The first Social Security check was issued to a woman named Ida May Fuller in 1940. The amount of the check was a whopping $22.54. Apparently back then Social Security had no problem funding the payment. Unfortunately, that is no longer the case as the entire system teeters on the verge of insolvency. If you are basing your long-term financial planning and retirement future on Social Security it might be time to rethink your options. Even if the system doesn’t break down, it probably won’t be enough to live on comfortably.