123. From Empty Nest To Encore Career: Finding Direction in Your 2nd Act

When your children launch or your career ends, a strange silence can set in—and with it, the big question: What’s Next? 

In this inspiring episode, Jack Calhoun, founder of Encore Career Lab, shares a hopeful, practical path from drifting to purposeful direction. He discusses how many of us face an identity crunch when titles no longer define us—and how to use agency, values, and curiosity to craft a second act that truly fits.

Jack unpacks the paradox of choice—why having too many options can stall momentum—and offers a straightforward antidote: start with your why and non-negotiables, identify your caring audience, and run small, low-risk experiments. He emphasizes that purpose often follows action, not the other way around, and shows how both career-related and unrelated paths can thrive if your heart is in it.

This conversation challenges outdated retirement scripts, reframing work as a fulfilling, energizing part of life’s ongoing journey. Expect honest talk about fear, ego, and indecision, along with tactical advice on surfacing your “wisdom fingerprint,” setting boundaries, and testing new ideas without risking everything.  

Key takeaways:  

• The rise of entrepreneurship among ages 55-64
• Identity enmeshment with career and parenting
• Finding purpose through purposeful action
• Defining your core values and non-negotiables first

Jack Calhoun Bio
Jack J. Calhoun is the founder of Encore Career Lab and a seasoned entrepreneur with over two decades of experience managing a wealth management firm. After selling his business, Jack faced his own post-retirement questions about purpose and fulfillment, inspiring him to help others navigate similar transitions. He specializes in guiding high achievers—particularly those aged 50 and above—toward designing meaningful second careers that blend passion, impact, and income. Through his insights and frameworks, Jack empowers professionals to turn uncertainty into opportunity and create purpose-driven encore careers that enrich their lives well beyond traditional retirement.

Find Jack Online: LinkedIn, Website

Chapters

• 0:00 Framing Agency And Autonomy
• 0:28 Welcome And Episode Setup
• 1:07 The Rise Of 55+ Entrepreneurs
• 1:16 Meet Jack And His Pivot
• 3:46 Identity Tied To Work And Parenting
• 7:56 Paradox Of Choice And Overwhelm
• 10:56 Defining Purpose Through Action
• 12:56 Client Stories And Career Adjacent Paths
• 16:45 Values, Non‑Negotiables, And The Why
• 21:16 Fear, Ego, And Analysis Paralysis
• 28:04 Redefining Work As Life’s Work
• 31:49 Wisdom Fingerprint And Strengths
• 37:00 Closing Reflections And Next Steps

Transcript

SPEAKER_03: 0:00

We have two things that we would have really dearly loved to have had more of when we were younger, which is agency and autonomy. And that's the ability to decide what we want to do and the capability to make it happen. And so we need to find things that are going to align with our values and are non-negotiables. I think that's what's important is to get clarity about that ahead of time so we don't spin our wheels and stuff that ultimately is just not going to be the right direction for us.

SPEAKER_00: 0:28

Welcome to this Empty Nest Life, the podcast dedicated to helping you embrace this transformative season with purpose, passion, and joy. In each episode, we explore stories, strategies, and insights to help turn your empty nest into an exciting new chapter. Whether you're redefining your identity, pursuing new passions, or finding peace in the pause, you're in the right place. Here's your host, the Empty Nest coach, Jay Ramsden.

SPEAKER_01: 0:50

Hey there, my emptiness friends. There are so many possibilities in our emptiness life to consider: downsizing, moving, second careers, maybe even retirement. But here's something I learned that just might pique your interest if you've ever thought, hey, I have an idea for a business. Right now, there's a surge in Americans aged 55 to 64 leading the way in entrepreneurship, making up nearly a quarter of all new startups. Today I'm joined in studio by Jack Calhoun, founder of Encore Career Lab. And after selling his successful wealth management firm, Jack faced his own what now moment. And from that experience, he created a powerful framework to help others craft the meaningful, impactful, and fulfilling second acts. And we're going to get into it right now. Jack, welcome to this emptiness life.

