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Harness the Power of Stewardship with David R. York

On this week’s episode of The Leadership Habit podcast, Jenn sat down with David R. York to talk about The Gift of Lift: Harnessing the Power of Stewardship to Elevate the World. David is an attorney, a CPA, and a managing partner of York Howell & Guymon, named an Inc. 5,000 Fastest-Growing Company. David works with closely held business owners and ultra high net worth clients in the areas of tax and estate planning. He has authored multiple books, Entrusted: Building a Legacy That Lasts, and Riveted: 44 Values that Change the World. But today, we are going to be talking about David’s newest book, The Gift of Lift: Harnessing the Power of Stewardship to Elevate the World! Enjoy.

Meet David R. York, Author, Estate Planning Attorney and CPA

Jenn DeWall: Hi everyone. It’s Jenn DeWall. And on this week’s episode of The Leadership Habit podcast, I am so happy to be sitting down with David York! David, thank you so much for joining the show today. How are you doing today?

David R. York:I am doing great. I’ve been looking forward to our conversation.

Jenn DeWall: Oh, great! There are so many things that I talk about that I knew I remembered from our pre podcast call that I’m sure will come up here, but David, you know, you are an attorney, you’re a CPA, you’re a CPA, you’re an author of The Gift of Lift. Tell me a little bit about who you are and how you came to be.

David R. York: Yeah. You know, I always tell people as an attorney and a CPA, I’m two of the most boring people in the world wrapped into one. You know, and I’m someone who knows an awful lot about very little. But when I came into estate planning, I came from a really technical background being a CPA. I did taxes for years, and I came to look at estate planning as the how and the what, right? How do you do estate planning? What is estate planning? And what I came to realize is that those are not the right questions to ask. It’s about the why of your wealth and who is around you. And it’s so much more about the purpose and people than it is about property or profits. And so, I’ve been kind of on this journey of, of, re-discovery of what wealth is and impact and all those things.

Jenn DeWall: Gosh, how do you think you would’ve defined wealth? Like, you know, earlier in your life versus where you are today?

David R. York: Yeah. You know, early on, it was about what’s on your balance sheet, right? Show me your assets, and I’ll tell you what you’re worth. And it wasn’t too long before I realized that there’s really little correlation between that. You know, I see people who live with such meaning and purpose and direction in life, they have such clarity, and it has nothing to do with how much or little they have in the bank account. It’s all about knowing who they are and knowing the impact they wanna make in life. And so, what I came to realize is people who have a lot of money tend to have one thing in common. They’re good at making money. Right? But that doesn’t necessarily tell you that they’re happy, content, fulfilled, engaged, or any of those kinds of things.

Jenn DeWall: Right. And I feel like it’s something that I guess if I speak from my own experience, I think even the initial messages that I received in life were– I remember this, I wanted to join the Peace Corps. And the first thing that, you know, my mom had said to me was like, but that’s not gonna make you money. Yeah. And it was the starting of the lessons of, oh my gosh, should I be more concerned about the financial situation that I create? And should that be the purpose of like how, or should that be the motivator of how I choose or what do I choose to do? And I feel like, I don’t wanna say how many years later, but it’s many years later, I am on the other side of that. Feeling like you can have the money, but it’s not necessarily going to grant you happiness. And you wrote your book, The Gift of Lift. What inspired you to write your book?

What Inspired Your New Book, The Gift of Lift?

David R. York: Yeah, it was interesting. It was actually an experience I had six years ago with a client of mine and talked about success. She, her name’s Gail Miller, owner of the Utah Jazz, and one of the wealthiest women in, in the United States. And we were sitting down working on a trust that was gonna transfer the ownership of the Jazz with the golden intent of keeping it in the state of Utah. If you’ve never been to salt lake, we have beautiful scenery but not necessarily a lot to do <laugh>. And so, you know, the Jazz are really important to this community. And so she wanted to make sure it was. It stayed there. And so we were working on this trust and finalizing the details. And during the review of some of the documents, I just happened to ask her, I said, so how will it feel to no longer own the Jazz?

