The Long Strange Trip Episode 33: Why Your Kids Stop Listening to Your Wisdom | Steve Legler

About the Episode:

We all like to think we're passing wisdom on to the next generation.

But there's a problem.

People don't usually want to be lectured by the people who raised them.

I've learned that the hard way.

We can have decades of experience. We've made mistakes. We've built businesses. We've raised families. We've learned things the hard way.

And then we try to tell our kids what we've learned.

Sometimes they listen.

Sometimes they don't.

And sometimes the harder we push, the less they want to hear.

I sat down on The Long Strange Trip with Steve Legler, a family facilitator who works with wealthy families, to talk about something that sounds simple but is anything but: how do we actually build better relationships across generations?

Wisdom Is Better Pulled Than Pushed

One of the ideas Steve shared really stuck with me.

Wisdom is better pulled than pushed.

That makes a lot of sense.

You can't force someone to learn something just because you learned it the hard way.

And the older I get, the more I think that's true.

Sometimes the best thing we can do is create enough trust that someone actually wants to ask us what we think.

That's very different from sitting them down and saying, "Let me tell you what you're doing wrong."

I've been guilty of the second one.

Your Kids Aren't Your Employees

This one hit home.

Successful business owners are used to giving direction. We solve problems. We make decisions. We tell people what needs to happen next.

That can work pretty well in a business.

It doesn't necessarily work very well with your kids.

Steve and I talked about how easy it is for parents to unintentionally treat their children like employees.

You see a problem.

You have a solution.

You give them the solution.

And then you wonder why they aren't grateful for your advice.

Maybe the problem isn't that they don't value what we know.

Maybe they don't want to be managed by us.

There's a difference.

What Happens When We Admit We're Wrong?

I think vulnerability gets harder as we get older.

We've spent a lifetime building an identity around being competent. People come to us because we know things. We've made decisions. We've solved problems.

So admitting, "I screwed that up," can be pretty uncomfortable.

But Steve and I talked about how powerful that can be inside a family.

Sometimes saying, "I was wrong," does more to repair a relationship than ten pieces of good advice ever could.

It changes the conversation.

It makes the other person safer.

And maybe it gives them permission to be honest with us, too.

Family Conflict Doesn't Get Fixed With One Conversation

We also talked about sibling conflict, forgiveness, and rebuilding trust.

I've come to believe that trust isn't rebuilt with one big conversation.

It's rebuilt through small things.

Showing up.

Listening.

Doing what you said you were going to do.

Admitting when you got something wrong.

Giving someone a little more room than you might normally give them.

Those things don't feel particularly dramatic.

But over time, they add up.

And the same is true of forgiveness.

Sometimes we want forgiveness to mean that everything is suddenly okay.

It doesn't.

It may simply mean we're willing to stop carrying the same argument forward.

Family Harmony Isn't a Finish Line

I liked something about Steve's approach because he doesn't make family relationships sound like a problem you solve once and then put away.

They're not.

Families change.

People change.

Our relationships change.

The things that worked when our kids were young may not work when they're adults. The way we communicate with a sibling at 30 may not work at 60.

So maybe family harmony isn't something we achieve.

Maybe it's something we keep working on.

That takes humility.

It takes curiosity.

And sometimes it takes being willing to change our own behavior instead of waiting for everyone else to change theirs.

I'm not coming at this as an expert. I'm a fellow traveler trying to figure this stuff out in real time.

And maybe that's the uncomfortable question Steve and I were really exploring:

Are we willing to change ourselves if it means having a better relationship with the people we love?

Because we can spend a lifetime trying to change other people.

I'm starting to think the more interesting question is what happens when we change ourselves first.

Transcription:

Intro

Welcome to The Long Strange Trip. I'm Josh, the host of the show. We're going to dig into six areas together, finding real work-life integration instead of that brutal 95/5 split too many business owners live with. We're going to approach retirement as an actual reinvention rather than just stopping work, and we're facing death honestly and avoiding PTSD around death.

We're also building resilience when life throws us curve balls, we're sharing wisdom across generations, and finally, we're understanding the patterns that show up in all our transitions. I'm not coming at this as an expert. I'm a fellow traveler figuring this stuff out in real time, especially now as I navigate my own dual cancer diagnosis at 73.

