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Reinventing Retirement: Jack Calhoun Shares Wisdom on Purpose, Identity, and Encore Careers
26th March 2026 • Don't Retire...Graduate! • Eric Brotman
00:00:00 00:35:07

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Welcome back to Don’t Retire… Graduate! In today’s episode, we’re exploring one of the most critical and overlooked aspects of retirement: transitioning your identity, purpose, and fulfillment as you move into the next chapter of life. Joining me for this conversation is Jack Calhoun, the founder and president of Encore Career Lab. Jack isn’t just a seasoned entrepreneur after leading a wealth management firm from $50 million to over $1.5 billion in assets and selling the business in his early 50s, Jack faced the emotional and identity challenges that often come after a primary career ends. Through his own post-career journey of “wondering and wandering,” Jack discovered firsthand that financial planning alone is never enough.

Jack and I dove into the parallels between our journeys, both as liberal arts majors and as people who built companies, stepped away from the top job, and then wondered “what’s next?” Together, we unwrapped the deeply personal and often daunting process of redefining yourself and finding meaning once the “what do you do?” The question no longer has a simple answer. Jack candidly shared the psychological hurdles many face upon retirement, especially for high achievers who tied their identity so closely to professional success.

We discuss the pitfalls of thinking retirement is only about “doing the math,” and the dangers of the so-called Striver’s Curse where career-driven people lose their sense of purpose and can become rudderless once the striving ends. Jack’s experiences and research led him to develop Encore Career Lab, a program designed to help successful professionals regain their “rudder,” starting with “why,” then the “what,” and finally, the “how.” We explore his three-phase approach to post-career transformation, the importance of generativity (the drive to give back and pass on wisdom), and why building a roadmap for fulfillment, not just finances, is vital in modern retirement.

5 Key Takeaways:

  1. Identity Challenges After Retirement: Jack illustrated how even strong, career-driven individuals can underestimate the existential impact of leaving their professional roles, discovering that so much of our identity is tied to what we do and contribute.
  2. Purpose Is More Important Than Leisure: We debunked the myth that endless recreation leads to fulfillment, revealing that humans are wired for purpose, meaning, and generativity and that’s what produces happiness beyond financial freedom.
  3. Start with Why: Jack’s work with Encore Career Lab emphasizes discovering your “why” before choosing what you’ll do and how you’ll do it post-career; clarity on purpose leads to choices that align with your values and lead to true fulfillment.
  4. The Risk of Losing Your Rudder: Without intentional planning, retirees often become overwhelmed, dabble without direction, or feel paralyzed by too many options; a structured process is vital to avoid feeling rudderless or self-conscious about your next steps.
  5. Generativity as the Common Thread: As people mature, the drive to give back and share accumulated wisdom becomes a universal impulse. Jack observed that everyone drawn to his program feels a compulsion to help others and leave a legacy making mentorship, teaching, and service recurring encore themes.

Join us for this inspiring conversation on redefining the very nature of retirement from a finish line to a commencement. If you or someone you know is approaching a new phase of life and seeking more than just financial security, this episode will open your eyes to the possibilities of true graduation. Don’t forget to subscribe, rate, and share this episode with anyone eager for a purpose-filled future!

Transcripts

Eric Brotman [:

Welcome to Don't Retire, Graduate, brought to you by BFG Financial Advisors. We're here to rethink what retirement really means to you so you can graduate into your next chapter of life with purpose and with passion. I'm your host, Eric Brotman, and in this, our 7th season, we'll be bringing you interviews with guests who will share their money stories with us every other Thursday. If you haven't already done so, please subscribe so you never miss an episode. Today, I'm pleased to be joined by Jack Calhoun. Jack is the founder and president of Encore Career Lab, where he helps high-achieving professionals reinvent their lives after their primary careers. After leading a wealth management firm from $50 million to over $1.5 billion in assets under management, Jack sold the business in his early 50s and faced the emotional and identity challenges that often follow retirement. Through his own post-career journey of wondering and wandering, He discovered that financial planning alone isn't enough.

Eric Brotman [:

We also need a roadmap for purpose, identity, and fulfillment in our later years. I couldn't have said it better myself. Jack, welcome to Don't Retire, Graduate.