And she looked at me, and she said, well, I don’t own the Jazz. And she went back to review her documents, and I, I was like, mm, you know, that, it, it kind of surprised me. And you know, here I am, I’m her attorney and helping her with estate planning. So I’m like, mm. You know, she’s a really smart lady, but I was like, well, no, you actually do own the Jazz <laugh>, and I’ll never forget she stopped what she was doing. She looked over at me. She said, no, I’m a steward of the Jazz. And it was honestly one of the most powerful experiences in my professional career because I saw somebody who had actually transcended ownership. You know, for most of us, we think the highest thing you could be is an owner, right. I own a piece of property. I own a business. I own a sports team. And yet she, she was above that. She had something that was, was bigger than ownership. And so it really made me sit back and spend years thinking about, okay, what is a steward and what is the mentality of a steward and what makes them different?

What is Stewardship?

Jenn DeWall: Who is this? I mean, I wanna get into like, what is a steward, because I think that this might be something, again, I would put back to myself, like it used to be like, I want the ownership because ownership was equivalent to success to feeling like you’ve made it, for lack of a better description, not to say I’m here today, but that was probably some of the earlier lessons that I had. So when you think about who you had in mind for this book before we kind of dive into understanding it a little bit more, who are the people that you had in mind?

David R. York: Yeah. You know, it’s interesting. I’m probably gonna date myself here when I say this, but it’s kind of like playing slug-bug, you know, when you start looking for Volkswagens, you know, you start seeing them everywhere. And so, you know, the first thing I had to grapple with is, okay, what is a steward? And what I came to realize is that a steward is someone who’s fully invested in something bigger than themselves. So, at the essence, they have two things they have investment and they have transcendence. In other words, they’re all in, but it’s not about them.

And as I started to look at that, I started to see examples of people, you know, one example, Nelson Mandela, obviously spent years in, in prison in South Africa trying to end apartheid. What most people don’t know, though, is he was actually offered his freedom six times. He had the opportunity to walk out of, Robben Island prison six times. And each time, he refused— because every time he was offered freedom, it was conditional. He had to leave the country or you could never speak in public, or you could never run for office. They always put conditions. And for him, his transcendent value was freedom. And he knew that you are not truly free unless you’re fully free. And so, for him, he was willing to continue to pay the cost and make the investment because it was about something that was more than just him. If it had been about him, he would’ve walked out the front door. But it was about something more, and it’s powerful and it’s life-changing. That doesn’t mean it was easy for him. You know, I also think of, Susan B, Anthony, you know, she was one of the leaders of the suffrage movement. She actually died 14 years before women got the right to vote, but it was because of her and her efforts, and she was all in, and she was all about equality for women. But it took her years and years and years. And so you start to see these people who just live fundamentally different lives and the impact that they make because of those two elements of investment and transcendence.

Jenn DeWall: I never realized that Nelson Mandela was offered release. That is, you know, just to think about how purposeful, how intentional and the sacrifice that he had to make, to be able to stand for the cause. That is an incredible example. How do you think in, I mean, do you notice any moments that maybe that people start to make that shift or is it more intention or is it life forcing you to that?

Stewardship is a Mindset of Investment and Transcendence

David R. York: Yeah, you know, I think it’s about a mindset and unfortunately, and, and this is where I kind of saw it coming from an estate planning perspective because what’s the opposite of a steward? Well, it’s someone who lacks any investment and lacks any transcendence and, you know, I call those people consumers. Unfortunately, we see consumerism and the effects of consumerism all around us, right. That’s why the average American inheritance lasts 18 months. So you think about that, what people build and accumulate over the course of their lifetime is on average spent and consumed by the next generation in 18 months. And, and why is that? I, I think by and large is because what we say is we are gonna give you something that costs you nothing. So there’s no investment and there’s nothing bigger than yourself about it. And then we’re shocked when it’s consumed.

And, you know, I’ve had a lot of clients who they see that issue, or they see that consumer mentality, or they’re afraid that all their hard work is just gonna be dissipated. So they come in and they wanna put a lot of restrictions and limitations on how their money can be used and how it can be spent. But the, the opposite of consumerism isn’t minimalism. It, isn’t less, it’s about something fundamentally different. And I think that’s what we, we see in society a lot, right. Is this consumer mentality is I’m not gonna invest in anything and there’s nothing bigger than myself. And we have a whole lot of really unhappy people as a result. So, yeah, what I want people to understand is it is not about being a world leader. It’s not about being a, you know, a billionaire it’s about having a mindset of being all engaged, but about something more than just you.

Jenn DeWall: Yeah. It’s greater than you. Greater than what you’re there to do. And I like the perspective of thinking about it as a consumer approach that, you know, I think we’ve almost been conditioned to always think what isn’t it for me? Why should I care? What should I invest in? Instead of being like, but how could I help? How could I solve, how could I do this? In your book, you describe different types of leaders through your perspective. I’m curious. Could you tell a little, tell us a little bit more about the types of leaders?

