Understanding The 4 Phases of Retirement & How to Thrive in Each One w Dr. Riley Moynes (EP. 35)
20 Oct 2025 · 34 min
In this episode of the Ideas by Mike podcast, host Mike Milligan interviews Dr. Riley Moynes, author of The Four Phases of Retirement and a former teacher, financial advisor, and TED speaker. Moynes explains his “unique ability” to synthesize complex, disconnected information into clear guidance, a skill that underpins his research into retirement. He describes the four‑phase framework: Phase 1 (the short‑lived “vacation” phase), Phase 2 (a period marked by depression, substance misuse, and loss of purpose), Phase 3 (a stage of failure and possible regression to Phase 2), and Phase 4 (a service‑oriented phase where retirees find lasting fulfillment by contributing to others). Moynes shares insights from his three‑year, 200‑interview research project, noting that only about 10 % of retirees reach Phase 4, and even they may need to reinvent their service over time. The conversation highlights common misconceptions about retirement, audience reactions to his TED Talk (over 5 million views), and the importance of moving beyond a purely financial focus. Moynes discusses his personal legacy work—a family foundation, a “life‑legacy letter” that includes a memoir, lessons learned, and a list of five most influential people—and how he encourages others to create similar artifacts. He critiques the financial‑advisory industry for failing to help clients envision a holistic retirement vision, mentioning his firm’s “Retirement Chi” model that integrates community, health, and impact. Finally, Moynes reveals his next project: adapting the Give Five volunteer‑matching model to his local community, aiming to connect retirees with service opportunities. The episode concludes with practical resources (updated book, workshops, thefourphases.com) and a call for listeners to engage with the material.
Chapters
Welcome to the Ideas by Mike podcast, where your one-of-a-kind life meets a one-of-a-kind financial plan. Every episode, we provide insights into financial markets, discuss strategies for navigating Wall Street, and explore how to make informed decisions in a constantly evolving financial landscape. All with the goal of helping you. So sit back, relax. This is not your typical money show. We're going to be all in on helping you live a one-of-a-kind life. Well, welcome back to the Ideas by Mike podcast. This is Mike Milligan, your host. Today's guest is someone who's changing the way we think about life's greatest transition. Please welcome to the show a man dedicated to helping others live boldly and intentionally.
Thank you, Mike. It's nice to join you this morning.
Well, Riley, you, you, you know, around here we help people build one-of-a-kind lives, not just a financial plan. Your story is the definition of a one-of-a-kind life. When you look back at your journey from the classroom to the boardroom, to meeting with thousands of retirees, to the TED stage, what's been your guiding star?
I guess my guiding star has been one, what I consider to be my unique ability. And I consider that unique ability to be able to take information that might, at first glance appear to be very complicated or disconnected and kind of make sense of it all. That's what I did as a teacher and that's what I tried to do as a financial advisor and it's what I try to do in my speaking and in my writing. And that combined with my life's mission, which is to make a positive difference in the lives of others through education. So that combination is really what has guided me in virtually all of the things that I've worked at over the years.
Now, The Four Stages of Retirement was not your first book, if I've done my research right. What else have you written about over the years just to show people the breadth of who you are?
Well, when I was involved in education, I was author or co-author of a number of textbooks, one including History of Russia. One was about world religions. In the financial area, I did a book back in the early '90s called The Money Coach, which was an attempt to kind of simplify, if at all possible, using a lot of graphics and colors and so on to make it as interesting and as easy as possible to understand some of the basics. And then more recently, when I retired, I found myself discombobulated, which led me to work on what ultimately turned out to be The Four Phases of Retirement. Oh, wow.
And so I'm intrigued, right? You said you co-authored a textbook on Russia. Man, I know you've gone back and you've updated The Four Phases of Retirement. Have you ever thought about going back and updating the textbook on Russia?
No, no, no. That was long ago and far away. No, I haven't thought about that one.
And in multiple iterations, you've left that one in the past.
I have left that one in the past.
That's right. The 4 phases of retirement. I mean, on TED Talk, right, on YouTube, it's gotten over 5 million views. And I know you know this, but many of our listeners probably don't know this, but 5 million views on YouTube for a TED Talk. puts you in the top fraction of 1% of all TED Talks. I don't want us to go through that video because we cannot— you could do it justice, but me as an interview would not bring justice to what you've done there. What I'd like to hear though is the why and maybe get some updates on your continued research you've done.
Sure.
So give us a glimpse into what you were thinking about As you kind of walked onto the TED stage and what those, you know, what impact you were hoping this would hit?
