Retirement Yenta has touched on this tip before, but it bears repeating. Start to “try on” retirement. You don’t want retirement to hit you like a ton of bricks; you want to ease into it and savor every moment. A friend of Retirement Yenta’s just retired at 55, after a steady career in an industry that is dramatically transforming. He says, ” Everyday is like Saturday!” He did say he was overcome by anxiety a few times during the year before he stopped working. He got over it. Pre-retirement anxiety is something the Retirement Yenta knows all about. Start to see a shrink.