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Summary:

In this episode, Mallory Mejias sits down with UX and content strategy expert Bryan Kelly to explore how the longevity economy—a massive shift toward a population dominated by adults over 50—is transforming digital experiences. Bryan dives into why designing for older adults is less about age and more about behaviors, values, and life stage. He breaks down the common UX mistakes organizations make and shares practical strategies for building trust, clarity, and confidence into every member interaction. The duo also discusses the powerful, and sometimes dangerous, intersection of AI and age bias, and how associations can prepare for a more nuanced, age-inclusive future. Bryan will also be keynoting at digitalNow 2025, so consider this your sneak preview!
 Bryan Kelly is a UX and content strategy leader focused on creating digital experiences that work better for adults over 50. He’s delivered measurable results for brands like McAfee, Premera Blue Cross, EXPRESS, Home Depot, Orange Theory Fitness, and FedEx by transforming user insights into revenue-driving features. Blending product strategy, UX expertise, and business acumen, Bryan helps organizations better serve this experienced and influential audience.
 
More About Bryan Kelly:
https://www.linkedin.com/in/bryankellynow/

Timestamps:

00:00 – Introduction to Bryan Kelly
01:55 – Bryan’s Podcast Legacy: Association Mavens & Pushing Send
04:00 – Bryan’s Journey into UX and Content Design
07:38 – The McAfee Moment: Discovering the Needs of Older Users
09:42 – What Associations Get Right (and Wrong) About UX
13:15 – The Age vs. Life Stage Myth
18:05 – Rethinking the 50+ Opportunity
24:08 – Breaking Age Stereotypes and Language Norms
28:18 – The Hidden Potential for Associations
37:27 – Actionable UX Strategies for Serving Older Members
48:29 – The Age Bias Lurking in AI
53:58 – Closing Thoughts

 

 

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🛠 AI Tools and Resources Mentioned in This Episode:

 

Claude ➔ https://claude.ai
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MIT AgeLab ➔ https://agelab.mit.edu
Stanford Center on Longevity ➔ https://longevity.stanford.edu

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Amith Nagarajan is the Chairman of Blue Cypress 🔗 https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

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Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space.

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Read the Transcript

🤖 Please note this transcript was generated using (you guessed it) AI, so please excuse any errors 🤖

[00:00:00] Amith: Welcome to the Sidecar Sync Podcast, your home for all things innovation, artificial intelligence, and associations.

[00:00:14] Mallory: Hello everyone, and welcome to today's episode of the Sidecar Sync Podcast. My name is Mallory Mejias, and I'm one of your co-hosts along with Amit. And today's episode of The Sidecar Sync Podcast, we're exploring how the longevity economy, which is a massive demographic shift toward adults over 50, is reshaping digital experiences, membership models, and the way organizations design for audiences.

[00:00:40] Our guest today is Bryan Kelly, a UX and content strategy leader focused on creating digital experiences that work better for adults over 50. He has delivered results for brands like McAfee, premier Blue Cross Express, home Depot, Orangetheory Fitness, and FedEx, blending product strategy, [00:01:00] UX expertise, and business insight to help organizations better serve this high value, often overlooked audience.

[00:01:08] In our conversation today, Bryan shares why designing for older users isn't about age necessarily. It's about behaviors, values, and life stage. The biggest UX mistakes organizations make, including so-called senior modes and how to avoid age bias, practical ways to build trust, clarity, and confidence into every single member touchpoint and how AI fits into all of this, where it can personalize and enhance experiences and where it's hidden age biases can quietly cause harm.

[00:01:41] This was a really fascinating and relevant conversation and I left it feeling energized about how associations can prepare for this next major demographic shift. Everybody, please enjoy this interview with Bryan Kelly. Bryan Kelly, thank you so much for joining us on the Sidecar Sync [00:02:00] Podcast. Before we have guests, I always like to chat, uh, for a minute on Zoom, and I was asking Brian if he was familiar with podcasts, if he had done podcasts before, and I didn't realize I was in the midst of kind of a, a podcast legend.

[00:02:13] Bryan, if you could share a little bit about that and then tell our audience more about you, more about your background as well.

[00:02:20] Bryan: Absolutely. So yeah, I've got a, a pretty close association, long history with the team behind, um, sidecar and all the Blue Cyprus families of companies. And so I probably about 13 years ago was the VP of marketing at Appify.

[00:02:37] And we had a, a show called Association Mavens that if you're watching this and you remember that, um, we had a good time interviewing some really fascinating people in the association space. And, um, it was great to be able to share those interviews. And I've done a number of other podcasts for Rasa. Um, we did Pushing Sin where we did like a narrative style podcast.

[00:02:58] It was overly [00:03:00] produced and had like narration and music and interview clips from, from these experts. Um, so that was a lot of fun and we did that for I think two seasons. Um, is it still out

[00:03:11] Mallory: there? Is pushing send still out there? I

[00:03:13] Bryan: dunno if they, I don't know if they still have the live, um, audio. I, I know they've got like the show notes and all the episodes on the Rasa website there's a section called Pushing Send.

[00:03:23] Um, and, and they've got all that. And I think actually the email newsletter for rasa, like the weekly newsletter, right. I think they still call that Pushing sin. But, uh, yeah. Well that's awesomes the story. Maybe we have, maybe we have some

[00:03:33] Mallory: listeners let us know. Uh, you can actually send us a text from the link in the show notes and let us know if you watched or listened to Association Mavens.

[00:03:42] I did not. That was a bit before my time, but we are honored to have you on the pod, Brian.

[00:03:48] Bryan: Yeah, thank you. Great to be here.

[00:03:50] Mallory: Can you share a little bit with everyone, your background, kind of where your expertise lies, um, and what you're up to now? [00:04:00]

[00:04:00] Bryan: Yeah, so as I kind of mentioned, I, my career started in content marketing.

[00:04:06] Um, had one of the, I wouldn't say first blogs, but like an early, early blog like circa 2005, um, that I started. It was based around a company that I, I had owned with a couple of partners, and we use that to attract, you know, our ideal customer and then ultimately. Connected what we were selling, um, to that audience.

