The One Question I Never Want to Hear Again

It's both ageist and rude.

By

Casey Glass

 
Published January 23, 2026
Kiersten Essenpreis

Dear everyone: Please stop asking me when I’m retiring. The answer — though it’s none of your business — is that I happen to love what I do. In fact, I may never retire. I didn’t work hard for years to position myself as a leader in the literary/publishing world only to walk away..

I am 60 and I could have 20 more years of this!

The widely accepted norm to retire by 65 was established in 1935, with the creation of the Social Security Act. This was based on the average American life expectancy at the time, which was 60 for men and 64 for women. Obviously, this has changed as we all know vibrant, healthy, still-employed people 80 and beyond!

I don’t want to retire, and why the heck should I? I have some older friends who have been retired for a while, and they all complain about boredom and being depressed because they no longer feel “relevant.”

Every morning, I look forward to my job, evaluating book proposals and then reading the finishing manuscripts. Each project is spent flexing my brain, fanning my creativity and feeding the lifelong learning that is essential to fuel longevity. So unless you are a financial planner with some quick ideas on how to turn thousands into millions, you should not be asking me that question for a number of very good reasons.

I want to make it clear that I don’t begrudge anyone making different professional decisions. If you’ve done well enough and are inclined to retire and travel the world, or pursue full-time philanthropy, congratulations. I’m sure you worked your butt off and deserve what you earned. Enjoy every minute of it!

And in your case, being asked the “when are you going to retire” question is a welcome opportunity for you to share the good news — that you have enough savings to live your dream and finally relax. For most people, however, it is a loaded question that forces them to decide in a nanosecond whether they want to say: “It’s none of your darn business!,” or “I love my job, why would I stop?” Or the half-joking response that often has an element of truth to it: “I can’t afford to retire!”

However innocent you might think the question is, asking someone if they are retiring does have an undercurrent of implying they can afford to ditch the job. It also comes off as a query into the way they’ve handled their personal finances, i.e., “Did you invest and save wisely over the years? Or were you profligate?”

The question could also bring up a misfortune experienced by an older person still on the job. Maybe they endured a 401K wiped out by a stock market plunge, or a bad investment that cleaned them out. And imagine how a victim of age discrimination would feel being asked that question.

When I hear the question, it is essentially age-profiling me. I hear: “You look old.” Really? Well, this is what a woman in her 60s looks like! And what the person is not seeing is my energetic and engaged mind and heart.

They don’t witness the joy I experience every morning when my alarm goes off and I welcome a new day full of opportunities to be productive and to learn something new about the world. They don’t feel my excitement of discovering and nurturing the next best-selling author. Remaining an active professional keeps me eagerly looking forward to the stimulating challenges of tomorrow; if I were to retire, that magic would disappear.

Asking me when I’m retiring is an example of small talk that pretends to be universal but is actually quite personal. Women in particular have to contend with nosiness disguised as small talk throughout their lives. For example, when a single woman is in her mid to late 20s, she starts getting asked about her timetable for settling down with a significant other. After that, the question becomes “When are you having a baby?” Once the baby arrives, look out — there will come another blizzard of other invasive questions.

Breast or bottle? Stay at home or working mom? Isn’t she walking yet? Still no teeth? What blah blah blah percentile is she? Are you thinking about having another? And if the answer to that question is no, here comes my favorite: Why not?

There will be other such intrusive questions asked over the years because your offspring will eventually grow hair and teeth and start applying to schools, having relationships and making career choices. This creates a rich palette of new-generation private decisions for people to pry into. And then one day, of course, you’ll be old enough to get asked the retirement question.

Is it possible that in some cases the person is just trying to make conversation? Sure, but how about: Seen any good movies lately? Theater? Museums? Or how’s your game of cribbage going?

If you know enough not to ask rude questions like “Is that a hair extension?” or “Are you on Ozempic?," then you really have no excuse. So the next time you’re at a party and you feel the urge to ask someone when they are retiring, try to remember that the person is there to have fun, not to reluctantly divulge private information and contemplate their mortality.

Play it safe and stick to the weather.

Casey Glass is still very much enjoying her decades-long career as a book editor. She works with incredible authors, many of them bestselling, who teach her something new every day. She lives and works in New York City with her family.