Fear of Flying

One of the most frustrating situations you can encounter is to see clients acknowledge the need to embark on a positive course of action, and then shoot themselves in the foot.

How can you bring a self-sabotaging pattern to your clients’ attention in a way that helps them move toward financial and emotional security and serenity? The approaches I’ve suggested below may give you some idea of how to tackle this delicate task.

My client, a widow in poor health, knows she needs to update her will but has put it off repeatedly. I have warned her about the possible consequences for her family, but she says she hasn’t decided on all the changes she wants to make. What can I do to help her get moving? I would encourage this client to take her best shot at updating her will now, and make any further alterations later on. My guess is that you have already suggested this, and that something else is preventing her from taking action.

To help, you need to find out what is really blocking her. It may be a control issue with her family, such as her not wanting them to know what she has decided to do with her assets. She may wish to treat some of them differently than others, and is afraid of being shunned or hated if they learn about it. Or she may irrationally fear that once she makes a new will, she will die.

You might begin by calling her bluff. Suggest that as an objective third party, you will be glad to help her sort through her ambivalent feelings. If she is willing to discuss these reservations with you, keep asking questions like “Can you tell me more about that?” to see if she will eventually open up about her true concerns.

Once you feel you understand her blocks, try to suggest ways around them. For example, you could tackle the “fear of dying” myth by telling her about other clients who made out their wills years ago and are still alive and well.

For everyone’s sake, I think it would be desirable for her to meet with each family member and explain what she is planning to do in her will. Another possibility is for her to talk to them all in a family meeting. You might take part in this gathering if you wish, perhaps with a counselor or therapist on hand to address any complex emotional issues that may arise.

Although this direct communication may seem difficult and scary to your client, it can pave the way toward more intimacy with her relatives. But even if she does not feel brave enough to open up to her family about her wishes, I hope you can persuade her to see an estate attorney. By recounting the risks of dying with an outdated will–or worse, intestate–you may be able to light a fire under her at last.

Our senior partner recently brought his son into the firm. Although this young man has all the right credentials to succeed, he recently started an affair with one of our married clients. I found out about it through the office grapevine, so he hasn’t done much to keep it a secret. People expect me to take care of this situation since I’m a friend of the family. What’s the best thing to do? What a mess this guy has gotten himself and your company into! Assuming that his father hasn’t yet gotten wind of this ethical breach, you may be able to quash it by talking privately with the son.

Try to find out what’s behind his behavior. Was he reluctant to join his father’s business? Does he secretly want to be fired? How does he feel about the fact that the affair may cost him his colleagues’ respect and his credibility with other clients? Is he infatuated to the point where he doesn’t realize the ramifications of his actions?

It would also be interesting to ask if he’s ever been in a similar situation where something he’s doing prevents him from getting what he wants (a tactful way of finding out whether he is prone to sabotage his own success). Of course, if he really isn’t happy working under his father, you may discover that his behavior isn’t self-sabotage in the classic sense, simply an indirect way of getting the message across that he doesn’t want to be employed there.

Once you learn where he stands, you’ll know better what to do next. If nothing positive has been accomplished by talking with him, you need to consider speaking to his father. This will position you as a stool pigeon, though; and if the father backs up his son, they may both end up so angry with you that your job is in peril. So I would hope you are successful in helping the son resolve his own tricky relationships with his dad as well as his inamorata.

My client, an artist, just had her first successful year. But instead of funding the portfolio I’ve recommended, she wants to invest most of her earnings in a restaurant that her new boyfriend plans to open. She has a history of supporting unreliable romantic partners, and I’m afraid this could be a similar mistake. How can I warn her, when she’s so starry-eyed? Do it very, very gently, and not all at once. I’d begin by telling her that romance may cause people to lose their moorings for a time. Sudden wealth can have a similar effect. Given this double potential for unclear thinking, you feel responsible for giving her a down-to-earth perspective on her situation.

If she agrees to listen to you, urge her to do nothing right away. Have her write down her life goals, not just her hopes for this relationship. At your next meeting, discuss how these goals may be affected if she loses her investment in the restaurant.