SPEAKER_03: 1:39

Jay, thank you so much. I appreciate your uh your invitation and I love the the work that you're doing here. So it's it's a privilege to be here with you.

SPEAKER_01: 1:46

Well, thank you. I'm excited. Like the idea of Encore career. Like, I love a the phrase encore career. It's just like perfect and forgetful thinking, like, oh yeah, I could have a second thing here. But you you sold a business that was thriving, and then you ended up asking yourself, what now? So take us through that. Like, how did you end up from there to Encore Career Lab? Well, impulsively. All good decisions are impulsive, I've heard I heard.

SPEAKER_03: 2:16

The classic ADD creative type. And uh, I uh backed into the investment industry. My dad was was in it. He had a small firm. He had been a stock broker and he didn't like the commission pressure, so he went independent and just took some of his clients with him and around the late 80s, early 90s. And I was off in the liberal arts land. I was a journalism major and it was in sports marketing, but I was getting the itch to do something on my own. I also realized I was far too ADD to ever work for anybody else. So uh so I went to work with dad, who was just like me, except even more so. And so we were a dangerous combination. Lots of ideas, not always a lot of execution, but um, but we found some people who were great for executing and implementing, and uh and we grew and we did well, and I learned the business along the way. And one of the things that probably contributed to some imposter syndrome on my part was being a creative in a very analytical industry. Um and in hindsight, I realized that was a real advantage for me because there are dime a dozen analytical types in the industry, but not many people that can communicate. And um, it's one of those things you appreciate in the rearview mirror, right?

SPEAKER_01: 3:37

Exactly. I see some parallels here because I was the same way. I was a tech, I was a chief information officer in schools, again, but creative. Not like I learned the tech stuff because I needed to be able to talk, I needed to find people who could do the tech stuff so I didn't have to worry about it. But you're right, there is something there in terms of how do we make this work? And I I think I should probably reintroduce this episode as welcome to this ADD life because I sit in that same circle as you.

SPEAKER_03: 4:02

Yeah, well, there's a big market for that too. So maybe you and I can join up on one of those.

SPEAKER_01: 4:06

But there you go. Um tell me, yeah, tell me about the Encore career and what is that exactly? What does it look like?

SPEAKER_03: 4:14

Yeah, so I had I ended up buying the company from dad, and then I ended up selling the company, and there was a lot of MA and consolidation and wealth management about 10 years ago, and and I didn't really see it coming. It was that the the offers started coming to us, and that's when I was like, oh, hmm. Well, I'm almost 50, or maybe I was 50, and I thought, well, I've done this for 25 years or whatever, and and it's been fun, and we've done good work. I didn't wake up every day when I was eight wanting to be a registered investment advisor.

SPEAKER_01: 4:50

It was not on a dream chart of eight years old.

