The Buddha affirms that as long as there’s still craving in the mind, you’ll continue to have opportunities to pursue happiness even after death. In other words, if you want to be reborn, you will.

"Belief in the principle of rebirth helps to counteract one common reason for fearing death: the fear that death means total annihilation. The Buddha affirms that as long as there’s still craving in the mind, you’ll continue to have opportunities to pursue happiness even after death. In other words, if you want to be reborn, you will. At the same time, if you’re afraid that death will separate you from those you love and those who love you, the Buddha offers reassurance that loved ones who want to meet again after death will do so if they develop, in common, four qualities: conviction, virtue, generosity, and discernment.

Still, repeated rebirth is at best an iffy proposition. To begin with, even if you don’t want to be reborn, you’ll still have to take rebirth as long as there is ignorance and craving in the mind. And as for hoping to meet again with your kin and loved ones, how many of them can be relied on to develop right view and maintain it all the way through death? The number of human beings reborn in at least the human realm — to say nothing of the higher realms — is infinitely small when compared to the number reborn in the lower realms. We love our loved ones because of their goodness, but the goodness of individuals can be a fickle thing. Rather than focusing on the goodness of particular individuals as you face death, you’d be safer to focus on goodness itself.

Think back on the Buddha on the night of his awakening. He was able to attain release by focusing not on the beings who were doing actions, but on the actions — and their results — themselves. In a similar way, you’re much safer in hoping to rely on your own good deeds, so that you’ll meet with goodness wherever you go. Kinship with those deeds is a more secure refuge than kinship with individual people, no matter how loving or kind. As the Dhammapada puts it:

A man long absent
comes home safe from afar.
His kin, his friends, his companions,
delight in his return.

In just the same way,
when you’ve done good
& gone from this world
to the world beyond,
your good deeds receive you —
as kin, someone dear
come home. — Dhammapada 219–220

Conviction in this principle motivates you to look inward to examine your friendship with the qualities of your mind. As the Buddha noted, we tend to go around with craving as our companion. We’d do better to become companions with the principle of heedfulness and the good deeds it will inspire us to do.

Yet even the refuge offered by this relationship is not totally secure. Your good deeds can find expression in your meeting with new loving people in the next life, but then those relationships, too, will end. And when you think in terms of the Buddha’s deep sense of time, you have to realize that these relationships have been formed and dissolved so many times that it would be hard in this lifetime to meet with someone who had not, at some point in that long stretch of time, been your mother, your father, your sister, your brother, your daughter, or your son (SN 15:14–19). Think about that the next time you walk along a crowded street. People who were once your closest relatives — people over whose death you shed more tears than there is water in the ocean (SN 15:3) — are now random faces in the crowd. Think about that the next time you see the ocean. How many more times do you want to establish new relationships that will end in more oceans of tears?

This thought, as the Buddha noted, should be enough to give rise to dispassion for the prospect of rebirth, and for a desire instead to gain total release."

~ Thanissaro Bhikkhu "Mindfulness of Death"