I’m having a tough time coming up with an answer to this question. I can’t think of any phase of my life that was difficult to say goodbye to. Every time some major life period ended, there was something better waiting in the wings to replace it.
High school was replaced with college and even though the first time around in college was a mess, it was so much better than high school.
College the first time ended long before I wanted it to and getting a full time job afterwards was anything but a positive experience, at that time though college was becoming a nightmare and it had to end. I couldn’t figure out how to move forward academically, apart from starting from scratch, so I put it aside for a few years… and then started from scratch.
Graduating from college and moving into a career… you’d think that would have been tough to say goodbye to, but really I was ready for it. I had been a student for a long time and I used to joke that I was really a career student. By the time I graduated though, I was ready for that phase to end and I welcomed what came next.
I was depressed when my 20’s ended and became my 30’s. I didn’t want them to end, but I was already so low that I wasn’t sad to see them go. I was, but at the same time, not really. You know? My 30’s started out bad but I was 36 when I met Jen and 38 when we got married. Once I had started a life with her I was ready for whatever the universe could throw at us. I looked forward to time passing and phases… phasing. I was sad to see my 40’s end, but only because I don’t want to be old. I accepted that I was already old though so it didn’t actually change anything.
So I guess the answer to this question is that I never really had a phase in my life end that I had a difficult time saying goodbye to. Sorry if that’s a lame answer. I guess I am just a super mature dude who is able to roll with the changes, as the song says. Maybe I should pat myself on the back for that.
Inside the Red Head's Head 
You said that when one phase of your life ended, something better came along.
Maybe a follow-up question to ask is “did you know something better would be coming king among when one phase of your life ended?”
For this prompt, I wrote about my marriage ending. It certainly led to better things for me; but at the time, I wasn’t ready for it to end.
LikeLiked by 1 person