Are You Emotionally Ready to Retire? Eight Questions to Ask Yourself

It’s one of the most important decisions many of us will ever make. And we often get it wrong.

I’m talking about retirement—and specifically, when to do it. If you are lucky enough to be able to determine your own retirement date, be grateful that this change is not being forced upon you. But also be aware that it isn’t a simple decision. Many of us know friends who thought they were emotionally ready but later regretted having retired. And we know colleagues who thought they were not ready, and then got sick or died young, filled with regret that they had missed out on a phase of life that could have been wonderful.

It doesn’t have to be this way. After seeing hundreds of individuals and couples in psychotherapy over many years, and writing a book on retirement, I believe that retirement-timing mistakes can be the exception rather than the rule. The key is to know what questions to ask yourself—and how to understand the answers.

To that end, here are eight questions that I think can make all the difference.

1. Every Sunday night, as I anticipate returning to work, do I look forward to finishing tasks, seeing friends and colleagues, and perhaps learning something new? Or do I dread another week of tedious tasks and difficult people?

To answer this takes a little soul-searching, especially after decades of simply accepting your weekly routine. But if you pay attention to your gut feelings at the end of the weekend, or at the end of a vacation, you’ll know whether your stomach is in an unhappy knot with worry, a happy knot with anticipation, or somewhere in between.

One CEO, whom I saw weekly from ages 59 to 69, had been in his position for 18 years. Although he would tell you he loved his job, he hated the angst he felt at the office every day—especially on Mondays.

Over time, he realised that he was hanging onto work as his refuge—the place where he found success and recognition—to avoid confronting issues he had at home.

People were shocked when he announced his retirement at age 67 because they thought he had nothing else in his life. But he knew the decision was right for him. For the next two years I saw him learn and grow and find other sources of happiness with his family. His stomach had told him what his mind was unable to see.

2) Have I thought carefully about my financial picture? What expenses am I prepared to cut if money becomes tight?

By this age, you should know what resources you need to live on and what you will have in income and savings for your retirement years. But people sometimes screw up, or circumstances screw them up. Maybe they (or a financial adviser) mismanaged their nest egg. Maybe the market collapses in a totally unexpected way just after they stop working. The unknowns are unknown.

So it’s a useful exercise to imagine cutting expenses if you ever have to. How might your life change in that way, and how would you feel about that? Are you emotionally prepared for it, or would it be best to keep working, at least for a while?

3) What do my already-retired friends, relatives and colleagues think?

You are unique, yes, but you can learn a lot from people you know and trust.

In my experience, seeking the advice of trusted friends is particularly important for successful women, who are prone to second-guess themselves and feel insecure about next steps, especially when it comes to retirement. They have often worked harder than men to establish their success, and the job has given them identity and independence. They think they will go crazy without work. But almost all are surprised how much they love retirement, how quickly they fill up their time with meaningful projects, and how much better they feelwhen they control their own time.

I have one friend who loved her job, and while she wanted to make some kind of change when she turned 65, she feared she would suffer a recurrence of her lifelong depression if she left work and had nothing to do.

Her husband advised her to continue working. Instead, she got a group of professional women friends together, and they told her: “Do it now! You’ll be glad you did.”

Their encouragement gave her the courage to see that she was ready for retirement—even if her fear didn’t allow her to see that. She found volunteer work with a political candidate she admired, she started speaking at schools about career choices, and she started discussion groups at the local YWCA, helping others make the retirement decisions that had been so hard for her.

4) Would I like part-time work for a more gradual retirement, or is “cold turkey” better for me? Is part-time work even realistic in my field?

The easiest emotional transition away from full-time work is sometimes a part-time or consulting contract, either with a new company or with your existing employer. It’s a question many would-be retirees should be asking themselves.

It often works well, allowing a retiree to test the waters if they aren’t absolutely sure it’s the right time to leave the workforce completely. But people need to do their homework before they assume the answer is yes. I saw in therapy a former chief financial officer who at 66 wasn’t quite ready to retire fully. So he took a job handling the books for another company. He learned within the first week how different that system was from his old one, how upset he felt when he couldn’t quickly pick up nuances from his underlings and how angry he got when his boss criticized him. He quit within one month.

Although in the end it turned out well—thanks, in part, to therapy, which helped him to improve his marriage and understand the possibilities in retirement—it was a traumatic period that could have been avoided had he answered this question with more care.

5) Do I have hobbies or interests that could fill my time? Is there volunteer work that I’d like to do?