SPEAKER_03: 4:52

I wasn't on my dream chart, and uh so I felt like I had done that and I was ready for a new challenge. And I thought, well, I'll take some chips off the table and I'll reinvent myself. And I'm a creative guy and and this will be fun. And it was really naive. I was really naive because having been in wealth management, I I knew a lot about retirement planning and all of those things that go into a sound retirement. What I realize now is the industry is really missing a big holistic view of this experience, right? It's spot on it. Very, very obsessed with solving for X, right? You have Y amount of money, you have you know X amount of years, you have Z amount of assets. Does this formula work? And if it does, go forth and party down. And if it doesn't, keep working. And and that's the view. And so I thought that's what I was supposed to do. I've got money or whatever you want to call it, and and now I can go do something fun and and reinvent myself. What what I mis uh understood or didn't value properly is how much of our identity gets wrapped up in our work. And I think with empty nesting, it's very much your work for a lot of us is parenting, too. And and when that goes away, there is this sort of existential crisis for a lot of people, uh, particularly if if you were really invested in in what you did. And if that became, and this is like I say, we did one of my clients is a recently retired OBGYN. And he he he didn't say I help people have babies, he said I'm an OBGYN. And say I help people with investing, I said I'm an investment advisor, right? I am what I do. And if someone's a full-time parent, you might say I'm a full-time mom or dad or stay-at-home mom or dad, and and that's what you and so then that goes away, and then there's just this sort of vacuum, I think. And and I know you've touched on this repeatedly in your episodes and with your guests, but it's real. And and I think for my case, people who were very invested in their careers, it it is this sense that who am I without this thing idea, right? And and I didn't see it coming, I guess, because I didn't think I wasn't this super type A guy working 80 hours a week, sacrificing everything for the sake of the company or whatever. I had a pretty balanced life, and and really I considered parenting and being a good father and husband to be my top value and priority, and work was a big part of that because of the other family stuff. And and so I thought I was pretty balanced, and when it went away, I thought I'll just reapply this to a different area, and and it was really hard. And one of the things that I realized is when you can do anything, how do you define what anything is, right? Oh, yeah, I love that. Yeah, and it's this called the paradox of choice, right? It's like we have too many. And I was my wife, Nancy told me to go get some toothpaste at the grocery store a few weeks ago, in addition to other things. And so I'm on the toothpaste dial, and there's like 50 varieties of the same three brands of toothpaste. I'm like, I just want the toothpaste, man, you know, and and it was overwhelming. I just stared at this wall of toothpaste for three minutes until finally I just grabbed something and kept going. And and that's kind of a metaphor for what we face when we leave our career behind. It's it's it's well, we've got to actually start defining things. And in some cases, I think closing some doors so that we don't have this overwhelm. And we start to get a sense of confidence that here are some directions that that resonate with me and that potentially resonate with people that would want to work with me. And and let me pursue those because I feel good about those. And so the the purpose of the program, Encore Career Lab, is really to help people gain that sense of confidence that they're headed off in the right direction.

SPEAKER_01: 9:16

Yeah, I love that. And and you touched on like the the idea of choice and that the way you framed it. Like I call that the Baskin and Robin syndrome. There's 31 flavors, like, where do I like what do I do? Where do I go? And I think that best describes how empty nesters look at this next stage. It's like, oh, there I there are so many choices, I choose to do nothing, or I just choose to wait to be involved in my kids' life, wait for the engagement and the wedding and the grandkids, rather than saying, oh, how do I seize an opportunity here in my second life? In wealth management, you're looking at retirement, and I'm looking at, hey, how do you maximize your life between the time the kids launch and retirement? Right. But I I think you talk a little bit about, ooh, when we get to this point, we hit this thing, I think you call it the drift. Right. That leads us to into, I'm just just floating.

SPEAKER_03: 10:12

Yeah.

SPEAKER_01: 10:13

So what what does that look like? And how do people, when they come to you for the encore career, when they come to you, like how do you help them through the drift to get them like headed in a direction where they actually have a rudder?

SPEAKER_03: 10:24

Yeah, that's a great analogy. And and I think the phrase that that I've used is is the wandering and wandering phase, um, which is which is basically what the drift is. And it's let's be honest, this is kind of a first-world problem, right? We're we're blessed to have this problem and and food and shelter taken care of, and we have some means, and and so in a sense, what a blessing, right? But also it's still real and it's still kind of overwhelming and paralyzing. And so I think it's important that we look at finding things that are that feel like they are aligned with who we are, how we like to work, what we feel like we have to offer, and things that feel purposeful to us. And people get obsessed about finding their purpose. But Chip Connolly, who founded Modern Elder Academy, had a great phrase that I loved. He's like, Let's work on doing things that are purposeful, and then purpose will follow from that, right? Love that. Um, and so I didn't feel a lot of purpose from sound investment principles when I was in college, but 20 years later I felt a lot because I'd invested myself in it, right? And and I felt there was a right way and a wrong way to go about it. And so, but that came over time. So I think when we get to this phase, there's so much emphasis on finding our purpose that we don't know maybe what our purpose is, right? And parenting might have been a purpose for us, probably was, and career, and when those go away, it's well, I gotta find my purpose before I can get going. And actually, I think it's the opposite. I think we get going on some smart, relatively low friction, low-risk directions and and try stuff and have some fun with it and just take all this perfectionism pressure off of it. Does that make sense? It it makes perfect sense.

