You are asking these questions from the point of view of an individual, but you could ask the same questions from the point of view of our government.
To keep the entitlements going, the government needs more than 222 trillion dollars in present value savings. It is impossible to save that much from the taxes coming in. See this:
The entitlement system WILL collapse. It is just a question of when. Many of my family members are retired and living of social security, disability, and military pension. I understand how dependent they are, but it is a dangerous situation to be in. The government checks will buy less and less over time, and one day the checks may stop coming.
The politicians have created a royal mess by making promises to buy votes. There is no easy way out of it.