The S&P 500 recently marked its fifth straight record closing high, a streak not seen since July 2024, prompting questions about investment opportunities. For retirees, like the 66-year-old with $200,000 to invest, the timing of entering the market is crucial. Financial advisors typically recommend a diversified approach, considering risk tolerance and long-term goals. While the S&P 500's performance is strong, market corrections are always possible. Consulting with a financial professional is advisable before making significant investment decisions, especially in retirement.