[00:04:29] And it, it was a very successful business. Uh, that was when content marketing was easy. Mm-hmm. Um, but kind of over the year, and I've always been involved in tech, um, in some way, shape or form. Early on the, in my career, mostly on the marketing side. Um, and there's kind of this gray space, uh, depending on the, the organization and it really, really the size and maturity of an organization where there's marketing and user experience.

[00:04:57] Um, a lot of times marketing is making UX [00:05:00] decisions, uh, about websites for other digital experiences. Maybe not necessarily applications, um, or apps and web apps, but. That was where I kind of had some exposure. And then the last several years I've been working as a, as a consultant with, uh, larger brands on their user experience strategy, and I.

[00:05:25] You may or may not know what that is. It's a term that gets thrown around quite a bit. Ux. Mm-hmm. So I can define that real quick, but really like what UX strategy is, is it's defining the vision for how a user or a website visitor should experience a digital product or service. And then it's kind of making sure that that user experience supports what they need as, as the customer and ultimately like what the business goals or the business objectives are.

[00:05:54] So it's a balancing act to try and figure out like what's the thing that's most helpful to them, but also helps us [00:06:00] achieve our goals. Um, so there's a lot of things involved with that. Things like creating, uh, user journey maps and figuring out all the touch points through like a sequence of, of steps, or we call it like a user flow, um, and making, you know, improvements to those experiences and suggestions on how to make them better, less frictionless, et cetera.

[00:06:24] So there's a lot of research that goes into that and data that guides those decisions. But ultimately that's like the focus of UX strategy. Then I've specialized in an area called content design, which really is driving the overall user experience and also, um, the ui, AKA, the user interface, um, for all sorts of digital experiences.

[00:06:48] But the focus is on language and information and making sure that when somebody lands on a particular page. Let's say for example, um, in an app where [00:07:00] they're maybe like logging in and then like what happens next after they log in and what's the expectation of that? Uh, individual making sure that there's alignment with the content that appears or the directions that are provided or, you know, the.

[00:07:15] Text on the button or the label. So there's just a lot that goes into really thinking about the, the content decisions and ultimately how that supports the visual. And the way that the, the page itself, um, is, is architected, right? Mm-hmm. Built digitally, uh, in the digital environment. So anyways, that's what I've been focusing on and the last few years, um, kind of by happenstance I was working with.

[00:07:45] McAfee and McAfee, I was working with them as a consultant and after six months, um, they were trying to hire me and I was like, no, I, you know, I'm good with being a consultant. And then they kept pushing and so I ended up, I took a, a full-time [00:08:00] position with them and the deeper I got working on that project, um, I saw that there were a lot of older, quote unquote, older users that were using McAfee in.

[00:08:11] McAfee's strategy was really trying to go after a younger demographic, and there was just like this real hard or misalignment between the business goals and the reality of what the existing customers like, who they were, why they were important. Um, and so that kind of was one of the first experiences that I had that opened my eye to like, I, I think we're getting something wrong here.

[00:08:36] Um, I was able to begin to go down this, this road of understanding what exactly older users, uh, needs are when it comes to a digital experience. And, you know, from that point on, I started looking at, you know, I would actually do research studies with users experiencing like, how I gotta sign into this thing and being like, oh my gosh.

[00:08:58] Like this is something that [00:09:00] as a quote unquote younger user. Like, it just makes sense. Like you do this and you click that and you enter this information. But then to watch somebody from a different generation go through those, those steps and, and you know, like they're thinking something totally different.

[00:09:15] Their mental models are different. Um, so that kind of sparked the curiosity and led me to research that even further. And ultimately what I discovered was some pretty shocking things, uh, which we can get into. Um, but that kind of sets the stage of like what I've been doing, um, kind of, you know, what that actually looks like.

[00:09:36] And some of the breaking down, some of the jargon behind UX and UI and all of that. So yeah,

[00:09:42] Mallory: I really, I appreciate that, Brian. I feel like UX and UI are both phrases that are thrown around a lot, and I was thinking about this prepping for. The podcast, no one ever really sat me down and said, this is what UX means.

[00:09:55] Like, here are the core principles. Right? Because that's not what I studied in school. So it's, [00:10:00] it's very helpful I think when someone with that expertise shares exactly what it means. I love how you kind of ended on a cliffhanger there with. Shocking things about older users. We're gonna get into that.

[00:10:10] Yeah. But before we do, uh, I wanna at least spend maybe a few more minutes on UX and ask you from an expert's perspective, are there any major, or maybe one thing that you find organizations tend to get right with ux and then one thing that they tend to get wrong. I don't know if you can boil it down in that simple of a way, but that might help some of our audience grasp kind of what it entails.

[00:10:34] Bryan: Yeah. Um, well, I think if you are a user of any piece of software or app, uh, mobile device, you know, we're all using these things and regardless of, of our age or generation that we came from, like they're everywhere. They're ubiquitous. And I'm sure you've had frustrating experiences where you're like, ah, I can't find what I'm supposed to do with this thing.

[00:10:57] Or, you know, how, why are they making this [00:11:00] so difficult?

[00:11:00] Mallory: Yep.

[00:11:01] Bryan: Um, and so that's the thing with, with user experience design is it's, it's science, but it's art. Um, and there's, there's so many variables to account for that. It's, it's almost impossible to get it. Perfect. Um, and so I think, you know, you could probably think, you know, there's certain categories of apps that always are a bit more challenging.

[00:11:23] Banking tends to be one that's really, you know, cumbersome, um, or any type of financial related, um, digital experience. A lot of times, you know, there, there's some. Companies or brands that are doing really great things in that. But in general, like it's fi financials, uh, financial apps are like pretty tough to use, um, especially when it comes to banking.

[00:11:45] But then, you know, the things that I see being done right are the organizations that are really trying to understand who is using this. What's the most important thing to them? Like how are they coming to this [00:12:00] thinking that we're gonna help them with X problem and making sure that all the decisions that go into what that ultimate user experience ends up being is aligned around that.

