How Different Generations Work, Live and Connect With Kim Lear

by Ryan Goulart

Generational dynamics are more than just age gaps‌ — ‌they reveal how society changes over time. From shifting work habits to evolving values, understanding generational differences helps us make sense of the broader transformations happening around us.

“People love context,” says Kim Lear, founder and generational research consultant at Inlay Insights. “People love understanding their place in history.” Our natural curiosity about how we fit into the changing world drives interest in generational trends, Kim has found.

On this episode of Making the Ideal Real, Kim shares her insights into how generational shifts shape our work, relationships and values, and what leaders can do to foster stronger connections across age groups. During our conversation, Kim dives into the ripple effects of the pandemic, remote work dynamics and the growing focus on financial security among younger workers. 

Listen in as we explore how to better understand and engage with today’s multigenerational workforce.

Generational Change: The Power of Context

Understanding generational differences requires more than simply focusing on a single age group‌ — ‌it’s about recognizing the broader context of change. Kim has seen this curiosity play out in the types of questions people ask, such as: “How come my child’s childhood is so different than my childhood was?” or “How do I want to age differently than my parents are aging right now?”

These questions about generational change help people understand their place in history and the evolving world around them. Kim notes how, in her research, trends like the youth mental health crisis or the rise of social media use reflect the deeper impacts of cultural and technological shifts​. Each generation’s experiences are shaped by pivotal societal moments — like economic shifts, technological advancements or the pandemic — which continue to create ripple effects across different age groups.

By exploring these trends, leaders can gain deeper insight into what motivates different generations. Whether it’s the need for in-person social connection or navigating a digital-first world, these experiences shape how people interact, work and define success in their lives.

Remote Work and the Role of Generational Sacrifice

Context and experiences shape what different generations want to get out of work. For younger workers, especially those just entering their careers, there’s a craving for mentorship, social connection and meaningful in-person experiences. However, older workers, who have already built social capital, are often more productive working from home, creating a difficult balancing act for leaders.

Kim has found that changing attitudes towards work reveal broader generational perceptions of sacrifice. “There was a lot of personal sacrifice that went into that older way of climbing the ladder,” she says. “And I think, for a lot of good reasons, people are no longer willing to make those sacrifices.” These differences have led to a tension between the desire for autonomy and the need to build culture and connection​.

The challenge for organizations is to find a balance between honoring individual freedom and creating collaborative, in-person moments that build the kind of workplace culture people crave. “We can’t police time the way that we did in 2019, but there is this sweet spot that I still don’t think we’ve quite mastered,” Kim says. The need for flexibility is key, but so is the importance of meaningful in-person experiences that help teams thrive.

Attitudes Toward Money and the Generational Divide

Different experiences and evolving perceptions of sacrifice naturally lead to differences in how people across age groups make financial decisions. “From a generational perspective, definitely [for] a lot of young people … the security and stability of their work, of their finances, it has become the most important priority,” Kim says. 

However, there’s also a growing contradiction. Despite young people prioritizing financial security, their spending habits — particularly on social media-fueled lifestyle choices — don’t always align with those goals. For many people, spending habits aren’t fully aligned with what they value most. “People just feel better when those things are in harmony,” Kim says. Finding that balance between financial aspirations and day-to-day spending requires greater self-awareness and intentionality.

This generational tension between security and spending is emblematic of larger cultural shifts. As Kim notes, the younger generation is navigating a world of increasing contradictions, where values like body positivity coexist with rising consumerism in industries like aesthetics. Understanding these contradictions helps leaders and advisors guide younger generations toward financial well-being and more thoughtful decision-making.

From the ripple effects of the pandemic to the evolving values around work, relationships and money, Kim’s insights provide a valuable roadmap for leaders looking to connect with and support their teams across generations. 

People in This Episode

Kim Lear: LinkedIn

Transcript

Kim Lear:

I think from a money perspective, we have a lot of people where the things that they say and the way that they’re behaving are pretty far off. And people just feel better when those things are in harmony. I think that is an opportunity as well for advisors to provide a little bit of that friction to make sure that people are spending or saving their money in a way that really aligns with where they want to go.