Some people are so consumed with hobbies already that they barely have time to work, while others have never had a hobby and doubt that they can think of anything in retirement. But being able to answer this question in the affirmative is often crucial: The most successful retirees seem to need either part-time volunteer work or hobbies that they love and that keep them busy.

Still, people who assume they would like volunteer work would do well to explore the idea fully before answering this question. If you fall in love with the concept of a volunteer job, it’s a good sign you’re ready to make the big move.

But it is entirely possible that you’ll find it tedious—especially if you’ve been a boss during your career. It is often a shock to offer your time, and then be asked to stuff envelopes or work in a boring gift shop. Or you may be honoured to be asked to be on a nonprofit board, but then walk into a hornet’s nest of infighting that you had thought you had left behind in your old job. You may also find that a large financial contribution is expected.

6) What friends do I have now that involve neither my career nor my partner?

This is a question that men, in particular, need to ask themselves.

People seldom think about which work friendships will continue in their postretirement life. In fact, they have no idea whether their co-workers are really friends or not. They are often shocked in retirement when they call former co-workers for lunch and are told “no.” Also, men have a tendency to think that their wife’s friends are their own; they are not. There is a famous quote: I married you for better or worse, but not for lunch.

In fact, a survey I did with groups I spoke to showed that on the question of “Who is you best friend?” more than 60% of men said “my wife,” while less than 20% of women said “my husband.” Friendship is not as easy for most men as it is for most women. Men think it’s a compliment to name their wife as best friend, but it’s really not. We all need best friends as well as spouses/partners.

So before retiring, think hard about whether you’re going to have those social connections that most of us crave and need to stay healthy, whether we think we do or not.

7) What role is my partner playing in my decision about retirement?

The decision should be yours as much as possible. You don’t want to blame your partner if things go wrong, as tempting as that will be.

Nevertheless, it is hugely important to understand the motivation behind your partner’s advice on whether you should retire. Is she already retired and pushing me to be more available? Is he getting ready to retire and doesn’t want to be bored at home alone?

Your relationship will thrive much more in retirement if you both know not only each other’s surface meanings but also the deep feelings involved. In other words, this question is important as a catalyst to a conversation—a lot of conversations—so that there are no surprises after the fact. Once one of you retires, a lot of those conversations that never took place when work was a refuge are suddenly on the table. It is much easier to have those conversations earlier rather than later.

I counseled one couple for four years. They were the same age, both accomplished and working in jobs they enjoyed. They had friends who were planning a year in Paris, and then a year in London. He decided it was time to retire and assumed she would feel the same. He was shocked when she said she wanted to work for another five years.

The repercussions were ugly. He accused her of ruining their lives, and their children all took his side. But she held her ground. Despite the pressure, she just wasn’t ready. After much discussion in therapy, they came to an understanding: He was ready and she was not. He came up with other interests to pursue while she worked, and they agreed they might spend two years abroad when she retires. They are still happily married and she hasn’t retired yet.

I am often asked whether couples should retire together or at different times. There are good individual reasons for each position, but I generally recommend that husbands retire first. This may happen naturally because women are usually younger and have gotten serious about their career later. In that case, husbands who have never learned to cook or clean or organize the home have time to learn these skills and then share more equally in these tasks after both are retired.

8) Do my partner and I have similar ideas about travel or where we want to live in retirement?

In my survey, the No. 1 reason people felt they might divorce after retirement was because they wanted to live in different places and have different lifestyles—the woman often wanting to be near grandchildren; the man wanting sun and sports. This is a difficult area in which to find compromise. But asking yourself whether you’re on the same page before retirement is a crucial first step, rather than just assuming you are seeing things alike. It could have a big effect on whether you decide you’re emotionally ready for retirement.

Similarly, travel can be another deal breaker if not talked about ahead of time.

A man I know has always loved to ski. After he and his partner retired, he became obsessed with planning trips to exotic ski destinations. But his partner wasn’t on board, preferring to play tennis and lie on beaches in warm climates. Their arguments grew more fierce. My turn/your turn didn’t work because they were both unhappy half the time. Finally, they tried separate vacations. Fortunately, that has worked like a charm—for now, anyway.

Had they asked themselves this question ahead of time, had they talked it out calmly when it was still in the future, they would have saved themselves a lot of angst and a near-breakup. They might have come to their separate-vacation solution earlier. Or one or both might have decided that, in fact, they weren’t ready for retirement.