Stewardship in Leaders

David R. York: Yeah. So then you think, okay, How do stewards express themselves in leadership? And I think they have a couple of things in common, first and foremost, and it’s kind of what we were talking about earlier. And that is, most of us live with what I call an if, then mentality of life, right? If I do this, then someone else will do this. Or if I accomplish this, then I will get this. And it’s all, it’s very, it is driven by expectation. And, and the problem with expectations is you either meet ’em, and at best you’re satisfied, or you don’t meet them. And then you’re unsatisfied, right? Steward leaders operate on a different mindset. It’s what I call the because/therefore, because of my transcendence, what’s bigger than me. Therefore I will do this. And what’s great about a because/, therefore, a model is it’s always achieved.

If you think about it, I say, okay, if I can grow and sell a business for $10 million, then I’ll be happy. Right. That’s sort of if then, and we see that in society. But if you say, because I value compassion, therefore I will foster a child. I will give to the local food bank. I will check on my neighbor. Who’s sick, right? No matter what, because/therefore will achieve, its purpose. You will add compassion to the world and that’s your driver. Right. And so, that’s, I think one of the biggest things is that, stewards are more about direction than a destination, right? A steward leader says, these are the values that I have as an individual. These are the values we have as a business. And we’re gonna advance that. It’s about direction, and direction creates pull. As opposed to destinations, which is all about either failing or arriving, but then you’re done.

Jenn DeWall: <laugh>. Yeah, it it’s, I mean, I like breaking it down like that. The, if, then the, this is what it is either we make it, or we don’t, if we are successful or if we are unsuccessful, this is what we’ll do. Instead of really leading with, I guess the core, the, I love the, because/therefore differentiator, because I think that, that one’s easy, maybe not easy, but from where I sit, sometimes it’s hard to find meaning in work when we live off of the, if/then like, okay, we’re just working like to, you know, get this job. But I like that therefore, because/therefore, or therefore, because like, I feel like it invites everyone into the conversation for how they can actually see themselves as a leader.

David R. York: Yeah.

Jenn DeWall: Instead of it just being a kind of person that’s out there, not really having control, not really maybe feeling like they let’s see, how am I trying to say that? I just feel like it’s more enticing. It’s more empowering to look at it in that way.

Finding Passion for Stewardship

David R. York: Oh yeah. It’s much more, it’s much more compelling. I, in 2019, back when you could leave the country and travel and have fun and do those things, I went with my family and went to Italy and, we got to tour a winery just outside of Verona, and beautiful it’s, but it had been around for– it’s a 130-year-old family business, fifth generation. And, we’re touring it. And we’re, I’m touring with, the daughter who’s running the family business now, raising the sixth generation there. And I asked her, I said, what’s the secret of a five generation hundred and thirty year old family business. And she said, it’s one word, you know? And I was like, geez, what is that word? You know, is it, family? Is it excellence? Is it wine? Like, what’s the secret? And she said it’s passion.

But I loved her description. What she said is it’s a beautiful work, but it’s also very hard. You have to both look up and see the beauty and look down and do the work. And I thought that was just a perfect example of stewardship because she was a steward of that land. There were four generations before her. She hopes there are four generations after her. So she was a steward. But for her, the beauty was the transcendence. But that beauty led to her engagement and that day-to-day work. Right. So she was able to do the work because of the beauty. Why was there the beauty? Because of the work. Right? And so they actually work really well together to create that passion that allows them to be around for that long.

Jenn DeWall: I love that perspective! So if you might be listening as David is talking about like even looking at what you’re doing and how it is, this cycle of things that can be fulfilling, that we are going to have, for lack of a better description, like the beautiful parts of our jobs that we love and the parts that we may not like that the work as you would describe it. But when we can merge those, when we put in that work, we can see that value, no matter what chair you sit in, or what title you have. So then let’s go to the other end of that. I know we’re gonna dive more in to really talk about what it means to be a steward. What’s the opposite of a steward at work?