[00:12:11] And so that's where you might have certain apps that you use where you're like, um, this just makes sense. Mm-hmm. This just mm-hmm. Is so easy and effortless and I can get in and I can get out, or, you know, I can find the information I'm looking for. Those are the, the situations where, you know, they're, they're, they're doing enough of the right things to make it, you know, and I'm sure even in those situations you might be like, yeah, but I wish they could also Right.

[00:12:35] Do this and include that. Um, 'cause nothing is ever gonna be perfect. And there's even with a, um, a cohort, cohort of users that are all aligned around certain values, um, or worldviews or, you know, the psychographic elements that make them want to use the app. They're all also, you know, a hundred different shades of, of variations from that.

[00:12:59] And so [00:13:00] it's never gonna be 100% perfect for mm-hmm. Every user. 'cause you know, typically you're, you're, you've got thousands or hundreds of thousands or even millions of people using these tools, and it's impossible to try and get it perfect for every single one of them.

[00:13:15] Mallory: Yep. That makes sense. Okay, so dialing into the longevity economy mm-hmm.

[00:13:21] We talked, you kind of like segued into this as a great podcast host would. Um, we have an older generation. We have older users that are using technology. Yeah. Um, digital applications, programs, software, whatever that may be. And so you mentioned that you have, you started to research this, you found some shocking things, but I guess can you kind of.

[00:13:43] Paint the picture first on why this demographic shift matters so much at this moment in time.

[00:13:50] Bryan: Yeah, it's fascinating because as I started researching on my own, you know, like what, what am I getting wrong as a UX strategist when it comes to understanding the [00:14:00] quote unquote older user, which is kind of a loaded term we'll talk about in a minute.

[00:14:05] But older users, um. There's a lot of older users, and with each year that passes between now and 2030, there's gonna be more and more. And so organizations that are focusing on, we've gotta, we've gotta do things for Gen Z, we've gotta start getting ready for Gen Alpha that's coming behind them. Um, you know, for the last 10 or 15 years, it was all about millennials and you know, that that is an important thing to consider.

[00:14:33] But when you look at the data. Um, and so I, I mentioned 2030 by 2031 third of Americans are gonna be over the age of 50, including the oldest millennials. So when you step back and you think about that, like that has tremendous implications for anybody who's designing, creating, architecting digital experiences, whether that be apps, [00:15:00] websites.

[00:15:00] Membership sites, whatever, anything that's digital and requires somebody to go to a device to access that service, that product, what have you. Like you're talking about a very large number of users that are older, and so when I mention this, this kind of shocking fact, a lot of people are like, okay, yeah, that, wow, that is kind of eyeopening and mind blowing, but.

[00:15:29] When I say 50 and older, right? People think senior and that's part of it. There are senior, quote unquote senior users who have certain, um. Things that need to be considered. Accessibility typically is something in user experience design circles that gets talked about. Um, you know, the size of the font on the screen, the, um, you know, the way that buttons are like on a, on a mobile [00:16:00] device where they have to tap, you know, making sure that like, that's big enough.

[00:16:03] 'cause they might, motor fine motor skills aren't quite the same as they were when they were younger. You know, there's a whole host of things like that that. Are, are pretty well talked about in user experience circles, but we're talking 50 years old. I'm almost, I'm not quite there yet, but I'm inching towards 50 myself.

[00:16:24] And when you think about it, I'm, I'm a cusper. I'm like Gen X. Slash gen, gen y, millennial. Um, so I was born on the cusp and you know, I don't really consider myself necessarily Gen X, but if we just look at like the right, the bookend, they typically say from like 1980 until, um, 95 I believe. And like, okay, we're all starting to get close to 50 Gen Xers.

[00:16:53] You know, the true, what I consider the true Gen Xers who are a little bit older than me, um. Like they, they are [00:17:00] 50, right? They're the oldest ones are, are 60 this year, like 60-year-old Gen Xers. Like these are people that grew up listening to nine inch Nails and you know, Dr. Dre and. You know, it's not what you're like, oh yeah, this, the, the six, whatever you think the, the stereotypical 60 something year old is.

[00:17:21] I can tell you that's not the Gen Xer and the Gen Xers don't see themselves that way. Um, even baby boomers, you know, they, they'll see like depictions of, of like, you know what everybody else thinks is a boomer. And they're like, that's not me. Exactly. Like, you've got it all wrong. That's not me.

[00:17:37] Mallory: Yep.

[00:17:37] Bryan: Um, and so there's this ageism that's just kind of permeated throughout all of our.

[00:17:43] Society, um, is certainly permeated through our, into our psyche and how we think about these things. And so, yeah, when I talk about this big thing that's happening underneath our feet right now, it's being overshadowed by ai. Um, in many ways it [00:18:00] makes sense. You know, AI is kind of this big crazy thing for everybody to wrap their heads around.

[00:18:05] That's gonna have huge implications, but it's kind of like being. Missed. Most people aren't really aware of this, this shift that's happening, happening demographically and the implications of that. And so that's where I'm really focusing a lot of my energy and effort is, is beating the drum on that and saying, look, when we think about building any type of digital experience, like we need to understand that we're not just, when we talk about the, if you, if you get the significance of this stat of 2030 and how the large majority of.

[00:18:39] People in America, but also globally are gonna be over the age of 50. You gotta stop thinking, well, okay, well now we need to shift gears and start designing for quote unquote older people. It's like, no. When you talk about the 50 plus demographic, it's a very nuanced, multi-generational group of people that have all sorts of different [00:19:00] worldviews, um, values, beliefs.

[00:19:04] Like there's a quite a number of things. And the thing that I've learned, um, in fact we were talking about this before we started recording at age 45, I moved to the world's largest retirement community and built, um, uh, like a winter, winter home. So I spent half the year there. And that experience taught me that if you talk to one 65-year-old, like you literally only talk to one 65-year-old.