Jack Calhoun [:

Thank you, Eric. I'm excited to be here. It's a privilege to be here with you.

Eric Brotman [:

I will tell you that I think in lots of ways we're living parallel lives. So I expect this to be— I expect to have some of the Encore Career Lab be labbing on me today because we're kindred spirits doing a lot of the same stuff. Why don't you share with our audience the story of not only a little bit about how you built your firm, but more importantly, how you decided once you were ready to monetize your life's work, what you wanted to do with the next chapter of your adult life?

Jack Calhoun [:

Sure. Yeah. Yeah. I guess I kind of backed into the industry a little bit. I was a liberal arts major. You know, I was a newspapers major of all things in college. And it only takes getting out and trying to live on $13,000 a year to really hone your values and priorities. Life.

Jack Calhoun [:

So fair. I decided that perhaps the SpaghettiOs was, was overrated and it would be nice to have some income. So I ended up moving into sports marketing. I had a background in sports communications in college and, and that was fun. Uh, but that was a family business that I was working for and I wasn't family, so I knew how that was gonna go. So my dad was what we would today probably call a breakaway broker. He was working for a big wirehouse in the Southeast in Atlanta. He didn't like the pressure to— back then it was all limited partnerships and you didn't feel good about it.

Jack Calhoun [:

So he went independent back when nobody was really doing that, uh, in the late '80s. And, and he just kind of took a small book of business with him. And, um, at that point I was realizing that like him, I was probably way too ADD to ever work for anybody and was probably not gonna be employed for long cuz I couldn't sit at a desk for more than an hour and a half. So. Um, you know, but I could communicate and, uh, and I had, you know, sort of that AED entrepreneurial urge, itch, whatever you want to call it. And, uh, so in the late— so I went to work with him, and in the late, uh, '90s, accounting firms started coming into the industry. I'm sure you remember that. And it was a very formidable group to come in as competitors.

Jack Calhoun [:

You know, they'd always been referral sources. They, they had the entire trust of the client as well as the knowledge of what the client was up to. And so it was going to close off a lot of opportunities for referrals. And so I decided to create a program, uh, that was a partnership program where accounting firms used us for the money management. We provided the marketing materials, communications materials, we did the mechanics of the management, and they handled the relationship. And, um, took a while, but ultimately it really took off and it became a really good program for us. And And it became the engine of growth for the firm. And so, um, about 2005 or so, we bought my dad out of the practice.

Jack Calhoun [:

I became the managing partner, majority owner, with a few other partners that were friends and key, key partners. And, uh, and we really grew. And we, you know, survived the 2000s and the two bear markets and actually did really well on the other side of them because, you know, we did things the right way, right? Just like you do. And so people find you in times of trauma when you're doing things the right way. You become a lifeboat for a lot of people. And so that's essentially what happened. The accounting firms started getting covered up with requests for help. They sent a lot of money to us.

Jack Calhoun [:

Our assets grew. And so at the same time, all of this M&A activity started happening in wealth management. And firms were rolling up wealth management firms. And so we started getting offers. We were, as you mentioned, north of a billion in assets, and they were pretty compelling offers. And I hadn't really thought about it. I hadn't thought about selling. I was right about 50.

Jack Calhoun [:

And, but it got me thinking, you know, and one of the things that got me thinking was I'm kind of your creative entrepreneurial type personality and a very, buttoned-up finance-driven world. And, you know, I was pretty good at what I did and I was good with clients, but I never felt like, you know, I was put on this earth to be a financial advisor. I respected it. I thought we did good work, but I thought, you know, this was something I did and I'm proud of it. And now let's go do something different and fun, right? Something new. And now I have the wherewithal to decide what that is. And so that was the entirety of my deep critical thinking of selling my company. Wow.

Jack Calhoun [:

Your butt.

Eric Brotman [:

Wow.

Jack Calhoun [:

A little impressive.

Eric Brotman [:

Well, let me, let me, let me bring some of our parallels to light. First of all, I was also a liberal arts major. I studied English.

Jack Calhoun [:

All right.