Ryan Goulart:

That’s Kim Lear, founder of Inlay Insights. We’re talking about how to prepare for the future generational shifts. I’m Ryan Goulart and you are making the ideal real. Kim, welcome back to “Making the Ideal Real.” You were one of our first guests in our inaugural season of this. And I’m sorry it’s taken us this long to come back to this, but welcome back.

Kim Lear:

Thank you. It was wonderful to be here the first time and I was excited to be back again. Thank you for having me.

Ryan Goulart:

You’re welcome. I’m excited to jump into this topic because I know it’s a topic that you are passionate about and people love to hear, and that is trying to understand other people. And your vantage point on trying to understand other people is looking at it from both a micro and macro standpoint of generations. So do you perceive that people get more excited to learn about the younger generations than their generations that they’re currently in?

Kim Lear:

I think it kind of depends. I never create any content on only one generation because… I think that what excites people the most, even if on the surface they say, “What I’m really interested in is the youngest generation, and kids these days, and why is it different, those types of things.” I think actually what people are really interested in is change. And I think this topic of generations, it’s the most human way to look at change, to ask ourselves these questions. How come my child’s childhood is so different than my childhood was? Or how do I want to age differently than my parents are aging right now? These evergreen questions float around in our mind. Yes, I do still have clients who are like, “We want you to come in and it’s just Gen Z.” It genuinely would not be as interesting because people love context. People love understanding their place in history. That is what I like to do. That’s the type of material I like to read, and therefore it’s the type of material I like to create.

Ryan Goulart:

Again, what you just said about how people are assessing change, what are some macro trends that you’re observing in your research of what’s happening with change, particularly right now?

Kim Lear:

I mean, where do I start? It’s funny because I’ve been doing this for such a long time where I understand that every moment in time has this sense of urgency, this feeling of like, oh my God, change has never been happening faster. And some of these generational opportunities or generational points of friction have never been hotter, but they have been. So there’s always these big things that happen. 

I think some things that are really top of mind for me that have been interesting is still looking at the ripple effects from the pandemic. And I know that people are so over the pandemic, which I get and I am too, but we’re only now just far enough away from it to begin to comb through a bunch of data about school closures, about an unceremonious catapult into adulthood, about remote work. All of these big issues we’re only now just far enough away to really understand some of these ripple effects. And so to me, I think that’s been really interesting to see.

Even between Gen Z and Gen Alpha, some of the trends, some of these Gen Z ethos that there’s a pendulum swing away from and some an acceleration of. Gen Z was really the first to have this phone-based childhood, and we’re already seeing with Gen Alpha, with today’s teenagers that we’re really shifting away from that. From a parenting perspective, from a policy perspective, but also from kids themselves having a really different idea around what technology, social media, phones, what it does to them as a fifteen-year-old. And there’s also more young people sitting in the driver’s seat of this relationship. That’s been really interesting.

The youth mental health conversation has changed quite a bit. The youth mental health crisis started in 2012, and that’s when interventions started to be placed into the K-12 environment. And so again, now we’re far enough from that 2012 intervention to measure the effectiveness of those interventions. And some things really helped. There were some things that really benefited young people as they worked through this crisis, and there were some things that had negative unintended consequences. And so with youth and mental health, there’s a lot going on there around what have we learned, what went right, what should we expand on, what went wrong, what do we need to get rid of. The tribalism created by social media and how do we get things back on track, put in some guardrails so that people can build bridges to one another, I think that’s been an interesting topic.

Some differences between young men and young women. I know that there’s been a lot of conversation about this, weirdly in the political space, which I’m like, “I don’t really understand what’s political about this.” But this story of the era right now being like, “Oh, I didn’t even know that this was so political.” It’s something that I might’ve even talked to this audience about before because it’s a trend I’ve been following of young women at this point now they’re the majority of PhD holders, the majority of graduate degree holders, the majority of undergrad students. 70% of high school valedictorians are young women. I think it’s an interesting thing because when I go through these statistics, some audiences have this feeling of like, yeah, or did. And now there is much more of this, of like, what’s going on with young boys in America? There’s something going on with each of these groups.