[00:19:29] They're all very different. And, and to say like, oh, well, somebody who's in their sixties is, you know, X, Y, and Z, and somebody who's in their seventies is this or that, you know, it's totally missing the boat by focusing on age. Um, and so that's where I'm trying to steer the conversation is away from demographics.

[00:19:48] Even though understanding the demographic pieces important, but when you are thinking about how to improve your experiences and. Connecting this to associations, this is pretty [00:20:00] significant. Um, you know, when you think about member experience and all the digital touch points, you have to understand that we can't be breaking it down by age.

[00:20:10] We have to look at it using psychographic data, which ties into those things that I mentioned, like values, world views, beliefs, um, and the other key thing is life stages. So, you know, I think about myself. My, my wife and I are in our, our mid forties, mid to late forties. We, we don't have any kids. Um, we are snowbirds and we work, but we kind of, kind of work on our, our own, own terms as like consultants and stuff.

[00:20:41] So. Our life stage is very similar to actually a number of the people that I, I have as neighbors. Um, in, in the retirement community where they're kind of working still, they're, they're like, you know, semi-retired, but they don't, they don't want to quit working. They're just [00:21:00] kind of doing what they want to do and not feeling like they have to work a nine to five or be super focused on a career like they, they were earlier at a different life stage.

[00:21:10] Their kids are gone or grown up, you know, they're, they're married and, and have their own families. They oftentimes are, many of them are snowbirds as well. So it's like we're, we're in a similar life state, even though we're from different generations and we have different world views. Um, but there is overlap in similarities.

[00:21:30] And so if I'm trying to design a digital experience or optimize a digital experience for somebody who fits those psychographic, you know, data points, well I can't, I'm gonna totally miss the market if I'm like, oh, well, 65 year olds, right? And then you're gonna exclude people of my age who are close to 50 or in their fifties, that are in a similar life stage as those that are in their mid sixties.

[00:21:56] Vice versa. I mean, we can kind of make that argument all the way up and down [00:22:00] from age 50 to age 100. Um, I actually know a number of 90 year olds that are doing some pretty incredible things and like I aspire to that. Um, and so yeah, it's, it's just this really fascinating multilayered, textured conversation.

[00:22:18] And the, the keynote that I'll be delivering at, um, digital now, this fall in November. Is really gonna be tying this, this whole kind of multifaceted thing together into why is this important, why does it matter for associations? And like even connecting this into ai, which we can talk a bit about, um, further in our discussion.

[00:22:41] But that's ultimately why I think that this mega trend is significant because it's happening whether we're aware of it or not. Um, you know. AI is everywhere, right? But this demographic shift is bigger and more certain and it's impacting everything from [00:23:00] workforce strategy to consumer behavior. And when we talk about 132 million people roughly being over the age 50, um, in just less than five years, you know, four and a half years from when we're recording this, um, that group drives.

[00:23:17] Over $8 trillion in annual economic activity. And it's growing fast, it's going to continue to accelerate globally. When we look at the numbers, it's $22 trillion annually. So this is a massive market and if you're not accounting for that in how you design and serve and lead your members, your customers, um, you know, AI is not gonna save you from becoming irrelevant if you're not thinking about it.

[00:23:45] It can be a very powerful tool. And I also think that there's an opportunity here. Um, but yeah, it's, it's crazy that we're heading to this very, very significant shift. Um, like it's coming and it's also at the [00:24:00] same time it's here already. So yeah. Any, anything that is kind of mind blowing to you as I've ran through all of that?

[00:24:08] Mallory: All of it, all of it's mind blowing. The fact that you live in a retirement community at age 45. But no, Brian, I really appreciate you sharing the nuance of, of what we mean when we say older users. Also, I wanna just ask you, since this is an area that you actively research and talk about, what is the appropriate term, like as I move through this podcast, is it older users?

[00:24:30] Is it users over 50? Like what would you say?

[00:24:32] Bryan: Yeah, I think, um. It's actually funny. I, I've had a number of these conversations and kind of what the preference is. I can tell you, I can tell you what most quote unquote older adults do not like as being called senior.

[00:24:46] Mallory: Oh, I've definitely said that before on the podcast.

[00:24:48] Okay, so not senior, senior leaders.

[00:24:51] Bryan: I, I've been, I've been guilty of that. You know, like, like, you know, the senior, it's like, yeah, it's, that's, everybody thinks you get your ARC card at whatever age they start sending [00:25:00] those out and, um, right. And you're, you're a senior citizen, right? Mm-hmm. Um. But, and that's the thing too, is like the, again, I'll pick an age, let's say today's 60-year-old or 65-year-old, since that's kind of like the traditional retirement mm-hmm.

[00:25:16] Target age is way different than the 60 or 65-year-old from 20 years ago and earlier. Um, they are pioneering like a major shift in how people think about retirement, how people think about. Longevity itself when it comes to like, you know, physical, uh, fitness and ability. Um, they're redefining so many things and, and bucking the norm of what we think about.

[00:25:45] And that's what's been fascinating about living in, you know, America's largest retirement community is there's a lot of people that are living the traditional kind of. Myth of retirement, right? The myth that's no longer becoming [00:26:00] viable for the majority of us, like most people are like, I can't retire at 65.

[00:26:04] Like I'm nowhere near financially being secure enough to do that. I'm gonna have to keep working. And there's people that are like saying, you know what? I don't. I want to stop working. I enjoy working and it's gonna evolve and change. Or maybe I'm gonna start a second or a third career, I'm gonna go back to school.

[00:26:22] But like, this is the shift that's happening. Um, that just makes this a situation where you can't. Think about the assumption, you know, the typical assumptions of older age. And so because of that, I think that's where there's a lot of rejection of the labels that typically come with being older. And so senior is definitely a word you, you don't want to use or you know, senior citizen or senior adult.

[00:26:46] Right, right, right, right. So yeah, to answer your question, I, I think the things that typically are accepted are older adult, you know. Age 50 plus. You know, the terms that I've kind of thrown around a little bit as we've been talking about it. [00:27:00] Um, I do think there, there's some that actually really like to be called elder, not elder Lee, but elder, um, such nuance.