David R. York: Yeah, it’s that consumer, right? It’s that person who says, what’s in it for me? And they lack that investment. They lack that transcendence. And so unfortunately it can either lead to, like I said, two, two things, your expectations are met, but how many of us actually get a bump in happiness when we get exactly what we expect? Right. it doesn’t really do much for you. Or your expectations aren’t met, which leads to anger and frustration and even depression. and you know, I see this with people who own businesses, right? You know, they, a study showed that is upwards of 70% of people regret selling their business within a year of the sale of their business because they thought it would bring them all of these things. Right. Like if I go and I do this and I build my business and I sell it for a bunch of money and put it in my bank all, all, then I’ll be happy. And the reality is it does not bring that happiness and contentment that they, they thought. And so, that’s the problem with being that if then it’s very, quite frankly, it’s self-centered, and it’s very expectation-based.

Jenn DeWall: And so if we look at that, what that looks like in a workplace, then it might be, just trying to think if there’s something off the top of my head, like maybe it’s, well, I don’t really wanna do that cause it doesn’t serve me. And then you, or what does, like, how do you see that show up for people’s work-lives or in people’s work lives?

Stewards Have Clarity of Purpose

David R. York: Yeah. You know, I think it’s a couple of things. One is I think when you can have clarity of purpose in a workplace, you actually draw people who are compelled by that. You know, and I tell people when you care about everything, you really don’t care about anything. Right. And we have to just realize that we are finite beings and we can’t care about everything. So what are those few things that really inspire us, guide us, direct us and make us tick. And so when you can be clear in a business about what your purpose is, you actually can draw other people who are like-minded and you get synergies from that. And the other huge benefit of having clear purpose is it actually makes decisions a lot easier. So, I worked with a family office, that they had just sold a business that had a great name brand, and you’d know the name brand.

And, they were looking for their next things that they were gonna do. So we went through an exercise to say, okay, what do, what do we want this, this company to be known for? And they wanted to be known for three things. They wanted it to be known for loyalty. They wanted to be known for integrity and they wanted it to be known for excellence. Now, unfortunately, the acronym was lie. So let’s set that aside, but <laugh>, they were like, okay, we didn’t think through that. But, that afternoon they were going through and they were deciding on what they wanted to do with an investment. And there was an investment that they could make, they’ve been thinking about it for months. And it was one that they could make some good money on, but it was kind of geographically remote and it would take a lot of time and effort.

And so they were kind of hemming and hawing, we could make money. What do we do? And I just asked them, I said, let me ask you this. Can you do this project with excellence? And they said done, we’re not doing the deal because yeah, we could make money, but we can’t do it with the excellence that we want to be known for. And that thing that’s bigger than us. And so, because we can’t do it with excellence, we’re not gonna do it. And so for them, it turned months of decision-making into a two-minute decision, because they had that clarity of that thing. That’s bigger than them. And, and it helped them drive what they decided to, how they decided to deploy their resources.

Jenn DeWall: I feel like, think about how much stress you could save humanity if you helped them get clear on, you know, even three things that will just get that around your passion and purpose. Just, gosh, I’m thinking about decisions that I’ve waffled on that if I actually started with that first, how I could have saved myself stress or even, I mean, what my, my husband would say too, is that sometimes I say yes to a lot of things, because I feel bad. Yeah. Not because it’s what I want to do, but it’s because I feel in some way that someone, you know, might be upset or not as happy. And then I feel like how that shows itself is being overscheduled not doing things with excellence in the way that I would want to, which had, I actually started with that, you know, purpose that would’ve been different.

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Practicing Stewardship

Jenn DeWall: Let’s think about the starting point. Where do you start? So if someone’s picking up your book and they’re thinking, how can I develop, you know, how can I develop into a better steward? How can I truly practice this? Where is the place that you would recommend that they start?

David R. York: Yeah. You know, it’s really good because when you’re talking about that thing, that’s bigger than yourself, inherently, that’s a really deep and personal question. And I think you, you, you hit the head on the nail on the head and that is for some of us, the problem isn’t about caring. it’s about caring about too much, right? Like the world gets so overwhelming and there are so many things. And so it’s really just about understanding that core of who you are. And the only way I think you can do that is through questions and stories. You know, I, I like to say it this way, knowledge and information inform, but questions and stories transform, you know, and I think one of the knee-jerk problems we have in society today is we live in the information age. Right. So what we think we lack is information. We’re like, oh, if I just had all the right information if I had, if I just had the podcast that told me the one thing I need to know, I can use that information. But the reality is I think we need transformation. And transformation comes from sitting with questions. So, you know, in the book, I actually, I’ve got like 50 questions and it’s, there are just things for you to sit down and ponder, like, for example. So I’ll ask you, what is the greatest compliment that you could, you could receive?

