The Ben Mulroney Show - The Dilemma Panel - Should you ever lend Money to family?

Episode Date: March 12, 2025

Guests and Topics on Today's Show Guest: Jennifer Hollett, executive director of The Walrus Guest: Alex Pierson, Host of The Alex Pierson Show on AM 640 If you enjoyed the podcast, tell a friend! For more of the Ben Mulroney Show, subscribe to the podcast! https://globalnews.ca/national/program/the-ben-mulroney-show Follow Ben on Twitter/X at https://x.com/BenMulroney Enjoy Learn more about your ad choices. Visit megaphone.fm/adchoices

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stands for Total Fund Savings Adventure, maybe reach out to TD Direct Investing. Welcome back to the Ben Mulrooney show. And now it's time to shake off the news of the day. It's going to come back. It's going to hit us again pretty hard, probably in the face. But for the next couple of segments,

we want the cleansing palette. We want to cleanse the palette with a nice sharp tonic It's gonna come back, it's gonna hit us again pretty hard, probably in the face. But for the next couple of segments, we want the cleansing palette, we wanna cleanse the palette with a nice sharp tonic that we like to call the Dilemma Panel. This is when we ask you, our listeners, to send us your everyday dilemmas, and then we as a group try to solve them. We ultimately fail, but we have fun doing so.

And so let's welcome to the Dilemma Panel, Jen Hollett, Executive Director of The Walrus and my very first colleague in television. Jen, welcome, thanks so much for joining us again. Great to be back. So I guess this is less news, more personal drama. Correct, yes. I mean, the politics can be personal,

but I think we're gonna be politics free for the next couple of segments. And which I don't know how my other guest is gonna deal with that, because every time we talk, we talk politics. Alex Pearson, the host of the Alex Pearson show on AM 640. Alex, thank you so much for being here. My dilemma is there's not enough time to get all the news in, but I beat you on the working with Jen Hollett. Oh really? Oh yeah, because when she was back in Much Music and I was

over at the other newsroom, she'd be in the makeup room where we'd all collide. Really? And talk for like 30 seconds. Oh, no, but if she was at MuchMusic, that was after I worked with her. Oh, yes, we worked together in 2000, 2001. Well, around the same time. What does that tell us? I know. Well, I'll tell you this. Alex and Ben, you know that we actually develop expertise on giving advice in the makeup room when you work in TV. So we do have that background. Solicited or unsolicited, you would get our advice. Okay, let's jump right in to the very first dilemma.

Hey, Ben's panel, I've been working at my current job for a while now and recently I've become increasingly uncomfortable with a situation involving one of my coworkers and our boss. There seems to be an inappropriate relationship forming between them and it's hard not to to notice they're constantly spending time together outside of work hours and have this unspoken dynamic that feels off. What's even more concerning is this co workers getting a lot of favorable treatment,

preferential shifts, assignments that seem to be outside their usual job scope, and even praise and meetings that feels unwarranted. I'm not sure how to approach this. I don't want to make accusations without being sure, but it's hard to ignore what's going on. Should I speak up or is this something I should just let go? And if I do decide to bring it up, who do I even talk to about this? Oh, that's a really good question.

I'm gonna put this, we'll invite Jen to answer first. Jen, what are your thoughts? Eee, this is a tough one. And actually a friend of mine navigated this at her job where she saw her boss tickle a coworker and knew, okay, this isn't normal. That's really flirting and not appropriate in the workplace. And so everyone was gossiping about it, but they weren't sure how to address it.

Now we don't know if this is like a big business or a small business. If it is a formal workplace, I would bring it up to human resources once there's more concrete evidence, which they'll probably be able to gather. But if it's smaller, like maybe start by asking another colleague if they've noticed this.

Yeah, I was thinking that as well. I thought maybe there might be safety in numbers and then you go to the boss as a group, but I see Alex is shaking her head. Stay out of it. Mind your own business. And I get it, but what if it is actually having a negative impact on your, not your ability to do your work,

you should be able to put your blinders on and do your work, but if the opportunities aren't coming your way, you are working your best, you are showing up, you are hitting your KPIs and all of that stuff. And yet despite that, this person is getting preferential treatment. At that point, I think it's incumbent upon you to say something.

It's gonna create a toxic work environment. There's a way to do it though, right? Cause a squeaky wheel doesn't always get the grease. And so I would say document it quietly, build your case. If you truly think you're being overlooked for opportunity because people are playing footsies, then you take it to HR. But the gossip, if you end up contributing through gossip

and doing the old, oh, did you hear? You're gonna end your career. You're gonna make it worse. Yeah, I agree. So to Sweeney, what I think we're saying is approach this analytically, do not approach it emotionally, and make sure that whatever you do, you document it so it's backed up with facts and you're insulated.

