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For Daniel Ryan, turning 40 and 50 came and went. But sometime around his 61st birthday in July, he said he had an “old man crisis.”

He did some simple math and quickly concluded that living another 20 years would be considered a “full life.” Even if he remained healthy for another 15 years, he figured he might only be able to maintain his active lifestyle of skiing, hiking and mountain biking for another decade.

“Looking at the rest of my life this way hit me like a ton of bricks,” Ryan said.

Five months later, he retired. After spending 36 years in sales and marketing at MillerCoors, the beer company, he was in the enviable position of having a pension and ample savings. The challenge, he said, is that his wife, 58, is still fully engaged in her interior design business, where she often logs 12-hour days. So he has to negotiate both his new play schedule and his wife’s work schedule.

“There is no easy answer,” said Ryan, who lives in Milwaukee but spends a considerable amount of time skiing in Utah, which, he said, means his wife comes home to an empty, dark house. “Hopefully we both stay healthy and the strength of our 36-year marriage will help us ride out these bumps until we get at least near the same page.”

With more and more baby boomers retiring each year, either by choice or because they lost their jobs in the economic downturn, many couples must coexist, if only temporarily, in different phases of life. Living two different realities can lead to a variety of challenges, both financial and emotional, from brewing resentments about how a partner is spending free time to how to reconcile the spending mindset of a retiree and of someone still collecting a paycheck.

“A lot of people carry around this misunderstanding that if you disagree about something it’s a problem,” said Susan Zimmerman, a financial consultant and marriage and family therapist in Apple Valley, Minn. “A big part of what I do is remind people that disagreeing and having varying opinions on how things can be isn’t a problem, but necessitates more discussion.”

One of the first big discussions for a couple retiring at different times should revolve around the retirement schedule itself. One partner may be more than willing to sell the family home so they can more easily (and quickly) afford to retire, while the other may want to continue working. One partner’s job may still be thrilling, as is the case with Ryan’s wife’s work, or perhaps the working partner simply feels less anxious by remaining employed for a few more years and saving more.

Starting the dialogue with the facts, experts said, is one way to lessen the chances for conflict. It’s hard to argue with the numbers, particularly if you have an independent financial expert use different timetables to analyze how long your retirement portfolio could potentially last, given your expected cost of living. To figure out how much it might cost to live, however, couples first need to spend time thinking about what they’re going to do to fill their days.

Jeff Hazlett, a retired trial lawyer in Dayton, Ohio, had many conversations with his wife, a physical therapist, before he stopped working in September. The stress of litigating cases for 33 years took a toll on his blood pressure and his ability to sleep; he said he had lost three friends in the field in the past two years, two of whom committed suicide.

But since he was only 57, they needed to prepare for a significant loss of income. They approached the process carefully and set financial parameters that had to be met before he stopped working.

“We asked ourselves questions about what things we will do differently, what things will we not do at all, and what things will remain the same,” Hazlett said.

Once those ideas are sketched out, couples need to go through the age-old preretirement exercise of estimating “absolutely necessary expenses,” said Paula Nangle, a financial planner in Doylestown, Pa., as well as costs where there is some control (eating in versus eating out) and completely discretionary expenses, like travel.

Hazlett took on more household chores to make his working wife’s life easier, but he said he did not anticipate such a steep learning curve. Then there was the matter of reinventing himself in a way that made him feel relevant – he took up photography, remodeled a bathroom and plans on hiking the Appalachian Trail. But what really took him by surprise were his newfound feelings about spending money.

“When I retired, there was an insidious shift in my mind from ‘our money’ to ‘her money,’” Hazlett said. He said his wife expected to work for at least eight more years. “When I stopped working but still spent, at times I felt guilty for doing so. That has been a tough one to get over.”

Conversely, working spouses may want to continue to spend money on niceties like restaurants or new shoes to reward themselves at the end of the workweek, something that suddenly makes retirees uncomfortable.

“The mental shift that occurs when income from work comes to a screeching halt is colossal,” said Zimmerman, the financial adviser and marriage therapist. “Even when retirement is well planned financially, dipping into retirement fund accounts is frightening, with several unexpected emotions.”

Part of the solution, she said, is probably easier said than done.

“When spouses have different retirement timing, they need to start with, and accept, that mental difference,” Zimmerman added. “Then, make sure someone has done the math. Most likely, they both need to adjust some of their habits – both mental, emotional and actual ones.”