Ep50 Howard Kaplan—The Wealth Manager Who Quit Believing in Retirement

Ep50 Howard Kaplan—The Wealth Manager Who Quit Believing in Retirement
The Pressures of Privilege
Ep50 Howard Kaplan—The Wealth Manager Who Quit Believing in Retirement

Sep 06 2026 | 00:58:22

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Episode 50 September 06, 2026 00:58:22

Hosted By

Diana Oehrli

Show Notes

In this episode of Pressures of Privilege, host Diana Oehrli sits down with Howard Kaplan, CEO and founder of Personal Strategic Design, who spent 30 years as a Harvard MBA, CPA, and wealth manager telling accomplished people how to retire, before his own life forced him to admit that doing everything right hadn't delivered what he actually wanted. 

Now he helps successful people in the second half of life find health, happiness, and emotional prosperity, drawing on life design training with Stanford's Bill Burnett and personal mastery work with Srikumar Rao. He didn't build his own next chapter until his 60s, and his upcoming book is proof the door doesn't shut when everyone says it does.

Howard traces the moment that changed everything: a month before turning 50, sitting at a Cheesecake Factory with his wife Sherry, then wandering into a Barnes & Noble and picking up a book called "Are You Ready to Succeed?" That single afternoon led him to call the author, enroll in a 10-week immersion program, and start unraveling why a Harvard MBA and a thriving CPA background still hadn't made him feel like he'd succeeded.

They get into why Howard now refuses to use the word "retirement" at all (he says it literally means coming to an end), what he calls "the gift years" instead, and the health scare he had to face before he could ask anyone else to change their life.

By the end of this episode, you will know...

→ Why Howard believes the word "retirement" is the actual problem, and the "gift years" reframe he uses instead.

→ The Cheesecake Factory afternoon that sent a Harvard MBA, CPA, and 30-year wealth manager into a decade of what he calls "personal R&D."

→ Why he hid a type 2 diabetes diagnosis for years, and what becoming "the role model" for his own son finally forced him to confront.

→ The "internal operating system," beliefs, patterns, self-talk, and identity that Howard says have to shift before anyone can design what's next.

→ Why real change requires both pain and a clear vision, and what happens when people escape the pain without ever building the vision.

→ The five areas Howard uses instead of the traditional "wheel of life," and why it stops being about money once someone reaches this stage.

→ Why he split his own practice in half once he studied the Experience Economy, keeping products and services on one side and transformation on the other.

This episode is for anyone who has done everything they were supposed to do, built the career, hit the number, and still feels like something hasn't clicked yet.

Chapters

  • (00:00:00) - Why Poverty Is Good for People
  • (00:00:40) - Howard Kaplan on the Pressures of Privilege
  • (00:06:20) - The Search for Excellence in Accounting
  • (00:09:56) - Are You Ready to Success?:
  • (00:15:11) - In the Elevator With Srikumar
  • (00:16:55) - The Courage to Live to 100
  • (00:24:04) - The Secret to Retirement: Connection
  • (00:32:21) - The Importance of Passion in Your Work
  • (00:39:48) - A Woman's Exit From Her Job
  • (00:40:53) - The Power of Experience in Business
  • (00:46:12) - In the Elevator With Positive Psychology
  • (00:49:19) - Designing a Lifetime of Success
  • (00:56:10) - A conversation about emotional prosperity
View Full Transcript