Well, I was hoping that it would be of help to people because I'm very much aware, I personally became very much aware of the fact that there is much more to retirement planning than the traditionally kind of narrow confines of retirement planning, which tend to focus on investments and estate planning and wills and powers attorney and all of those critically important things. But there's more to it than that. And I discovered through my own personal experience that there are significant changes and challenges that almost always accompany retirement. And I was kind of blindsided by those when I stepped back from my work as a financial advisor and kind of considered myself to be semi-retired, at least if not fully retired. I was just As I say, I was gobsmacked by the changes and I tried to kind of figure it out because that's what I always try to do is to try to make something that's complicated easier to understand. So I went through the research as I always, that's my fallback position is to, what does the research say? Well, the research said what I've just indicated to you, and that is that most retirement planning focuses on investments and estate planning and that kind of stuff. And again, it's critically important, but just not what I was looking for. So I decided then that I would probably be best served by talking to people who I had been told had figured out retirement, whatever that means. So I put together a series of questions. I always finished up with the question of how do you squeeze all the juice out of retirement? That was my Final question, always. And, uh, one thing led to another. And so I started talking to a group of people and then they would refer me to other people. Oh, you should talk to so-and-so because they've got it all figured out, or they'd love to talk to you. And it went on for about 3 years and I did, oh, probably close to 200 interviews. And then I had this massive amount of information that I had to try to make sense of. Uh, and that was a challenge. But again, my unique ability, I think, is that I'm often able to do that. And the end result was The 4 Phases of Retirement in book form, in workshop form, and then ultimately, and more recently, of course, in TED Talk form.
So I know you just in March of this year came out with an updated version of the book. Any insights that have changed since the TED Talk? that you've discovered through more conversation and through more real-life application, not only for you, but your friends also who are still in retirement?
Yeah. Well, I guess the one thing would be that even if one reaches phase 4, and phase 4 is distinguished from the other 3 phases by a commitment to service to others.
Mm-hmm.
That's what separates phase 4 people from all the other phases. It's a commitment to providing service to others. So what I've discovered is that more recently is that while one may have decided what their focus was going to be in that regard that provided service to others, maybe it runs its course and we need to be kind of reinventing ourselves even in phase 4 as to other ways of providing providing service. And so I personally have experienced some of that, and some of the folks that I spoke to originally and that I continue to be in contact with have said something similar. So I thought originally that when you found out what it was that was kind of, that represented your sweet spot, that it would perhaps remain for an extended period of time. And while in many cases it does, I found that it doesn't always do that. And that was a bit of a revelation to me.
In your questioning, when you were in the discovery phase before the development that ends up being your final project, and then updated since, what are some of the wildest things you've heard from retirees that showed a lack of really understanding about what retirement is?
Yeah. Well, I guess first of all, I would say, Mike, that most of the advertising that is put in front of us suggests that phase 1 represents the ideal form of retirement. And in phase 1, I call it the vacation phase. It generally doesn't last for more than about 2 years. And taking into account that many baby boomers will be living up to 1/3 of their lives, perhaps 30 years in retirement, to try to spend one's retirement as a phase 1 person where it's all about you is simply impossible and it's not gratifying. That certainly has become very clear to me. Secondly, I would say that in phase 2, where I've heard stories that have just shaken me to my boots about The depression, the giving up that people have encountered, the frankly opiate misuse, gambling. Those are the sorts of things that I was simply not aware of the depth and breadth of in phase 2, which is where millions of retirees find themselves. In phase 3, I have found that, although it's clear to me that one has to be expecting failure in phase 3, I've heard some horrific stories of failure and people actually reverting and falling back into phase 2 and becoming part of the very, very destructive kinds of situations that develop in phase 2. So it has not been an entirely fun journey, but it's been one that I have really gained from, and I hope that I've been able to contribute to others as a result of.
I went to YouTube, right? Because it's not often you find over 5 million views on a topic. And I picked out some comments and I don't know if anybody's ever done this with you before or if you've ever gone and listened to the comments.
Yeah, I've checked them from time to time, but not for a while. So sure.
It's, I mean, some of these are just absolutely amazing, right? A guy named Tom writes, I've retired from a busy and stressful corporate life at the age of 65. I migrated straight to Phase 4. Clearing invasive weeds and regenerating degraded infested rainforests opposite our home, found complete enjoyment and immense satisfaction. You know, 2 years later, I've cleared out 7 acres, right? This is somebody who recognized the phases and went straight to where impact is. I've read another one. This video really hits home for me. Retirement has been such a rewarding chapter of my life. My wife and I worked hard to get here and we're incredibly thankful for where we are today. Now we're debt-free with a net worth of $3 million and that investment income supports us every week. We're enjoying the fun stuff. Thank you for the video. Just another one said, just accept— this hit me. This is a lady named Miranda. She said, just accept that you are not important. Not when you are working and not only after you're retired, just do what makes you happy and be the person that makes you happy. Can you, I mean, when you hear somebody who's watched one of your videos and say, just accept you're not important, what do you think when you hear that?