[00:27:09] Yeah. There, there's a, a guy named Chip Connolly who was one of the. Co-founder, I don't think he was an original co-founder, but the co-founders of Airbnb brought him in as like a senior advisor. They were young guys that had all these interesting ideas, but they didn't have experience. And so they brought Chip Connolly in as another co-founder.

[00:27:28] And, um, he, he's since gone on and he's created, um, this organization called the Modern Elder Academy, and it helps people in midlife. Um, you know, kind of around their, their fifties and older to kind of understand what this shift means and all the things that are happening, um, that are changing in our world and what older age looks like now in, you know, as we get further and further into this millennial.

[00:27:54] And so, yeah, he's, he's kind of coined or, or labeled this, this thing elder. And [00:28:00] so a lot of people are like, yeah, I like that. You know, it's kind of, I'm mature, I'm experienced, I have, you know, wisdom that I can pass along to, um, those that. Are following behind me. Um, but then there's others that are, they, they associate very closely with the word elderly and they're like, I don't want to be, don't, please don't call me elderly.

[00:28:18] Mallory: Yeah. Okay. So there, there's some personal preference there, but thank you for sharing that. Hopefully that's, you know, it's very useful for me and hopefully for some folks in our audience too, because when you first, when we were talking about the topic for this podcast, I definitely had a moment of, you know, ooh, like that, that might be tough to discuss.

[00:28:35] And how do I approach that in. A polite way and in a correct way. So yeah, I think it's good to have these conversations. Um, Brian, and I'm assuming this is what you'll get into at digital now, so I won't make you share too much, but do you feel that associations are kind of sitting on this big trove of untapped value when it comes to users over 50?

[00:28:59] Bryan: Yeah, [00:29:00] absolutely. I think, um, I mean I can't speak for every association out there obviously, but. Um, I do think that there has been a, a, a major focus on AI for, and again, like I mentioned earlier, for a very good reason. Um, like it's not, I'm not saying that there, there's anything wrong with that. I think it's one of those situations where it's AI and the longevity economy as all the experts call it.

[00:29:27] Um, there, there's a group out of MIT. It's called the MIT age lab. And, um, there's a, a gentleman who kind of runs that. His name is, um, Joseph Kauflin. He wrote a book a few years ago called The Longevity Economy, um, which I think is where that, that term kind of originated from. It was his, his labeling of what this market is, um, and all the economic activity related to it.

[00:29:54] But they're researching, um, you know, this topic in depth and, and [00:30:00] specifically to like its impact on society at large. Um, and I'm taking a lot of what they're uncovering and filtering it through the lens of user experience design to kind of talk to my field and my industry. Um, so anybody that's involved in product management, um, product design, you know, tho those things, building and maintaining digital experiences.

[00:30:24] Um, I think there's, there's a number of people that are focusing on this in the advertising and marketing space, um, that are starting to, to beat the drum on that, which I think is good because marketing and advertising have a, a great deal of influence over society and how we think about things. Um, but I know there's a long way to go there.

[00:30:41] So when we think about associations. Um, being able to understand this first and foremost, I think is, is the first thing. And then looking at it and, and saying like, how is an association really poised for taking advantage of this, this [00:31:00] shift? And I think it's interesting because I've read a number of studies where there's, there's almost like.

[00:31:09] Experts are advocating for like a re-skilling of the age 50 plus adult. And especially when we think about some of these things with, there's a labor shortage, things are changing dramatically with what the workforce looks like, and there are going to be more people with a lot of, um, collected experiences, wisdom.

[00:31:37] Et cetera, they're potentially gonna be either forced out or they're, you know, gonna buy the, this myth of I'm gonna retire at 65 and like, I'm, you know, it's time for leisure. It's, it's not time to continue working. And so for those that are either rejecting that idea or that myth, [00:32:00] or, you know, whether it's by choice or whether it's by.

[00:32:03] They don't have a choice. They have to keep working. Um, there's a huge opportunity to re-skill them. Well, ideas have been batted around, amongst experts, around, well, what's the best way to do that? And typically, the last handful of years, the conversation is steered towards community colleges being really in a great position to help this cohort reskill or upskill, and do so in a way that's quick effective.

[00:32:32] You know, it's not gonna incur hundreds of thousands of dollars of additional debt going to like a traditional university. University programs are slow moving. What you're learning today is maybe not relevant today because it was right. The curriculum was developed two or three years ago. Um, and it's fast moving as everything is right now and accelerating.

[00:32:52] Like they're just, they're not set up for that. So community colleges, that's been one idea that's been batted around. Interestingly, I did [00:33:00] find, um. There's, uh, an expert out of Europe, um, who's been really pushing and working with the educational systems, um, and, and like the traditional universities to start to build programs that help and are targeted towards the older adult, um, the lifelong learner, or as they call it, the long life learner.

[00:33:23] Um, but like, I think Harvard's starting to pioneer some of these things and, um, I think Cambridge University is another one. It's very early days, but again, I mean that's, I I'd say those are the exceptions, uh, to the rule. So when I look at it and kind of my background, um, working with associations for a handful of years, um, that I think that this is, this is, I mean, no organization is probably better poised.

[00:33:51] To help older adults re-skill, and especially if we're talking about in specific trades or professions, um, whether [00:34:00] it's, you know, we could use AI as, as kind of an example of, of one thing that, that you could be re-skilled or up-skilled on, but. Whatever is relevant to the particular industry. It's like, hey, there's an opportunity.

[00:34:13] Not every older adult right now is, is I think maybe thinking along those lines. But when we look at Gen X, the mindset of, of a Gen Xer who's in their fifties, um, or you know, approaching their early sixties, they're like, I'm either not retiring or I can't retire. And there's a whole movement right now going on that's called Unre Retirement, and it's this idea of thinking about.

