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 realized 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 honored 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?
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