The only time I would tell someone they are "obsessing" about the past is when all they can do is think about all their past mistakes, regrets, etc. to the extent that they are not living and enjoying their life in the present. It looks like you are looking back on things in your past that you are proud of @Frank Sanoica...and there is nothing wrong with that in my opinion. I love to look back at the years I birthed and raised my own children...it is one of my favorite past areas to visit and "sit for awhile" in. Yet, I don't want to spend to much time there because living the present with my grown children and grandchildren is such a wonderful season in my life too that I don't want to miss a minute of this time in my life either. Some of us had a lot of pain in our pasts and don't want to go there at all...and I understand this too. For each of us revisiting our past can bring joy or sorrow, a mixture of the two, or just one of them. And while revisiting our pasts is part of life...it isn't good if we want to just keep living in the past. We can't change the past, but there is a lot we can change in the present (and often the future)...even if it is just our attitude sometimes.
I suppose that's probably the best way. Not wait until you're loaded down with grief and sorrow, but start out right and with an advantage from the beginning. Still, I keep thinking...the roads less taken is not taken for a reason, maybe , huh?
I probably would have taken my Dad up on his offer to teach me to fly a plane. Both my brothers have their pilot license. I'd study harder in school, with the goal of being a military pilot. Having been around planes most of my life, would have been nice to fly one of those 'puppies'.
If I could do it all over again - what would I do ................. I would take the same path that led me to you I'd sing for evermore of the face I adore - and dance till me knees hit the floor ...............
Before I wrote this short piece I had considered my own life, the road taken that has brought me to this point in time. My first thoughts were of regrets, poor decisisions made, bad judgements, the way I have treated some in my journey. I was decidedly sure I would change many things. That I would and should have taken that other road. But after reading some of your thoughts on the matter and thinking further, I'm not so sure. One can never be certain what might be encountered on the other path. The way taken might seem like the land of milk and honey if we knew well the journey on that road less traveled. And would I be prepared to give up what I have. A good woman, good kids, a very good retirement in spite of health issues. I flipped the coin and took the well travelled pathway. After consideration I have regrets but would not change the known for the unknown. Cheers.