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Financial Planning > Tax Planning

Taxed to the Max

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Just when we thought we’d put 2002 behind us, along comes April 15 to remind us of it all over again. And worse yet, to make us pay for having been through it.

With tax time piling more pressure on top of the anxiety many people are already carrying around, it won’t be surprising if some of us act a little dysfunctionally this month. However, there are ways to make tax stress less toxic to yourself and your clients. Here are some ideas:

I’ve just met with a new client who is about to be married for the second time. Several years ago, he neglected to pay taxes while his business was failing. The IRS caught him, and he is still paying penalties and back taxes. He intends to be honest with his fianc?e about this, but I’m the one he wants to break the news to her! Should I agree? Though I understand your client’s desire to have you do his dirty work, this won’t serve his marriage well–it positions him as a child, rather than as a responsible adult who’s cleaning up his act and moving forward. He’d be better off broaching this delicate subject privately with his fianc?e before they see you together.

Urge him to find an relaxed time to talk with her. He might open the conversation with something like this: “Honey, I want us to have a marriage based on trust and open communication. There’s something I did in the past that I feel ashamed about, even though I’m making up for that mistake. I need to tell you about it, and I hope you won’t judge me too harshly.”

Having set the stage, he can then tell her about his tax debt. When they subsequently meet with you, she will have had some time to grapple with her feelings and reactions, and they can talk to you about the best way to move forward.

Yesterday a longtime client ranted at me for half an hour about his IRA, his stock portfolio, and his estate plan–all of which will need to be revisited if the President’s proposed tax changes go through. I didn’t know what to tell him, except that I’m just as frustrated as he is by the constant changes in tax law. How should I handle this? I think it’s a good idea to validate his feelings of frustration and confusion, just as you have. It’s extremely hard to plan for a future that holds so many unknowns, but remind him that he chose you to help him chart the best course amid all these uncertainties.

Once he feels calmer about the situation, you can counsel him about his choices. Some people feel more in control if they focus on a single possibility, while others prefer to consider all the alternatives and then prepare for the worst case.

So if you have a good idea of his personality type, consider tailoring your response to whatever will best calm his stressed reaction. For example, you might run several scenarios for him, and suggest how he would want to reposition his assets in each case. If you think the law isn’t likely to change anytime soon, advise him accordingly.

My client, a retired professor I’ve known for years, is so angry at the government’s plans for military action in Iraq that he wants to protest by not paying his taxes this year. As a planner with CPA certification, I’m not comfortable with this choice. He knows I don’t agree, but how can I dissuade him? I would begin by giving him time to vent his feelings of alienation. After listening empathetically, see if you can support some of his perceptions so he feels he is not alone. Even if you don’t agree with his views, you may be able to say something like “I know you’re not the only one who feels this way. I’ve heard other people say similar things.”

Once you have supported his stance to the extent that you can, you might brainstorm with him about more proactive ways to express his opinions. For example, he could join organizations of like-minded folks, write letters to major publications, call his Congressional representatives, and write the President.

Whether or not he elects to take positive action of this kind, I think you should make sure he understands the eventual cost, complications, and other repercussions of tax evasion. If his decision was made impulsively, remind him that hastily made choices rarely prove to be the best ones over the longer term.

Ideally, the combination of empathy, brainstorming about activist alternatives, and more consideration of the real-life cost of evading taxes will help him choose a less thorny path. But if he persists in being a refusenik, make sure you keep a record of your advice to protect yourself from being implicated in his choices.

I recently met with a potential client, a widow in her 70s, who insists on maintaining an enormous cash reserve in case she ends up owing more income tax than planned. I tried to explain that keeping so much money in a checking account is not very productive, but don’t think I got through to her. What else can I say? Before you can help a client who has tax anxiety, you need to know what caused it. Did something happen in her childhood or marriage, or to a relative or friend, where a lack of money to pay taxes led to dire consequences or personal humiliation? Or is she simply unfamiliar with managing money, and dreads being caught short?

When you understand the source of her anxiety, you may be able to gently reassure her that she has more than enough money put aside, even under the most unlikely scenario. Once she calms down, remind her that your job is to help her become more financially secure.

You can then recommend what she should do with her excess cash. Or if she prefers to have choices, you might suggest several alternative courses of action that will allow the money to work harder for her.

I’ve been working for years with a client couple, both of whom are Type A personalities. At a recent social event, the wife confided to me that she hates it when April comes around, because she and her husband get into heated arguments about their taxes. Last year, they ended up not speaking to each other for weeks. She told me they would both appreciate my advice to prevent this from happening again, but I don’t know what to say. Any suggestions? I would try to find out what upsets these clients so much. Is there an actual tax trauma in their past? Or is this annual eruption a symptom of money conflict that bubbles under the surface all year long?

To start working toward possible solutions, you could do a “stress inventory” for them–perhaps individually at first, then together. This is an assessment of ways their marital tension manifests itself around tax time, and ideas to help them avoid stress triggers. Ask them to think about stressful events they have handled well together in the past, and what they did that was different from their tax season meltdowns.

With what you learn from the stress inventory, you might go on to explore specific ways to defuse the April 15 time bomb. For example, if blowups tend to occur because they get in each other’s way, they might divide up tax preparation tasks: one prepares Schedule A deductions, say, while the other collects capital gains information for Schedule D. Or if last-minute procrastination fuels their fights, they could address different aspects of their return in stages before the tax-filing deadline. On January 31, they could tackle their investments; on February 28, their deductions; and on March 31, the 1040 itself.

As part of this process, they should commit to communicating respectfully with each other. Urge them to avoid blame and recriminations, and monitor their tone of voice as well as the words they speak. If communicating orally about taxes is likely to push emotional buttons, you might suggest that they request information from each other in written notes or e-mails.

There’s a good chance you can help this couple by encouraging them to remember ways they have coped with stress in the past, and asking them to envision how they might handle it better in the future. But be prepared: if they’re truly “stressed to the max” at tax time, they may find that moving toward harmony is very difficult. If so, they may need to seek professional counseling before this season of living dangerously rolls around again.

A client has asked me for advice about her 24-year-old son, who has his own business as a computer consultant. She recently learned from his roommate that the young man hasn’t filed a tax return since graduating from college. When she asked him about it, he said airily, “What the IRS doesn’t know won’t hurt them.” This is a tough one! What would you suggest? I think the next step has to be for your client to approach her son again. Coach her not to be accusatory or confrontational, or he may simply dig in his toes. Instead, she might begin by saying something like this: “Son, I’m feeling bad that I may not have educated you very well about money and taxes. I’m also worried that by neglecting this responsibility, you could get into serious trouble, including fines and even jail time. Will you help reassure me by finding out more about this from my financial advisor?”

If you can get the son in to see you (preferably alone), you’ll have an opportunity to help him resolve this tax issue. Most people find it easier to take advice from an objective third party than from a parent or authority figure with whom they have an emotional history. It may also be possible at that point to explore what’s behind his “What, me worry?” attitude.

Remember that when people are under stress, as they tend to be when compelled to cough up thousands of hard-earned dollars, they will almost always revert to their oldest, most dysfunctional mode of behavior. Think of it as their primitive survival mode, and you won’t be far wrong.

By preparing yourself in advance of tax season, you may be able to avoid slipping into this mode yourself. Get enough rest, and factor tension-relieving activities into your schedule. This will put you in a better position to help your clients move from a “taxed to the max” anxiety mode to a more rational level, where they can hear and absorb your sound financial advice.


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