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Wednesday, November 11, 2026Nov 11

Kennedy: Filing for Social Security feels scary and exciting

With an estimated 10,000 baby boomers retiring every day, the Social Security Administration must be a busy place. / AP Photo/Jenny Kane, File
With an estimated 10,000 baby boomers retiring every day, the Social Security Administration must be a busy place. / AP Photo/Jenny Kane, File With an estimated 10,000 baby boomers retiring every day, the Social Security Administration must be a busy place. / AP Photo/Jenny Kane, File

There are certain milestones in life. For me, they include: baptism, marriage, birth of our children and filing for Social Security retirement benefits.

I began to clear the Social Security hurdle last Saturday morning. I tried to be very intentional. I woke up at 7 a.m., cleared off the dining room table, gathered some old tax documents and booted up my laptop. Oh, and then I ate a blueberry Pop-Tart (unfrosted) for energy.

Next, I took a deep breath and placed my hands gently on the keyboard like a concert pianist preparing to play. I had mentally set aside the time for this a few days before, and I settled into the task with a mixture of fear and excitement.

I had literally been preparing for this day for decades. I’m one of those people who has been thinking about the pieces of the retirement puzzle for 30-plus years, a consequence of my banker mother explaining the magic of compound interest to me as a kid.

With an estimated 10,000 baby boomers retiring in America every day, the Social Security Administration must be a busy place.