SPEAKER_01: 12:21

And I I think too, like people who are listening, like, oh, I don't even know how to get started on you. No, my purpose was my kids. I can't imagine another type of purpose, right? But you but through assistance and help and somebody kind of showing you multiple ways that that could happen. Well, let's take a look at it. So, could you give us an example? Let's put this into like practical terms for folks of someone who went through your program and discovered a new purpose, and maybe maybe what was one of their biggest breakthroughs in doing that?

SPEAKER_03: 12:57

Yeah, I think I've got that's interesting. One of my clients is uh CIO, former CIO for a big manufacturing company in the upper Midwest. And he was early retired, as I call it. It's the it's the proverbial offer you can't refuse, right? And this is the way that big corporations do these things, right? You know, you may not get this package again. And it was one of those. And so he wasn't mentally ready for that. He was early 60s and he really felt like he'd been there since he was out of college, right? So this was his identity. And he was, you know, there was some he was embittered a bit when we started working together. And I get that there's a grieving that goes to it when it's not on your terms. Um, but we worked through that over some time. Well, one of the things that he's done is taking up distance running, and he didn't start until he was 60 years old. Now he's like 65. And he is now preparing to run the Chicago Marathon. I think it's his ninth or tenth marathon that he will have run. And he didn't start until he was 60 years old. There are other younger runners coming to him asking for help, asking how he's doing it. He's got this Yoda stoicism when he goes about this running that is appealing. And so we're working with him on potentially being this running coach, is something you can do online, right? You can do it. Absolutely. A lot of ways to do it. And it's gratifying and it's potentially lucrative to him. So that's one path that we're working on. But there's also the path of what he did in his career, and people are coming to him asking him for help with consulting. And this is really this distinction David Brooks, the writer, has made it it's it's career adjacent and non-career adjacent for your encore career, which means doing stuff, a different variation of what I did before, but more on my terms. Okay. Or something completely different. What I find is that high achievers, people who are career invested, our logical brain says, I've got all of this experience, I should probably just do something that's related to what I've done, right? I get it. On the other hand, our heart a lot of times isn't still in it. And we're burned out on it. But in my case, writing was one of my fortes in the investment business, right? I I was good at kind of John Bogle plain talk investing stuff. And I knew I could teach that to other advisors who probably weren't, it didn't come naturally to them. That could probably be a lucrative encore career. And I started down that path, and then I was so sick of writing about the top, just was like, I don't want to do it. So I think, and I have a dentist in the program, same thing. He was very successful, really an entrepreneur disguised as a dentist, and uh and he has wants to keep going with something. When he started thinking about consulting with younger dentists that are behind the line or timeline where he was. But then I've found that he keeps talking about it. It sounds like work when he talks about it. And I'm like, well, we got to figure this out because what I do know at this point in life is if our heart isn't in it, we will not see it through. We might get intrigued by it, we might start down that path, and then we'll get stuck if it's in conflict with our values. And so I think it's really important to get clear on the why before we get into the what and the how.

SPEAKER_01: 16:38

Oh, absolutely. Yeah, touching a little bit into Simon Civic's work there. Yeah. I I love that you bring it up. Like, that was me. Like when I left my previous career, known nationally in independent schools and tech leaders, and was the chair of the board of our professional association right before I pivoted. And I I left like people were like, you're gonna crush it as a leadership coach for people who are tech folks. And I was like, I tried it, and I was like, my heart, my heart wasn't in it. Do I believe in leadership? Absolutely, 100%. I'm not saying I don't, but I knew I wanted to have a bigger impact, right? And so it's tied to purpose, and that's where I ended up with this, and maybe a couple other things that I'm working on, but it's also oh when you leave an entire community and identity behind, it does rock your world a little bit. It does.

