Anonymous Mailbag

It’s Tuesday, rejoice, it’s time for the anonymous mailbag.

As always you can send your anonymous mailbag questions to, anonymity guaranteed.

Okay, here we go:

“I’ve been stewing about something for several months now and after your well composed advice in last week’s mailbag about inheritances, I think you’re the right person to offer some guidance.  

My 22 year old son is an active member of Antifa. He concealed this from my wife and I until I outed him after seeing him on television terrorizing people who attended the Trump rally in Minneapolis.  He was dumb enough to wear a personalized sweatshirt that my wife and I purchased for him for Christmas and a local news camera caught him in action.  When we spotted him we paused the screen and stared at it for at least an hour.  We were in shock. He didn’t respond to our texts or call us for several days afterward. 
I can handle the fact he has different political views than I have but what I can’t handle is his alignment with such a violent organization.  I’ve already cut off my financial support (he was on our cell phone plan and on our car insurance among other things).  
I’m now contemplating the decision to write him out of my will.  Right now he and his sister are set to receive an equal stake.  Unlike last week’s letter writer, there are significant dollars in play.  My wife feels that I’m overreacting but I don’t think I’ve done enough to send the proper message.  
I don’t want my life’s work to fund an extremist organization. I’ve had a while to think about this and cool down but I still think my move is to leave him with nothing.  What say you?”
Let’s remove the politics from this completely and just say that your son is engaging in (borderline) illegal activity. Do you have an obligation as a parent to facilitate or encourage that behavior? The answer is, of course no.
For instance, let’s pretend you found out your son was an ISIS adherent and was sending your money to help fund an Islamic caliphate overseas. I think most people reading the mailbag would agree that you would be justified in cutting off any money that you gave him because of the purposes he’s using it for. Closer to home I’d imagine most readers would agree that if your son was using your money to run a criminal drug enterprise, you’d be well suited to cutting off his funds.
So I see nothing wrong with your decision to cut off his cell phone or car insurance payments. (Arguably this is just good parenting as well, since most kids need to finance the costs of their lifestyles at some point in time).
Cutting your son out of the will is, however, a bigger decision. Especially since you say there’s a substantial inheritance he’d otherwise been entitled to.
This is a fascinating question with many angles.
So let’s unpack them.
The first point of analysis is this, while your son may well be an idiot right now, he is only 22 years old. How many people reading this right now made incredibly stupid decisions when they were 22 years old? Virtually every single one of us, I’d wager. Most of us, thankfully, come to make better decisions as we age, thereby helping to cancel out some of the stupidity of our youthful decision making.
The good news for you: even ANTIFA supporters grow up at some point in time.
It’s likely this is a form of youthful rebellion from your son; he’s rebelling against the wealth and privilege you have provided him by engaging in destructive behavior. In other words, from a psychological perspective he may want you to know about his decision-making because he’s trying to hurt you. You say he was dumb enough to wear that unique sweatshirt. But what if he intentionally chose it in the hopes you might find out about it? You don’t say that he’s made any attempt to deny his behavior. That makes me think he may very well want you to know about it.
If that’s true then by taking him out of the will you might well be fueling his behavior. In other words, how often do teenagers stay in relationships just because their parents disapprove of them? Frequently. We all know a couple that should have never been together, but seemed to use parental criticism of their relationship as fuel; the result: far from breaking them up, that criticism became the glue that held a dysfunctional relationship together.
So my fear here is this: if you make your disinheritance known to him, he may very well take this knowledge to his ANTIFA allies and use this as a badge of honor. They may view your son skeptically — who is this rich kid who claims to be down with the cause? — but the minute he’s disinherited it becomes a legitimizing force that further binds him to his ANTIFA brethren.
The other issue here is this: how stubborn is your son? One of my sons will make bad decisions — and stick to those bad decisions even when he knows they’re wrong — simply because he refuses to acknowledge my wife and I are right. In other words, he doesn’t behave rationally in a conflict or disagreement because of his stubborn nature. He’d rather lose and be wrong than amend his opinion and make the right decision because that would require validating his mom and I. Is your son the same way? If so, your decision to disinherit him may serve to commit him further to the path he’s on today.
Finally, and this is the biggest question of all, I think: to what extent should a potential inheritance be used as a means to encourage favorable behavior? Like many things in life, that depends. For instance, what if you conditioned your son’s inheritance on attaining an advanced graduate degree of his choosing? I think most people wouldn’t view that as a necessarily bad choice since, in general, most of us view attaining higher degrees of education as a benefit. But our view for that conditional behavior might change if, for instance, you specified that your son had to attend medical school and become a pediatrician in order to achieve his inheritance. In other words, the more specific the requirements for his inheritance, the less most of us would feel that is appropriate behavior for a parent. (Obviously we could extend the specifics to a ridiculous degree. An inheritance which only vested if a son or daughter married a Jewish cinematographer from New Mexico who was the third daughter of a third daughter would strike many of us as patently absurd and controlling behavior).
Tying an inheritance to lifestyle choices is permissible, I think, but only to a point.
Here your decision is relatively benign — just don’t be a criminal or a violent supporter of a political organization — and you will inherit substantial sums of money from me. That seems like a lenient and fair standard. But your goal is essentially two-fold here: 1. don’t allow your son to spend your hard earned money on a life philosophy you vehemently oppose and 2. I believe you also hope that receiving knowledge of this disinheritance might cause your son to reconsider his behavior.