Well, I'm very gratified to hear that because the essence of Phase 4, in my opinion, which is the the level that we should all be aspiring to, in my opinion, is based on service to others. And it's not about you. It's all about you in phase 1, the vacation phase for a very short period of time. You've worked hard and maybe you have a bucket list of things that you want to take care of. That's great for a period of time, but you cannot build a successful 30-year retirement when it's all about you. So what that person has said is that they're not important. Exactly the case. You have to contribute to something larger than yourself, and that gives tremendous satisfaction over and over and over again. And it's something that seems to be virtually not discussed or hardly discussed at all in the retirement preparation phase.
To me, this is where I feel like Wall Street, Main Street, the financial advisory community fails retirees.
Absolutely.
And like, I think that the lack of being able to cast a vision with somebody sitting in front of you who's thinking about retiring is one of the greatest failures that kind of the one-size-fits-all financial world has done. Like, you know, in our firm, and I mentioned this to you ahead of time, but we have developed something called Retirement Chi, which is creating the vision for retirement. Chi is a Far East component about inner peace, bringing harmony. Sure. But we think if you define what your community is, how you're going to focus on your health and what your impact is, that then you could transition over to start talking about how your money accomplishes that. And so, you know, I like, like the 4 phases of retirement does a great job. One other comment that hit me that I want to end on the comment side is that this talk is for people who did not develop and nourish a life outside of work.
Yes.
And that's a problem. That's a problem that many countries and many people have. They devote everything to work. Yeah. And then they come to retirement, they don't know what to do. I would, I'd love to, for somebody who's done that, who's given it all at work and that's their social network and that's what there is, how do they transition to retirement? What is the, what's your advice for that?
Well, I have met in all of the research that I've done and in all of the interviews that I've done, I have met 2 people Only 2 people who remain in phase 1 and say that they are happy there. I believe that they're delusional, but that doesn't matter. They believe that they're in the right place for them. And one of these folks was a, who, he managed a very large law firm in Cleveland, Ohio. He said that he did it for all of his working life. He worked, he was exhausted virtually all the time, and he has nothing left to give. And so it is all about him. So he wants 2 things only in this world at this time. He wants a regular 10 o'clock tea time, and he wants at least one Manhattan at 5 o'clock each and every day. Those are the exceptions to the rule.
Right.
But when you mentioned, Mike, about how some people go to phase 4, and I've discovered that that's true, I believe it only happens to about 10% of the people, of retirees. But these are people who for the most part had discovered a life outside of work while they were working or while they were working at home. Wherever they were committed, but they discovered a life outside that. And maybe it was coaching, maybe it was art, it doesn't matter. Maybe it's photography. It doesn't matter what it is or what it was. These people seem to be able to move seamlessly from phase 1 right to phase 4 because they want to spend more time doing what they have wanted to do for all of their lives, but their routines prevented them from spending nearly as much time on it as they Right.
Um, uh, you're married with kids and grandkids, correct?
Yep. Yep.
So, uh, you are, you're finding yourself in phase 4 where you're trying to squeeze as much juice out of life as you can.
Uh-huh.
And, uh, you and your wife have turned the page now and started focusing on legacy a little bit. Can you tell us, can you tell us what you guys are doing? Um, you know, on a daily or building or, or what you're building out from a legacy standpoint for your family?
Yeah, well, we, we, we both do some volunteer work every, every single week. We have created a family foundation that provides funding for things that we're— that are important to us and that will last beyond, beyond us. And in addition to that, we have undertaken to write, and it's not finished yet, we've been working at it a long time with huge intervals in between, something that I discovered while I was doing my research that was referred to as a life legacy letter. And it's kind of a combination of memoir, family history, advice that we want to pass along to our children and lessons that we've learned, that kind of stuff. And there was kind of a rationale behind it. And one was that we discovered that oftentimes during family gatherings, they tended to be perhaps at celebratory times of the year. And the kinds of discussions that were possible were pretty, pretty not very deep. And so my wife and I came to realize that our children and our grandchildren don't really know what some of the things that are truly important to us are. I also came across a research study provided by Manulife Insurance Company, and they discovered that The more children know about their family history, the happier they are. And those 2 things have kind of combined for us to make it important for us to do what we call our life legacy letter. That we're, as I say, it's kind of a history. It's good advice. We think it's good advice. It's things that our children and grandchildren would never know about us except as a result of this. And so it's a work in progress. We're closer to the end than the beginning, and we're happy about that. But I haven't quite figured out what the format will be for that finally. But we know that it'll have a readership of probably fewer than 10, but we've invested a lot of time and it's important to us.
