Drake said she tried to be savvy. She moved to a school district that compensated teachers well and offered a pension. She bought a house. She saved for her children's education. After those expenses, she had little left in her paycheck.
It wasn't until 15 years ago that Drake saved her first dime for retirement.
"Retirement? How was I supposed to pay for that, too?" Drake asked.
"I wish someone had sat me down and told me I had to figure this out," she added.
Laura Kay House, owner of Silver Connections, a social networking group for single baby boomers, is very familiar with the fairy tale many of her clients held dear.
"Many of these women were raised to get married and have babies," House said. "Life didn't go as planned and they weren't prepared."
Watkins, the financial counselor, said the older baby boomer women didn't get the financial lessons their children have, even though they were entering the workforce and earning their own money.
"They were poorly educated about their retirement," Watkins said. "There was this old mythology that women weren't good with numbers and they shouldn't fuss over them."
Philips said her retirement plan was her husband. She figured they would rely on his military pension. But he became an ex two years ago, and she said she got none of that.
To make matters worse, Philips lost her full-time job months before and has struggled to find steady work since.
Once upon a time, Philips, a former banker, did have a retirement account. The bank where she worked even matched her contributions. But the bank eventually closed its office in her town, leaving her jobless with few prospects.
She cashed in her retirement to keep from losing her house.
Philips said she's been turned down from more jobs than she can count. Another challenge: the missing years on her resume she spent staying at home and raising her daughter.
Last month things got so dire that Philips applied for food stamps.
Financial planners say single women often get caught saving for big-ticket items other than retirement. The biggest: a child's education.
"They are doing their best to save for their kids' education," said Jim Trull, certified financial planner with Keystone Financial Partners. "All of a sudden, they wake up one day and realize they are 55 and have only $100,000 in their 401(k) and they make $70,000 a year."
In 2009, Margaret VanDeCar of Raleigh had a great accounting job and was on track financially to retire in her 60s. Then, a layoff notice landed on her desk.
She was 58 and counting heavily on her earnings to fluff her retirement nest egg.
"I never anticipated that setback," said VanDeCar, who divorced her husband 17 years ago.
VanDeCar competed with women half her age for open positions. It took 18 months before she landed another accounting job through a connection.
"I just never thought about having to navigate a job market at this age," said VanDeCar, now 59.
Many of the single boomer women who had already stepped into retirement are facing the same cold reception as they try to wedge their way back into the job market.
Arnita Woodard, 61, of Garner, N.C., took early retirement a decade ago from her management job at Duke Energy. She figured volunteering to take a buyout would spare another employee who still had young children. She had already gotten her son into college.
Woodard, a divorcee, imagined finding other work to help supplement her pension. Those jobs were hard to land. Finally, a year ago, Woodard decided to start her own business, offering companionship and organizational help to older seniors.
"For me, this is the difference between paying my bills and getting to have some fun," Woodard said.
Drake, the retired teacher, is also looking for the same sort of supplement. She earned $2,200 a month from her pension plan, but she has been nibbling at her savings to cover fun activities and travel. She has already spent the $40,000 profit she made when she sold her house last year.
Drake imagined finding work as a substitute teacher. But, with the state budget crisis, those jobs have grown scarce.
She did get a job as a clerk at a women's clothing store, where she earns $8 an hour. Drake figures she spent three times her paycheck shopping. She quit and has vowed to stay out of the mall.
For all the single boomers' efforts to save enough money to cover their expenses in retirement, they are caught flat-footed on a critical issue: long-term care insurance.
None of the women in this story have purchased policies that would cover the costs of skilled care help or an assisted living facility if they need it.
That is a common trend. The AARP said boomer women are ill-prepared for long-term care needs. According to a survey of boomer women, more than half of female baby boomers do not have a long-term care insurance policy, and two-thirds said they couldn't afford the premiums, according to the AARP survey.
That gap promises to be an enormous problem because these women are expected to live to age 85 or older.
Many of the women sheepishly said they'd turn to their children if they needed help.
"My son said he'll take care of me when I get to that point," said Woodard of Garner.
The average cost for an assisted living facility in 2010 was $38,000 a year. A private room in a nursing home was nearly double that.
"We're probably in denial about it," said VanDeCar, the accountant. "We think we're the caregivers and we don't need the care. But I guess that won't be the case forever."
Drake, the retired teacher, refuses to be a burden to her children. Years ago, she had a stern talk with one of her daughters about how to handle her if she is sick.
"I told her to take me to a mountain top and leave me there," Drake said. "There's only so much I can worry about and this isn't one of them."
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