Episode Transcript

[00:00:00] Speaker A: More than anything else, people want to be out of serious pain, so they get really motivated. And so if they have a vision, they have something to follow. It's good for them because there's somewhere they want to get to, so they have the motivation. There's somewhere to get to. There's the chance for transformation. That's what we're after. [00:00:20] Speaker B: I'm Diana Earley, and I've spent most of my life learning firsthand what privilege actually costs. The legacy control, the family expectations, the guilt of feeling trapped in a life everyone thinks you should be grateful for. If you've ever wondered why having everything still feels like something's missing, you're in the right place. Welcome to Pressures of Privilege. My guest today is Howard Kaplan, CEO and founder of Personal Strategic Design. He spent 30 years as a Harvard MBA, a CPA, and a wealth manager telling accomplished people how to retire. Then his own life turned him around. He'd done everything right and found out it didn't deliver what he actually wanted. Now he helps successful people in the second half of life find health, happiness, and emotional prosperity, and he gets them there. He saw it coming early and. And went and mastered the fields to answer it. Life Design with Stanford's Bill Burnett, Personal Mastery with Srika Morao, and more. He didn't build his own next chapter until his 60s, and his upcoming book is proof. The door doesn't shut when everyone says it does. Howard, welcome. [00:01:37] Speaker A: Diana. Great to see you once again, as always, and thank you for having me. [00:01:43] Speaker B: We know each other a little bit. [00:01:46] Speaker A: Yes, we do, on a whole bunch of levels, from client to collaborators to, you know, respecting each other's work to friends. There's just many roles we've taken with each other, which is such a great relationship to have. That's. That's really what the work is all about, you know? Right. Right there. Well, that's certainly one of the areas for happiness. The Harvard study, which everybody points to, certainly talked about deep human relationship was the number one thing that underpinned, strategically, happiness. Of course, there's much more to it, but also the notion I talk about of bringing the personal and professional together. Our relationship did just that, which really leads to emotional prosperity. It's very efficient because you have all kinds of ways for us to generate positive emotions with each other. [00:02:50] Speaker B: It's funny because I was drawn to you because of the cpa, Harvard MBA profile, and then getting to know you, I realized it's all emotional, what we talk about. It's not. Not talking numbers. We're not talking no Not. [00:03:06] Speaker A: Not at all. Which is, you know, because we're talking, you know, your podcast, you know, privilege, the pressures of. Privilege, the pressures of having some degree of wealth, you know, depending on the. The individual. But, you know, I'm the ugly duckling story. You know, I was swimming in the pond, the financial services pond, and doing all, you know, given my background, my identity, starting as, you know, a cpa. I mean, I was recruited by every major accounting firm in the country. But that never was really fulfilling to me. And it's when I found out what was, and it even related to me personally. Wow. That's when I turned into the swan. That was the ugly duckling story. So, you know, but. But, you know, it's such a big deal for me because, you know, I really said I truly do care about people. Very high in my values. That's the life I live. I was an only child, you know, with older Jewish parents. Relationships meant everything, you know, to me. But if you really care about someone, don't you want to see them do the best they can with their life, make the most of their life? So how did we get there versus just saying, what's the number? Having enough. What's that number? Is it all about just having the number? No, actually, the majority of work is not the number, but it's looking at the life. And how do you help them strategically and as well as going deep to really get where they want to go. Not just need, but where they really want. Want to go. [00:05:00] Speaker B: Well, the thing is, you're so good at numbers. Like going like you've told me your history and going back to 1973 when you worked in that New York City credit union. [00:05:09] Speaker A: Yeah, that's when I graduated high school in 74. So that was one of the first internships I had because I was finally of age. [00:05:21] Speaker B: Yeah, and you placed seventh in the state in your CPA aptitude test. So you're really good at numbers. [00:05:29] Speaker A: Yes, I'm really good at numbers. I've always been good at numbers. But the interesting thing, it was something I was good at. So we're talking skill. But it wasn't something I enjoyed or was really into. It's just that when you're young, I put it aside. Gee, that must be how it is. You're not supposed to be happy. You're not supposed to enjoy something. You just do it because you're trying to get somewhere. I think there were a lot at these ages like me because I had Jewish parents. So Dr. Lawyer account became one of them. You were Good. And if not. But why did they know about happiness? They went through the Great Depression, actually, my parents. So for them, it wasn't happiness, it was being able to make a living. [00:06:20] Speaker B: Well, there were a few hints along the way that helped you realize that perhaps numbers weren't the thing. Like, for example, when you were working for the accounting firm and you found yourself planning those company picnics. [00:06:31] Speaker A: Yes. This was my third stint in accounting in my first four years out of Michigan, and I was still trying to get this figured out. And I couldn't find a place that I was really enjoying. Well, I was like the number one accounting recruitment. When I came out of school in the country, it was difficult to find out that I actually didn't like it. I didn't kind of get off on it. I didn't feel fulfilled by it. So this was my third stint, and it was Goldstein, Golub, Kessler Company, Park Avenue. They were the largest single office accounting firm in the country. And I ended up realizing that I enjoyed, actually I got to help them do the company picnic. And I ended up enjoying that so much, and not the accounting. It kind of said to me, maybe this wasn't your way, but that just meant, oh, so now I go back to law school or medical school or business