Jenn DeWall: You know, I think the greatest compliment I myself could receive is that I have in some way, inspired someone to see their life in a different way that they are yeah. That it’s for, and that one is probably that one’s yeah. I think it would be along with that of like feeling like they have the confidence and that they feel good enough to do something.

David R. York: Yeah. And what I love about that one, is it gives you a good insight into what your core values are, right? Like what, what do you value? Who are you? And then what I loved about, and, and this is a critical element of stewardship, is it’s about other people. Ultimately stewardship is about other people. And they realize that, that others’ perspective is actually what brings value. And so it’s really just a matter of, of that. What, and I mentioned it earlier, it, it, you described it, but, you know, if you could be known for three words, what are they, you know, what three words do you wanna be described as these are just questions that as you ask yourself and you wrestle with and you ask other people, you start to get that clarity. And then that clarity actually becomes a great rubric for you to go through and decide what to do in life. So as life tosses you all these different things, you can look through with that perspective of what is bigger than you, that you, you are going to invest in it.

Jenn DeWall: What’s what if, like, what’s the opposite in the, you know, if I think about the answer I just gave and is there, is there such a thing as being too much of a steward?

Finding Balance, or Counterbalance

David R. York: Yeah. No. The great thing to me is, you know, it’s funny, one of the buzz words you hear in the world today is balance, right? Like, oh, we need to have balance work-life balance, all of that. And to me, balance is about more or less. but I actually think we shouldn’t seek balance. We should seek a counterbalance. And counterbalance comes when you, actually balance two things against each other to give more strength to the other. And so, think about an elevator, an elevator works based on counterbalances. It actually doesn’t take a lot of energy, because all it takes is a little bit of effort on one side and you’ve got the weight of the other working together. So, you know, it’s kind of like, salty and sweet together, right? How, how good is salted caramel ice cream, right?

It’s not about, oh it need to be more sweet or less sweet. It’s about adding that salt. That brings something different. And so, what I tell people is you get far more power when you combine that transcendence and that investment together. So, it’s not about titrating life up or down. I need to work more. I need to work less. No, this needs to be about why do you work? And that why will actually lead to that, that deeper engagement, but because it’s bigger than you, it actually takes some of the pressure off. Because it’s not something that you can achieve. It’s something that you can express.

Jenn DeWall: It’s not an end destination. No, I feel like there, there has to be, I don’t know someone listening to this podcast, hopefully feeling like I now have freedom in some capacity, freedom to understand the purpose, but to let go of what I feel. And maybe this is my self projecting. Like there’s often this vision of perfection that is supposed to hit everything. And I think that can be really restrictive. It can challenge the way that I might look at success, how resilient I might be, whether or not I pursue it or I give up in general. And I like that. It’s, you know, it’s the journey. It’s, it’s the journey. It’s what you’re doing in the middle. It’s not, I think too often we get caught up in the, in the outcomes, as you’re saying, like we get so caught up in, what does success look like? Or how will I know when I’ve made it?

Avoiding Perfectionism

David R. York: <laugh> yeah, no, I totally, I totally agree. And then I think the other thing you hit on, which is huge is this problem of perfectionism, right? And there are actually all these studies out there that show that the levels of perfectionism are going up, like the expectations we have on ourselves, the expectations we have on others, just keep going up and up. And there’s a guy named Barry Schwartz, I think. And he came up with this term called “satisficing“. And basically, it’s about getting to the point of being satisfied with good and achieving an expression of what you value as opposed to, well, it’s gotta be perfect or I can’t do it at all. Right. So we just create these binaries of it’s gotta be absolutely perfect or I’m not interested. As opposed to, taking a step back and realizing, you know what, I can do a good job on this. and I, I may not be a perfect friend. I can be a good friend. I may not have the perfect advice, but I can beef with someone. Right. And just helping to, to again, take some of that pressure off, because it’s not about achieving it’s about advancing

Jenn DeWall: Well, and it’s that’s that achievement is just rooted in that judgment. I remember in my twenties when, you know, I just can remember the first time that I had a boss tell me, Jenn, it’s about living in the gray. Yeah. But I think that was the hardest leadership lesson to really understand, because up until that point, life was a destination, there was enough judgment to tell me if what you’re doing is right or what you’re wrong, which then adds into that level of perfectionist thinking of like, I must do this as a right way. Like how do you even begin to think in the gray? Like if you, like, what are some of the questions that not even, this is kind of putting you on the spot in maybe a more conceptual way, but like how did you start to learn to live in the gray of like good enough?