***

Retirement is wonderful, but it can also be difficult. “Am I ready?” is an emotional journey into yourself, as well as an assessment of your situation. There will be no perfect decision, but you’ll fare better if you consider all of the options carefully.

There is usually some excitement in every new stage of life. After raising kids and working hard and doing the best we can, this is the first time that most of us have had total control over our lives. It can be the best time ever—time to learn a lot about ourself, finally “growing whole” in so many ways. Are you ready for that?

LIKE MARVEL VILLAINS, most fashion writers have origin stories. Mine began with a navy nylon Prada purse, salvaged from a Boston thrift store when I was a teen in the 1990s. Scuffed with black streaks and sagging, it was terribly beat-up. But I saw it as a golden ticket to a future, chicer self. No longer a screechy suburban theatre kid, I would revamp myself as sophisticated, arch, even aloof. The bag, I reasoned, would lead the way.

That fall, I slung it against my shoulder like a shotgun and marched into school, where a girl far more interesting than I was called out, “Hey, cool bag.” After feigning apathy —“I don’t know, you could use a Sharpie on a lunch bag and it would look the same”—we became friends. She introduced me to a former classmate who worked at a magazine. That woman helped me get an internship, which led to a job.

Twenty years later, I still wonder how big of a role that Prada purse played in my future—and whether designer bags can function as a silent partner in our success. Branded luxury bags took off in 1957, when Grace Kelly posed with an Hermès bag in Life magazine. (Hermès renamed that bag “the Kelly” in 1973.) The term “status bag” was popularised in 1990 by Gaile Robinson in the Los Angeles Times, describing any purse that projects social or economic power. Not surprisingly, these accessories are costly. Kelly bags cost over $10,000; ditto Chanel’s 11.22 handbag. Some bags by Louis Vuitton and Dior command similar price points. The cost isn’t repelling customers—both brands reported revenue surges in 2023. But isn’t there something dusty about the idea that a branded bag carries meaning along with your phone and wallet? How much status can a status bag deliver in 2024?

Quite a lot, said Daniel Langer, a business professor at Pepperdine University and the CEO of Équité, a Swiss luxury consulting firm. Beginning in 2007, Langer showed a series of photo portraits to hundreds of people across Europe, Asia and the U.S., then asked them 60 questions. Those pictured carrying a luxury handbag were seen as “more attractive, more intelligent, more interesting,” he said. The conclusion was “so ridiculous” to Langer that he repeated the studies several times over the next decade and a half. The results were always the same: “Purchasing a ‘status bag’ will prepare you to be more successful in your social actions. That is the data.”

Intrigued, I gathered various Very Important Purses—I borrowed some from friends, and others from brands—to see if they could elevate my station with the same unspoken oomph as a “Pride and Prejudice” suitor.

First, I took Alaïa’s Le Teckel bag—a narrow purse resembling an elegant flute case and carried by actress Margot Robbie—to New York’s Carlyle Hotel on a Saturday night. The line for the famous Bemelmans Bar stretched to the fire exit. “Can I get a table right away?” I asked the host, holding out my bag like a passport before an international flight. “It’s very busy,” he said in hushed tones. “But come sit. A table should open soon.” I sank into one of the Carlyle’s lush red sofas and sipped a martini while waiting—a much nicer way to kill 30 minutes than slumped against a lobby wall.

Wondering if this was a one-time thing, I called up Desta, the mononymous “culture director” (read: gatekeeper) who has worked for Manhattan celebrity hide-outs like Chapel Bar and Boom, the Standard Hotel bar that hosts the Met Gala’s official after party. “Sure, we pay attention to bags,” he said. “Not too long ago at Veronika,” the Park Avenue restaurant where Desta also steered the social ship, “we had one table left. A woman had a Saint Laurent bag from the Hedi Era,” he said, referencing Hedi Slimane , the brand’s revered designer from 2012 to 2016. “I said, ‘Give her the table. She appreciates style. She’ll appreciate this place.’”

Some say a status bag can open professional doors, too. Cleo Capital founder Sarah Kunst, who lives between San Francisco and London, notes that in private-equity circles, these accessories can act as a quick head-nod in introductory situations. Kunst says that especially as a Black woman, she found a designer bag to be “almost like armour” at the beginning of her career. “You put it on, and if you’re walking into a work event or a happy hour where you need to network, it can help you fit in immediately.” She cites Chanel flap bags made from the brand’s signature quilted leather and stamped with a double-C logo as an industry favourite. “People love to talk about them. They’ll say, ‘Ohhh, I love your bag,’ in a low voice.” They talk to you, said Kunst, “like you’re a tiger.”