You 100% can control the first outcome.
But you 100% cannot control the second outcome. My concern, as illustrated above, is that in notifying your son of his disinheritance you may well encourage him to continue his behavior longer than he otherwise would.
I also think you have to consider your daughter here. What’s her relationship like with her brother? How will it change if she receives all the family’s money on you and your wife’s death? Does she agree with your choice? Or will you also create further dissension in your family with this choice?
Your age also factors in here. Your son is 22. Let’s say you were 34 when he was born and are presently 56. According to mortality tables you’d have at least another 20-25 years to live, potentially many more. Think of all that could change during this time. Your son will go from 22 to 47 over the next 25 years. Sure, he could be a middle-aged ANTIFA activist, but odds are he’s going to get married and have kids. I don’t see a lot of ANTIFA activists running around with strollers.
Having kids and getting married tends to de-radicalize even the most radical among us. And if it’s any consolation to you, maybe your son will have a rebellious son as well. Who knows, maybe he’ll rebel by embracing conservatism and you can give him the inheritance instead.
Finally, it’s important to recognize that according to most mortality tables your wife will outlive you. How committed is she to your opinion? Because the two of you can make the changes to your will, but in almost every jurisdiction your wife will be the beneficiary of your estate. Once you die she can make whatever decisions she’d like with most of your estate. (This obviously leaves out certain technicalities — you could have trusts set up for instance which skip past you and your wife and go directly to your heirs, but I’m talking in generalities here since I don’t know the particulars of your estate.)
When you consider all the angles here, I think it’s fine to change your will, but I’d counsel against notifying your son of the changes. Because I think it may lead to him pledging even more fealty to a cause you abhor rather than leading him to abandon it. He may well view your behavior as attempting to buy his loyalty, which is exactly what he’d expect from a rich plutocrat like you and your friends. Better to simply tell him you think he’s an idiot for engaging in the behavior he is and make your own private decisions as you see fit.
That way you get the satisfaction of ensuring — at least during your life — that your money isn’t going to support violent causes you abhor, but you don’t have to worry about your decision strengthening his resolve and providing further distance between you.
Good luck.
“About 4 years ago I became involved in a relationship with a lady who had been a friend for several years. At that time, I was single and she was exiting a bad marriage. I had also been friends with her entire family since moving to the city I now live. I’m still close with her family.
We were together about a year. She needed help financially, and I had the means to help. It was clear from the beginning that it was a loan. I told her there would be no interest, and she always responded when asking for help with “I’ll pay you back if it’s the last thing I ever do.” 
Cut to the chase, I loaned her $125K. Some were medical/dental expenses, a lot for her daughter’s wedding, some to get another daughter started in college. Then I started catching her in lies, and ended things.
We have both moved on. I remarried a little over a year ago. She remarried a few months ago. 
Question is, I don’t want to ruin my relationship with her parents. To my knowledge they don’t know about the money she owes me, but probably assume she had help and it was me. 
Since news came out I was getting married, she’s never brought up repayment again. And I’ve kept it private. What’s the fair play here?
Yeah, I know I got played. I’m not looking for revenge. Just need an independent perspective on what is fair. It’s not something I need to discuss with friends.”
The fair play here is she should repay you all the money because she made a commitment that she would repay the money you loaned her if it was the last thing she ever did. That money, as you say, wasn’t a gift. It was a loan and she promised she’d repay you, meaning she knew it wasn’t a gift.
But I think you know she’s unlikely to ever repay you if you say or do nothing regarding this debt.
So that leaves you with two options if you want your money back: 1. you can hound her demanding repayment and making everyone in her life aware of the money you gave her that she hasn’t repaid or 2. you can pursue legal action seeking repayment.
Let’s start with the latter. What evidence do you have that this was a loan? You say there was no interest rate on your loan. I’m also guessing there was no signed contract on the loan. What’s more, you paid for college tuition for her daughters, which means the adult daughters received the direct benefit, not her. Were you payments to her in cash? In check? You’re setting yourself up for a substantial legal battle here to try and prove you gave her a loan and that these were not gifts given in the context of a relationship.
What’s more, both of you are now in new marriages. This threatens to drag your new spouses into this legal battle as well. And, again, I’m not sure how successful your legal battle would ultimately be.
That leaves you with option one, hound her for repayment.
So ultimately your decision comes down to this: how much do you need the money? You gave a woman you were dating $125k, which is a lot of money to most people, but if you’re worth several million dollars it may not be money that you need. It sounds like based on your email this is more about pride than finances to you.
That’s a lot of money to give a woman in a year, but the positive is it’s probably a lot less than it would have cost you if you’d ended up married to her.
In the end, I don’t think you’re in the wrong by approaching her and letting her know that you’d like for her to repay the money you loaned her as she promised she’d do. I don’t even think it’s wrong of you to say that you’re willing to set up a ten year payment play where she gives you $12,500 a year for ten straight years. That’s a little over a thousand dollars a month at zero interest.
You know what kind of financial situation she’s in now. Is that in any way possible?
As for her parents, I don’t see why this harms your relationship with them. You loaned their daughter money when she needed it. There’s nothing wrong with requesting the money back for that loan. Especially where, as here, there’s no interest rate attached to your loan and you are no longer together.
If you want your money back, I think you have to go to her directly and seek repayment. If she refuses, I’m not sure you have a ton of great options.