You’re like, it doesn’t have to be perfect. Like, I don’t know if you had any tips that you used because I still find that’s hard. It’s hard to know that we’re supposed to live in the gray, but then still assess ourselves as either winning or losing. And so I don’t know if you have any tips for how you’re able to come back and be like let’s refocus or is that always coming back to the why and the purpose and the passion? Or am I stacking way too many questions into this podcast where I’m at right now to even answer, it’s probably a mix of all.

David R. York: No, I think it’s great. And I think, first of all, when I figure it out, I’ll let you know. Right. We’re all on a journey. <laugh> but, I think one of the issues that we have again is just such a lack of self-awareness. and I think we struggle so much. They did a study a couple of years ago, and they were looking for like the key characteristics of leaders in businesses. Like what, what is the key characteristic of, of highly successful businesses? And, they were like, we think we found it because we were not looking for this. But they said the number one characteristic of successful leaders is self-awareness. That they knew who they were. They knew their strengths, they knew their weaknesses. And again, counterintuitively, it takes a lot of the pressure off when you can understand fully who you are and you know, the gaps that you need and the people to surround yourself with.

Self-Awareness is Key to Leadership

David R. York: And it actually brings a huge sense of, humility, when you can actually be self-aware and humility is a great antidote to pressure and pride and all those things. it is kind of funny. I did see a breakdown the other day between male leaders and self-awareness and female leaders. And so they, they did a study and it was like 4% of male leaders were self-aware and 19% of female leaders were self-aware. So depending on how you can look at it, you’re like, oh, women are five times more self-aware than men. Or you can say no 80% plus aren’t self-aware either. Right. So yeah, but I do think it’s interesting because in general you do find women who are more relational. They, they tend to ask a lot of questions and tend to just understand a bit more of who they are. But I think that’s the key, is understanding that self-awareness and who you are. I think it makes you a better leader. It makes you a more mellow leader, and I think it makes you ultimately far more impactful.

Jenn DeWall: I love, I love that stat that you just gave to even think. Yeah. 80% of people actually aren’t as self-aware as what they probably think they are. Yeah. Because I bet most of those leaders probably I think if you ask, if I ask that question to a class at Crestcom, I’m sure the majority of people would say like I’m pretty self-aware.

David R. York: Yeah. In fact, what are the markers of a lack of self-awareness is if you think you’re self-aware! <Laugh> Like <laugh>, You know, like they did a, they did another study. I saw like, if you, if you think you can multitask, you actually can’t. They said it’s actually the people who don’t think they can, that actually can, because it’s such a small percentage, but honestly like a truly self-aware person is gonna be open to maybe there’s something I don’t know about myself. so yeah, if you, if you’re certain you’re self-aware, it’s probably an indicator that you’re not.

Jenn DeWall: I feel, oh my gosh, I’m just laughing. Cause I’ve definitely heard, you know, I’ve seen the example in leadership where I’m talking to a leader and they would be the self-described, like I’m a people person. Yeah. And then you watch them and you’re like, but you are the opposite of a people person. I’m not sure if you can see that about yourself, but I don’t know. Or did someone tell you that and not maybe give you that feedback throughout the way? Because you do see that like I’ve absolutely hear, that’s not even, I’ve heard that a few times of someone saying like I’m a total people person and in my head I’m like, but I don’t think you realize like how your words are actually impacting all these people and they may not describe you with that language.

David R. York: <laugh> yeah, yeah, absolutely. You know, it’s so funny when I was a kid, my mom told me once that I was, I was patient I’m like such a patient person, because I like to, to, I was go, I went fishing and I could spend hours doing that. She’s like, you’re so patient. So, I grew up thinking I was patient. It was not until like 10 years ago I realized I am so impatient. I’m like the world’s most impatient person. but someone told me that and I believed it. The only reason I was patient, I liked fishing. I was impatient getting there. I was impatient heading home. I just happened to like that. And so I agree with you. I think sometimes we get these things both positive and negative in our head that are not truly who we are. and it takes some of that internal work. Like even just like, like what does a counselor do at the end of the day? All they’re doing is asking your questions. because you have the answers. You just, you need to be asking the questions to actually get to who you are.