It has impacts on the dating market. It has impacts on the marriage market. It has impacts on the ability to have children for those who want to. I mean there’s so many things that happen from that that I think are worth exploring. So it’s an election year. Really interesting polling data. Something that I’m looking at closely is how Gen Z is much more ideologically diverse than millennials were at the same age. The millennials, from my perspective as a researcher, were a little bit easier to study politically, especially during that Obama era because they voted as such a block during that time. Gen Z really doesn’t. I mean, it’s quite diverse. And so I think that’s been interesting and has implications on messaging, values and priorities and all of these things. So those are some of the trends. Those were my most top of mind.

Ryan Goulart:

Yeah, it is fascinating too when you start to talk about just the way in which… And I didn’t have the experience of having to do class online. I didn’t have the experience of having to graduate basically on a camera, on screen, and then you get this weird introduction to, guess what? You’re an adult. And that remote work piece because I definitely see that. I think there was something I saw on Bloomberg a few days ago about… It’s a mining company in Perth, Australia where the billionaire CEO says that you have to be… Pretty much if you’re not working at your desk, you’re not working at all. Which is like, “Whoa, what are you talking about? I have a laptop.” But there’s a lot to say about that. So speak to what type of remote work, hybrid stuff you’re seeing.

Kim Lear:

I tread lightly on this only because I don’t want it to come off as I’m like, all right, everyone back into the office. I’ll get into data in a second, but before that, I’ll start with just a theory that I have, is that our country is very, very divided. And I do think that a lack of in-person meaningful moments, of experiential moments with people who are different from you contributes to that. There’s a million things we could say about echo chambers and social media and optimized algorithms and all of that, but work was really the last bastion of ideological diversity. Because all the way back in the late ’90s, sociologists were writing about the big source, which was that even neighborhoods were becoming ideologically homogenous and churches were becoming ideologically homogenous.

Based on someone’s zip code and where they worshiped, you could predict very accurately who they vote for, what they believe in, all of these things. But work was still this place where it’s like, you got to row the boat in the same direction with people who are very different from you. And so there’s part of me that I hold onto that because I think there’s something very civilizing about the work experience and the workplace itself that forces rowing that boat in the same direction towards a worthy goal. So there’s that aspect, which I’m like, “I feel like that’s almost a bigger conversation that we just have to be like, what future are we trying to create here? What are the levers that could be pulled in order to help with that?” So that’s one aspect.

The other is that a lot of young people do want some in-person work. There’s a lot of reasons for this. I think one that people forget about is that statistically people are less likely to marry their high school and college sweethearts, and so we have a lot of young people who are single. And after college, you meet people at work and then you all go to happy hour and one of your work friends invites their college buddy from Michigan and whatever. It’s just a way that people meet. And so there is a craving for some of that social outlet. There was also a really interesting study that was done between the New York Federal Reserve, Harvard University and University of Iowa where they were looking at remote work and its impacts on mentorship, succession planning, all of those things.

One of the findings was that older workers are more productive at home. They already have social capital, reputational capital, they’re in an executionary phase of work. They know what they’re supposed to be doing and what they’re supposed to be delivering on. But younger workers, there hasn’t been a great way to really transmit mentorship, organic relationship building, some of these teachable moments over a screen. So leaders are in a very difficult position right now because they’re basically being asked to sacrifice older worker productivity for the sake of younger worker growth. And I don’t know the quick answer on that. That is very difficult. But there is this misconception that it’s like, young people don’t want to come in and it’s all these older people that want to come in.

If anyone’s followed what’s happened in New York. Manhattan was the first to be like, “All right, everyone’s back in.” I’m like, “Half your leaders live in Palm Beach. What are we doing? What is this facade?” It felt like a weird skit. You need to look at how do we get leaders back in, in a really generous, meaningful way? How do we create these workplaces that are more experiential and more immersive? And we can’t go back to the 2019 work environment. That’s for sure. And I think people don’t want to be taking PTO to go to a one-hour dentist appointment. We can’t police time the way that we did in 2019, but there is this sweet spot that I still don’t think we’ve quite mastered.

Ryan Goulart:

Ryan here. Are you interested in learning more about what drives you, what drives others? I’m excited to share with you our 2024 State of Values Report, packed with understandings on what drives people. Download your copy at think2perform.com.

