A recent New York Times article by Tim Gray explores the unique challenges faced by family business owners planning to retire and provides some fascinating real-life examples of family-business handovers.

Citing a 2007 U.S. Census report, Gray notes that large numbers of family business owners will be dealing with succession issues soon: One-third of small-business owners were 55 years or older, and that about a quarter of small businesses were family-owned.

One tricky issue for family business owners is assessing whether their successors have what it takes to keep the business successful. On this matter, Gray quotes Toronto family business consultant Kelly LeCouvie:

"One of the first questions you have to ask yourself is, 'Do I have financial security if my kids run this business into the ground?' It's a possibility. You may have enormous faith in your children, and often that perception reflects reality, but sometimes it doesn't."

Read Gray's article here.