Jenn DeWall: Oh my gosh. It’s I love that. It’s it really is questioning yourself in a kind way, in a curious way. Or I guess what advice would you have in terms of how they should be asking these questions? Because I think any, like, do you have any pitfalls that they should watch out for? Because I think again, we might just be starting with like, well, what does, you know, hitting the millionaire circle look like for me, this destination? I think it might be easy to even ask your yourself leading questions. So I don’t know if you have any pitfalls that you would maybe avoid or any guidance around like questions of open-ended. I mean guess is, is the first one of like open ended, but how do you answer ’em do you write them down? Do you just reflect and meditate on them?

David R. York: Yeah, I, I think it really is. I think it’s a matter of just, and the big thing too, I think is avoiding the posing, right? Like we’re all supposed to give answers a certain way. And I think the key is just to ask yourself the questions and then give yourself honest answers. Not like, what are you supposed to say? Or not, what other people think. But, but honestly, what do you think? I, I really think that’s the key, but it does take time and it does take effort.

Jenn DeWall: Yeah. It’s well, and it’s hard. I think that for some, depending on where you are in your life and what’s going on, when you’re asking yourselves these questions, your answers might lead to things that require some heavy lifting or some different choices and changes that I’m sure can elicit all of the fear or emotions or feelings of well, if I go back to like what really matters to me, you know, and it’s having that imprint or I forget the exact question that you had phrased, like, and then you find out, oh my gosh, is this, where is this where the midlife crisis happens, David? Is that why we start answering the question is too late in life. And then we’re go, we go into panic mode and buy the sports car.

David R. York: <laugh> yeah. I mean, honestly, one of the nice things about the mirage and not getting there, is it still drives you forward. Because you think once I, you know, if I get there, then I’ll be happy. And I see that with, with so many people. And I remember, I mean, geez, even when my, my wife and I got married, I’m like, okay, if we could save up a thousand dollars, then I’ll feel completely financially secure, right? Like you’re living paycheck to paycheck and you’ve got nothing. And then you get that. And then it’s like, oh, if we could get just a little bigger house, if we could just have this or that, and you finally hit enough of those destinations and they don’t actually move the needle in life, I think that’s what midlife crisis is, is honestly, when you’ve checked off enough boxes that were supposed to make you content and happy and they didn’t. Then you’re like, then you start to realize, well maybe the next five boxes I’m working for. Aren’t gonna do that for me either. So maybe it’s not about checking boxes.

Asking Yourself the Right Questions

Jenn DeWall: Yeah. It’s about asking deeper questions. Well and understanding. I mean, I’m not sure. What do you see with, with how, like writing this book? Like, I don’t know if you notice those times then? Is it, do you ask the questions when we’re going into that new promotion or going into a new field or becoming parent or is any time the right time to ask the questions of yourself?

David R. York: Yeah, I think it, every time is good! And it actually, it’s good to, ask your, to continually ask yourself. Because the reality is we are affected by life experiences, by good things and bad things and struggles and trials and difficulties. And actually you see so much growth. I see so many people who have gone through difficulties in life, and you talk to ’em about it afterwards. None of them would go back and not have that struggle or trial. They don’t necessarily wanna go through another one. Right. But it’s in those times of struggle and pain and difficulty where we actually get to an understanding of who we are, because a lot of stuff gets stripped away. And so I do think it’s good to re-ask yourself because who I am and what I value and what I believe has changed over time. And that’s not a bad thing. So I do think constant that self-reflection is really valuable.

Jenn DeWall: So once you get those answers, like what, what is it like, how do you actually transcend? Like, is that as a result of small steps? Is it, I don’t know if you have any tips and techniques on like, you know, once you realize what that purpose is, how can you live in alignment with it?

David R. York: Exactly. Yeah. That’s the right question is once I understand that thing that is bigger than me, then how am I gonna invest in that? And, and everybody has three things they can invest. You can invest your time. You can invest your talent, you can invest your treasure, right. You know, you can invest. And your time is really the most precious commodity. That’s the interesting thing I’ve I noticed is I don’t care how much resource financial resources you have. We all have the same amount of time. And that becomes the most precious to people when they have, extra financial resources. But where am I gonna invest those things in that thing? That’s, that’s bigger than myself. So actually, I find the investment side is actually easier. Once you understand the direction you want ahead. You.