Yeah. It’s a fascinating distinction between what younger workers are craving and the experience of the older worker who has amassed that experience while working in an office and somehow discounts it as a way to you should get here too type of thing. What we’ve seen in the values play that we’ve been amassing data on of where people are experiencing their values. One of the things that resonates with what you just said was that for younger workers, they value categorically interpersonal relationships and financial security. So they’re in their job amassing that type of event. For those that are in the older demographic, what they value are traditionally, again, categorically care for others or impact. What you’re looking at is just again, the wisdom and the experience that they’ve accumulated over time, placing a higher value on impact and care for others versus the relationship component. And the way we perceive that was that it’s just a higher level of interpersonal relationship, yet it’s a one-to-many, not a one-to-one.

Kim Lear:

Oh, that’s so interesting. I can’t wait to comb through this. And that interpersonal relationship piece… And again, I talked about this the last time I was with these groups all those years ago. I was looking at this uptick of enrollment in tech-free summer camps for kids. I was looking at this rise of Montessori and Reggio pedagogy for children. There was already this focus from parents, but then also, like I said, in some ways coming from children themselves that this in-person, that this interpersonal human connection had to be put back in some ways at the forefront. Because it doesn’t need to be the default anymore, which means it requires a little more intentionality. And this is the first year with this group of students that I’m with for 10 years. I started with them in 2020. So this past summer I was with them and doing the research. This was their first year in the workplace.

There was a difference between those who were working this first real grown-up job in person and those who were doing it either primarily remote or primarily hybrid. There was a difference. There was a difference in this feeling of forward momentum. There was a difference in loneliness. There was a difference in optimism. So it’s something that we just have to follow. And the thing is… I know people are so over the pandemic. But if someone were to ask me in 2004 how I think 9/11 impact millennials, I would’ve been wrong. I wouldn’t have said the right thing. We don’t know for such a long time. So you have to stay dedicated to the following of it, to the study of it, to understanding how these black swan moments now trigger this series of events that we could not have foreseen. And if as a researcher you buy into the fatigue of like, “All right, it happened. Let’s get over it. Let’s move on,” then you miss the story and you stay with the wrong story that you concoct in the haze of the aftermath.

Ryan Goulart:

Yeah. And as a researcher, you have to have a long-term view. I mean, behavior change is subtle. A lot of the research that you do on all of these movements is about change, and change is subtle. It happens slowly, and the actual impact won’t be realized until 2030 at minimum. One of the things, too, that I know you do quite a bit of work on too, is just attitudes about money. Money is so emotional. And it also transcends generations, it’s a human thing, but people view it differently. So how is money working for generations and how is it not?

Kim Lear:

I mean, it was interesting what you said about your study of showing that young people… Did you use the word security or stability?

Ryan Goulart:

Stability.

Kim Lear:

Yes. And so Boston Consulting Group, they do a longitudinal study of looking at priorities at work, and they’re ranked in the top 10. And I believe they started this in maybe 1980s. So it’s been a long-term data collection. And it’s a study of youth. This year was the first time, since they have done this, that financial security and stability was the number one priority of young workers. And so from a money perspective, I think that part of what happens is all people have their own amount of risk that they can stomach. And I think the world feels risky. We could argue all day about is it actually riskier, and there’s this thing. But if we go by what people feel, I think that’s part of it. And so I do think that there are a lot of people across the board, but from a generational perspective, definitely in a lot of young people where the security and stability of their work, of their finances, it has become the most important priority. Which again is why I think for advisors it’s…

If you’re a good advisor right now, it’s just nothing but opportunity. Because people are so anxious, people are worried, I think people are letting some of their fears stop them from trying. And so it really is an opportunity. So yeah, from a money perspective, I believe that that’s part of it. And some interesting money trends are things, again, that have been followed for a long time. But the lifestyle that is portrayed on social media at this point, even in this current era of authentic social media, it’s very expensive lifestyles. And so I think one of the attitude-behavior gaps that we’re seeing with young people is saying, financial well-being, financial stability, financial security is my top priority, but their spending habits still feel a little out of control.