school. Which master's degree was I going to take to. To get me out of here to figure something else out? So I went to business school. It was going to be law school first, and then I changed and became business school, and I applied to only one, Harvard, and I got in. [00:08:03] Speaker B: Wow, that's amazing. So you got to Harvard Business School and did that solve the problem? [00:08:12] Speaker A: No, no, it should have. I was going to be the Harvard mba, Michigan bba. I should add that cpa. Everyone with my background would be thrilled that they get into investment banking or any other part of institutional finance. Yet there was something coming to me going. I didn't think I really wanted that. And I ended up going to Macy's, believe it or not, because the CEO of Macy's at the time was a Harvard mba. And long story short, I ended up going there. And they had this thing at the time, they're being known for what was called store design, which intrigued me, which I love. But it was very confusing because my background, my identity still was being the accountant. It didn't go away. In fact, when I was recruited, that's really what everyone wanted to talk about to me because that's what they saw on my resume. [00:09:18] Speaker B: Yeah, it's impressive. [00:09:20] Speaker A: It's impressive. But inside it wasn't giving me the answers. I went down another road that I was still the ugly duckling. I pivoted back into financial services because of the cpa and I spent a couple of years almost with Macy's. Again, why am I here? I don't like this. So what's next? So I pivoted back into financial services again because of the background in accounting. [00:09:56] Speaker B: And then there was a moment when you're the cheese Cheesecake Factory, literally a [00:10:01] Speaker A: month before I'm turning 50 myself. And we know what that means for most people turning 50. You know, some evaluation of where your life's going, what's it all about. That's where people used to have what they call this, a midlife crisis, you know, because it wasn't just making a living, you know, holding up the family, you know, et cetera, et cetera. And I tell this story with just everybody knows me. We were at a Cheesecake Factory for brunch, myself and my wife Sherry next door. We went to Barnes and Noble, by the way, we have blue laws where I live. So that was the only store that actually was open. There was an exemption for bookstores. So we went into Barnes and Noble. I'm walking around and I see this book called are you ready to succeed? And it spoke to me. Now you hear my story a little bit. So I was not someone who felt he had succeeded yet from the background that I had because I had classmates at Harvard Business School who were multi gazillionaires already and I hadn't lived up to, to that competition. So yeah, I picked it up. Are you ready to succeed? And amazingly, it was patterned after a program at Columbia Business School. And so I thought it was speaking to me. Cause I'd been to two business schools, not just one, but two major business schools, undergrad and grad. The author, Srikhar Mah Rao, an amazing guy. Well, I called him up, I found his number, called him on the phone because I used to do programming at the Harvard Business School Club of New York. I wanted to ask him if he'd like to talk. We really hit it off. And so he said to me, you know, I'm going to be teaching the class at the Columbia Business School Alumni association, so you could go, you should consider taking the class. But he said to me, it's not just the meeting on Saturdays with the group, it's 10 weeks, all the reading and writing you're going to do. And sent me a 70 page syllabus. And in fact that 10 week immersion for me Because I decided to do it created the shift that was the start of the journey where I started finding myself a bit. But it was also very interesting because there's a whole field called positive psychology which has been developed at major, major schools that are the most popular programs at the schools now because they actually speak to happiness and emotional prosperity and choices you're going to make. But that wasn't at those schools. I mean, I went to Michigan and Harvard, but positive psychology hadn't been developed back when I was there in the 70s and 80s. And I thought, hey, maybe there's a lot of others like me. But that got me going in this interest now. It took my 50s, believe it or not, fits and starts and who I was and what my identity was. And I was still working as the retirement planner and financial practice. But most of us do this anyway. Fits and starts, back and forth. Am I worthy? Am I going to be. I had a major decision. If this is really what I wanted to do in my life, am I going to be the role model? How can I not be the role model and talk about this to other people at the deep level that I wanted to? So I made the decision to be a role model for everyone who knew me, that this was what I was about, this is what aligned with me. This was not just me finding clients for my financial practice. This was actually doing the work. In fact, I had to put my financial practice on hold in terms of the growth that it would have had to put the 10,000 hours in of really going deep about this work with positive psychology. Life design, which I believe was a niche of positive psychology, as I looked at it, personal strategic planning, not just strategic planning on an institution or business level, but actually doing it for human beings. And to the point of actually studying implementation. Because great strategy can be destroyed by poor implementation. And particularly when I was dealing with individuals or families, real human beings, that whole notion of implementation was all on their shoulders and was key. So that's a little snippet, but what [00:15:15] Speaker B: I'm interested in is you were feeling like the ugly duckling until you were working with Srikumar. [00:15:21] Speaker A: Well, I've always felt that something was off, that something wasn't clicking, that I wasn't getting the level of, let's call it positive emotions out of doing something. There were values that I had around family and around, you know, and those are deep. And so I wanted to do right by my son and my wife and so forth. But in looking at myself, this is not what was feeling fulfilled. It doesn't Mean, you know, I don't believe the money side of this is crucial for everyone. I certainly do. But it wasn't enough. Having enough wasn't enough. Having enough wasn't being enough for many, you know, many people. So