The record for an item remaining on my To-Do list is 17 years and 7 months.
The item: Get a copy of photo with George W. Bush.
On July 28, 2000, my jazz trio played at a private party in Woodside. When I was hired to play the party, I wasn't told that it was a fundraiser for Bush's campaign. When the planner later requested full legal names, birthdates, and social security numbers of the musicians, I asked her why she needed them. "The secret service are requesting it" she replied. That's when I found out.
The event was pretty low key. George said a few words, mingled a bit, then left. As he was walking out, he made a detour across the lawn to where we were playing. A couple secret service guys and the photographer followed him. As he shook hands with each of us, introducing himself as "George W", the photographer took pictures.
Even if he's not the president I would have chosen to shake hands with, it still seems like something. Not sure what, but something.