Jenn DeWall: So if I was, so if I was thinking about how can I take it? Because I love your book is gonna drop on June 6th. We want people to get The Gift of Lift. You know, we rise by lifting others. How can we become that steward first starts with asking you the questions, you know, and then thinking based on those answers, where are you going to invest your time, your talent, or I love that your treasure I’m like, do I have enough treasures to invest myself? I don’t know when you say treasure. It makes me feel like I need to have a big chest with a lot of gold coins in it. <laugh> and I dunno if I have that, you know, but I’m teasing, but really thinking. So that’s the investment of that going through and thinking, how do I want to invest my time, talent or treasure? What are other tips that you have for people as they’re really embarking on this life of stewardship?

Stewardship Lies in Meaning and Impact, Not Money

David R. York: Yeah. I, again, I do think it’s important to realize because you know, to me, we think money is a lead indicator of investment, right? Like the more money you have, the more investment you can make, the more impact, I oftentimes find money is a lag indicator. It comes after your investment of time and hard work. You know, I cannot tell you how many clients I work with that, come from absolutely nothing and they have that high level of cost. But the reality is that cost is the only thing that actually brings value. and when we, we try to bypass cost or pain or work, we actually end up undermining value. So, honestly, I just think it’s a cop-out to say, well, I don’t have enough money, so I can’t make a difference in the world.

I mean, go back to the people in your life that made the biggest impact in your life. You think about those people. I think about an eighth-grade math teacher who believed in me. I don’t think she had a lot of money. She made a lasting impact in my life because she actually believed in me and it was one of the first teachers who ever did. Right. So, I think we just need to reframe what impact looks like. And it really is just a matter of taking your time and investing your talents and, and most people who have financial resources it’s because they invested those first two things.

Jenn DeWall: My gosh, David I’ve loved our conversation because I feel like it’s, it’s soul-filling. When we really think about our purpose, which is often the legacy that we leave, that we, I think that’s the last question that we actually think about is like, did I do it right? I love your approach and really thinking, how do you wanna show up today? Like how do you wanna live your life? Not the destination you’re going to because we make a lot of assumptions. I mean, you see it from the perspective as an estate planner, I maybe watched it in terms of watching both of my parents, everything they worked for, be gone within a matter of years. And then you really that it’s through those situations that I think they force those questions, but everyone that’s listening to this has the opportunity to ask yourselves those questions. Now, instead of waiting for that situation where you might be forced into it, this is your opportunity to think about what your life can look like. What benefits have you seen? Because in closing, I, I wanna, I wanna sell it. Like, why do people need to hear this right now? If they’re going through blank? Like why do they need to hear this message right now?

David R. York: Yeah. Because ultimately, the most content, the most impactful people are the ones who seek meaning in life and not happiness happiness is just such a fleeting temporary thing. And honestly I think a lot of us come to realize that, you know, it’s just the, it’s the hit of adrenaline that doesn’t last. But meaning comes from being deeply engaged in having other people involved. And so I think that, you know, maybe that’s a question you need to ask yourself, is, am I living life for happiness or am I living it for meaning? Because it’s gonna look very different.

Jenn DeWall: Oh my gosh. I love that. As a closing question, are you living your life right now for happiness or are you living your life for meaning, David? How can people get in touch with you? Your book drops June 6th, where can they purchase it? Tell us all the details.

Where to Find The Gift of Lift on June 6^th, 2022

David R. York: Yeah, it’s on all the natural resources, you know, Amazon, Kindle, Barnes & Noble. We’re working on an audio version for those like me who like to listen to books, but then you can also go to DavidRYork.com. I’ve got a Ted Talk on there about wealth and looking at wealth differently, and some other resources as well.

Jenn DeWall: Oh my gosh. Thank you so much for your insights. Thank you so much for just your perspective. And I hope that the questions that you posed today brought some people to powerful answers so how they can live their life with more meaning. Thank you so much for being on the show, David!

David R. York: Anytime! I loved talking with you.

Jenn DeWall: Thank you so much for listening to this week’s episode of The Leadership Habit podcast. I hope that you enjoyed my conversation with David and that you are leaving feeling inspired, wanting to ask yourself some questions so you can find more meaning. If you want to pick up your copy of The Gift of Lift, just remember it, it drops on June 6th, but you can actually get special pre-launch pricing for Kindle now! And if you want to connect more with David, find more resources that he has available, or just check in, see how you can book him for speaking head on over to DavidRYork.com and finally check out, his Ted talk all about building wealth.