I had to go further. I didn't have a choice. It was a calling, you know, for me. And I feel blessed now that I had a calling like this and I was able to take it somewhere because most people actually want this. They want to love what they do. Most people don't. And it's a shame. But I don't believe it's just an athlete or an entertainer who gets to do that. In fact, the model, she's no longer with us, but so many people would point to was Betty White. And she lived within months of being a hundred and worked through almost all of that because she loved her work. [00:16:55] Speaker B: So you sometimes talk about the regret that was underneath all of the work you did in those 10 weeks. [00:17:02] Speaker A: Oh, my God. It was, well, very simple. What was wrong with me? I didn't become an investment banker. I'm in a cpa, Big eight firm at the time, two major business schools, like everybody else with that background would become an investment banker. So why didn't I. And what was wrong with me? Because I didn't do it. Something must be wrong with me. That's one regret of many. But these things are deep. These things are deep. Things like that can create. Can create emotional holes for us. I mean, Diana, you've studied a lot and worked with a lot, you know, trauma, you know, different. You know, for me, it was food. You know, for others, it's alcohol or drugs and trauma through that. And that's how people try and fill their emotional holes. Too often for me, it was food. So, in fact, I'm turning 50, and I was suffering from type 2 diabetes and hadn't dealt with it. Not only was it created out of this angst in me, and so I had a food addiction from when I was a young child. But I wouldn't go to the doctor. I wasn't taking any meds for it. I hadn't been. And this was. But this was part of me being the role model. I said I couldn't do that anymore. To be the role model, to show my son, for instance, be a role model for my son. And I feel blessed today because today in what's going on with med tech in particular now, it's not only longevity living past the hundred, we're really not just talking about, but it's really here. But for someone like me with a major condition. There are plenty of people at these ages who have major conditions. And now it's not a death sentence. But there are ways to intelligently manage this, to have a full life expectancy, you know, and now I embrace all that. But this took a radical transformation in me to get to this place. [00:19:34] Speaker B: Yeah. And also Srikumar got you to see what was already there. [00:19:38] Speaker A: Well, let me. Let me give you a great shift because it was me understanding, it was no one else saying, here's what success is to me. It's me coming up with my own definition of success. So instead of me going, oh, my God, I'm not an investment banker, so I'm not worth a gazillion dollars. In fact, I live in one of the greatest towns in the country. I have the house with the white picket fence, in actuality. And there's a lot of good stuff going on in my life if I would take the moment to see it. [00:20:26] Speaker B: Yeah, I mean, you've got a love. I mean, Sheri is. [00:20:29] Speaker A: Yes, everybody loves my wife more than me. And I've been very lucky and fortunate. But I almost. And I don't know how many out there can understand this. I almost threw it away because of where I was at. I almost threw it away. But I'm grateful. I think about that every day, how grateful I am now, because these things happen in my life. And it's not to say, by the way, and I will say it, it took courage. It was scary at times. Bill Burnett talks about. We were talking today, actually, because he's now my partner, you know, who I took Life Design. He's known throughout the world, his whole work on Life Design, him and Dave Evans. But we were talking about how one thing that people seem to respond to is this whole notion of curiosity. How do you get more and more curious? I said to him, I think curiosity goes with courage a bit. Taking the courage to become curious. We came up with, actually around this and working together, this process of how people get there. Because it went from me focusing on me to me focusing on everybody else to try and bring this to them, to who we can help, particularly a niche with wealth. Because where I was coming from, you know, out of a financial practice, but, you know, we looked at all this and we love the process. We actually call it personal R and D, personal research and development for each of us to do. It's not just the company, but why does the company do it? Because that's where they'll go. That's how we Find our next big thing. That's how we discover the new, the different, the better the and it's fantastic process of curiosity. So we took that to an individual, a personal level to be able to do that with a human being and get them to this amazing place really focused on not just need, but what they want. And by the way, with that, it's amazing. I learned this from Bill. Want is like an 8020 thing. And that's one of the failings of the financial advisor who thinks they, most of them think they do this or can do this, but they really can't. Because when they ask someone what they want, they're actually accepting in a short meaning that what they're being told is true. And in fact the 8020 here is that 80% of people either don't know what they really want or can't articulate it to a level that is helpful to them or anyone working with them. That's where our work is very deep. Because we're not accepting. We'll start there with someone, but we're not accepting of that's truly what they want and they know how to tell us. [00:24:00] Speaker B: Yeah, because otherwise they wouldn't be reaching out to you if they knew what they wanted. [00:24:04] Speaker A: Well, that's some of the people we work with because they're really, they're in more pain than others around this. But unfortunately there's so many people who actually are in this place who don't admit it to not even other people, they don't admit it to themselves and they don't know how to find anything different. So they just go, oh, here's what I want. But in fact, that's why we have a whole methodology and process here to work with people so that they can come up with that. Because when we're working with people in their 50s, 60s, 70s and beyond, it's not about money anymore. What it's about is about time. Think about it. It's how do we help these people at these ages make the most of their time going forward. Whether it's you're in your 50s and now you