I've always had difficulty saying goodbye to circumstances and people that I am attached to. The thought of a good thing not being present in the future can be unbearable.
I went to summer camp every year between kindergarten and my senior year of high school. I usually went alone, and I bonded with the other kids and my counselor. At the end of the week I was very sad to say goodbye to them, to leave this place where I felt part of a community that accepted me and helped me to integrate things like exercise, socialization, and new activities into my lifestyle. I cried every time.
Hiking the Pacific Crest Trail was a lesson in goodbyes -- with the people, and within the trail itself.
You meet other hikers every day, and you say goodbye to them every day. Everything is in a constant state of flux, and it is obvious that nothing in the future is guaranteed. When you are hanging out with someone in town, and then you leave to get back on trail, you don't know whether you will see them in an hour or if you will never see them again. Sometimes your paths cross many times, but this is often not the case. So, you learn to say goodbye in a way that will be appropriate in either case: not overbearing or overly attached, but sincere and appreciative.
Many times on the trail, you go over a "pass"; usually a saddle point on a ridge, the lowest and easiest route from one valley to another. At the top of the pass you can see everything that you have been hiking through, perhaps for the last day or two, and you can also see the unknown landscape into which you are about to descend. I sometimes felt an emotional tug when I had to leave the area I had just been living in and experiencing. I was leaving that memory behind. Yet, there was no choice but forward, and I learned to replace the sadness of leaving the old landscape with curiosity about what was to come.
The best thing about goodbyes is that they are closely linked with hellos. Any painful goodbye is evidence that you have said hello at some point in the past and developed something meaningful. Also, saying goodbye to what you know sets you up to experience what is unknown... new places and people, and the lessons they bring. The only way to avoid the pain of saying goodbye would be to never love, never grow, never connect.
I've made friends with two people here in Moab who are fellow van-dwellers, only here for a short stay as part of a longer journey. I just got a text from one of them while I was starting to write this post; he has left town and is almost to Telluride. The other is probably leaving tomorrow. It is hard to connect with people and then watch them leave; but, that's what I've chosen, so I need to embrace it. That's part of what nomadic culture is all about.
We can't hold on to each other forever because we all desire the freedom to go where we please. It's a lesson in setting free that which we love. I can either choose to see it as heartbreaking, or as the start of something exciting: I may never see these people again, but there's no reason we can't stay in touch, and someday in the future when we happen to be near each other (or if we remain close and plan a visit intentionally), it will be all the more exciting to see them again. "Remember how we met so randomly in Moab and how much fun it was?" And I will have an instant sense of home with them, wherever we happen to be.
I think death is scary to me because it is the ultimate goodbye. I don't think it is rational to remain afraid of what is known to be inevitable, so having a lot of practice with endings makes sense to me; meetings and partings are like a constant reminder of the impermanence of our reality. Whether it's a friend you only met for a day, or a lifelong partner, there will always be a goodbye at the end of it, and we never truly know when the last one will come. It's a reminder never to take any person, or place, or time, for granted. To live fully in each day. Because time is limited, and we can only choose to make the most of it while we have it.