SPEAKER_03: 17:31

It does. It's your because it's your comfort zone, right? And you know the people and you know the players, the landscape. It's it's literally comfortable to you. Yeah. And when we push outside of that, it triggers a lot of fear and imposter syndrome and things like that. One of my current clients is a very high-ranking military member who's just retired, been in the Pentagon and commanding forces overseas. And it's the same kind of thing. It's it's it's even at that level where you'd think that person could write their own ticket, and really they can, but it's still a completely civilian life, is something he hasn't experienced in 30 years. Sure. It looks like it does. It comes for it comes for everybody, but I also think that's where a lot of the really fertile ground is. Think about reinvention and doing stuff that you know maybe it it's tied into stuff we loved when we were a kid. But it's it's a more grown-up variation of that, right? So our program is really we start with the Hawaii, we try to surface a lot of things. We're really focused on helping people get in touch with the wisdom that they've acquired. I call it their wisdom fingerprint. We all have our unique kind of amalgamation of experience and perspective and natural gifts and talents that creates our sort of unique wisdom brand, if you want to call it that, right? Nobody has the same amalgamation as anybody else. And there are other people that really can benefit from that. And this is an age where, you know, the the cerebral energy, the fluid intelligence, if y'all have ever gotten into that, that high synapse firing stuff that we had in our 20s and 30s is declining at this age. It's that it's that cerebral energy that we had when we were younger. But what we have in droves now is this wisdom, this crystallized intelligence, perspective, and judgment, and you know, the was wisdom of the elders. So it's really what we're about is trying to help people surface what they've got to work with, where their passions are, where their capabilities are, the people that they think that they would like to work with. And then we get more into the what, and then we get into the how. And uh and let's take this in a logical progression as opposed to just trying stuff and getting stuck, right? Yeah. Pretty much what my recipe was when I sold my company.

SPEAKER_01: 20:03

Yeah, oh, absolutely. Yeah, the who before the how is so important. Yes, right, yeah, yeah. And the why fits into there in advance of that, but if you don't know who you want to be or what you want things to look like for yourself, then it makes it really difficult to kind of even take that next step.

SPEAKER_03: 20:20

It does because our values, you know, are we we spend a lot of time on non-negotiables because we didn't have that luxury when we were young. We didn't get to decide who we were going to work with all the time and how and where and when, and and parenting too. And so now we do. We have two things that we would have really dearly loved to have had more of when we were younger, which is agency and autonomy. And that's the ability to decide what we want to do and the capability to make it happen. And so we need to find things that are going to align with our values and are non-negotiables because we won't put up with the crap, excuse my French, like we did back when we were younger because we don't have to. And so I think that's what's important is to get clarity about that ahead of time so we don't spin our wheels and stuff that ultimately is just not going to be the right direction for us.

unknown: 21:19

Yeah.

SPEAKER_01: 21:19

What what's kind of like the very first question you have people answer when they come to you?

SPEAKER_03: 21:59

Well, do they have a sense of clarity about where they think they're going? If they do, then we spend some time on that, and I helps me understand what their thinking is. Most of the time it's it's cloudy. And so I think what we try to do is to help realize that that's not atypical. People one of the things I find at this age, and I I had it happen with me, is we're an age where we feel like we're supposed to have it all figured out, right?

SPEAKER_01: 22:27

I mean, oh yeah, 100%.

SPEAKER_03: 22:29

If we're empty nesters, presumably we launch some children somewhere in the world. And we're we are either at the top of our careers or we exited at the top of our careers, however, we define that. And so there's this sense that, you know, I should have this figured out, right? I tell my kids I do. And so when we get stuck and we can't figure out where to go next, there's this kind of sense like, oh my gosh, it's me. And insecurities surface. And what I find is that people tend to go internal. Uh we we we get in our heads, we want to get it figured out. We don't want to worry people that we're stuck that we care about, and it's a little embarrassing to us. And so we just start reading and we start consuming and we we get all locked up in our head. And and that is a sure recipe for analysis paralysis. And and so I think the first thing I try to reassure people is it's not you, it's this phase of life. And genealogically, we're really the first generation that's grappling with this, right? True. True. Grandparents, even 30, 40 years ago, and really even our parents, and that wouldn't have thing, they weren't thinking about a thriving third act, right? No, they were thinking about martinis and viceroy cigarettes like my grandparents were. Um yeah, cocktail hour. Not coincidentally, they didn't live that long. Um, and so now we do. We expect to have years and and and really decades left. If you if you hit 60, you have a 50-50 shot of seeing 90. And you have a life expectancy of about 85, and it's just gonna get longer as technology improves, right?