Eric Brotman [:

Uh, and I worked for the school newspaper. Um, so, and, and, but I worked on in the sales side doing advertising, not actually doing the writing, which is sort of an interesting one-two. Um, went to work for a brokerage firm in the legal department. Like most English majors, you're either going to teach or go to law school. I decided on on, on law school and then decided not to go and found financial advising. So, so it's interesting because, you know, you're talking about the, the M&A opportunities in our industry and the offers are silly. They're really off the charts silly. And, you know, we're trying to take a different approach here, which is to do something fully internal and to be buyers rather than sellers.

Eric Brotman [:

And for better or for worse, I stepped down as CEO 6 weeks ago as we record this. But the first—

Jack Calhoun [:

I didn't know that.

Eric Brotman [:

Well, congratulations. Yeah, no, I stepped down as CEO. I have not sold. I have been selling gradually to other folks. We now have 9 equity partners here. That's great. And I'm a growth officer and looking for M&A opportunities and doing a lot of speaking and podcasting and consulting and, you know, trying to figure out what I want to be when I grow up. And I'm not going to ask you yet.

Eric Brotman [:

We're going to hold everybody in suspense until we get there. But quite, quite candidly, one of the things that we've done on this show for 7 years is talk to people about moving towards something rather than from something. Something at quote unquote retirement. And so you're now in the business of helping successful people who run the risk of losing their identity and sometimes become depressed or forlorn or feel like they're no longer contributing at that moment. I don't know if you experienced some of that on your own. I'd love to hear your experience and then sort of we'll springboard that into how you're helping other busy, successful people who suddenly are less busy but still successful and need to figure out how to, how to find purpose in their lives. So let's share your story because you did this. You were in your early 50s, which is, which is right where I am, Jack.

Eric Brotman [:

I mean, we're— it's, it's astounding how similar in so many ways we're in the same kind of boat. So tell me what that— tell me what it felt like for you and sort of what some of the epiphanies were as you were as you were going through that process? Because it can be daunting.

Jack Calhoun [:

It can and is, I think. And I underestimated it. I was kind of naive about it. I thought, doing what we did, what you do, what I did, it's like we work on solving for X, right? Here's how long we project you're going to live and here's the money you're going to need to sustain you. And it's a pass/fail kind of thing, right? And if they passed, then it was like, well, go forth and recreate, have fun. This is your time. And, and what I couldn't understand was so many of my clients, um, males in particular, but, but successful, uh, females too, which is kind of— and it didn't happen immediately, it happened over time. And I guess, you know, I was in my 30s and 40s at that time, and I didn't understand it.

Jack Calhoun [:

It wasn't until I lived it that I realized— I was like, oh, The money's just one part of it. And what I underestimated was the existential part of this and how much of my identity was wrapped up in what I did. And I guess because I felt like I was a little bit of a fish out of water in financial services, right? The creative, you know, and all of that. And I thought, well, you know, it doesn't define me who I am and I'll reinvent myself. And I underestimated how much of my identity I took from the work. And just casual conversation, people are like, what do you do? And I'm like, you know, wealth management partner, whatever. And then when I sold the company, it's like, what do you do?

Eric Brotman [:

I'm like, eh, it's the, it's the, I used to be a, right. I used to be a blank. Well, okay. But what are you now? You're not, you're still fog in a mirror. Let's do something. Right. I mean, you're, This whole used to be is not a healthy thing. No.

Jack Calhoun [:

And it's a conversation killer. You know, it's like, what are you doing? Like, you're just kind of futzing around. You know, it's like, well, okay, thanks. We'll move on. And so I started getting self-conscious about it, which, you know, I guess it's a little ironic because, you know, we think the whole brass ring ideal, right? We work our butts off. We achieve what we want. We grab the brass ring and go off and enjoy our time to recreate and and enjoy the fruits of our labor. But as it turns out, the fruits of our labor is a big part of the whole purpose of life anyway.