literally could live potentially 50 more years because you could go past 100 or the 60s thing. This whole notion around retirement, that just doesn't make sense anymore. But most people still line up at this retirement line because the conditioning has been so massive for decades. Or the 70 year olds that are in this period where it's not about decline, it's not about this, is it? It's about the bucket list. No, they want to still be productive yes. They want to do more in terms of their happiness. What with family and connection. And we strategize to. It's so amazing to me. If the biggest altar putting the happiness is personal connection and relationship, then who plots strategy around it? I haven't met anyone who says to me. They've actually been asked and discussed creating strategy around all that, which we do. So we really believe this is a stage of a different stage of life because of what's happened with longevity and med tech and so forth. And it needed to be rethought. This retirement thing just isn't making sense anymore. [00:26:27] Speaker B: You don't even call it retirement. You call it the gift years. Right. [00:26:31] Speaker A: One of the things we think about, we go, these are the gift years, not the golden years. The golden years, the gold watch, the. All of that doesn't make sense anymore. Why? It starts with one thing. What does the word retirement actually mean? And the word retirement actually means coming to an end, retreating, decline. Why do you want to put that in people's heads when that is not what's going on now? Now, I get that everyone's been so conditioned, but it's about time to not start with retirement and how we're trying to retrofit that thinking because everybody is in different places now. No, get rid of the word. Don't even think of we. We actually have lists of words we call the renewal, rebirth, reinvention. Pick your own reword that gets you fired up to go through a process to see where you actually want to go. Not this thinking that's been so prevalent out there. I mean, I think this whole notion of retirement is the next blockbuster. It's time to go on to a different level of thinking around all this to make these years. I love. I love when I say to people, what if all these years up till now when you're with me was the regular season and now what we're in is the playoffs and championship. Ooh, gee, it doesn't that far E up. [00:28:16] Speaker B: Yeah. That's really cool. [00:28:19] Speaker A: That's the way we want people thinking that the amazing experiences and for some people, the wealth they have now. How do we take all that to really do amazing things with the time they have left and by the way, with the whole longevity thing, which is so hot now. Yeah. People are getting a bit that all this stuff about connection and we relationship that we. And we don't just go human, we go many levels of this. But they're starting to get what a big deal that is in terms of longevity all the Longevity. People are now talking about social connection and what a big deal that is and not being lonely and so forth. We were there already many years ago, you know, and we built something very special. If someone, by the way, wants to get our whole connection exercises and are thinking around that, they can just email me if they'd like. Howardersonalstrategicdesign.com and I'm happy to send it off to them. [00:29:30] Speaker B: That's so cool. So they can just email you and you give them some exercises. And then what? [00:29:35] Speaker A: Well, then we see. I mean, my book's coming out in the fall, which we're very excited about. We have a program working with people we call Designing what's Next, which I do with Bill Burnett. Between the two of us, that isn't like the normal program because it's not just going for a weekend to have infotainment. That was coined by Tony Robbins, by the way, who. I'm not putting him down. Anyway, I love personal development work as much as positive psychology. But what we're really trying to do is we're trying to find what you want. We're trying to help you get started, get unblocked. It's amazing. But the most successful people still have blocks, still have robots, because we're all human beings. We're all not perfect. We all have our flaws. We all have stuff going on. Even though we may show to the world everything is great. We all have stuff. So when we're really working with someone. So some people like yourself go through. You went to dwn. That's been evolving. But then we have some clients for our consulting practice as well as our coaching. And that's what you've experienced, Diana, and that's been working in development for the last few years. And we just get excited about that. And as this field keeps growing, I mean, everybody who might listen or watch this, it's a big deal to understand how new this is the type of thinking we're talking about today. Maybe it's the last few years that people are getting excited, the whole longevity thing and all that. If five years ago I had talked about this, people wouldn't know what we're talking about. They'd still be in the whole retirement thing. But now it's starting to go, hey, there are things that just don't work for me around this. How do I get fit to what I'm trying to do? So that's where they're trying to retrofit retirement. I just say get rid of it, because it doesn't serve many of the people who have been particularly successful, people who have achieved in some manner in their life, they're finding it's not as fitting to just go, give up achievement, stop wanting to do that. Well, that's what the retirement thing basically says. You're coming to an end, you're stopping. We say, if you've been an achiever, why do you want to stop, keep doing it. But we have a way about it that doesn't cost you your connections and relationships. In fact, it spurs them on. It's amazing. It becomes strategically important when you create looking at connection and relationships. [00:32:38] Speaker B: So it's. So you break happiness into connectivity and productivity. [00:32:42] Speaker A: Right. I didn't want to use the word work. Why? Because most people have bad connotations with work because they weren't fulfilled. It didn't make them particularly happy. I think there was a study I saw Deloitte did. I'm trying to remember how it's at least five years old, but it said like 87% of the people they surveyed in business didn't love their work, weren't passionate about their work. Know, I look at it this way, even with work, isn't it amazing? You know, we're in such a competitive