For high-stakes jobs that rely on commissions—sports agents or sales reps, for instance—a fancy handbag can help establish credibility. “It says, ‘I’m succeeding at my job,’” said Mary Bonnet, vice president of the Oppenheim Group, the California real-estate firm at the centre of Netflix reality show “Selling Sunset.” As a new real-estate agent in her 20s, Bonnet brought a fake designer bag to a meeting. To her horror, a potential buyer had the real thing. “I work in an industry where trust is important, and there I was being inauthentic. That was a real lesson.” Now Bonnet rotates several (real) Saint Laurent and Chanel bags, but notes that a super-expensive purse could alienate some clients. “I don’t think I’d walk into [some client homes] with a giant Hermès bag.”

Hermès bags are supposedly the apex predator of purses. But I didn’t feel invincible when I strapped a Kelly bag around my chest like a pebbled-leather ammo belt. The dun-brown purse cost $11,800, a sum that prompted my boyfriend to ask if I needed a bodyguard. Shaking with “is this insured?” anxiety, I walked into a showing for an $8.5 million apartment steps from Central Park. I made it through the door but was soon stopped by a gruff real-estate agent asking if I had an appointment. No, but I had an Hermès bag? Alas, it wasn’t enough. The gleaming black door closed in my face.

“What went wrong?” I asked Dafna Goor, a London Business School professor who studies the psychology behind luxury purchases. “You felt nervous,” she replied. “That always makes others uncomfortable, especially in a high stakes situation,” like an open house with jittery agents. Goor said recognisable bags from Louis Vuitton and Christian Dior are also often faked, which can lead to suspicion if not paired with “other signals of wealth.”

“You can’t just treat a bag as a backstage pass,” said Jess Graves, who runs the shopping Substack the Love List. Graves says bags are more of a secret code shared between potential connections. “I’ve been in line for coffee and a woman will see my Margaux [from the Row] and go, ‘Oh, I know that bag.’ Then we’ll chat.” Graves moved from Atlanta to Manhattan in 2023, and says she’s made some new, local friends thanks to these “bag chats.”

I had my own bag chat that night, when I brought Khaite’s Olivia—a slim crescent of shiny maroon leather—to a house party thrown by a rock star I’d never met. In fact I knew hardly any guests, but as I stood in the kitchen, a woman in vintage Chanel pointed to my bag and asked, “How did you get that colour? It’s sold out!” Before I could tell her my name, she told me the make and model of my purse. Then she laughed about her ex-boss, a tech billionaire, and encouraged me to buy some cryptocurrency. The token I picked surged nearly 30% in about a week. Now I was onto something—a status bag that might bring not just status, but an actual market return.

Thanks to their prominence on social media, certain bags have gained favour among Gen Zers. “TikTok and Instagram make some luxury items even more visible and more desirable to young people,” said Goor. I experienced this firsthand on a stormy Saturday morning, when a girl in a college hoodie pointed at my Miu Miu Wander bag as I puddle-hopped through downtown New York. The piglet-pink purse is a TikTok favourite seen on young stars like Sydney Sweeney and Hailey Bieber. “Your bag is everything!” yelled the girl from the crosswalk. “Thanks, can I have your umbrella?” I shouted back. She laughed and left. My Wander had made a splash—but it couldn’t keep me dry. I ran to the subway, soaked. The bag looked even better wet.

Changing the Status Bag Quo

Everyone loves an ingénue—fashion insiders included. Perhaps that’s why at Paris Fashion Week in September, newer handbags from Bottega Veneta and Loewe jostled for space and street-style flashbulbs.

“These bags, especially ones by independent labels like Khaite, are quieter signals of cultural access,” explained Goor. “Everyone knows what an Hermès Kelly bag is. So now there need to be new signals” beyond traditional status bags to convey power.

Sasha Bikoff Cooper, a Manhattan interior designer, says there’s a less cynical explanation for why these bags have captured celebrity fans—and more important, paying customers. “They’re fresh and also beautiful,” she said. “Hermès is always classic. It’s like a first love. But you want newness, too.”

The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.

Are You Emotionally Ready to Retire? Eight Questions to Ask Yourself

Too many people leave work too early or too late. It doesn’t have to be this way.

***

Some designer handbags like the Hermès Kelly have implied power. But can a purse alone really get you a restaurant table—or even a job?

Changing the Status Bag Quo