SPEAKER_01: 24:24

Oh, absolutely. Yeah. Some of the people forecasting it out like our kids, my kids' ages could live to be like 110 or 120.

SPEAKER_03: 24:31

Right. And so that's that's completely different perspective than anybody had 30 or 40 years ago. And even if they wanted to do stuff that was productive, they were very limited what they could do because this thing we're doing here didn't exist, right? There was no way to create your own thing online or whatever. You had to work for a big company, and when the big company was done with you, maybe you could open up a wine shop or something, right?

SPEAKER_01: 24:57

But yeah, there wasn't a whole lot to it, and now there's so many different avenues people can go down, so many different ways they can become an entrepreneur if they want to. I would imagine I'll say most, a good portion of the people listening probably have ideas like, oh, I thought about this or I thought about that. But then the cloudiness that you talked about, like I call it that's just fear, right? It's just fear getting in the way of not allowing you to explore that. Yeah. So what do you what do you say to people who are like, oh, yeah, I'm a little cloudy, or I'm afraid of taking that next step? I would imagine even a high-ranking military person is afraid at some degree of going into something new that's in civilian life because he hasn't done it before.

SPEAKER_03: 25:41

Yeah, yes. And and and and we all are. And I think that is something that we need to recognize is human nature. And our ego is there to, and its role is to protect us reputationally, and and it doesn't like it when we get out there and start trying to reinvent ourselves or do something different. So it will start chirping at us, telling us, well, it's fine to study and learn, but we're not gonna actually do anything. That's ridiculous. That's not who we are, right? I don't know anything about that. No, no, no, let's stay here where everything's known, right? But then you contrast that with the the deathbed question that is we see it all the time, what are you what are your regrets? And it's always not having the courage to do the thing you wanted to do. Whatever that thing is. And I think that's very real. And and so that's where I think we try to people bring process and structure to this experience is realizing there's a way to go through this where we come out the other side with a sense of not only motivation and enthusiasm and optimism, but also this clear vision of who we are and where we're going. And that to me is the the the secret ingredient of all this. When we are younger, we we don't have any problem getting a vision of our future selves, right? We can see ourselves as parents, we can see ourselves in career levels that we aspire to. Maybe we see ourselves in a neighborhood we want to live in for the schools that our kids could go to, or any of those things, right? They're all tangible. And we see ourselves in that life and it pulls us forward. And then we get to this phase of life, and the culture is completely geared around winding it down.

SPEAKER_01: 27:33

Oh, absolutely. You even get showcased retirement at this stage, 15 or 20 years of this stage, so spot on. It's not modeled.

SPEAKER_03: 27:43

That's what they tell us to do, is now you're just now you're just chilling. And so now it's about experiences, right? And then the positive experiences are cruises and antiquing and running through amber waves of grain with the sunlight glinting off of silver hair, right? And and the downside imaging is I've fallen and I can't get up, and stepless entry tubs, and all of these ridiculous things we see when we've got the flu on Wednesday at two o'clock and we're watching TV, right? And these are the models we're given of aging in this country, and they're completely divorced from reality and what things can be. And so the first thing is we have to get clear on this future vision. It can't just be I'm playing golf three days a week. It's fun, nothing wrong with it. It's part of what we want at this phase is that freedom to do what we want to do when we want to do it, but there has to be an overarching drive, purpose, ambition that's pulling us forward that we can see that future self uh down the road that's compelling to us and it's pulling us into that future.

SPEAKER_01: 28:51

Yeah. I uh personally, I want to be like Mary Lee. You're probably wondering who's Mary Lee? Mary Lee was a 74-year-old woman in our group of people who hiked Kilimanjaro. Oh, wow. She absolutely crushed it. And I'm like, that's what I'm like. She's an example. I want to be Mary Lee. And then I saw a woman who was like 80, I think 80 or 84, somewhere in that range, walking the Camino in Spain. It's like anything is possible. Why do we want to shut it down because society says you you go go, slow go, no go?