[00:34:36] Retirement totally different where it's like, I'm not, I'm not gonna retire. I'm just gonna evolve my, my career. You know, I've, I've built a very specific set of knowledge that's has value, and I'm looking at new ways to be able to deploy that value that looks a bit different than maybe the traditional job or career path that I've been on for the majority of my life.

[00:34:58] Um, and so [00:35:00] we're seeing more and more of that, and I think it, it'll be a, an. A very quickly accelerating trend over the next few years as more and more Gen Xers start to, to wrap their minds around what this means and what the next chapter of their life looks like. Um, 'cause I, I do know that they're, they're not thinking the Leisure v lifestyle, you know, golf and mm-hmm.

[00:35:21] Um, you know, social activities, that, that's, they're not interested in that. Uh, they wanna make meaningful contributions and they, they want to have, do it on their terms, but, um, you know, they're definitely looking at ways to explore that. So this is a great opportunity for associations to say, look, we have the resources, the channels, the experiences, um, you know, like when we talk about member experiences to help this cohort make this shift, to make this change, um.

[00:35:55] So, yeah, I mean, there's a, I'll get into it in the keynote, but there's a lot of things that [00:36:00] you gotta understand that are gonna resonate with the older adult. Things that are grounded in like clarity, respect, ease of use. Um, and not making the mistake that a lot of us make, and I've been guilty of this in, in my work as a UX strategist, is like dumbing it down and being like, Hey, let's make a senior mode, uh, for this experience.

[00:36:23] So I think, you know, that's one of the, the pitfalls of if you're an association leader, that's. This is resonating with, and you're seeing the opportunity and possibilities, like there's some pitfalls that you need to be careful to avoid when you start thinking about the overarching strategy and bringing in other key members of your team into the conversation.

[00:36:45] We are all loaded with so many assumptions about older age that when we think we're getting it right, we're abso absolutely, totally missing the mother. Um, so I, I have good news in my keynote. I'm gonna give you you some of the [00:37:00] things that you need to be able to, um, make sure that you're not stepping in it, um, and, and avoiding, um, what would come across as ageist mm-hmm.

[00:37:11] And offend those people that you're trying to actually help and reposition. Um. You know, your, your member experience around. So yeah, there's, there's a lot of cool things that I think are, are possible here and um, we're just kind of scratching the surface.

[00:37:27] Mallory: Mm-hmm. I'm trying to put myself in the shoes of our audience.

[00:37:30] And I imagine at this point in the conversation, surely everyone's nodding their heads and saying, ah, yes, we need to focus on the segment of our membership. This all makes sense. On the flip side, it also sounds very daunting and it seems like for. Resource constrained organizations like nonprofits, like associations, being able to capture the nuance that we've discussed in digital experience sounds very challenging.

[00:37:57] Uh, especially as you mentioned, you said there's [00:38:00] no 65-year-old that you've met in the retirement community. That's the same. And so given that I'm, you'll, you'll probably get into this in your keynote, but what are some like general. Directional advice that you could give to our listeners of, okay. If you're hearing me, if you're understanding that we need to focus on, uh, members over 50, here are some things you can do right now in preparation for that.

[00:38:25] Bryan: Yeah. Yeah. I've got some very simple practical tips. In fact, I just gave a, a talk, um, in May to a, a group of, uh, user experience designers and. It was a very short talk. I think it was maybe meant it was like a 30 minute talk and I was like, look like we, we have a whole workshop that we could go into of material.

[00:38:46] Yes. But I know you're here for some practical quick takeaways and so let me, let me just kind of give you some of the quick things that are gonna help if you wanna start to wrap your head around this. I do have a document that I put [00:39:00] together, um, that we can link to in the show notes. It's called Identifying Age Bias, A Framework for Age, inclusive Design.

[00:39:07] Well, it's content design, right? 'cause that's what I'm focusing on. But it has a lot of, um, very specific things that I think would apply to associations, because everything, not everything, but the majority of things that associations do is based in content, right? So I think there, there's a lot of good takeaways here, but the high level on some of this that I can share with you right now is that, and I alluded to this earlier in the conversation, the first overarching kind of principle or axiom is don't focus on age, focus on behavior.

[00:39:43] And so asking yourself questions like, what motivates this individual, this particular member. That's where you want to be building your, um, kind of strategy or brainstorming ideas of like, you know, what's really motivating this [00:40:00] individual, um, and getting into the psychographic level. Questions around, you know, what, what is the beliefs that they have?

[00:40:07] What are the values that they hold? What lens are they looking at the world through, um, at a particular stage in their life? And, and trying to really parse out those things and understand what does that look like for your membership? Bottom line. Do not focus on ho how old they are. Okay? That's, that's a huge mistake when you start to focus on age, like you've already lost that battle.

[00:40:33] Um, so throw that out. Any conversation that starts to gravitate towards age, nip it in the bud and, and regroup and start to focus on psychographics or continue to focus on psychographics. So that's the first one. The second one is. The other thing when it comes to older users that I've learned is you have to build trust and confidence.

[00:40:55] So when you think about those digital touchpoints, whether it [00:41:00] be the website, maybe even e, something that's relatively simple as email, um, or other types of digital communication, like how are you building trust and confidence, older users care about. Usability, clarity, security is another huge one. You know, like I said, I, I did a bunch of work for McAfee, um, or, you know, security, digital security, online security.

[00:41:24] I mean, oh my gosh, this is hugely important where when you talk to a Gen Z uh, individual, they're like. Like, what, why do I need, why am I concerned about online security? Like, isn't all my information's out there? That's the cost of being on the internet. Like they see no value in protecting their, their security online.

[00:41:44] Like it's crazy, um, for somebody who's older that's like, no, no, no. I want, I want everything locked down and I don't want anybody to have access to anything of mine on the web. So those are some of the key things that they're really dialed into when it comes to a digital experience. [00:42:00] So if you're asking yourself those questions, like, how do we build trust?

[00:42:02] How do we build confidence through these touch points? That's another thing that really is, is kind of a quick win to zero in on and start to help you. Um, the next thing is avoiding stereotypes. So I did talk about this a little bit, but again, no senior friendly. Shortcuts. Oftentimes we're guilty of, oh, let, let's make it easier for them.