“Please settle this debate between my wife and me. Which scenario is worse: a spouse who cheats or a spouse who secretly liquidates the retirement account? She says cheating. I go with retirement. My logic is that both actions qualify as a betrayal and would absolutely result in me filing for divorce. With that in mind, I’d way rather move on knowing some other dude nailed my wife than have $0 in the bank. (For purposes of the debate, spending the retirement would be for something completely selfish instead of being the victim of a con artist or substance abuse problem).”

I think most men would think secretly liquidating the retirement account is worse because it’s a tangible financial act of betrayal.

I think most women would think the cheating is worse because it’s a tangible emotional act of betrayal.

There are obviously members of both sexes who would not align with the majority opinion, but I suspect that’s the way most would see it.

As a married man, you probably already know this, but the odds of you convincing your wife she’s wrong are, conservatively, 0%.

“So January 18th or 19th I lost the biggest bet of my life. $250k+. Don’t they say that is the average cost of a child? Yep. My wife is pregnant… with our 3rd. 

So here’s the issue: I have never really wanted a 3rd child. My wife has wanted another ever since the 3rd trimester of her 2nd pregnancy. Going back to our premarital counseling, we’ve always been in agreement on 2 kids. That was the deal…until she changed her mind. 

Don’t get me wrong, I love my 2 girls (5yo and 2yo). If money and time were no issue, I’d have 10 kids. We are a late 30s couple living in a major southern city making a good income. We both work. I’m in a business where I’m basically self-employed and my income is solely tied to my production, which takes time to continue to build. My wife doesn’t want to stay home full-time, but would like to have the option to go part-time. We have other family goals and aspirations as well. All of these are dependent upon me growing my business. Herein lies a major problem. Ever since we’ve had kids my wife depends on me for so much at home that it gets in the way of me growing my business. My worst years of production have been during the birth of our children because the demands are so big at home. For instance, I do 95% of the meal prep, grocery shopping, cooking, and cleanup. If I work late, she refuses to even try to cook because she says it’s not possible to cook and also get the girls fed, bathed, and in bed. The business which will ultimately allow us to achieve our family (long term) goals gets sabotaged because of the day-to-day pressures, but when we don’t hit certain financial goals (car upgrade, home addition, vacations, etc.) it’s on me for not providing. 