SPEAKER_03: 29:26

And that's that's what we all bought into. And this is this is if I'm sanctimonious about anything, it's rejecting this whole retirement mentality that we've had as a culture for over a hundred years or about a hundred years, which came out of the Social Security Act. And and that that came out in 1935, and and and it was a safety net that's helped millions of people. So that in and of itself was was a good thing. But they put an earnings test in it that forced older workers out. And back then life expectancy was only 60 anyway. So and and the economy, yeah, and the economy was very heavily into manufacturing and agriculture, and it was physically demanding, and people smoked and drank, and they weren't in great shape. And so, yes, if you got to 60 or 65, you probably weren't worn out. You probably couldn't keep working, or if you were, you were clinging. And so that was designed to get older, tired workers out of the economy, bring in young, unemployed workers in the middle of the Great Depression, and it established this mentality in our culture. That when I'm 65, I'm done with work. Now it's my time. But nobody ever defined what my time was. And as people began living longer, they began, we began seeing this sort of inertia and this decline set in. And I'm not a scientist or physician. I can't speak with authority, but there's a lot of data that shows that the dementia epidemic we're seeing, at least in part, is from this extended atrophying that people are experiencing that people just didn't live long enough to experience 50 years ago.

SPEAKER_01: 31:09

Yeah, yeah, yeah. You you need to use it or you lose it. Now, there's some things that happen too with dementia that are beyond that. Right.

SPEAKER_03: 31:16

There's there's other aspects to it.

SPEAKER_01: 31:18

It's not just that, but it's like how do you stay fulfilled? Right. And and I'm not saying we work a career and that's always fulfilling every single minute of every day, but it does tie into your identity as who you are, whether you're primary caregiver, whether you work outside the home, whatever it looks like. Yep. Your identity does get wrapped up to that. And we talked about that at the beginning of the show. Yep. And it's it's a process of unwinding your identity to even begin to talk about what comes next. Yes. In this next phase. Right. And so that's like step one is unwrapping your identity from who you were before. Yeah. So that you can proceed. So how do you how do you help people in that process? I know how I do it when I work with folks, but what's your approach?

SPEAKER_03: 32:03

Yeah, the term you're spot on, the term is enmeshment. I think that really nails it. It's when our identity and our work get wrapped up together, right? Or it could be our identity and our our parenting, right? But it's when external things become part of how we identify ourselves. Then it goes away, and then we're disoriented. Um, what we try to do is to take people at the very beginning through some assessments that we've done, some are outside uh of what we've done, but like Clifton Strengths assessment, I'm a big fan of. And it gets back to your core of who you are, right? What's that unique blend of of your talents and your experience and your interests that comes together to make you who you are? And we think we know and we do, and and we think when we get to this age, it's like, I know me, I know my tendencies, but but then you step back and you you get an appreciation for what you really have to offer. And one of the things that I see consistently is that people undervalue this wisdom that they have and these capabilities and what they know. You know, and uh and I've seen some of the most profound coaching programs launched by people who've been cancer survivors or who've raised a special needs child and have learned so much the hard way. And there are people that are just going into that experience that are desperate for someone to help them through it and who can who's relatable and not just some expert from on high. Um, and and so sometimes those can make the best encore careers, and they're completely not adjacent to what people did in their first careers, right? And so I think that's part of what we try to do is is help people get back to what makes you you beyond your career. And then what do you have to offer that the world really needs? And and you get to decide that, and we can find ways to test it and see if the demand is there, but but it comes down to redefining work, and work for so many of us in corporate America and professional life is very grindy with high burnout work, right? And and so when people get to this age, a lot of times they don't want to hear the word work, it's the four-letter work, and so we really have to redefine that for this next phase into more of your life's work, and and and I love to point to people that are high profile, like the Rolling Stones, right? And Willie Nelson, and I was just watching a show the other night, and there was a cameo by Mel Brooks, who's 99, and he's working on a rooting of the producers, right? And that's not grindy have to work for these people, right? It's work they love to do. And yes, they're rich and famous, I get that. But if rich and famous was all there was, we we wouldn't have the 27 club, right? We wouldn't have all these tragic stories of people who died young. So it's because they feel like their work is their their purpose and not just the have-to work. So that's the kind of work we want to help our clients figure out and find in what we do at Encore Career Line.

