Robert W. Baird & Co. financial advisor Lori Gervais recently started working with new clients—a couple in their 70s with a small business—who are facing some harsh realities. The couple, who own a medical device company, have had their son working in the business since he was 15 years old and planned for him to succeed them in running the firm. Now feeling ready to retire, they envisioned that the son, 38, would buy them out of the business and provide them with $250,000 in annual income during retirement.

But they had never openly discussed those plans with their son, Gervais says, and he has now taken on a senior executive position at an international engineering company. He recently told his parents he had no intention of taking over the family business. "It was a surprise to them," Gervais says.

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