And then, you know, and maybe talk to a lawyer just in case. I mean, or don't listen to people in our business, right? Because when's the amount of time? All right, let's move on to the second dilemma. Hey, Ben, I'm in a bit of a tricky situation with a family member who constantly asks to borrow money. At first, I didn't mind helping them out

when they were in a tight spot, but now it feels like it's becoming a pattern. They always promise to pay me back by a certain time, and even though they do eventually pay me back, it's never when we agreed. I'm always having to chase them down, send reminders, and follow up repeatedly. I want to help, but I also feel like

I'm being taken for granted. I'm not taken for granted. I'm not sure how to set better boundaries without causing tension in the family. I don't wanna be the bad guy, but I also don't wanna feel like I'm being strung along every time. And that's from Sam.

I'll go first, Sam, like you're not the one causing trouble in your family. It's the person asking for the money. And in my opinion, Sam, I think you've gotta recognize that in this power dynamic, you have the power, you have the money, and they want your money. And in my opinion, Sam, I think you've got to recognize that in this power dynamic, you have the power, you have the money, and they want your money. Therefore, you can set the terms and you can start putting onerous terms on it. Look, if you don't pay me back by a certain date, here's what's going to be expected. Have them sign a document. Doesn't even have to be legally

binding or do it in front of family members. So you have witnesses who can say, no, I remember you promised to pay Sam back by a certain date and you didn't do it. And then you can hash it out at the dining room table. Jen, what do you think? Well, I remember once reading in the device column, because this comes up quite a bit, that lending money to a friend or family, it's a gift.

Don't expect to see it back. And I hear, Ben, your legal training coming through, because unless paperwork or a lawyer is involved, it's someone close to you. And it ultimately is something you gave them, you choose to give them, and it will be hard to get back. But I don't think, Alex, every family is different. Some families you can lend money

and others you just give. I don't think that just because it's a family member, it's an automatic gift. No, absolutely not. And look, the way I've always treated it, I go in with the expectation that I'm not gonna be paid back, right? So if you're gonna lend the money,

be willing to lose that money, otherwise you're gonna lose the friendship. Yeah, but this is a- And family, right? But then it's family even work. Like, let them in. You can't keep coming to money, but you have to say, happy to help you, here are the rules. But also, how important is family? You've

got to be able to say, I don't need it. But we're going to go through a lot of this in the next couple of years. This is happening all over the place. Oh yeah, the bank of mom and dad is an expression I've only really started hearing recently. With tariffs and businesses closing and layoffs, you better believe these conversations are being had around the table where people are saying, can I have some money? Yeah.

Accept it, okay? But on your rules, don't expect it back. Jen, a situation is only as complicated as you let it be. In other words, it can be the most convoluted complex and be the biggest amount of money ever. So long as you lay out a game plan, so long as you have a roadmap on repayment, doesn't matter how complex it will be simpler with that documentation.

And even say out loud, this could get complicated. I'm going to be very clear, I'm going to follow up if you're not comfortable with dealing it like this. And maybe this isn't the best ask. Yeah, I mean, just accepting that it's going to be awkward. But Alex, I totally agree. Tough times ahead. And you do tend to go to your family and friends first before the bank or a stranger. I mean, you should be turning to your community for support. Yeah. And look, but as I read this dilemma again, it does feel to me like this, this person feels responsibility to the

family. They want to, they want to help. They, they, they allow leniency when the payback doesn't happen at the right time, and then they take responsibility for quote unquote causing tension in the family. No, exactly. That's why I'm trying to look Sam in the eye and say, you're in charge here. You're part of the problem. Well, no, not part of the problem.

But you're in need of. No, but you're in control. Yes, right. Right, it becomes a problem if you don't assert that control. Right. Like they want your money. You have the money to lend don't assert that control. Right. They want your money, you have the money to lend, set the ground rules.

Business is business. Business is business. If you want to bring business into the family, we're going to treat it like a business. But you, Sam, have to be more assertive in this because clearly your family member has sensed this kindness that they are interpreting as weakness and they have been taking advantage of you. Also, what's going on? Ask the bigger question. Hey, there's a pattern here.

What's going on? Yeah. But if you're gambling and coming or there's an addiction issue, that thing will bankrupt a whole family. So what's the issue? Is it a business thing? Can you save the business?

