocked out, dreamless sleep are closest to what we would consider “experiencing” oblivion. We can correlate the lack of experience or consiousness to the what we “experienced” prior to existing.

I get what you mean though, we can experience a transition out of and into non-experience, but cannot, as a matter of course, experience non-experience. There is no good reason (by my measure) to believe that there is anything other than just non-experience in the before and after phase of life. To the individual consciousness there is no discernable difference either. The matter/energy you are made of existed prior to and will continue to exist after you are gone, all that will be left is your memetic and causal imprint on our small bubble of reality.