Jack Calhoun [:

And it's not just this life of endless leisure that has come to be associated with retirement. And that's a whole thing I've become really passionate about. We can kind of jump into the origins of that concept and how destructive it's come, you know, if you want to. But, but, but for me, I think it was very disorienting and I started getting self-conscious about it. And, um, you know, my kids would come home from college and I'd be like, what are you doing, dad? I'm like, yeah. And so it, you know, it just kind of ate at me. And now having read a book I would highly recommend, you may have referenced it or not, but it's From Strength to Strength.

Eric Brotman [:

Amazing. Amazing.

Jack Calhoun [:

I mean, that That was the epiphany for me.

Eric Brotman [:

Oh my goodness. I should have him on the show because I have been talking about that book since the minute I picked it up. I could not put it down and it changed so much of my philosophy and attitude overnight. It's so funny that you found the exact same thing.

Jack Calhoun [:

Me too. This is just, I mean, this is uncanny. Part of our curriculum. And by the way, back up your Brinks truck if you want to get Arthur Brooks on this show, but you're competing with Oprah.

Eric Brotman [:

But well, but listen, it's worth a shot. You get nothing you don't ask for. I'll try. I'll try. We'll see if our producers can make that happen. Let's look. Yeah, given that book is a life-changing event for me and it sounds like for you and Arthur, if you'd like to be on the show, we'd love to have you fully support it.

Jack Calhoun [:

I would love it. I think you'd be great. So a big part of what the epiphany from that book was that he called it the Striver's Curse. And I think for people who are very invested in their career, career becomes identity. We only know one thing, which is to set our sights on objectives and goals and strive to accomplish them. And that comes out of this sort of meritocracy that we've created in this country and Western civilization society, striving to get in the right schools. And, you know, get our foot in the door of the right firm and then get to an income level and we'd get the house in the right neighborhood to send our kids to the right schools. And it's just the whole game that we all play.

Jack Calhoun [:

And then when that goes away, we feel rudderless. And, uh, yeah, and in the sense that we're just gonna cool our jets and, and be, you know, proud of what we've accomplished and now it's recreation time, it turns out it's just a terrible idea. We're not wired for that. We're wired to do things that matter and that have an impact and to feel like we matter. And that's the part that I realized quickly is like, oh, we're missing a big part of this in wealth management. And it's not really wealth management's fault. That's sort of the limitations of that area, right?

Eric Brotman [:

Oh, it's interesting you say that. I think it is our fault as an industry. I think we're not preparing people for the psychological, social, spiritual, mental, intellectual challenges, just the financial ones. And I, you know, AI can do that, Jack. AI can do the financial. It's a math problem. It's algebra.

Jack Calhoun [:

Yeah.

Eric Brotman [:

It's the human side of it that makes this so great. I don't know, are you familiar with the Anya Institute? Have you ever heard of them?

Jack Calhoun [:

I am by reputation. Yep.

Eric Brotman [:

Not deeply, but so, so I am part of their second cohort group this year. Oh, wow. I could not be more honored and thrilled to be a part of it. But it's really about integrative wealth and how to bring the concept way beyond money. Because to your point, money's a tool. Money's part of it. I mean, certainly you need resources, but it is— if that's all you live for, boy, are you going to be disappointed when you finally have that pot of gold. It's just not rewarding.

Eric Brotman [:

It's nice, but it's not rewarding by itself. You got to have things to do. So if you're not familiar, or it sounds like you are familiar with that group, that That might be up your alley too because it is.

Jack Calhoun [:

Yeah, I will definitely check that out.

Eric Brotman [:

It's a special group of people.

Jack Calhoun [:

Oh, and you've touched on— Yeah, okay. I appreciate that. And you've touched on what I think is a significant point, which is that we think it's about the financial, and that's just as a society, the way that we're sort of groomed for this. And then you get the numbers right and you feel like, okay, well, I guess I'm supposed to be happy and fulfilled now. And then when you don't feel that way, then you feel like you're doing it wrong. And, you know, in my case, having been an advisor to high-net-worth people for 20-plus years, telling them if you do these things, you're going to have a happy retirement, you know, I felt a little bit like I was a hypocrite.

Eric Brotman [:

Yeah.