What's the plan? Or are you out doing nefarious activities? Now we only have a minute left before we go to break. So I don't want to start another dilemma. Instead, I'm gonna ask Jen. Jen, how are you out doing nefarious activities? Now we only have a minute left before we go to break. So I don't want to start another dilemma. Instead, I'm going to ask Jen, Jen, how are you doing? I'm doing well. And I think what I really like about this segment and thanks so much for the invite

is we often aren't speaking directly about the things that are consuming us. And I always try to do that in my life, whether it's about news or politics or checking in with folks. And I think often we're spending so much time at home or behind screens that we've lost the muscle to have these conversations.

So even just asking, how are you doing? I think can prove these types of dilemmas. Well, and also I find that you get to know people a heck of a lot better when you don't just speak to them about the same things every single day. I get to know more about Alex. I get to know more about you when I hear how your brains work. But when I hear how your brains work on things like this,

it makes it so that I understand you guys a little more and get to know you a little more deeply. All right, more of the dilemma when we continue, including are stepfathers allowed to harshly discipline kids that aren't theirs? That's next on the Ben Mulroney Show. Welcome back to the Ben Mulroney Show and welcome back to our Dilemma panel

where me and my fun guests, very exciting, interesting guests, try to solve your everyday dilemmas. Let's welcome back Jen Hollid and Alex Pearson. Guys, thank you so much for sticking around. Our pleasure. Happy to be here. All right, time for another Dilemma. Hey there, I'm having a hard time

with my child's decision about their university major. They've chosen a field that doesn't seem to have strong job prospects or align with their strengths. As a parent, I wanna be supportive, but I'm really concerned about their future. They're excited about it now, but I worry they'll regret this choice

once they're out of school and facing the job market. I've tried having conversations with them about exploring other options, but they're very set on this major and aren't open to suggestions. I don't wanna push them too hard, but I also want them to make a decision they won't later regret. How can I best support them while also ensuring they're setting themselves up for success in the long run? Alex, as you sit here, your

son is next to us. And so what would happen if your son came to you and said, I want to study? Look, I want to pick one out of thin air, but something that you know, is not reflective of what the market is going to want in 10, 15 years. Then he'll pay for it himself. Yeah. Right. That's how that goes. That's the conversation. We've we've had these conversations or we're having more than I want him to get a trade and he's going to get one just to have it because you can never go wrong being able to do jobs when you lose another one and you can pick up stuff. Right. That's okay. He can go to do what he wants, but if it's not going to lead to a job, then he can pay for it. We've got education money set aside, but that is for a job to be trained in

life. If you want to go off and do 30 years of philosophies and all these sites, there's value to it, but not value to get a job. So you pay for that on your own. Jen, your thoughts? Friends of mine adopted their first son. And if you know anyone who's been on adoption journey, courses are required as part of the process. And they had to do this exercise where all the soon to be parents were asked to write down your dreams for your adopted child. And then they said, now rip them up.

These are your dreams, not your kids' dreams. And I wish everyone could take this course because I think so often parents have ideas of who their children like should be or what their interests are. And it doesn't always line up. I also have no problems with kids paying for, well, I have no problem with that.

And I contributed to paying all types of different bills growing up. I think that's a great way to teach responsibility. Yeah. And look, I think there's, I think a lot of things can be true at the same time. I think we want to support our kids and we want them to dream big. But you also have to realize that reality is going to smack you in the face one day. And reality trumps dream when it comes to, you know, paying your bills and responsibilities in life.

And we all have dreams that go unrealized. We all have dreams that become other dreams. And we are the parents for a reason. And so I have my own personal experience. Like I was a history and a political science major. And then I went to law school and law school was not, I realized I didn't want to pursue law, but I was, and I really hated being there.

My parents forced me to go and I didn't want to go, but I'm so glad they forced me to go because it opened up opportunities for me and it actually changed the way my brain worked. So I think to this Melinda person who sent us this dilemma, and I thank you for sending it, I really do think it depends on how you've been raising your child.

You may have missed the boat on having these important conversations earlier on. I don't know what kind of, it sounds like you care and love your child, and that's great, but you may have missed the opportunity to remind them that these are discussions, there are practical aspects of an education

that go beyond I'm following my dreams. And if that's the case, you know, it's a sink or swim sort of situation like, okay, you're gonna become a gender studies major. Good luck when all the jobs are in IT. Right, see, my son, who can't hear me right now because he's got headphones on, following me around on March break,

he keeps saying, well, I wanna be a YouTuber, to which I'm always responding like hell. That's not gonna happen. But I'm trying to say, look, if you want to be one, you have to understand how much work it is. To be a successful person, to do that kind of stuff, you have to really grind, you've got to understand the business behind it. So you do need to get some skills. Having

said that, I'm like, if it were so easy, I'd have been doing it. But I've been grinding it out in hard news for the last 25 years. But get the expectations. What do you want from this? Where do you think you're going to go? I think a lot of younger people think things might be easier than they are. At least you say it's not as easy as you think. I'm 49, I can promise you. Trust me. It's a lot harder today than it was a few years ago. I go do it now.