Welcome to The Long Strange Trip. I'm glad you're here.

Josh

Hey, how are you today? This is Josh Patrick. I'm with an old friend, Steve Legler, who I've known for I don't know how many years through an organization called Purposeful Planning Institute. And I found Steve one of the more erudite and smart people there, he is going to help us understand you, not gain wisdom, but how you impart wisdom to others.

He works with wealthy families and, um, there's a lot of facilitation there. So instead of me talking about it, why don't we have Steve talk about it? So let's bring him on. Hey, Steve. How are you today?

Steve 01:46

Uh, very well, thanks Josh. Uh, I, I don't know that I've been described as erudite very often, but I'll take it. It's, that's one of those 50 cent words

Josh 01:58

It's a word I really like, although my favorite word is sesquipedalian, means user of large words.

Steve 02:07

Okay. Okay, there's a meta thing going on with that one

Josh 02:11

Yeah, so any rate, that's been my, uh, sometimes I like ridiculous words. But any rate, let's talk about wisdom. I mean, you deal with, with wealthy families that have really big problems with how to impart the wisdom from the senior generation to the junior generation and have them listen. So first of all, is the problem with doing that?

Steve 02:41

So, thir-- everyone always asks, "At what age do you start?" You know, when do you start to tell the children that we're a wealthy family, and when do you... And I always say earlier is better, and going slowly and using the dimmer switch is better than having them in the dark and then flipping the lights on and blinding them, right?

So, so going slow and sharing over time in digestible bits is very important. The issue that, that sometimes occurs is somewhere in the teens to the early twenties, um, there's almost this natural, "Whatever my parents are saying is stupid, and I don't wanna hear about it." And you've gotta be able to get through that and onto the other side where they're willing to come back and realize that, you know, Mom and Dad are actually...

They have some interesting things to share with me. But the hardest thing for some parents is they feel like they need to push the wisdom down, and the wisdom works better when it's pulled down. So in pushing on us

Josh 04:01

experience. Go ahead, sorry

Steve 04:04

So it's the pushing on the string problem, and people think, "Well, I'm pushing and they're not taking it, so I better push harder." And the other, the, the real answer is, "I better stop pushing, and I better try and create the conditions where they will want to pull it." And that comes in, in meeting them where they are and learning to listen to them and not have the discussions be a one-way street.

Because for young people to be lectured by their parents gets old real quick, especially when sometimes the, the parents are just a little bit judgmental about things like work ethic and things like that. Um, so many parents end up turning off their kids from what they have to say, and it's, it's hard to sorta realize that, that laying off is better than pushing harder.

Josh 05:04

So one of the areas that, you know, one of my six areas here I talk about is how to run a business without treating your children like employees. A- and I'm going to bet that many wealthy families are led by a patriarch most of the time, sometimes a matriarch, has built a very, very successful business, probably was really involved in the business when the kids were young, and the kids didn't get much of mom and dad while they were building that, and the resentment stays way past 23. Stays with them their whole life. How do you deal with that?

Steve 05:48

So the, the hardest people to deal with are those entrepreneurs to get them to change their perspective of what they're doing because what has been successful for them for decades usually at work has worked quite well with employees, and the things that work with employees don't necessarily work with your family members, right?

So getting them to want to listen to what you have to say without you acting like, "I am the expert, I know this, you don't know it, so just listen to me." Um, there's so much more in the delivery of it than... It's, it's not what you say, it's how you say it, it's when you say it. I saw something the other day about, about feedback and, and feedback is not what you say, it's when you say it, how you say it, where you say it.

There's all the little details of how you go about transmitting this wisdom that you have that you want others to pick up. But acting like, "I am the smartest and you are lucky to have me to learn from," is not necessarily conducive to having that go well. So having the parents actually... This is one of the things, um When there's been a successful business, it's rarely been a, you know, a straight shot from zero to millions, right?

There are always hiccups along the way, and one of the things I am often telling to these people is, "Can you share some of the mistakes you made? Can you share some of the things, some of the challenges you had to overcome?" Because I don't think your kids recognize that, and they have a tendency...

