Since the father had not really done integrated planning before, we started by having him gift the bypass trust income to the kids, since he did not feel attached to the income. We then made substantial gifts to each child and funded 529 plans for the grandchildren. Our client worked closely with her father to be sure he felt comfortable with the strategy.

But then, because no good deed goes unpunished, one of the brothers complained about how his tax situation was changing and the other brother indicated that his financial planner told him he needed more money gifted into the 529s in order to fully pay for college.

My client was hurt and frustrated. She had mistakenly thought that the real issue was to make the best decisions about the disposition of her father’s estate. But that wasn’t really the issue. For one of the brothers, the minimalist, the real issue was trying to understand how money could potentially change the life he was living. Or it was about the responsibility of stewardship. Or it may have been about being rich while his friends were poor.

For the other brother, the issue might have been that there could never be enough money because he had grown up in a financial situation vastly different from his current one. He might have been wondering why his sister was the one in charge of his father’s finances. Or it could have been that he still did not feel successful after being blessed with these riches.

And our client was likely asking why she was not appreciated for doing the right thing. Why did all sorts of family history have to be acted out in such a harmful way? Could she have possibly done something wrong?

Since there are multiple parties involved, each with only limited information about the others, there are a number of possible issues at play. So in this case, identifying the most important one was probably impossible.

Instead, we tried to find clarity about everybody’s intentions. We communicated with the brothers about what they could expect to receive going forward and why the grandchildren would be gifted only the annual exclusion amounts. We also talked about people’s behavior: for example, why it was inappropriate to go behind their siblings’ backs to lobby Dad.

This approach helps our client understand why she is making decisions, identify how they are consistent with her role and give her brothers needed information related to what they can expect. They may also be able to find their own help. What the approach doesn’t do is put an end to everyone’s issues, because everyone has sovereignty over their own dysfunction (and by the way, that includes all of us planners).

Couples pose a different problem when we are trying to get to the real issue behind financial ones. For example, if we identify overspending as a problem for a couple, is creating a better budget the solution? How many of you have had clients who overspend no matter what budgeting tools you use? Guess why. The spending wasn’t the issue. It was why they were overspending. Maybe they felt unsuccessful and wanted to prove otherwise; maybe they felt as if they had a hole that could be filled by buying things. Maybe they had little control over their impulses.

Trying to get clients to open up about what may be causing this allows us to get closer to helping them. One of our recently divorced clients was in a habit of splurging on things for herself. She had put herself on a number of budgets, crossed her heart and hoped to die several times, pinky swore, and did everything except tie herself to the mast like Ulysses when she wanted to stop spending.