Okay, let's move on to, I think probably our last dilemma. I've been a stepdad for just over eight years now to two wonderful children aged 14 and 12. My relationship with my stepchildren has been positive. I've always tried to be a supportive father figure, but now that they're hitting their teenage years, things are starting to change. They're beginning to talk back, challenge rules,

and push boundaries in ways they didn't before. I feel like the respect we had for each other is slipping and I'm not sure how to handle it. I know this is a normal part of adolescence, but I'm feeling a bit stuck. I don't want to come across as overly strict or authoritarian, but I also want to maintain respect in our home.

Plus, my wife always told me it's not my place to dole out harsh punishment. I'm not sure how to navigate this shift in the relationship. How do I balance being a stepdad who is both a friend and an authority figure during these challenging years? Kirk is in a little bit of a pickle. Alex, how would you solve this dilemma? I had such an amazing stepfather.

I was so, so lucky to have an amazing stepfather who's no longer with us, who I would always call when I got into trouble, like when the cops caught me with beer. So I would call my great stepfather, Ted. We had a wonderful relationship. But yeah, absolutely. He's paying my bills and raising me with my mom. He has a say. So I think this guy absolutely has a say.

I don't agree with a wife. You've brought this person into your life. If he's good enough to pay the bills and raise this child, then he has a say in here's what we've got to do. Having said that, it's a balancing act, right? My stepfather was a friend to me, but he was also kind of a father figure in the sense that there was a balance. And Jen, Kirk hasn't given us the whole picture.

We don't know where the actual father is in this dynamic. That being said, I agree with Alex, like this is, this is a home that they've built together. He is, whether you like it or not, he is an authority figure in his own home that he is paying for. And I wouldn't accept anybody talking back to me in my own home, especially when I know how hard it is to keep a roof over everybody's head. And the fact that the wife has sort of tied one hand behind his back, limiting his ability to be who he needs to be in his own eyes, right? I think is a little bit of a problem. It depends on the details and the setup. So I have a mom and I have a stepmom. I was a teen and I remember as a teen, it was really hard for me to have two moms because my mom was raising us as a single mom. And I was seeing my stepmom just a

few times a year with my dad. So I would say something for Kirk to consider is like his role as a parent in the setup. I would argue might not be a friend, but a role model and a partner. And I think by being a partner to the mom, then you are actually the person that the kid may call like Alex did. And that's a very special valuable role. And you know, I've often- A lot less grief. I've often said, and it applies to parents

more than step-parents. I can't speak to step-parenting, but I always tell my kids, I say, I don't wanna be your friend. Friends are a dime a dozen. You could throw a stone and hit a friend. I am the only father you will ever have. I am as unique as a snowflake.

This is the most special relationship that you will have next to the relationship with your mother. Do not diminish this relationship by saying that we're friends. And far too many parents sort of bootstrap themselves, or hamstring themselves rather, by saying, oh, I'm not just their parent, I'm their friend. You are diluting your relationship by saying that.

And I think ultimately- And they'll appreciate it though later. Possibly putting roadblocks in front of you later. Jen, thoughts on that? Yeah, I would agree. I think it's really tough to be around teenagers. I say this as a cool auntie because they're full of hormones, they're testing limits,

they're getting their Alex, thanks for like just being true about how it is to be a teen. And it is really tough and parenting styles and trends have changed. I've become a back of my day person and as someone without kids, of course, you know, I'm an expert on parenting. But I actually think to have these conversations

and to really define roles, I think there is a really special and valuable role for step-parents, but it is different than being the father if the father's in the mix. Yeah, so back to Kirk's actual problem. I mean, maybe a family meeting, maybe a sit down family meeting. Oh, I like that. And they sit down and Kirk says,

listen, you all know your roles. They were defined by biology. Mine is defined by society. And therefore, as a mini society in this house, we need to hash this out. But he has to talk to the wife too. You should have a private conversation with her. Like I'm either in this or not.

And if I'm a part-time. A pre-meeting. Yeah, a pre-meeting. A pre-meeting. You either on the same slide or not. Well, you have to be, regardless of whether it's birth parents or step parents, the authority figures have to be singing

from the same hymn book. United we stand. The kids are very sneaky and they know how to find the seams and use those seams as leverage. And so don't do your kids' job for them. Their job is to figure out how to sneak around you. Your job is to create a united front. But anyway, I wish we had time for more dilemmas. The good news is the Dilemma Panel will be coming back again next week.

But to Alex and to Jen, I say thank you and keep those dilemmas calling. Have a great week guys.