environment when it comes to business and work, et cetera, you know, so who's going to win in a competition? The person who's passionate about what they're doing or the person who isn't? I think that's, that's an easy one. So I think this, this issue of passion is a very big deal. So when we talk productivity that we use the P's, that's what we think about purpose. You know, Bill just came out with a book, in fact, you know, his third book that was about this notion of meaning and purpose, et cetera. We think about play. Yeah, we should come back to play at these ages. That was always important. If you're playing, you can be into what you're doing. How do we build that in, not put it aside practice, you know, everything is not this one time project. Many things we go to, we want to go from project to practice. It's about daily, weekly, monthly practice so we don't have to think about it so much. So there are underpinnings to this notion of productivity. I always think of it this way, you know how many people think they should be playing golf at this point in life? Because that's what people say, oh, you're retired, you're gonna go play golf. Like, you should love it. It's part of retirement. I look at it and go, why should you do that if that's not something you're into? I'm not into golf, I don't need to play. But if you're someone who looks at it and goes, hey, that's something I want to master, that's being productive, where they look at it and go, the reason I love playing golf is I love the foursome that I go out with. So it gives me some great time to be with others that I'm really into being with. So that's a great reason. So there's intention, there's reason. It's not done. Because I hate this word should. You should do it because others said that you should do it and somehow you give them weight. No, you do it because it's actually aligned with who you are. I hate the notion of balance. That's fine when you're really young, but balance actually just creates lots of shoulds and that's never helpful. This notion of alignment. How do we find alignment with who you are, with the choices you're creating and making for yourself? For some people, they're very lucky. What they're struggling with is they have too much choice, particularly with wealth, they've too much choice. So how do they narrow down from the too much to what really is about who they are? That's where alignment comes in. Getting deeper, knowing themselves, the self talk, even all of their reality. How do you get into that to find what they really want versus oh, they should do this or they should do that. [00:36:31] Speaker B: Yeah. How do you get them to narrow things down too? [00:36:35] Speaker A: Well, that's where we talk about what we call the internal operating system. Think of this. Everybody today gets computers. So you have software in the computer that runs on top of an operating system. So as human beings, it's really the same thing. What we see with our reality runs on top of this internal operating system. What's in the internal operating system? Things like beliefs, patterns, self talk, identity, purpose. So that's where you use the iceberg. That's where we're trying to get below the surface. Not just on top, but the big deal is below. And we work with people in looking at and them understanding and working themselves with this internal operating system so we can shift patterns that they have or create a shift in terms of beliefs or work on their identity. All of this. Now for some people they get lucky, they can do it quickly. For others it's the so called journey. Because to get started, to get them unstuck, moving forward, this is deep work. But it's Such good work. And most people really get into it because what's it all about? It's about themselves. Some of the greatest that they could look at and work on is themselves. And, boy, it also impacts their family. The person that's so important to you, potentially a partner or a spouse. A spouse. It could be a business partner, you know, someone that's so important in your life, you know, and, you know, it helps everybody make, you know, decisions. There was. There was a woman we worked with who came in to work with us, saying to us, God, everything has been so great with her spouse except this thing called retirement. She felt she couldn't talk to him. He didn't get it. They weren't getting somewhere. So literally, she came to work with us. Of course, we follow life design. That's where we think people fall down, by the way. They go to programs, they read books, et cetera, but they never develop anything from it. We're all about. We're all about development. So we taught her how to do ideation and brainstorming. So she came up with 40 different ideas. She looks at the list. She says, I'm going to try the top. What she felt was the top three. The first one she tried with her spouse. All good, everything corrected. She went on. And in fact, we've worked with her and kept in touch. It's been a couple of years. She's just leaving her job because she wants to go to find something more fulfilling to her than where she was at. So she's really had some major transformations in her life. And that's what we really focus on, being transformative, focusing on change, getting someone to do that, understanding. Sometimes even it's important to exit something. It's actually like the Beatles. You know, the Beatles lasted like 10 years, and we thought it was all terrible that the Beatles blew up. But for their personal lives, each one of them, maybe it was the right thing because they had their life to go on, and it wasn't just being part of this group. So even exit sometimes is very important strategically to move forward in someone's life. [00:40:53] Speaker B: Yeah, because you've often said that in order for transformation to take place, you need both clarity of vision and pain. [00:41:01] Speaker A: Well, that's something that goes all the way back to Harvard Business School. For me, we learned this great model about change, which I still exists, human beings, even though Harvard Business school was, what, 40 years ago? Plus, for me, it's still the same. But they said it's on one end, great pain, on the other end, a real vision of where you're going. And if either of those are missing, there's a real tendency not to transform, not to change. So that's something that we look at that's so important. But something Tony Robbins said that I always catch that I think is so interesting, that does create the impetus for change. But sometimes the pain is a problem. Why