Sometimes the problem is the parent has been so successful that the, that the offspring are looking and going, "Oh my God, I'm, I'm living in the shadow of a giant. I can never live up to that." And that creates its own challenges as well. And so having the parent maybe have a little humility and admit that they're imperfect, show that they have things that they can learn from their kids as well, which technology kind of helps with that often enough that like, you know, my, my kids are helping me with stuff on my phone all the time, and I t- I could just look like some, "Oh, okay, Boomer, you don't get it.

I'll fix it for you." But at least there's a little bit more of, of an adult-to-adult re- relationship, and that's the, the issue. I sa- I read something just the other day about parenting, and the guy who wrote it, Mike McRan, and he wrote, " An eight-year-old always needs parenting, an 18-year-old sometimes needs parenting, and a 28-year-old should not be parented."

And if you take a certain definition of parenting being, you know, hands-on, I agree with that. And so somewhere I have clients where the kids are 38 and 48, where they're still... the parents are still trying to parent them. And, and

Josh 09:32

Yes

Steve 09:34

that, that rarely works well. The later, the later, the later you wait to stop the parenting part, the harder it's gonna be

Josh 09:44

So what do people do when they're 50 or 60 or 70 they finally realize that they've blown it with their kids, and their kids really don't wanna have a whole lot to do with them?

Steve 09:58

That's, that's hard, and it's like that best time to plant a tree thing. The best time was 20 years ago, but the next best time is today or tomorrow. And, um, I think the big mea culpa, uh, uh, humble, honest, I'm sorry, I screwed up. I know I did a lot of things. I did them for reasons that I thought were right at the time, and I'm realizing now that the way I went about it had a lot of shortcomings.

I'd like to try again. I hope you'll let me try again. Um, I don't know that all parents are able to s- to actually say those words and say them in a way that's believable. But if somebody said, "I really wanna do this. What do you think I should do?" Uh, that would be probably the first thing I would say. A- and then don't expect that you saying that one time will flip the switch, and they'll come running back.

You, you have to demonstrate that probably on a number of occasions or repeat it and find ways to demonstrate it, to build up the goodwill, to put back some of those deposits in your goodwill account with your kids that, that maybe you depleted over the years with treating them in a way that, in retrospect, you realize you were probably harder on them than you really wanted to be

Josh 11:24

Or needed to be.

Steve 11:26

or needed to be.

Josh 11:28

Yeah, which

Steve 11:30

Yeah. And they're not the same

Josh 11:33

No, they're not. I, I'm guilty of that, so I, I know that, that plan- that world really well. it's a struggle I'm having with, you know, my kids, is that, okay, we have a relationship, it's superficial. They never really wanna get into anything deep. And breaking through that has been an incredible challenge. Um, so it's, you know, it, it's something I think that you work on for years, and years, and years, and years. you make a little bit of progress, you slip back two s- so it's sort of like one step forward, two steps backwards, three steps forward, one step backwards. And as long as you're going up to the right, you're probably gonna be in a good place. Hopefully you don't die before you finish

Steve 12:21

And, and, and you really have to understand as you start that it won't be a straight progression, and that you're gonna have... You, you, you need to expect that there will be stumbles along the way. And, and, and this is where my, one of my favorite expressions is, you know, it's, it's, it's not about the destination.

There is no destination. It's all a journey. And if you can learn to enjoy the journey, and take the small wins, and learn from the steps back to try and do a little bit better next time, and be open about the fact that you're not perfect and admit it. And like the, the humility I'm talking about, about demonstrating, there's always another chance to do that.

And, and, and admitting the struggles that you're having it, but without blaming the other people of, of accepting your part of the blame and, and asking for forgiveness. And if there's, if there's things that you need to forgive the others, um, forgiven- forgi- forgiveness is something you do for yourself, right?

If I forgive someone, it doesn't change anything for them, but it changes a hell of a lot for, for me.

Josh 13:37

Ja

Steve 13:39

and somehow in many relationships, there, there's, there's been hurt from both sides. And, and forgiveness and, and, and saying sorry and things like that, if you go first, you make it easier for the others.

