“It wasn’t a great deal of money, and if we never got it back, we’d be okay. But should we maybe just write a provision in our will to withhold that amount?”

How would you answer? Here’s what I told them—and what I still think:

Carefully consider what you’re trying to accomplish. Unintended consequences are just as impactful as the ones you meant.

Your will is essentially your final statement to your family. And last words, as the saying goes, are lasting words. Those sentiments will stick in minds and hearts. They’ll be remembered—as much as anything else you said during your life. 

So, choose your words carefully.

If your goal is to exact revenge through your will, a will can be a very useful tool indeed. This is the stuff of mystery novels and legal thrillers. The family gathers around the family lawyer, who reads the will with the verbal intonations of a Shakespearian actor.

“And to my worthless, shiftless son, Charles, I leave this cheap $5 wash bucket, full of the same empty promises he always made to me!” The red-faced Charles storms out of the room, while the rest of the family smiles wryly at just desserts delivered in style.

Nothing in your question makes me think you want revenge. So, let’s look at another option.

Is your goal to bring about justice in your will? That’s what it sounds like. You’re thinking of leaving a generous inheritance to your son, minus the amount he took and never paid back.

If you took this approach, the money would indeed be “paid back” at last. And any other children would be “made whole.” However, you would also mark your son—the one you say has turned his life around—with a brand he’d never be able to wash off. He’d always be “the one who stole from Mom and Dad.” Absent any other actions, that’s what I believe would happen if you pursued justice through your will.

There’s another option—in my opinion, a better one—if you really want to make things right. 

Deal with this situation face-to-face, not through a document. Deal with it while you are alive, not after you are gone. If need be, have a trusted third-party facilitate what might be an awkward conversation.

Tell your son what you are really thinking and feeling. Say something like:

“Son, you know that we love you. We’ve been making out our wills and that triggered the memory of the stolen money. We’ve never brought it up; and neither have you. We know you were sorry, and you’ve done such a fine job of making a good life for yourself. We’re proud of the man you’ve become. But we do feel the need to resolve the outstanding issue of the money you stole.
“What do you think is right? Do you want to pay us back? Or would it be better if we just made a provision in our wills that addressed that issue upon our deaths? We can do that in our wills, but we didn’t want to take that action without talking with you first.”

You get the idea. Don’t limit yourself to these words. Make them your own, and say them in your unique way. The specific words that come from your mouth are not as important as the sentiment that comes from your heart. If you’re kind and gracious, and your desire is for true reconciliation and peace, that’s what will be heard loud and clear. 

Justice done through a will too often comes across as vengeance. 

A loving conversation can work wonders. And it will be immeasurably healing to your family after you’re gone.

If you’re wrestling with good questions like this one, make sure you ask all the right ones. Email me at bmoore@argentadvisors.com and I’ll send you my free list of “30-Something Questions for People Who are 60-Something.”

Argent Advisors, Inc. is an SEC-registered investment adviser. A copy of our current written disclosure statement discussing our advisory services and fees is available upon request. Please See Important Disclosure Information here.

I’m retired and widowed. My two adult sons still depend on me to pay some of their bills—even though one of them has a job. (The other can’t seem to keep steady work.) I’m worried that when I’m gone, they are going to fight over my money, even though I don’t have much. Should I consider a trust?

Sadly, I see this problem more often than I’d like. It’s never pretty, and it rarely ends happily. It typically starts when parents confuse leniency for love. 

Children can always sense when a parent is afflicted with “leniency-love confusion.” And they will manipulate the heck out of those that do.

“Johnny, go finish your homework.”

“But I wanna watch TV!”

“Now, Johnny, you know the rules…”

“You don’t LOVE me!” 

(Nothing eats at an insecure parent like that statement.)

“Okay, you can watch. But just this once.”

Ugh. This dynamic is bad for kids, it invites trouble for parents, and it’s cringeworthy for onlookers.

I love those rare occasions when a parent quietly flashes “the look.” You know, the stern glare that says, “You just messed with the wrong Marine!” 

Instantly, the offending child shrinks and slinks away, knowing he/she is in serious trouble, with a capital “T.”

May I state the obvious? If nothing is done to squelch this kind of behavior early, the manipulative seven-year-old will grow up to be a manipulative 17-year-old…and a manipulative 27-year-old and… The longer you wait, the more complicated the cure becomes—if it can ever be cured.

We often think of parenting as “raising kids.” A better goal is raising responsible adults, who can stand on their own two feet financially (and in other ways). 

So, let me say this as clearly as I can:

It’s not healthy for a healthy adult child to be dependent on regular infusions of “rescue cash” from mom or dad. 

My greatest concern for my questioner is that this unhealthy pattern is draining her assets at a time in life when she can least afford it. Here’s what I advise:

• Tell your sons that the gravy train just ended. If they can’t manage to pay their own bills, you can’t count on them to take care of you when your money runs out. 

• Create a trust in your will. If you don’t have a will, have one drafted by a competent attorney. The will should stipulate that the assets of your estate be placed in trust, to pay an income for life to each of your sons, equally (if that is your wish). 

This way, there is nothing to fight over, and they can’t get their inheritance right away and spend it all. (And, yes, they would.)

• Get a professional trustee to carry out the specifications of your estate plans. Your trust document contains your estate plan. Your trustee is the one who must carry it out. 

Parents who financially support their able-bodied adult children obviously do that out of love. But I encourage you to start loving them with “tough love.”

It will be best for them…and best for you.

To help you think through such issues in greater detail, I’ve created a thorough checklist of financial questions for people who are 60-something. It’s free if you’d like a copy. Email me at bmoore@argentadvisors.com, and I’ll send it to you right away.

Argent Advisors, Inc. is an SEC-registered investment adviser. A copy of our current written disclosure statement discussing our advisory services and fees is available upon request. Please See Important Disclosure Information here.