[00:42:28] 'cause they have challenges with technology. Like that's a really common assumption that many of us make about the quote unquote, older user. And it's simply not true. There are older users that maybe, you know, are a little bit challenged when it comes to technology in a certain way, but look. They have been using technology longer than we have and you know, especially when we talk about baby boomers, like, I mean, man, they've been through so many major shifts [00:43:00] in the last 60 some odd years.

[00:43:03] They've been with it every single hype cycle. Um, AI being no exception. And so they're just a little bit more, you know, conservative, reserved. Like, I'm gonna sit back and wait and see like what actually happens with this thing. And then, okay, well maybe I should be using this and how do I use it? So they're, they're very adept to technology.

[00:43:22] The data shows that, you know, over 70 some odd percent of, um, again, older users. Are using technology, the web, they're using mobile phones, like it's, this is not like a minority. It's a majority of people in this cohort are using those things. So you gotta recognize that. And when you recognize that, that helps you avoid falling into those traps again, of stereotyping and saying like, oh, well this is what an older user needs.

[00:43:51] They need bigger fonts and they need that. That is part of it. Right? But there's more to it than that. It's how you're messaging. [00:44:00] It's how you're understanding their mental models when they're going through a sequence of things or they're trying to engage with something digitally. How are they understanding it?

[00:44:10] You know, what are they bringing to the table to make meaning of what you're putting in front of them? Those are the things that you should really be, um, putting a focus on and, and not getting into that like, well, this is what, this is what we know, or this is what we think. Um, avoid that. And then the last one, kind of the fourth and final one, is you can do a quick audit of your current content and that's where, uh, this download that I mentioned that you can grab, um, is something that you can put to work pretty easily.

[00:44:41] It's, it's a quick little reference. It's like a two pager PDF, and it's got, I believe, four steps that help you audit your content quickly. Just to, just to surface like where are there any age assumptions? Where are they showing up in your, your content or your experiences, your [00:45:00] messaging? Um, because I think that that's again, kind of a quick low hanging opportunity to be like, survey the land of all your digital touchpoints and be like, are we doing, like, are we missing the mark?

[00:45:12] Are we okay? You know, there's a difference between being okay and and optimizing it, but at least you get a sense of where you might need to start focusing to make some of these changes. So yeah, these four. Kind of guidelines or principles I ran through are the things that can get you started. There's a whole heck of a lot more that you, you need to understand.

[00:45:36] And, you know, I'd be happy to talk with anybody about it. But, um, these are very helpful, low hanging fruit opportunities to at least start to head the right direction and shift the conversation. Within your team and within your organization around how you're gonna engage with this, this kind of shifting demographic.

[00:45:59] Now the interesting thing is, [00:46:00] I'm sure you know there's probably a good percentage of the audience that's listening right now that's either my age. Older, um, that's like, yeah, like I totally get this, this makes sense to me. But when you think about the organization and you think about, um, kind of the core initiatives, like have, have these conversations been happening?

[00:46:23] My guess is probably not, and again, we always tend to think about like, well, the next coming generation, you know, we've gotta prepare for, and we've got to understand like what's important to them. I don't disagree that that is an important conversation, but when you look at it through the lens of they're the minority now, it's not, it's, you know, I, I think historically when we think about even like communications, like advertising, marketing, that has driven a lot of our stereotypes and assumptions about age for the past 75 years, thanks to the Mad Men, going back to the 1950s, [00:47:00] um, there's this idea that.

[00:47:05] You know, it's, it's like just ingrained in how we think and how we approach things. And so baby boomers fueled that baby boomers were the Gen Z of their time. You know, when in the, in the 1950s and sixties, this was a massive opportunity for businesses, organizations to build everything around this youth culture.

[00:47:28] Since then, it's created this cascading trend of each youth culture that's, you know, risen up from generation to generation until now has had a dramatic shift. I mean, we think about millennials. Millennials, they're a massive group, but we look at the situation we're now, where their birth rates are declining, um, in our country and across the globe.

[00:47:50] There's less and less young people. And so this is, again, that major shift that I'm talking about that's happening right now is we gotta stop focusing on youth culture and [00:48:00] really obsessing around this, this younger generation or cohort. We need to shift our focus to how are we serving the older cohort, because there's more of them in an increasing number of them with each passing year.

[00:48:13] Um, and so it's just this paradigm shift that is hard to wrap our heads around, but. Again, that's where I think the opportunity is. And so you can use these tools, these very simple tools, as a starting place to shift that conversation in your organization.

[00:48:29] Mallory: Mm-hmm. And I, I totally hear you. I've been to. I would say many at this point, conferences that are dedicated for association leaders and many of the most attended sessions are very much like how to Get Activate the Gen Z segment of your membership and so on and so forth, which is exciting and new and I understand that that's important as well.

[00:48:49] But I think. You bring up an excellent point that, uh, we're having less and less young people, so why don't we focus on, um, the bigger segment of membership. I do wanna talk just a [00:49:00] second. I know we're kind of at the end of our conversation and we've talked about AI scattered throughout. I just wanted to ask you about the intersection of the longevity economy and artificial intelligence as you've been speaking throughout this conversation.

[00:49:13] In my head. I'm thinking of hopefully a near future where we have personalized experiences within associations within the brands that we love, where perhaps we have content and landing pages that are. Kind of being optimized for us as individuals real time based on that psychographic data that you mentioned earlier.

[00:49:34] That's like where my mind is going in terms of the intersection of artificial intelligence and the longevity economy. But I wanted to know at a high level if there's kind of any other areas within that intersection that you think are wants to watch.

[00:49:47] Bryan: Yeah, I mean, I think in general, like AI and the longevity economy as two separate trends, like, don't think of 'em that way.

[00:49:55] Think of them as converging trends. Hmm. And I think the smart organizations are [00:50:00] gonna design for both. And I think that that convergence is really where the magic is. Um, because, you know, ai, like you said, the, the just a little use, uh, use case that you presented of like going to a landing page and it being like.