SPEAKER_01: 35:32

I love that. You it's interesting that you brought up the Rolling Stones. They're they're the number one brought up example of what's possible. I don't know why, maybe it's just our generation and they were bigger.

SPEAKER_03: 35:45

It seems so unlikely Keith Richards would still be kicking at this phase, right?

SPEAKER_01: 35:49

Exactly. Exactly. But this is like the third time somebody's brought it up as an example. I'm like, well, there's something there to it.

SPEAKER_03: 35:55

Yeah.

SPEAKER_01: 35:56

You talk a little bit about the the wisdom approach, right? We have this amount of wisdom now, or wisdom brand, I think is what you called it. Yeah, but oftentimes people say, well, I'll just volunteer or I'll mentor. Why is entrepreneurial ship so powerful instead?

SPEAKER_03: 36:12

Yeah. This is a really fundamental question that comes up a lot of times, and it's well intended. And I think what you find is that people that were uh it really invested in their careers or in their work with their kids or whatever, when that goes away, presumably we're in a better financial situation than we were when you were younger. We have more capacity, and we think, well, I I can give more now. There's this, it's called generativity, is the term. It was by Eric Erickson, the psychologist, and it's this compulsion we feel to give back as we get older. It's wired in us. And so I think that that's where we have to really look towards what is that going, what's going to scratch that itch for us, right? How are we going to find ways to give back um that are still in line with our values and our priorities and what's driving us at this point in life, and not end up spinning our wheels doing things that seem like they'd be interesting, but that we don't feel really passionate about? Does that I may have gotten off topic. So that answered.

SPEAKER_01: 37:23

Yeah, you're right there. Yeah, right on, spot on with that. It's it's this has been a fascinating conversation. I think one that's been hopefully super powerful for people who uh will listen to this episode because it is such a good example of what's possible once the kids leave home. And before I let you go, I I'm just curious, what's one thing you've learned about yourself in developing and creating Encore Career Lab and your journey?

SPEAKER_03: 37:59

It really lights me up seeing what people have to offer and seeing them discover that. And and it's there's a variation of that from wealth management, but it's not exactly the same. And the people that come into the program have so much potential and and they don't appreciate it, they don't see it a lot of times. They're humble people and they underestimate themselves. So it's really energizing to me to see them start to get excited about that because the downstream effects, the butterfly effect, you just you never know.

SPEAKER_01: 38:34

Yeah, the ripples and ripples are out there, and who knows if you inspire somebody else.

SPEAKER_03: 38:40

Just one person, who knows? Who knows? That might be the one person that changes the world, right?

SPEAKER_01: 38:45

I believe that 100%. Impact one or impact one million, there's no difference. Impact is impact. And when the kids leave home, I think we can still impact the lives of others, just not our kids.

SPEAKER_03: 38:57

Yeah, absolutely.

SPEAKER_01: 38:59

Jack, thank you so much for being here today. The conversation was fantastic, and I look forward to seeing how Encore Career Lab continues to grow and shine a light on what's possible for folks.

SPEAKER_03: 39:10

Thanks, Jay. I appreciate the invitation. It's been great being on, and I love what you're doing, so keep up the good work.

SPEAKER_00: 39:16

Thank you for listening to this Empty Nest Life. Remember, this chapter isn't an ending, it's an invitation to redefine, rediscover, and reignite your life. If today's episode sparks something in you, don't forget to take that first step and visit thisemptynestlife.com and click work with me to get the conversation started. Until next time, keep your heart open, your mind curious, and your spirit shining. This Empty Nest Life is a production of Impact One Media LLC. All rights reserved.