is it a problem? Because when people lower the pain, they have a tendency to fall back to old patterns. [00:42:04] Speaker B: Should they stay in the pain? [00:42:06] Speaker A: No, no, we hope they don't stay in the pain. But the thing is, is how do we turn pain to pleasure? How do they do it? Because it's at. We call it aspiration. Where's the aspiration? Because that will be more long term than just negating the pain. And of course, clarity of vision is key because that's where they're heading, that's where they go. And it's so important because it's about the journey, it's about the path they create, it's about being present in that. It's not just about the outcome of where they think they're heading. We can talk more and more and more about that, but we don't have the time today. [00:42:52] Speaker B: So the pain motivates them to go after that vision? [00:42:56] Speaker A: Yeah, more than anything else, people want to be out of serious pain. So they get really motivated. And so if they have a vision, they have something to follow. It's good for them because there's somewhere they want to get to. So they have the motivation. There's somewhere to get to. There's the chance for transformation. That's what we're after. That's the highest level of value. That's what we focus on to people we work with. Transformation and experience. [00:43:29] Speaker B: You said that because you studied Experience Economy and transformation sits at the top of the four, right? [00:43:37] Speaker A: I studied with Joe Pine and his co author, his last name is Gilmore. They wrote a book called Experience Economy. And they had the foremost consultants in the United States States around this notion of experience. So when I first got started with them, they showed me what's called the value progression. And it went commodity product, service, experience transformation. And basically it was that the highest level of value to people was transformation. So I looked at that and you heard my story. I'm the ugly duckling. I'm trying to figure this all out. So at the same time, I've been in financial services. So it came to me, I said, I think I'm going to split this in half because I think what's happening with financial services is that they're all in product and service for the most part. That's what they're selling, products and services. But they're all worried about being commoditized. I said the other half. How about for me? I'm focused on transformation and experience, and I'll give you a tip on that in a minute. And that the lowest rung is actually service. That's just the operations of how we focus on transformation and experience. Experience, by the way, so everybody gets that is just, you know, if someone says, you know, we're changing you, we're transforming, and you're part of that. If the journey sucks, you may never get there, or you'll attach certain things to it that will cause you not to get there. So we don't want the journey to suck. We want the experience instead to be a great one, because then you'll be more apt to want to be there. It's all about this whole notion of the human being to find the natural, the natural alignment, the natural path, what comes naturally to you. Because when you speak this, when it comes naturally to you, stress falls away. Right? And motivation increases, Emotional prosperity increases. That's key. That's very key. Sorry. I get so passionate about this. It's just so great. [00:46:12] Speaker B: It's great I could listen to you talk about this. [00:46:15] Speaker A: Oh, you're sweet. [00:46:17] Speaker B: For hours and hours. [00:46:18] Speaker A: We've always loved our conversations now for. I think we're kindred spirits with this and the type of work, and you're terrific. So. [00:46:30] Speaker B: Well, you've helped me through some very difficult patches. [00:46:33] Speaker A: You've been great because you've allowed us to work with you. I'm always grateful that when someone works with us, I'm always grateful to them for the opportunity to work with them and get to this great place. So I thank them. [00:46:52] Speaker B: But it's so funny because whenever I talk psychology with you, you, you refer to the Harvard Business School, which is making me think that Harvard Business School is actually a psychology school. [00:47:01] Speaker A: You know, this notion of positive psychology, which was developed. I mean, you know, I had studied personal development with some of the greats for years. Robbins, Brendan Bouchard, Jack Canfield, who went to Harvard himself, and then positive psychology, which was derivative of programs at Stanford, Penn, Harvard, Michigan, Yale. And they're amazing because it underpins. They usually use the word happy for the book or for their podcast or. That's easy. It's not just the word happy. There are hundreds, if not thousands of. Of words that are positive to someone or negative to someone. It's actually getting There, for instance, in actuality, fulfillment is a different word than happy. They're not the same emotion. So how do we work with all that to actually create emotional prosperity for someone being emotionally rich? Now look, if you look at these schools and go, how much does it cost to send someone now undergrad? What, three quarters of a million or more graduate? Who knows? Doesn't it kind of make sense that maybe it would be good to attach happiness and emotional prosperity to decisions one is making at that level of investment in themselves? So that's why they became the most popular. So, yes, this thinking of positive psychology is not about a disease. It's about how through research and science, we've captured methodology around bringing someone to a greater self to be more positive to the upside of things versus the, you know, where someone needs treatment, which is all important, important and skill there around the negative, something they're suffering from or a disease or a chemical issue, so forth. [00:49:19] Speaker B: So for someone listening who feels that the finish line is coming, Walk me through the first real step. What does day one of designing what's next actually look like? [00:49:31] Speaker A: Well, first I have to listen to them a whole bunch to see where we start and get going. It's what's attracted them to want to work on this. What do they think their greatest challenges have been looking at this. It's about listening because everyone is different. That's the whole thing. When you look at financial services, for instance, that isn't necessarily true. And that's not the way it's dealt with when