Jack Calhoun [:

And, and I was like, well, I guess I've been doing it wrong somehow. And so what I find is that we go internal. Um, we don't talk to people about it. And on some level, I think we just know how fortunate we are, right? I mean, cry me a river, right? I mean, I've got money and I'm secure, and who's going to feel sorry for me? Nobody. And I don't blame them. Yet when you're rudderless and you don't know what to do with yourself and you feel like you have a lot left to offer, but you have no idea what that is, then you do get stuck and you get self-conscious. And so what I find, I know this was my case, I find this with a lot of clients is we go internal, we try to read our way out of it, we try to think our way out of it. We sit in our basement and read personal development books.

Jack Calhoun [:

I can only speak for myself. And, um, you mean, you mean the man cave? Yes.

Eric Brotman [:

Yes. The man cave where I read things like strip and stream.

Jack Calhoun [:

Correct. And so, you know, what I realized was this is a really weird phase of life historically, genealogically. We're really the first generation that's grappling with this, right? Even 30 or 40 years ago, this wasn't a topic and it wasn't relevant.

Eric Brotman [:

Well, that, and a lot of that has to do with not only longevity and lifespan, but also healthspan. You know, when you, when you think about the traditional retirement and I, you know, I spend almost a chapter on it in my book because I think that it's, it's so horribly defined. But when you think about a traditional retirement, the idea was you would work from 15 or 16 or 18 until you're 65 and you're dead at 72. Right. That is no longer the human experience in most cases. We hit the workforce at 25. We might be in a hole financially because of student loans and grad school and all the things. We want to retire at 50 and could live to be 106.

Eric Brotman [:

And the math doesn't math. But beyond that, that is a very long time to be idle. And you know what idle minds are, right? I mean, that's, that's problematic. So there's a lot of different adventures, though. And I trust— and I, I'm going to ask you about the, the career lab that you're— that you've created, because I'm going to imagine that there's a choose-your-own-adventure for almost anyone and that some of those involve consulting or serving on boards, or some of them are volunteering. Some of them certainly are family and recreation. But there's so many different aspects of our lives that can be enriched by our freedom, flexibility, and hopefully financial independence. So, so talk a little bit about what you're doing and how you're helping people sort of regain that rudder?

Jack Calhoun [:

Yeah, I guess with everything, you know, in, in, in entrepreneurial world, you know, so much of it comes from your own pain. You try to reverse engineer your own mistakes and fix them for other people. Um, and you reference the wandering and wandering phase. That's what I call it. And, and that's the sense that, um, you know, you, you, you've got options, but you don't know what those are. And so you just kind of dabble, or, you know, in the South, my grandmother would've said, piddle around, quit piddling around with stuff. And I felt like I was just piddling around with stuff all the time because you not only have options, but you also have overwhelm. And if you commit to one thing, you're, you know, you're choosing that over other things, and then you, you don't— you're not sure.

Jack Calhoun [:

So that was what I realized was a big part of the problem, that we didn't prepare people for creating a thriving life after retirement beyond just the recreational stuff. And that that was what people really were going to need and do need for this next phase. To your point, because people are retiring earlier, a lot of times not by their own choice, right? They're getting the retirement packages. I mean, down here in Atlanta, it's Coke and Delta and Home Depot are just forever throwing early retirement packages at people in their 50s and they're taking them because they don't know if they're going to get them again. So, you know, they get this package and then they're 58 and they might live to be 98 or 106, right? And that's a very different proposition than our grandparents had, right?

Eric Brotman [:

That's right. That's right.

Jack Calhoun [:

And so what I've realized is, um, you know, we need a framework and a process to help us get oriented not only about what we're going to do but why we're going to do it, right? It's a Simon Sinek start with why concept, and I'm a big believer in that. Uh, and what I found with me, what I found with my clients, is we want to rush into the What, what are you doing? Because we get very self-conscious when we don't have an answer for that. And so a lot of times when something comes our way, we jump at it because it solves the what. But then what happens is we get in conflict with our values and our non-negotiables at this phase of life. And two of those preeminently are agency and autonomy. We've worked our whole life for it. And we're not giving it up. We're not going to work for anybody we don't want to work for or bringing in clients we don't want to deal with.

