Hoax, I can sympathize with your situation. I have noticed that retirement at "30 and out" looked a lot more exciting when I just had about ten years in, than now when I have more than 30. Personally, as a package car driver, I will probably leave before the next contract. I suppose that since you are in management, the prospect of a rumored buy-out would have to play in your decision. However, I have a good friend who left at 55, with 30 plus years in, and over 25 in management. Unfortunately, things changed in his personal life, and he found that he couldn't live on his retirement, and had to go work nights in an assembly line management position in a factory. He wanted to come back to UPS, but the company said the bridge had been burned. You need to be sure it's time to go, as you can't go back.