And it's hard to do. And it's hard to do

Josh 14:03

Yeah, that's been my experience. And yes, and that's been my experience. my, my... the w- the word I use all the time is vulnerability.

Steve 14:14

Mm-hmm.

Josh 14:15

I think that the more vulnerable you are, and I think this is a general thing in the world, by the way, not just with your kids. more vulnerable you are, the better chance you have of people thinking that you're authentic, your children. And it's a process, I will tell you, I, 'cause I through it myself

Steve 14:35

Yes, and, and I, and I bet you anyone who is a parent, uh, can relate to some part of what we're talking about. And one of the things, like, I often play a facilitator role for other families, and it's, it's unbelievable how often, like, parents will say to me, like, "Why do they talk to you about this, but they don't talk to me?"

And I, and I always... Well, 'cause you're their, you're their parent. I'm not. I'm like the safe uncle that, that they can, that they can talk to because I haven't been overseeing their lives s- often in too much detail for, for so long. So I can... I get away with, you know, hearing things. And then sometimes one of the things I do a lot now is I explain that my kids don't talk to me about this stuff either.

Like, I, I was at, at, at my sister's beach house a couple of summers ago, and my, my kids were upstairs on the rooftop deck with their aunt, and I was coming up the stairs, and then all of a sudden I stopped. I said, "Wait a sec. I'm... I can eavesdrop here." And, you know, she's asking them questions that I would never even ask, and they're answering it.

I'm like, I'm getting this information that they won't tell me 'cause I won't even bo- I won't even dare ask 'cause it'll seem like I'm prying. So it's not that I have this magic wand. It's just so hard to do with your own kids for many, many people, probably most people.

Josh 16:07

I would say most people. And it doesn't matter the, the level of wealth you have and, you know, Because, you know, uh, people with little wealth, you know, they often beat their kids when they were little and, and they made a mistake. And, you know, that never, they never do that. They never get over that

Steve 16:35

There are plenty of mistakes to make as a parent and, and, uh, I don't know, when my kids were born, it didn't come... they didn't come with a manual, right? And so you're making it up as you go along, and you do your best, and you're never gonna get every step right. And if you're vulnerable and humble enough to admit it, and, you know, a- admit that, "Hey, yeah, there's a lot of things I wish I would've done differently

Josh 17:05

Yes. Absolutely. So Steve, um, when you work with a person in your role as a facilitator,

Steve 17:12

Угу

Josh 17:14

go about helping bridging the gap between the two generations? From a facilitator's point of view, not from, you know, a family point of view

Steve 17:26

No. So for the facilitator, wh- when I started doing this work, I really imagined that the bulk of the work was when I would be in the room with the whole family. And yes, that is an important time, and that's where I really gotta be on. But the secret to doing that work well, that's like the game, you gotta practice before the game.

And the practice is all the one-on-ones you do with each family member to get each family member to trust you. So I need to develop the one-on-one trust with every single person in that family so that when I'm in the room with them together, they all know and believe that I am them- there for them. And yes, I'm there for their parents and I'm there for their siblings, but I am there for them and I have their best, best interests at hearts, at heart.

And I always jokingly say, I, I can only do my job as long as everybody agrees that I should be there. Because if I manage to spoil something with one person by sharing something that they didn't want me to share or whatever, like I'm effectively neutered. I can't do my job anymore as soon as one person doesn't trust me.

So I take that very seriously. It's, it's something that you can't read in a book how you do this, but when you're doing the work, you feel it, and you feel the, the pressure to, you know, be very discerning in what you say and, and when, and how you need to bring your calm to the room, and be able to ask people to rephrase something if you see that it didn't land well.

And, and call out things like, "Oh, did you realize that when you just said that, that didn't land so well out? Do you wanna try again a different way?" Or, "Can you share with your dad why you, you had that reaction?" And now you're kinda like trusting the person like, "Remember two weeks ago when we talked about this, you mentioned something.

Now I would like you to say it to your parent." Right? So, so it's all this stuff of developing this trust and trying to make sure that the right information comes out and is heard in the right way, and to just... It's really, when I first heard this term holding the space, I didn't like it, but now I love it because that's what it is.

