Just when should someone retire? Several studies have suggested that for a person to retire in reasonable comfort, he or she may have to work well into their 70s or 80s, depending upon the individual’s income level. But many factors come into play when deciding when to retire affordably. For example, when is the optimal time to start drawing down Social Security? Then there is the biggest wild card of all: long-term care expenses. Each individual situation is different, but saving now and cutting expenses are good places to begin a retirement plan.