Jack Calhoun [:

We're not. And so what happens is we say yes to a what and then find out it's in conflict with our values, which is our why, and we won't put up with it. And we'll have to extricate ourselves from it. And then it gets messy and then we feel bad. And so What I have found is it's much more important to start with the why and go through that. And a big part of what we focus on is what we call uncovering your hidden wisdom, you know, your wisdom fingerprint, so to speak. And it kind of builds on the crystallized intelligence concept from Strength to Strength. And that's helping people surface, take stock of, and appreciate how much wisdom they've they've acquired over the course of their lives and how not just valuable it is, but how critical it is to share that with the world and how much people are craving that.

Jack Calhoun [:

And it can be things that we spend our career dealing with. It can be what we call career adjacent, which I think David Brooks, the other Brooks writer, mentioned that one. That would be maybe consulting in an area of expertise that we had from our career, like financial services. Then there's non-career adjacent, and those can be great too. And sometimes those are the most fun, right, where you're doing something completely different from what you did. Yeah, you know, um, and so that's what a big part of our focus is, starting with the why, then the what, then the how. It's a 12-week online curriculum that we also have small groups and one-on-one coaching. That's the whole lab idea, right? And we're not only trying to open doors, we're also trying to close off some doors, right? Some, some, some, some things that might be interesting but maybe don't align with the, the values and non-negotiables people have at this phase.

Jack Calhoun [:

And so it's interesting to see what comes out of this. Some people very much gravitate to the career-adjacent stuff because their heart's still in it, right? Uh, and, and others don't. You know, I know for me, when I was contemplating what to do before I kind of hatched this idea with ECL, I thought about starting a program to help investment advisors communicate more effectively with their clients. You know, that was one of my unique abilities, as Dan Sullivan would say. Um, and I still help out with my old firm with some of their communication stuff because that's still my voice that the firm has. Um, but every time I would contemplate it, I would find myself procrastinating. And then I finally was like, you know what, I'm just kind of done with this. I don't, I don't feel it right.

Jack Calhoun [:

I know I could make this work. I could probably make a really lucrative encore career out of helping advisors get better with communicating, but I just don't want to do it. And that was okay. You know, nothing wrong with it. Of course. And so that was part of what I realized that we have to help clients with. It's not just what makes sense in your analytical— what is that? Your left brain. It's also your heart.

Jack Calhoun [:

It's got to really speak to your heart in this space.

Eric Brotman [:

So, you know, starting with why makes perfect sense. Figuring out the what makes perfect sense. And of course, you took the words out of my mouth because I'm sitting here thinking, all right, I think I know why this is important. In fact, I do know why this is important. And I do have plenty of ideas for what. And the challenge with that is selecting, prioritizing. I think Bill Gates said that busy is the new stupid. I mean, there's lots of ways to fill your calendar with nonsense and not feel— just because you're busy doesn't mean you're productive.

Eric Brotman [:

It doesn't mean you're happy. It doesn't mean you're fulfilled in any way. But getting to the how, I think is so important. How, and not the logistics how. I mean, if you want to serve on a board, there's ways to do that. You can figure out how. If you want to do consulting, if you want to do— how is— when we're talking about how here, we're talking about how to determine the what and the why for yourself, I would assume. Because how to do these things is, you know, you go on LinkedIn and you find people who can help you.

Eric Brotman [:

But in terms of the How to determine and really identify your why and then your what. That feels like the how I want to know about. So you have a, you have a program that's helping folks go through that.

Jack Calhoun [:

Yeah. Yeah. That's exactly what we do in Encore Career Lab. And we save the how for the end so that we can get to the foundational stuff at the beginning. And then the how for us is coming at it. Part of this is mindset. And this is the strivers thing that we were talking about. People put a lot of pressure on themselves to get this right and to make it something they're proud of.

Jack Calhoun [:

And that's great, right? We want them to bring that sense of pride and quality of work to whatever they do. But a lot of that is bringing our 30-year career mentality into this next phase, and it's completely different. We're not building a new 30-year career. We're not putting on what I call our professional armor like we did every day for 20 years and being impervious and infallible. This phase of life, I call it going from guru mode to Sherpa mode. Guru mode is you're managing $5 million for somebody and they don't want to know about your problems. They don't even want to know that you have problems. Sherpa mode is what I'm doing now.

