As others said, set up an account with SS. They have all the info you need. Their basic estimate assumes you will keep working at your current salary until retirement but they have worksheets that will allow you to plug in expected future salaries to do what if calculations. On your question number three, if you retire before your full retirement age (e.g if you go at 62). They begin to reduce your payment $1 for every $2 you earn over $18.960 (2021, that will go up each year). If you expect to earn significantly more that the limit, it makes no sense to claim early. If some opportunity arises by surprise and you earn more that you expected the penalty cuts will kick in. But all is not lost - SS will make up the missing amounts by increasing your payments after you reach FRA.