[00:50:16] Tailored to you as the individual. Um, that sounds like a dream. And unfortunately, I don't think we're there yet. Yeah. And we probably have a long, long way to go. I know there's a lot of really interesting things that people are doing to try and do that, but here, here's kind of a word of caution. One I talk about in one breath, the amazing convergence of AI and this demographic shift, um, which we're we're talking about is the longevity economy.

[00:50:46] AI, and, and in many cases we know this, when we talk about other biases or other specific groups that are usually marginalized in our society, um, [00:51:00] like. If, if I were to, to say, Hey, use AI to help you build out a strategy for pursuing this, this cohort, like I'd be sending you down the wrong path because you're gonna get very bad information because the systems have been trained and are, they've basically been trained on age biased content and materials.

[00:51:21] Um, and so it's always shocking to me to see what, when I've, I've used Claude or JGBT or. Gemini and some of the other tools like the output that I'm getting and I'm like, whoa,

[00:51:34] Mallory: really? This is, so,

[00:51:35] Bryan: yeah. It's so off the mark and so blatantly ageist. Wow.

[00:51:39] Mallory: Yeah.

[00:51:39] Bryan: Um, and I've used it, I've got, you know, some prompts that I've developed that I'm like, let's go back and like run this through the filter of.

[00:51:49] Like bias, and then it's like, oh yeah, like this, this phrase here is definitely an ageist phrase, you know, it's like, so when you bingo, when you dial it in right, it gets a little bit better. But [00:52:00] I've actually, um, kind of developed a GPT that I use for my own. Kind of quick research and brainstorming and things that's trained on a lot of the, the data that's come out of, um, organizations like MIT Stanford has a, um, the Stanford Center for Longevity.

[00:52:17] They're another, uh, group that's doing amazing research. Um, ARP obviously, um, which, if you're. Part of ARP and you're listening to this conversation, um, um, hopefully I'm doing you a serv, a, a good service here with what I've been sharing. Um, 'cause ARP has some amazing research studies that they've, they've put out there and they, they talk heavily about this shift.

[00:52:39] Um, but there, there's a lot of materials that I've trained, you know, my specific GPT on that I feel like, okay, like it's dialed in, but like just going to straight, you know, the raw tools themselves, um, you gotta be careful of that. So that's one thing that I would say is there is an opportunity when we talk about these two trends converging, um, and [00:53:00] what that means.

[00:53:00] But also if you're using it as a tool to help you think through how you can take advantage of, of this shift, you really gotta be careful, um, and, and be very, very, I mean, I feel like if you're using this tool, you're already kind of thinking along like, okay, is when is it making up? What it, you know, what's the bias or the slant, um, based on, you know, what it's been trained on.

[00:53:25] So we're already thinking about those, those, you know, along those lines. But I always say that age is kind of the last final group that, or, you know, people of a certain age, like they're the last final group that's really still, it's like acceptable to discriminate against. Um, and so. It's so per, you know, pervasive through everything that AI has even kind of become this tool that if you're relying on heavily to help you think through it, you gotta be careful.

[00:53:55] So sorry, that was my little soapbox moment. Um, I

[00:53:58] Mallory: appreciate it. I'm [00:54:00] kind of bummed out that it's at the very end of the episode. I feel like that is a really essential part. So maybe we'll, uh, I'll probably tease it at the beginning and say to find out what you shouldn't use AI for, make sure you listen everybody.

[00:54:12] Um. This has been a great conversation with Brian Kelly. He will be leading what I know is going to be a fantastic keynote at Digital Now, which is November 2nd through the fifth in Chicago, uh, in the year 2025. We're recording this right now in July. You might be hearing it a bit later. Brian, where can people keep up with you, find more about your work?

[00:54:33] I know we're gonna link that. Um, what was it? Uh, like template in our show notes. Yeah. Yeah. But yeah. Where else can I find you?

[00:54:41] Bryan: Probably the best place right now is LinkedIn. Um, so you can reach me at, uh, you know, it's linkedin.com/in, I believe, and then slash Brian Kelly now, and that's B-R-Y-A-N-K-E-L-L-Y.

[00:54:59] [00:55:00] So that's the, the quickest way to get me on LinkedIn. Good luck trying to find Brian Kelly. Um, 'cause there are so many Brian Kellys out there. There are. Um, but you follow that link and that'll get you there. Um, I am in the process of getting ready to launch a Substack newsletter that is going to provide like a weekly.

[00:55:20] Digest that provides insights into the longevity economy, filter through the lens of content design. Um, and then every probably six to eight weeks I'll be publishing specific case studies where I'm breaking down certain digital experiences. So it might be like logging into, you know, like the chase.com.

[00:55:41] Um. Banking app and kind of walking through, um, a, a breakdown or a teardown of that experience of what it's like to log in and call out. Like what are some of the opportunities, what are the, you know, the things maybe they're getting right, the things that maybe, you know, they're missing the mark on. Um, so I'll be publishing those, [00:56:00] those case studies on like a bi-monthly basis roughly.

[00:56:03] Um, so more to come on that. I'll probably have more to share at the keynote, um, this fall in November. But if you. Follow me on LinkedIn. I'll definitely share more information about that as it, uh, is launched.

[00:56:16] Mallory: Perfect. Well, Brian, thank you for joining us on the Sidecar Sink Podcast, and I've gotta say props to you on doing such incredible work for a demographic, for a segment of our population that is so often overlooked.

[00:56:29] I think it's amazing. So keep up the good work.

[00:56:33] Bryan: Will do. Well, thanks for having me. It was

[00:56:34] Amith: great talking with you mall. Thanks for tuning into the Sidecar Sync Podcast. If you want to dive deeper into anything mentioned in this episode, please check out the links in our show notes. And if you're looking for more in-depth AI education for you, your entire team, or your members, head to [00:57:00] sidecar.ai.

Mallory Mejias
Post by Mallory Mejias
November 2, 2025
Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.