It is holding this fragile space of family emotions and trying to make sure that all the conversations are productive

Josh 20:02

So the end of your engagement, do you believe that you have created family harmony or you've helped create family harmony?

Steve 20:12

That's the goal, and it's the North Star. And I don't know that there is something called family harmony as a destination, but I'm always trying to make the family more harmonious

Josh 20:26

Okay. So, um, how do you deal... 'Cause I, this is again a very interesting question for me. How do you deal with children that are very different, have a very different belief system about how the world should work, and specifically how their kids should be raised, and it's really different how they do it? How do you bridge this gap to keep them from hating each other?

Steve 20:48

Oh, so you're meaning between the sip, between each one?

Josh 20:52

the siblings

Steve 20:54

Um, okay. You're

Josh 20:56

I'm assuming, Steve, that one of the outcomes that uh, you know, first f- gen one clients want is that after they're gone, their kids talk to each other and they like each other

Steve 21:10

Yes, because all those decisions that they were making autocratically now need to be made democratically, and if the people aren't getting along, it's gonna be hard to make those decisions democratically.

Josh 21:22

Yes

Steve 21:24

And they are all so different, and then the way they are making life choices start to be in conflict with each other.

And so as a parent, the best thing I can do is show acceptance and understanding to each and every one. And understanding and agreeing are not the same thing,

Josh 21:50

Yes

Steve 21:52

right? To be curious enough to understand, so you say, "Okay, I understand. I don't particularly agree with it, but I support your right to do as you choose.

And your sister over here and your brother over there, they have different views." And if the parent is taking sides with any views, well, then it's kinda over already. So the best, the best a parent can do is show the acceptance and the understanding of... And a- and again, acceptance and agreement are not the same either, right?

Josh 22:26

No.

Steve 22:28

So if you can understand and accept even when you don't agree, if you can demonstrate as a parent the ability to treat someone with, with respect even though you don't agree with them, but because you love them and they are part of your family, and they have a lot of other good qualities, then if you as a parent can demonstrate that, you have a much better chance than if you are s- siding with one brother and sister against the other one over there

Josh 23:08

That makes certainly good sense. And unfortunately, um, I see parents too often siding with one side or the other

Steve 23:16

Yeah. Yeah, I, I see a lot of parents who do things that make me go, "Er, this is gonna be hard," because, because I can see

A, a, a little tweak that they could do that would make it not nearly as bad, and yet they, they won't avail themselves to that because they've, they've... That's just not how they roll, right? There, there's some parents, I, I, I read a blog every week, and I... One I wrote a little while ago where I, I brought up this tr- concept of, of the self-righteous parent.

You know, the, "Oh, well, I am right, and you are wrong, and I'm hardworking, and you're not hardworking enough." And okay, if you're gonna keep bringing that up and lording that over your kids, then don't be surprised when they don't wanna spend time with you. It's not rocket science.

Josh 24:24

Yeah

Steve 24:26

it go, 'cause you s- you really want the best for them, so you want them to be more hardworking, and you want them to appreciate how hard you work, and you want all that, and you can't have everything you want.

So if you wanna have all those things and you still wanna have a relationship with them, something has to give, and I'd rather give up on some of those other things and keep the relationship

Josh 25:00

So when someone starts working with you and their mindset is, uh, you know, um, ha- I would assume their mindset has to be somewhere in wheelhouse you can actually get some results

Steve 25:14

Yes. Oh, oh, a-absolutely. I, I, I've had, I've had, um, more clients than I care to admit that I've started off with good intentions and thinking that they had good intentions, and then eventually I had to stop working with them because I didn't enjoy banging my head against the wall, right? There needs to be some movement.

And I've had my share of clients who, uh, are somewhere between the, uh, immovable object and the irresistible force or whatever those terms are, and they, and they won't move. And, and so these are the kind of people who approach someone like me with a, um... I'm saying it semi-facetiously, but, "You know, my kids won't listen to me, so I'm gonna hire you so you tell them what I'm saying, and maybe they'll listen to you."

And, and, like, if that's your attitude, like, w- let's not waste any of our time because it's, it's not gonna work that way. This is a two-way street. And yes, I'm sure I can help you get your message, your important messages heard by your offspring. And if you're not willing to change anything in the way, in your part of this, then this isn't gonna be successful.

