Having a successful entrepreneur for a parent should inspire a child, not discourage him or her. But that's not the case in the Stewart household. Asa Stewart is founder of an industrial company in Pennsylvania. His son, Nate, is 20 years old and jobless. "My son, who is having trouble finding even part-time work, doesn't feel he will be able to surpass or even equal what his father has achieved," says Jenna Stewart, Asa's wife and Nate's mother. (At Jenna's request, I've changed names and all identifiers. In a world where employers routinely search for information online, Jenna didn't want to suggest anything negative about her son.)

A kid with no job. A parent with his own company. Would hiring young Nate provide a temporary solution or just make things worse?

With so many Millennials unable to find employment, family businesses can provide economic lifelines while preventing embarrassing resume gaps. But that can be hard on family relationships. Young adults hungry for independence don't want their parents bailing them out. Spending every day in a place that embodies the previous generation's accomplishments continually twists the knife.

And Nate's earlier experience with the business doesn't bode well. Last summer, Asa hired his son to paint the facilities at his company. "My husband was critical of the work Nate did," says Jenna. "He has an expectation that our son will perform better than his other employees. But Nate is a typical 20-year-old."

As Jenna sees it, Nate's sense of failure is a reflection of his father's attitude. Asa simply can't fathom why his son hasn't been able to find work. "My husband is an entrepreneur who sees opportunity everywhere," says Jenna. "He wonders why Nate isn't out there knocking on doors to mow the neighbors' grass. My husband says things like, 'When I was your age, I had three jobs.' My son wants to prove himself. But his father feels he's just not a hard worker."

Both Asa and Jenna want their son to gain work experience that doesn't involve reporting to dad. He should "know what it's like out there," says Jenna. It's an attitude they share with most entrepreneurial parents, even those eager to pass the company on to future generations. Young adults who work outside the family business return with new perspectives, skills, and contacts. Having tried other options, they can also make a more informed decision about whether joining the business is right for them.

But in a wobbly economy, do the same rules hold? In the Stewarts' situation, I think I'd do just about anything to get my kid working. Family-provided employment may hurt a child's confidence and self esteem. But long-term joblessness might lay waste to them. And, of course, just because the family supplies the job doesn't mean kids can't push themselves to excel in it.

Kids joining the family business--as designated successors or just employees--can create a hornet's nest of emotional and financial complications. A few safeguards are in order. Have your children report to someone other than you. Create systems to dispassionately resolve sensitive issues, such as compensation and performance evaluation. And be vigilant about keeping the family's accumulated psychic detritus from clogging the gutters of your nice, clean-running company.

Above all else, protect your relationship with your children. Otherwise, what's it all for?