Cheryl Menken thought she knew everything about her husband, Morris. She knew he cheated on his first wife. She knew how he got caught. (They were in a car accident and Morris broke his leg.) And she knew that when he became terminally ill at 67, he wanted to remain in denial about his illness and continue to work for as long as he could. It wasn't until after Morris died that Menken realized how much she didn't know, particularly about their marital finances. She knew he had amassed at least $4 million and that some of it was invested with the Carlyle Group, but she couldn't even access those accounts because he never gave her the passcode.

"My role was to pretend he wasn't sick as best I could. So for two years, I saw him die, and I didn't ask him about our finances," Menken says. "I tried to keep abreast of where things were, but it was almost impossible."

Reeling with grief, Menken says she staggered around for a while after Morris died, unclear about her future. She reached out to her husband's advisor at Morgan Stanley,  but she was away, so she decided to go with someone else. She contacted one of her husband's former business associates, and he suggested she contact James "Buddy" Thomas Jr., a CFP with Superior Planning, an investment advisory in La Jolla, Calif. Thomas was writing a book on widows at the time. That was four years ago. Menken still speaks to Thomas every Monday, whether she needs financial advice or not.

"When you're in grief, you can't think," Menken says. "It doesn't matter how much money you have. If you don't know what you're doing, it's traumatizing."

Menken's story is not unique. Advisors to the ultra-wealthy say no matter how much-or how little-one plans for death, they've learned to expect the unexpected. Widows can get depressed and fail to pay their bills. Children behave badly. Friends and relatives want money. And before long, the best laid estate plans go awry. Thomas says he spent almost a year with one of his clients, formulating a plan for the day his son would take over his international importing business. When the father died, Thomas met with the man's wife and son and the boy looked sullen. When the mother asked him what was wrong, he said he liked being a salesman. He didn't want to be a CEO. They wound up selling the business for a substantial profit, and the son now works for the new owner as a salesman.

"He wanted out. She wanted out. So we shifted gears and sold the business," Thomas says. "When you're working with a widow, you don't know where things are going to go. So you just sit back and let things unfold."

Thomas would know. He's made a business out of serving widows. He can reel off the statistics: Some 80% of surviving spouses are women. Their average age is 56. They generally outlive their husbands by about 14 years. Thomas says the hardest part is that they must file their estate tax return within nine months, a laborious and costly process that requires every asset and piece of property to be appraised, all at a time when the widow is dizzy with grief. And that grieving period can last about 18 months. Thomas says he had one client who lost her shoes and finally found them a day-and-a-half later in the microwave. Another client says she was on a ladder dusting a shelf and suddenly found herself on the floor, and she had no idea how she got there.

While he's seen children want to flee from the family business, Thomas says the more common scenario is for them to try to run things-whether it's the family finances or the widow's life. Some think they're helping. Others want more control over their inheritance. Thomas says the first widow he worked with in California had allowed her husband, a retired real estate developer, to control all of the couple's finances. While she ran a boutique, her husband sat in the backroom and played with their investments- until one day he got indigestion, was rushed to the hospital and died. Her son immediately wanted to swoop in and take over where his father had left off.

"I'm afraid he'll smother me," she told Thomas. "This woman's ideas about what she needed to be happy were different from her son's ideas."

Thomas says he came up with a financial plan for her, and when they were finished, she clutched that plan in her hand and began to cry. She'd never taken control of her own financial destiny, he says.

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