you're dealing with a human being at the levels we're talking about, everyone is different. So it's real important for us to listen. Okay, we're obviously looking for why they haven't started. What's happened now that's getting them going or a challenge, what's in their way, you know, how do we start functioning? Now we have a model that we use that we tried to get this to as small a model as we could. There's something called the wheel of life with coaches that. One of the things I don't like about it is it's seven areas or 10 areas and too much. So there are five things I look at with someone at these ages. And what we basically said, there was a great quote we saw from Laura Carstensen, who is the professor that now heads the Stanford center for Longevity, and she said something like, gee, we're there with quantity of life, the med tech. The real challenge and opportunity forward is going to be quality of life. And we, we took that Very seriously. So we said, how could we build quality of life for someone? Wow, interesting notion. And so ultimately I got to. And this took time. It's not just all of a sudden you stap your. I said, well, I think what everybody wants, if I look at everyone, is health, happiness and prosperity. But here it developed into. It's not just financial prosperity, it's emotional prosperity. So we look at five areas related to that. We look at health, we call it health, aging and longevity. How we look at happiness, the underpinnings to that we believe we see, like 90% is from these two areas which we were talking about connectivity and productivity, and then prosperity, money and emotions or emotional prosperity. And we focus in those different areas. Now everyone is different. So which of the areas do we start with? What do we emphasize? And that really is about listening skills, then questioning. Remember, one of the things I say about retirement is wrong problem, wrong solution. You know, you know, if you have the wrong. And I give Bill credit with this in. In studying life design with him, you know, because he's been my mentor, coach, client, partner, you know, so forth. But, you know, see, he says in design, you know, it's basically, if you're working on the wrong problem, you're going to come up with the wrong solution. So it was real key for us to come with health, happiness and prosperity. And you know how we work through that. [00:53:15] Speaker B: Yeah, the psychic problems, right? [00:53:17] Speaker A: Yeah, yeah. So that could be, for instance, that can come up in connectivity, a relationship that you just, you know, it can be a toxic relationship. We look at those. That could be where there needs to be some decision and strategy around exit because it's so toxic. Or that can be productivity. That could be, gee, I have the business partner. You know, we seemingly want different things forward in our life. I'm 60 years old. This is a pretty big deal right now. Do I exit this business? Do I go sell this business? There are many private business owners who struggle with that, who struggle with creating a vision. And without vision, they're not going anywhere. They don't have a good sense of looking at it. So that's our model. The process we use is this one of personal R and D. It's one side is research. How do we get into that internal operating system? How do we look at alignment, things like that? The other side is development. And I mentioned that's where people really struggle to develop something out of the books or the weekend programs or so forth. Remember when I talked about Srika morale and shifting? There's one thing that I learned there that most people don't understand because they don't get it. And it's called immersion. How do you create immersion for someone that'll shift them? I was with Srikumar for 10 weeks where he said that reading and writing the syllabus, working in the group setting. We believe groups are very valuable by the way as well, that collaboration with others who are on something similar to collaboration is a big deal. Leadership is a big deal. Us providing leadership, for instance, is a very big deal. But that's how we work with someone. We put groups together, we try and lead. It's unlike. We're ridiculous in this. We use AI. AI can be fantastic here for ideation and brainstorming. It's not about being perfect or 100%. You're just coming up with ideas and brainstorming that can be beautiful. So that's a snippet of how we work with some. [00:55:55] Speaker B: So if they, if someone takes that step, Howard, what do you want them to know is waiting on the other side? [00:56:01] Speaker A: Oh my God. The first thing we're going to do is it's really simple. It's just reach out to me, you know, the same email. Howardersonalstrategicdesign.com let's just have a conversation. I'll see if we'll talk about. Are you a fit to. We can't do this. We don't do this with that many people because this is deep work. This is serious work. At this point, we're not looking to. Let's have thousands of people on a webinar call. We're not looking for that. We're looking for handfuls of people that we can work on to really go deep, really develop. We don't just talk about this but you know, where are they really going? What's really in their way that does it? For some, it'll confined it in 30, 60 days. For others, they want to just keep working on this. Because you know something? At these ages we find people, many people love learning. What's the learning journey going to be at this. This point in life for themselves. And so they want to keep learning. They want to keep at it. They want to keep. So we have some that just keep working with us and others who it's a short term and we focus on certain elements. But it all starts with a conversation. It's just a half hour to 45 minutes. Let's see where they are, let's see what kind of fit. And we go from there. [00:57:36] Speaker B: Yeah. Well, here's to emotional prosperity. [00:57:40] Speaker A: Thank you. It was great to talk. Really appreciate it. [00:57:43] Speaker B: Thank you. Howard, if this episode landed for you, share it with someone who might need to hear it. And if you haven't already, subscribe so you don't miss what's coming. But here's the real thing. I want you to know if you're carrying something you can't talk about, if you have every resource except someone who actually understands what wealth costs. I work one on one with people like you navigating exactly that. You can reach me@diana oehrli.com thanks for listening.

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