It's impossible for words to describe what is necessary to those who do not know what horror means. Horror... Horror has a face... and you must make a friend of horror. Horror and moral terror are your friends. If they are not, then they are enemies to be feared. They are truly enemies. ....~ Kurtz
Yeah I always say "beware the man with nothing to lose".
Death is an old friend of mine, or maybe you might say, a "frenemy'. We have coffee regularly. I have priced in the coming death of our dogs, my surviving brothers (10 and 15 years older than me respectively), possibly yet another wife (she keeps insisting she will not outlive me; I think it reflects her general fatigue with life) ... I have become almost indifferent to all this stuff because it's priced in ahead of time.
Not much of a way to live, but I don't have it in me to let each new loss take me down. In the last 15 years I've lost a mother, brother, wife and son to "untimely" death, and that ignores the ones who died "when expected". If that doesn't teach you about impermanence, nothing will.
Sure, it will still hurt as each one drops off the mortal coil, but if you don't act like it wasn't supposed to ever happen, like it's some strange way of the universe picking on you personally, then you at least don't make it worse than it already is.