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updated 2/14/2010 1:16:16 PM ET 2010-02-14T18:16:16

Financial planners can advise, books can inform, worksheets can approximate. But they'll never replace the advice you can get from folks who have ventured before you into that great unknown: retirement. To help you avoid dead ends and pitfalls, we asked retirees to look back over their time outside the working world and talk about their smartest financial moves, biggest surprises, and worst mistakes.

Tim and Jackie Fehr
Park City, Utah

It was skiing, not snoozing, that Tim Fehr imagined when he thought about retirement. When the Boeing engineering executive retired in 2001, at age 60, he and his wife, Jackie, knew they wanted to live in a ski community. Every Christmas for more than 10 years the family had vacationed at ski resorts. Soon after he retired they settled on Park City for its many slopes, lively town, and nearby international airport. The Fehrs consider that move one of their smartest. But the absolute smartest thing he did, says Tim, was to work with a financial planner and hire an estate planning attorney to set up trusts for his wife and two adult kids.

The financial wrinkle he considers his biggest mistake came out of consulting work. A former client hired him as chief technical officer. He was paid mostly with stock grants and had to pay income tax on the stock's value at the time of the grant. When the stock traded below $1, that didn't seem like a big deal. The problem came when the stock rose above $10. When he got grants at that price, he had to pay a lot to cover taxes. He couldn't turn around and sell the stock — he was required by the company to hold it for a year, and, as a corporate insider, had other restrictions on when he could sell. He wound up tapping retirement savings to own a stock he had to wait to sell. "Lots of cash out and a lot of paper in," he says. "The risk was much greater than I was expecting."

The most unexpected aspect of retirement for Fehr is how work-life balance is still tough. He used to tell team members at Boeing that a reasonable balance was 60 percent work, 30 percent family, and 10 percent giving back. When he retired, his team asked what his percentages would be. He predicted 50 percent family, 20 percent work, and 30 percent giving back. The reality: 40 percent family, 40 percent community, and 20 percent work — though the line between working and giving blurs. He works for his wife's not-for-profit, the Wildlife Protection Society. "My challenge is to make it function as a legitimate business and meet IRS and state requirements," he says. "It requires me to tap all my MBA knowledge."

Carol Daly
Minneapolis

Carol Daly, 68, doesn't like the word "retire." It stems from a French word with the bleak meaning of "withdrawing" or going into "isolation," she says. Daly prefers to tell people she "left behind paid work."

For 25 years Daly worked at the University of Minnesota helping colleges and universities in the state develop lifelong learning programs. Although she and her husband never made more than a combined $100,000, they put three kids through private colleges. She planned on working until 65, but at 56 she lost a part of her work that she loved, as Minnesota state director for Elderhostel, the nonprofit for adult educational travel, when it restructured. (She worked both for the University and Elderhostel.) Three weeks later her husband died from lung cancer at 58. She continued working at the College of Continuing Education at the University of Minnesota until she could tap retirement accounts at age 59 1/2 in 2001.

What has shocked Daly is how well she's doing financially, given the economic trauma of recent years. For 25 years the University took 13.5% of her paycheck for retirement savings and she added another 2.5%. She takes out $6,200 a month from retirement savings and gets another $1,400 from Social Security. About $1,200 is set aside for taxes and another $1,500 is taken out so that she has easily tapped savings.

The best financial move Daly made was selling her home in the suburbs and buying a condo in downtown Minneapolis. The condo has become a hub of her social life. Biggest regret? Working from 2001 to 2006 in the field of adult education, including for her former employer, UMinn, without pay. She stuck around because her identity was so closely tied to her work, she says. Now she's having a blast working on a city arts commission and taking adult education classes. "I wasted some time," she says. "I was too afraid of being discarded or ignored."

Jack and Terry Forsythe
Tucson and Chicago

A cancer scare was a big reason why Jack Forsythe decided it was time to retire in 2006 at age 59. He had been chief tax officer and senior vice president at Ecolab , the cleaning and sanitation company headquartered in St. Paul, Minn., and had worked there for two decades.

Real estate is at the core of both a good move and a mistake. The Forsythes had bought their Arizona home, which is on a golf course, at the height of the housing boom. But they love the climate. They also love Chicago and their condo there. The mistake was trying to hold on to a third home in a St. Paul suburb. The hassles weren't worth it, and they sold it. "I didn't lose money, but I didn't get what I would have if I had sold at the top," Forsythe says.

The surprise is how quickly he abandoned his identity as an Ecolab executive. He left and that was it. Instead, he and Terry travel the world, attending operas and chamber music concerts and visiting kids and grandkids.

Copyright © 2012 Bloomberg L.P.All rights reserved.

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