For many people, retirement can involve perfecting their golf game or taking a cruise around the world. But for Dave Duffield, retirement has taken an unconventional path.
Duffield is a billionaire who founded two famous HR software firms — PeopleSoft Inc. and Workday Inc. — before repeatedly finding himself “bored silly” in retirement.
“I tried to make model airplanes and failed, rocked away on the back porch, sort of failed at that too,” he told Bloomberg in a story published Oct. 7.
Duffield is the type of person to commit himself to the task before him. After a stint playing FreeCell, an online version of solitaire, his daughter says he became one of the world’s top players. Now, Duffield has set a new challenge for himself. Rather than sit on the sidelines and enjoy his estimated $15.4 billion net worth, the 84-year-old aims to take a third company public.
Duffield started his career as a systems engineer at IBM before leaving to go on his own. After three initial ventures, he started PeopleSoft, which he took public in 1992, according to Bloomberg, before retiring for the first time. He returned in 2003 after a hostile takeover attempt that ultimately ended with a $10.3 billion deal. Next, he started Workday in 2005, which grew into a $64 billion company, from which he retired as co-CEO in 2014.
Despite adopting his 10th child with his wife and serving on the board of WorkDay until 2022, this wasn’t enough to fill his days. So, in 2017, he started his latest venture, Ridgeline. He’s now invested $400 million in the company, which is a cloud-based platform that streamlines investment management. Bloomberg reports that Duffield hopes to take the company public in the coming years.
Duffield joins other retirement-age businessmen, including Warren Buffett, 94, who have ample money to enjoy a life of leisure but decided to keep going. Speaking at Fortune Magazine’s Most Powerful Women Summit in 2015, Buffett explained the motivation that likely keeps them all at their jobs instead of settling into retirement.
“It’d be crazy for me to leave my job, assuming I can do it,” he said. “I see these people, they spend a whole week planning their haircut. That’s not my idea of living.”
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If you’re bored in retirement, taking a company public may not be on your to-do list, but you also don’t have to sit around and play solitaire. Instead, consider your passions and find ways to bring meaning and joy to your life.
You may want to start a business like Duffield, and retirement may be a great time to do it if you’re in a financial position where you don’t have to make a big profit right away. As long as you’re not risking your retirement security with the money you invest, there’s no real downside to trying entrepreneurship.
Other options include volunteer opportunities, working a simple side hustle, or getting involved in community organizations. The sky is the limit once you no longer have a paycheck to earn, so if you’re dissatisfied with how you spend your days, don’t be afraid to try something new.
You may have more success in your second or third act than in your original career if it means being free to take chances and explore your passions without the pressures of early life.
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
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