I do a lot of work in the aesthetic space. Just as an example. So aesthetics, we’re looking at medical-grade skincare. Very expensive. We’re looking at Botox and fillers and all these different things. And the amount of money that Gen Z spends just in the aesthetic space is astronomical. And so this is also the generation that brought us body positivity, body neutrality. People are filled with contradictions. And so of course, a generation, it’s filled with contradictions. It doesn’t mean they don’t believe what they say, it’s just this is how people are. So I think from a money perspective, we have a lot of people where the things that they say and the way that they’re behaving are pretty far off. And people just feel better when those things are in harmony. I think that is an opportunity as well for advisors to provide a little bit of that friction to make sure that people are spending or saving their money in a way that really aligns with where they want to go.

Ryan Goulart:

It’s an intentionality thing. If they are more intentional or at least making decisions that have that mindset of this isn’t me. I guess it’s a bit of self-awareness of… If they were to have a little bit more… even just a fraction more in those situations of rather pulling out a credit card. Buying that thousand dollar trip to put on social media isn’t a great idea.

Kim Lear:

Yeah.

Ryan Goulart:

I guess I’m gutting it towards more individualistic.

Kim Lear:

That is individualistic, but I also… A question that has been on my mind for 15 years that I think I wrote about for the first time 10 years ago, is this question of generational perceptions of sacrifice. What am I willing to sacrifice? I mean, it impacts money, it impacts politics, it impacts consumer behavior, all of these things. And it is this question of… When I work with purpose-driven brands, this question is: What am I willing to sacrifice to align myself with a purpose-driven brand? Because sometimes those purpose-driven brands, they are not the ones that have the most convenient tech. Sometimes it’s not that. And sometimes people are like, “That’s fine. I don’t need the perfect app. I’d rather have this.” Different things have to be sacrificed. Or what am I willing to sacrifice for my job? There’s give and take and things like that.

What am I willing to sacrifice for the safety and security of my future? So that idea of sacrifice, of course, there’s an individualistic aspect of it, but there’s also a generational story that exists about what could be sacrificed. When you go back to traditionalists, the greatest generation, this generation that has this legacy of being builders, setting aside their individual needs in order to achieve the needs of the greater good. And so over time, that idea of sacrifice changes and shifts. And it’s not right or wrong, but it’s worth understanding what that is.

Ryan Goulart:

Older generations, they have more experience, but they in some cases made intentional sacrifices along the way and accidental ones too. So one of the tradeoffs with younger professionals is to understand that sacrifice more, right? And to just go in less blind.

Kim Lear:

I’m so glad that you brought that up. For years when I would do interviews with older people and ask them about their pathway to success, that pathway was filled with sacrifices. Along that way, there was failed marriages, missed anniversary dinners, there was missed ballet recitals, and missed softball games. I mean, there was a lot of personal sacrifice that went into that older way of climbing the ladder. And I think for a lot of good reasons, people are no longer willing to make those sacrifices. And I think in the long run … I try to be objective in the fact, I’m not here to decide what’s right and what’s wrong, but we’re trying to look at what is, and I do think that is a part of it.

And the original promise of technology was freedom. And when you go back and you even look at the science fiction of the 1960s, as these science fiction writers would write these amazing utopian stories about this time when you could live in a city, you could live near a stream anywhere, and everyone could still contribute, and everyone could still be connected. And it really was viewed as this possibility of utopia. And so sometimes I think it’s valuable to even look at what were we promised with this technology. And freedom was such a core part of that. And people are not willing to give that up, which I think is… I don’t want to say good or bad. This is where we are. So that’s what I meant when I said with the remote work piece specifically, that there’s still a lot of experimentation going on so that we find that right balance between honoring autonomy and freedom without completely sacrificing culture.

It’s that balance that we’re still in. And even though people are over the pandemic, and even though people are like, “That never even happened, let’s just ignore it.” It did happen, and it completely transformed the way that we work, the way we connect, the way we communicate, the technologies that are possible. And so it’s why I still think it’s important that we stay connected to where we are because we are in a time of experimentation. But if you imagine that landing pad, that place when we do finally find this way to be free and to find meaning and togetherness will be remarkable. That’s what we wanted. And in some ways, that’s what the promise of technology was.

Ryan Goulart:

Awesome. Well, thank you very much, Kim, for coming on.

Kim Lear:

Thanks for having me.

Ryan Goulart:

As we wrap this episode, we’re committed to helping you make the ideal real. If you found this program helpful, share it and help someone else make their ideal real, too. Until next time. For think2perform, I’m Ryan Goulart. Take care.

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