All of the pressure provided by 2 kids is enough for me. There is already enough stress and anxiety around our house. We’ve had behavior problems with the 5yo, potty training issues with the 2yo, etc. As it is currently, it’s about all I can handle between work and home. I’m fearful of adding more to our plate. 

I’ve been really excited about the next phase of our life (no…diapers, potty training, bottles, etc.), but more importantly being able to take an entire day to spend with my girls and not having to worry about nap time. I was also excited about becoming empty nesters in our mid 50s so we could be very active with our children when they are in college and beyond. 

I know many marriages and families are built to handle multiple kids, I’m just not sure mine is.

The number of different emotions I’ve felt since learning this is crazy: stress, anger, resentment, depression, apathy, etc. I’m afraid my lack of excitement and emotions will also come out when we start telling people in a couple of months. I know I’ll love the child like my others when he/she is here (high odds it’s another girl), but am I an a-hole for feeling like this? Do I have a right to be upset that she reneged on her commitment to 2 kids? Or, do I just need to suck it up and DBAP?”

First, if you 100% didn’t want any more kids, you could have gone and gotten a vasectomy. For any dads out there reading this right now who want to ensure they never have another kid, go get that done.


If you don’t do that then there’s always the possibility, no matter how safe you are, that you have another kid.

Now let’s dive into your particular concerns about baby number three.

Your concerns are shared by any number of working parents across the country. The truth of the matter is this: it’s hard to be incredibly successful at work in a competitive job environment and also be a great parent. It just is, that’s true whether you are a man or a woman in 21st century America.

That’s made even more challenging for you because, as you state in your email, your wife expects you to pick up much of the slack when it comes to parenting a newborn (and taking care of the other kids while she parents a newborn.)

We have three kids and I think I’m a very active dad, but I also work a ton. If we’d had no kids it’s probably true, however, that I would have been even more successful at my jobs because all I would have had to focus on is my work. (If you look around the sports media universe at people with jobs like mine it’s interesting how many of the most successful people in our space are either single or don’t have any children: Skip Bayless, Dan LeBatard, Bomani Jones, and Pablo Torre for instance, are all my daily male TV contemporaries who don’t have children and/or are single. Women like Michelle Beadle, Erin Andrews, Jemele Hill, and Charissa Thompson don’t have any children either. Now maybe some of these guys and girls will one day have children and/or get married, but in the meantime that frees them up to focus on their careers and still have time left over for themselves.)

The point is that kids make it harder to devote as much time as you might prefer to your job, no matter what that job is.

Here, specifically, you’re pointing out that your income suffers — since you’re self-employed — when children are born. That makes total sense to me as well.

In reading your email you don’t need to be asking me for advice, you need to have this exact conversation with your wife. You need to sit down with her and lay out the case you made in this email — how your income takes a hit every time you add a child to the family — and you guys need to prepare for baby three in advance, in ways you didn’t for babies one and two.

In particular, your spending needs to be dialed back in a big way — preferably in advance of this baby being born — and she needs to understand the financial impact that comes from a third child. That is, she can’t be griping about needing a new car when you’re working as hard as you can to take care of your work responsibilities and the added responsibilities of a new baby.

Anyone who has had a newborn in the household knows that it’s impossible to be as effective and efficient at work when a baby isn’t sleeping at home. The entire family lifestyle is a zoo. The more kids you add the more of a zoo your life becomes.

Having said all of this, you will survive having a third kid and my expectation is you will quickly come to see it as impossible to imagine not having that third kid in your family.

I say this because I have three kids myself.

My youngest is five years old now and every couple of months I say to my wife — who was on the fence about having a third child — can you imagine if we didn’t have this guy? I honestly can’t remotely imagine our lives without him. I’d wager a ton of money that the same will eventually be true for you as well.

But none of that changes the difficulties inherent in your work-life balance in the short term. Rather than share those challenges with a guy you don’t know on the Internet, you need to share them with your wife.

Right now.

Long before the chaos that arrives with a newborn in the household. Once that baby is here you will all be sleep-deprived and incapable of dealing with stress in anywhere near as rational of a manner.

Good luck with that conversation.

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Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.