Jack Calhoun [:

Hey, I've been there, done that, and I went down this path, and let me show you some things that I learned the hard way that I can help you avoid.

Eric Brotman [:

Have you identified trends now that you've been doing this for a while where there are certain types of humans where there's enough data in your lab to say, all right, these are the 3 or 6 or 29 personality types and paths that people take? Are you seeing a lot of similarities between folks? Just at least anecdotally?

Jack Calhoun [:

Yes, I am. And the thing that really jumps out over and over again is this word generativity. I didn't coin it. It was coined by Erik Erikson, who was a preeminent psychologist in the 20th century. And I heard Chip Conley mentioned it, who's the founder of Modern Elder Academy, and it really jumped out at me. And generativity is this compulsion that we feel as we get older to give back. And to share what we know. And it's the wisdom of the elders.

Jack Calhoun [:

And our generativity impulse gets stronger as we get older. So there is one constant with every person who's come through this program, and it has been, I feel like I have a lot to offer and I want to give back. I want to do, to do things that I care about for people I care about.

Eric Brotman [:

Now, is that a self-selection thing? In other words, are the people— is that— let's talk chicken and egg. Are the people who realize they have something they want to give back the people more likely to do your program, or the people who do your program more likely to discover that there's a lot they want to give back? It might be self-selection. You're not taking a random walk with humans into your program. You're taking folks into your program who already, I would think, identify that they have something to give and that they want to create purpose. And that's why they do it in the first place.

Jack Calhoun [:

Correct.

Eric Brotman [:

I doubt you're changing minds.

Jack Calhoun [:

Well, I'm not changing minds from people who have zero interest in this subject matter, uh, and there are a lot of people for whom work was putting food on the table and keeping a roof over their head so they could go on and live their lives outside of work, and that is totally honorable, totally respectable. I get it. Um, then there's a whole other class of people— not class, but group of people— for whom work became a big part of their identity, and they feel disoriented without that. And so the messaging, I think, helps to self-select, right? And that needs to resonate with people. But I think when people come in, it's sort of this vague feeling like, I have a lot left to offer. And that's kind of it for a lot of people. And so a big part of what we do and that lights me up is helping people figure out what is it, right? And also what isn't it, if that makes sense?

Eric Brotman [:

Well, it makes perfect sense. Yeah.

Jack Calhoun [:

Yeah. All right. I got off into a venture. Yeah, please.

Eric Brotman [:

Let me put you on the spot. Yeah, I'm going to put you on the spot. I'm going to tell you what my, what my, my own personal path looks like. And you tell me if I fit into one of your groups. All right. Because here's, here's where I am right now. I'm in a position where I am almost empty-nested, have hit financial independence, and I'm in a position where I'm working for fun and I, I love it. I'm enjoying it, but I'm working for fun and I find myself working more than ever and not creating a lot of balance because I'm still saying yes to lots of projects.

Eric Brotman [:

And I think there's a part of me that thinks if you start turning down projects, you're going to stop getting offered projects. Is that head trash or is there some truth to that, that it being super selective? I've heard lots of people say pick your projects carefully. And if I'm taking on darn near everything, I can't— that becomes problematic. But there's a sense, and I've always heard this with media, I've always heard if you, if you have media contacting you for an interview and you can't do it, they're going to find somebody else and stop calling you. Is that, do you think, true with the consulting, particularly the career adjacent mindset? Do you think there's some Is there any truth to that or is that head trash on my part, Jack?

Jack Calhoun [:

I think there's some validity to it in that if we get so selective and so precious about it that we're just not saying yes to hardly anything, then inertia kicks in pretty quickly. And what I have found is that it's really within about 2 years of the line, the line being retirement or career end, whatever you want to call it. People who are within about 2 years of the line or just over about 2 years of the line are sort of our ideal group to work with. Within 2 years, they know that this is coming. They can't avoid it. They need to deal with it and they want to have a plan. On the other side are people who have discovered that they were, um, maybe they feel misled or they were just not ready for this life of endless leisure that we talk about and they want to get back into it and they want to find what it is. Beyond that, inertia does kick in, and I find that people who have been, you know, fully retired and doing the, you know, life of pickleball and cruising, and that's great and that's it, they don't want to hear it.

