Q: I’m retiring. I’m surprised how consistently I’m asked what I’m going to do. Any suggestions? After I organize my house, go through my reading list and get a good gym regimen, what’s next? What does successful retirement look like? — Portland, Oregon

A: I recently encountered a man who was retired and taking a scenic train ride through the American Southwest. At the time, his retirement was very fresh — so fresh he could still revel in its novelty among strangers. He confided to me that his new workless life had required “a short period of adjustment — about 10 minutes!” That’s a perfect joke, and he delivered it flawlessly. Practicing this joke so you can incorporate it into your repertoire will eat up a couple of minutes of your abundant free time.


Your retirement will be successful by virtue of the fact it will take place — a circumstance neither I nor my friends (an ironic term referring to my enemies in competition for the Earth’s dwindling resources) will ever experience. People who ask about your plans for the chapter of your life when every day will be Saturday afternoon are not looking for a reasonable reply. They are dim-eyed soldiers who, their lower limbs having just been blown apart by German artillery, are posing to you the blood-choked, hopeless question: “What will happen to me now?”

The appropriate response (accompanied by a smile): “A scenic train ride through the American Southwest.”

Work Friend is a cheeky New York Times advice column to help with careers, money and the sometimes grim, sometimes hilarious maze that is the contemporary office, from a rotating cast of advice-givers. Email questions to workfriend@nytimes.com.