Josh 26:34

Yeah.

Steve 26:36

two sides to a coin.

And, and when people are this far apart, you can't expect that, you know, it's gonna be this or that. There's, there's gotta be the easiest ways for each one to approach the other. Now, it doesn't necessarily have to go fast, but they all have to do some of, some of the movement. And, and sometimes the feelings in the, in the rising gen have been so-- they've been so turned off that they don't wanna make a move, and very often the parents are so set in their ways that they don't wanna move either.

And my best bet in situations like that is to just try and chisel away a little bit, a little bit, a little bit as to just micro-moves in the right direction. And then pointing out to this side, "Hey, you notice, you know, your parents actually agreed to something which, you know, a few months ago if I would've told you that they would do that, you might not have believed it."

And on the other side, "Hey, you know, you didn't think they would do this, but now they're starting to show up to the meetings and take a little bit of responsibility, so we're making progress." And just to, to me, as long as I can finish a meeting and have the next meeting on the schedule and be 99% convinced that all the people are gonna show up again, and we're gonna do this again, and we're gonna talk a bit further, and we're gonna move the ball a little bit further down the field.

If I can know that they're gonna come back together and, and reconvene for another meeting, then that's a large part of the battle that I have, is to just keep them coming back and continuing the discussion. And having thought about the things that were discussed in between on their own and also with me and in perhaps in small groups, and then get ready to all come back together and say, "Okay, last time we talked about this.

You said you were gonna do this. You're gonna look at this. Where is this now? How are things evolving?" And just, just move slowly but surely. It is a des- it is not a destination. It is the journey, and I am there to accompany them on this journey and help it go well and help these conversations happen in a productive fashion.

Josh 28:50

Cool. And Steve, we're gonna have to leave it there 'cause we are out of time. So, so, um, what would you like people to do after they watch this podcast or listen to it? How do they contact you, and do you want them to contact you?

Steve 29:08

Um, if anything I said resonates with you, I'm always willing to jump on a call and talk about particularly a family situation, whether it's, whether it's someone from a family or someone who works with families who, who understands what I'm talking about but wants a little bit of guidance on, on how to help families move forward.

Um, I'm very active on LinkedIn. I have an easy name to spell, even the ... And it's not common, so I'm easy to find. There's only one vowel. It's an E. It shows up twice in my first name, twice in my last name, Steve Legley. You can Google me. If you put family business or whatever, I'm sure to show up. Hit me up on LinkedIn, and, uh, sign up for my blog and read my blog.

Listen to the podcast that I host and, and I'm on, and if anything resonates and you wanna chat, I'm al- I'm almost always happy to do that. If you're trying to pitch me something, probably less likely, but if you just wanna chat about this kind of work and working with families to help them have better conversations to in- increase the chances that their transition of their family wealth from one generation to the next will go well, that's the work that I enjoy.

Josh 30:44

Cool. I've got two things I'd like you to do. first is please go wherever you're watching this podcast or listening to it and give us an honest rating and review. If you love us, you give us five stars. You hate me, give you one star. I will cry big crocodile tears, but you won't see it, so that's the way it is. The second thing is, if you think you'd be a good guest for the show, I'm always looking for great guests, just send me an email. We'll set up a time to talk and see if this is right for you. My email address is [email protected]. That's the number two, and solution is singular. It's [email protected]. is Josh Patrick. We're with Steve Legler here at the Long Strange Trip podcast, and I really do need to have, uh, Truckin' as our outgoing song because this is a Grateful Dead title. Um, but thanks a lot for coming by, and I hope to see you back here next week.

Outro

Thanks for spending this time with me today. I really appreciate you being part of this journey. I'd be grateful if you'd leave an honest rating and review. It helps other people find these conversations, lets me know what's landing with you and what isn't. If you love the show, give us five stars, and if you hate it, give it one star and I'll just cry a little bit.

Keep asking the hard questions. Keep being honest about what's difficult. And remember, we're all just trying to figure this out together. I'll talk to you next time on The Long Strange Trip. Thanks for stopping by