My husband and I are preparing our wills. We have two adult children: a daughter who is more successful than we are, and a son, who has been down on his luck for years. He also has three young children to educate. Everyone, including our lawyer and close friends, tells us that we should leave our money to them in equal shares to avoid hurt feelings. But that doesn’t seem right. Our son needs the money. Still, we don’t want to hurt our daughter. What would you do?

Anonymous, Chicago

Stop listening to everyone. It’s your money, and they’re your children. Who better to walk this perilous tightrope than you, especially if we set up cushiony nets beneath you (unlike Burt Lancaster in “Trapeze”)?

Your advisers have a point. You don’t want to hurt your daughter by leaving all the goodies to your son. (I hear that even wildly successful people have feelings.) Talk with her privately and say: “We always imagined leaving our money to you and Bobby 50-50. We love you both. But you’ve become so successful, and Bobby really needs our help. How would you feel if we left him a bigger piece of the pie?”

Then listen. You will be perfectly placed to hear how your daughter feels. Make sure she knows that you are not looking for an immediate answer, only to start a dialogue. And be clear that if anyone’s circumstances change, your estate plan will, too. It won’t be the easiest conversation you have this year. And I’m not suggesting that your daughter’s feelings should be paramount. (It’s still your money.) But by talking it out sensitively, mindful that even the sanest people can go bonkers where cash is concerned, you stand a decent chance of walking through the fire unscathed.