Ryan shares a story with the viewers about a friend, and how she ran into some trouble when she filed for Social Security. Ryan explains that just because someone is able to file and collect Social Security does not necessarily mean that they should file and collect Social Security. Someone very close to Ryan ran into issues when they filed for Social Security, but were still working and earning a significant amount of money. They did not understand, nor did the advisor who recommended that they file understand that if you make over a certain amount of money and file prior to full retirement age, then a portion or all of your Social Security could be penalized and forfeited. That is why it is always important to work with someone who specializes in retirement planning to know what to do and when to do it.