Retirement Guilt. Do You Have It?

There’s a ridiculous question being posed to retirees: do you feel guilty you are retired? It’s not as if retirement is an award you win in a competition. It’s something that you have worked for and saved for your whole life. Or it’s something that was thrust upon you after you lost your job, inherited money or became ill in your later working years and couldn’t work anymore. So, I really don’t understand the question being posed. What the heck are you supposed to feel guilty about?

Retirement is a phase you go through in life. Do you feel guilty you’re a teenager or a thirty-something-year-old? Do you feel guilty you’re married, divorced, single or widowed? I’ve been retired since I was 50 years old all because I despised working for a living. I therefore made some good investments over the years to get me out of a job. Am I supposed to feel guilty because I’m smart and others are not? See how preposterous this line of thinking is?

The real question that should be posed is: do you feel jealousy, envy or even hatred towards others who have retired and you didn’t/can’t/won’t? Or to be more specific, do you feel these negative feelings towards other retirees who have retired better than you? Perhaps guilt might come in at this point if you think you’re the one who has retired better than anyone else. Then it’s just a case of pure narcissism and should be completely discounted.

I don’t feel guilty I’m retired. In fact, that emotion never once entered my mind. If so, then I’d feel guilty I can brush my teeth in the morning because there are still people in the jungles of the ancient ruins of the migrant rain forest who can’t. If I felt guilty about being retired, then I should also feel guilty that I have running hot water in my home, can shop for foods in amply supplied grocery stores, wear shoes in cold weather, can pop an aspirin whenever I have a headache and have paper to wipe my butt with after I take a poop.

I don’t feel jealousy or envy when I come upon fellow retirees. Much in the same manner I don’t feel envy or jealousy when I encounter someone younger than me, richer or poorer than me or driving a bigger, larger RV than me. Those feelings are ludicrous, stupid and foolish.

What I do feel, however, is pure, unadulterated hatred whenever I encounter a retiree who is a liar and a cheat. You know immediately that they are lying about their so-called ‘amazing‘ retirement because their mouths are moving. They’ve got photographs galore depicting their extravagant, jet-setting travel adventures, 4500 square foot penthouse retirement-gated-community homes, electric Bentleys, perfect golf scores and public displays of their actual CPA-approved spreadsheets showing exactly how well their investments are doing. The collars and the cuffs just don’t match. You know it, because you’ve a brain and you’re smart. They’re just plain braggarts.

rich retiree
This rich retiree ‘made it’….now F you!

What I do feel also, however, is compassion towards the elderly who, for whatever reason it may be, just aren’t doing that well in their later years. No judgments. No blame. I encounter them all the time. I’ll see them at the grocery store scrounging for some cash to buy their food. I’ll see them in the park, sitting on benches, poorly dressed but ever so proud. I’ll see them walking along the side of the road, clutching plastic bags filled with light foods, as they make their way back home, by foot, because they don’t have cars or bus money. I see how badly the outside world treats the elderly. Service workers won’t wait on them, won’t give them fair pricing or the time of day. They’re ignored, ridiculed and disdained all because they are guilty of one thing: simply growing older.

I once bought an old woman a cup of tea because the waitress wouldn’t serve her. I often pay an elderly person’s restaurant bill whenever I see them struggling to come up with the money to pay their check. I’ll cover an elderly person’s grocery bill when I see them putting items back on the shelf or off the conveyor belt because they can’t afford the price of the food. I admonished a sales clerk once when she wouldn’t sell an elderly woman a loaf of bread. (I reported the clerk to the bakery owner and I bought the woman the loaf of bread she wanted) If I see an elderly person struggling, I stop and ask them if they need a hand. I help them cross the street. Get up out of a chair. I hold the door open for them. I give them advice. What I don’t give them is any feeling of my guilt, because I don’t have any. I give them my respect instead. Something most people will not do.

I don’t make donations to charities because that’s just a cop-out to ease one’s feelings of guilt. I prefer actions to just making a mindless tax write off. Not everyone in this world is smart. People make stupid mistakes. Some people have done the best they could have done.

A few years ago my husband was complaining to me that the $15 sneakers I bought him at Wal Mart fell apart. Nick and I were going through some real financially hard times back then. I had to catch a train to NYC because I was babysitting for my granddaughter that afternoon. When I got off the train at Grand Central, as I was making my way up a ramp to the exit, there was an elderly man in front of me, dragging his feet.  It was a cold February morning. When I looked down at the man’s feet, I saw that he had no shoes but his feet were wrapped in several plastic zip-lock bags. That man would have been ever so thankful if he were wearing those $15 sneakers my husband so carelessly tossed away. I stopped the old man, who smelled, was dressed shabbily and I looked him in the eye as I handed him my only $20 bill. “I love you” I said to him. “God loves you“.

Retirement guilt? No. Compassion? Absolutely.

Should I say to myself: she’s got cash in her hand, I’m not giving her anymore? Should I blame her because she didn’t prepare for her own retirement better? Should I feel guilty because I’m retired and still flush?



  1. Cindi the first part gave me a good laugh , thank you. I too agree feeling guilty , how absurd. Compassion and your kind of charity is what I do too and was spot on. Lara


  2. Cindi, I am moved by your compassion. We’re in NYC and I often give the money in my pocket to those on the street in need. We also support excellent charities in NYC like City Harvest and Housing Works which provide help on a larger scale. It feels good to do both.


    • Hi. Thank you. I have a special spot on my heart for the elderly and for those who can not help themselves. I often stop and talk to those in NYC who approach me for money. The worst are those who get me after I leave a restaurant and ask for my leftovers. I usually give them enough money to buy a meal for themselves. Heartbreaking.
      Thank you for your comment.


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