Retirement for the Restless

If you love to work, the thought of stopping entirely can be terrifying. So don’t. See how these overachievers are redefining retirement.

By Lisa Belkin

Managing Money — and Time

My mother has been a whirlwind all her life. "Change careers at least once a decade," she always warned me, "so you don’t get bored." And she practices what she preaches. After starting out as a teacher, she earned her PhD in counseling while her three kids were in elementary school. The year I graduated from high school, Mom graduated from law school. There were a few years spent as a business consultant, and some time as a professor, and a side gig as a travel agent in order to subsidize her frequent globe-trotting. Although she’s 70 now, she has never even come close to retiring.

I’m only 47, but these days I’ve been thinking a lot about my own future, in part because of my mom’s example. What does retirement look like for women who live life at full throttle? Can a type A personality, someone who can’t sit still and always has to be learning and working and doing, suddenly collapse into a rocking chair one day just because the calendar says she is 65? I’d wager Mom has not even looked at a rocking chair recently, and I don’t plan to either. Which is why I am watching her — and others like her — so closely, studying their choices for any clues I can use when I need to make decisions of my own. There is much advice out there on how to manage our money so it lasts for the rest of our (extended) lives, but there is little on how to manage our time. And if you have always seen work as a joy and an outlet, then how to use that time may be the bigger issue.

Some women have to learn the hard way that old-fashioned retirement is not for them. Consider Sue Welch, 56, from Gloucester, Massachusetts. She worked around the clock, and loved it, during the years she built RockPort Trade Systems, which created software that allows large retailers to track their inventory. In those days Welch thought of work as a means to an end, a way to amass enough cash to walk away. Sure, she knew she loved to work and that she had "a hard time relaxing," but she thought of money as the prize, and when she sold RockPort for $103 million at the age of 48, she assumed she would spend the rest of her life blissfully traveling and maybe writing the occasional novel.

That was seven years ago. For the first eight months, she woke up at 5:30 every morning and spent the next eight hours crafting her murder mystery. The 340-page manuscript, in which a lot of venture capitalists lose their lives, is still in a drawer. "I never intended to publish it," she says. "I just wanted to see if I could write it." Months of travel followed, but rather than lying about on beach chairs in foreign countries, Welch arranged meetings with government officials to learn about trading with overseas factories, "just in case I wanted to jump back in," she says. Within a year, she did. "I was getting depressed. When you’re not working, the only person to exchange ideas with is you, and you can bore the hell out of yourself."

She is now the CEO of TradeStone Software, which connects her old retail clients with the smaller international suppliers she cultivated during her "retirement." Now she knows she will never stop working. "I can’t," she says. "People like me will die on the job. I would never retire again."

Replacing Work with Work

Neither would Mellanie True Hills, 56, of Decatur, Texas, who was a pioneer in the early days of the Internet, finding an adrenaline rush in a series of start-ups. "I am not type A," she says. "I am type A plus plus." Her creations include the Web site, and for years she crafted Internet and e-business strategies for Cisco Systems’ customers, a job that kept her on call 24/7. "Every day was like jumping from a plane with my hair on fire," she says, in a tone that suggests the pressure wasn’t a bad thing.

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