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.

I would also ask her to consider whether she has ever been in past situations of showering unconditional love and financial support on a romantic partner. What was the outcome? (Pretend you don’t know.)

You might tell her about “another client” who was on the verge of becoming financially successful. This client was so uncomfortable with the possibility of succeeding that she purposely sought to give away her money and independence. Perhaps she feared no man would want her if she were successful, or that her wealth would intimidate them. How does your artist client view this other woman’s attitudes and actions?

By discussing these painful situations and scenarios, you may be able to prompt her to reconsider the impulse to give her new guy so much of her hard-earned money. An acceptable compromise might be to invest less than she had planned, or to make it a low-interest collateralized loan.

Ever since my client’s online business failed, I’ve been urging him to move to a nearby city with better job opportunities. He lives in a rural area with little prospect of employment, and is beginning to have difficulty keeping up with his alimony and child support payments. Today he told me he has bought a horse for his daughter to enjoy when she visits him. Obviously, there’s no way he can move now. How should I handle this? You may be able to unravel this knotty situation by proceeding in steps. First, take some time to help your client explore his feelings about the demise of his business. If he has not really mourned this loss, suggest that he join, or form, a support group of entrepreneurs whose businesses have not succeeded. If there aren’t enough people locally in this situation, perhaps he can find a group of job-hunting professionals.

Ask him how expensive it will be to keep the horse, and how he plans to pay these bills. Eventually, you may feel comfortable inquiring how he feels about a move to the city to find work. In buying the horse, did he intend to make it clear that he was taking this option off the table?

If your client is depressed, acquiring and caring for the horse may actually help him. On the other hand, he may be in denial that he needs to change his situation. Or he could be so angry (at God, the fates, or whoever) over what happened to his business that he’s essentially saying, “I don’t care if I don’t have the money; I’m doing what helps me feel better!”

If that is the case, all you can do is offer him options and scenarios, and see if he will eventually get on board with a plan that yields positive financial results. If he remains too angry or depressed to get mobilized, you can be of great service by preparing a resource list of experts who can help him. Give this client time, keep discussing his situation with him, and see if he moves into a phase that is less self-sabotaging.

A client I’ve been seeing for years has had many ups and downs. Whenever he has some extra money, he tends to lose it in some get-rich-quick scheme. How can I help him change this self-defeating behavior? I’m glad you’re willing to work with your client at this level. His habit of risking his profits on a big dream probably leaves him feeling depressed, embarrassed, and even ashamed when the long shot doesn’t succeed.

I think your best approach is to interview him, calmly and non-judgmentally, about this recurrent theme in his financial life. Does anything in his family history explain why he falls for magical fantasies of getting something for nothing, instead of building wealth in a steadier, more patient fashion? Did someone in his family set an example of this get-rich-quick attitude? Or does he simply think that more “sensible” investments are too boring? Maybe the thrill of living on the edge excites or feels familiar to him.

Whatever you find out, it will give you a better handle on how to talk to him about changing his pattern. You may not be able to persuade him to ignore investment tips that promise to make him an instant millionaire, but perhaps he will agree to venture only a fraction of his assets.

When clients behave in ways that seem to undermine their progress, be patient and accepting. Remember that many people are stuck in irrational, self-defeating behavior because they prefer old, familiar patterns, however painful, to the newness of change. If you allow yourself to ask about the history and motivation behind these seemingly weird habits, you may discover what fuels their self-sabotage.

Once you identify what’s keeping them stuck and suggest small actions to change their patterns, you will be showing them a light at the end of their myopic tunnel. They may well reward you with deeper trust and stronger professional relationships.

Olivia Mellan, a speaker, coach, and consultant therapist, is the author with Sherry Christie of The Advisor’s Guide to Money Psychology. E-mail Olivia at om@moneyharmony.com