I have had my share of hellos and goodbyes in life, from the death of close loved ones to many friendships drifting apart or ending through challenge. I would probably say I tend to embrace relationships changing more gracefully than many because I have had many end.
All in all, everything happens for a reason and it is far less stressful if we can release, grieve the letting go, and allow the new to fill its space. We are not heartless if we release people, often we are doing what needs to be done.
So go easy on yourself if you are coming to the end of a season/reason with someone, it's all part of the divine plan unfolding.