Eric Brotman [:

Well, I would think it's also extremely difficult to get back into it if you've, if you've gotten a— you stop working that muscle out for a while and it's the muscle, you know, I imagine. And there's lots of different ways we could translate that. We are, we are sadly getting short on time. And I've got to ask you first and foremost, because we've been talking about it for half an hour, and that is what, what's your plan? What do you want to be? Now, what do you want to do? Not sure what, but what do you want to be when you grow up, Jack?

Jack Calhoun [:

You know, I want to be a 100-year-old Sherpa. I love people like Mel Brooks, 99 years old. He's working on a reboot of The Producers. Thriving, all these people that are moving into these ages that we just thought were just like borderline vegetative and they're just thriving and, and there's such inspirations and I want to be that guy, you know, my subject matter is helping people figure out how to reinvent themselves post-career and, and I'd love to keep doing that and, and be that guy 40 years from now.

Eric Brotman [:

The 100-year-old Sherpa. That's, that's your book. There's, there's your book title, Jack. You said you were working on a book. That's your book title.

Jack Calhoun [:

Yes.

Eric Brotman [:

100-Year-Old Sherpa. I want some kind of credit or I'll write your— I'll write your foreword for you. How's that? Because we're all the same.

Jack Calhoun [:

Love it.

Eric Brotman [:

So how can folks who want to know more about you or more about ECL or the work you're doing, how can they get in touch with you? How can they find more online and so forth? Sure.

Jack Calhoun [:

Yeah. The URL for our site is just literally Encore Career Lab. Lab.com, lab, L-A-B, singular. And they can also email me at jack@encorecareerlab.com, or they can find me on LinkedIn. And please don't hesitate to reach out. I'm happy to have conversations with anybody, whether you feel like you're interested in the, in the program at this time or not.

Eric Brotman [:

Well, this was awesome. I have no doubt you and I are going to collaborate on projects over the next 45 years or so until we're 100-year-old Sherpas. And I love the concept. It was phenomenal getting to know you. Thanks for— thanks for being on the show. You've been a great guest. And we're hopefully— hopefully there'll be a lot of people checking out your stuff. It's good stuff.

Jack Calhoun [:

Well, listen, I appreciate it. You're doing great work. I appreciate you making this topic visible to so many people. And I enjoyed our conversation today.

Eric Brotman [:

Fantastic. I'd like to thank everybody for watching and listening today. If you enjoy the show, please share it with friends and family so they can join you on your journey to financial freedom. We'll be back in 2 weeks with another engaging guest. And in the meantime, next Thursday, be sure to check out BFG Financial Advisors webinar series, Diary of a Financial Advisor, which you can find at BFGUniversity.com. For now, this is your host, Eric Brotman, reminding you, don't retire, graduate. Securities offered through Kestra Investment Services LLC, Kestra IS, member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services LLC, Kestra AS, an affiliate of Kestra IS.

Eric Brotman [:

Kestra IS or Kestra AS are not affiliated with Brotman Financial or any other entity discussed.

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14. Income Strategies for Retirement Planning
00:30:00
13. How Financial Coaching Can Help Get Anyone Started in Planning for Retirement
00:32:46
12. Why tax planning is more than just filing tax returns
00:33:16
11. Using Home Equity as a Working Asset
00:32:32
10. How the Financial Media Encourages Bad Behavior
00:31:01
9. How Retirement is Not a Sprint, It is A Marathon
00:29:17
8. The Financial Freedom Formula
00:27:51
7. Housing in retirement. To downsize or not to downsize?
00:30:12
6. How to choose a financial advisor and when to know you need one
00:31:21
5. Estate planning basics – not only for the rich
00:29:36
4. Legacy planning – Leaving behind something more important than money
00:30:24
3. Preparing for Act 2 Career
00:27:37
2. Volunteering in retirement –time, talent & treasury
00:29:13
1. Envisioning Your Own Retirement as a Graduation
00:28:33