So I think a lot of people who are listening to this, right, are are going to say, well, how do I, you know, how do I structure a life legacy letter? And I'm sure you've got some wisdom on like how you, how you structure that. What, what's some wisdom you can pass on from that standpoint?
Well, we, we, we created some, some things that we wanted to include. And of course, one was some of, some of our of our life story. That was, that's part of it. Secondly, we wanted to include what we considered to be some lessons that we have learned that, that we think are important lessons that our children and grandchildren should be aware of if they're not already. I also have, have made a commitment, or I have identified the 5 most significant people in my life. And I acknowledge those 5 people in this life legacy letter, and I try to be in a fair amount of depth telling about what they have done for me, why I consider them to be among the most influential people, the 5 most influential people of my life. So those were some of the guidelines that we were looking for. It's organized More or less chronologically. But with those pieces of advice, lessons learned, mistakes made, all of that kind of thing that we've included as well.
I would, I'll give you, I told you that like Legacy is like one of my passion projects that I'm trying to push forward the legacy of Walter and Elizabeth Calder. Those are my grandparents, really my heroes in the grand scheme of things. And one of the things I would, Uh, when my Granny Elizabeth was still alive, she had dementia, but I could always bring her back to, you know, spots in time. And one of the things that my kids, so her great-grandkids, loved to hear her tell stories of was like the day my mother was born.
Mm-hmm. Right?
Like what, like what she was going through that day. Like, uh, and you know, like I might, my kids know that like when they were born, I have a, um, I had a, um, I had a meal that I ate every day on the birth of my kids. I ate pancakes. So my 3 kids, when they were born, I had pancakes on each of their birthdays. Right. And it's just something that I still do to this day. Like on their birthdays, I'll have pancakes. I have pancakes 3 times a year.
Right.
But it's just like those little small details. That's what light— to me, that's what lights up like the younger generation and gets them inquisitive. Like, You know, what else, Grandpa? You know, what else do you have? And those are like, I mean, the, the, the 5, I've never heard somebody say the 5 most influential people in my life. That, that just inspired me to, 'cause, you know, I wanna write that list. I mean, Granny and Pa are gonna be on that list, but I wanna write the other ones.
Yeah.
And I wanna let them know, 'cause at least if I had to think off the top of my head, 3 of 'em are still alive. I wanna let them know why they're alive. They're older than me. I wanna let them know how influential they've been on my life before they go.
Yeah.
So, uh, you're— you said you don't know how that is going to end up, and you said the viewerships or the readership's going to be less than 10. Um, yeah, you know, uh, have you ever— in the, in the 4 Phases of Retirement, do you talk about that in your new research, about that's something you're doing, or in your workshops, are you trying to encourage more people to do that?
Yeah, it's mentioned in, in the revised version of the, of the 4 Phases as a as a means of providing that kind of legacy. It's not something that I have included as much in the workshops where I want the focus to really to remain on seeking and attempting to achieve phase 4. And my concern is that it might kind of lose a little bit of its impact if I try to throw too much in. But it certainly is in the revised edition of the, of the Four Phases. Yes, indeed.
That's amazing. So I'd love to give people a way to connect, like if, like, like your workshops, or are they virtual now?
Some are. They're not nearly as powerful in my opinion. They're much, well, you know, it's real live in person is always better than virtual, but virtual is, if it's a necessity, it's a necessity.
So how do people connect with a Four Phases of Retirement workshop or how do they connect? I mean, obviously we're going to put a link in the comment section to your book, but how do they connect with you and your organization?
Well, probably the best way is through our website, thefourphases.com. That would be the best. And we can kind of go to books or workshops. From, from, uh, from that website.
And then, uh, and then my final question is, uh, what's next for you? I know there's probably something. I know it's the legacy side, but what else is next for you?
Well, uh, funny, Mike, you should ask. Um, I have become aware in my research of an organization in Missouri called Give Five. And, um, in the past couple of years, I made a kind of a, I guess one might say, kind of a half-hearted effort to, um, to incorporate some of the concepts of Give Five in our local community. But essentially what Give Five does is to attempt to connect retirees and near retirees with volunteer opportunities in their communities. I think that it is exactly along the lines of what I've been attempting to do, helping people to reach phase 4. And I have kind of, the folks who run it in Missouri have been so kind to me and they've been gently dripping on me over the course of the last couple of years. And as I'm winding down on some of my other activities, I'm going to, I'm going to put some time and effort into, in some way or another, introducing that concept in our, in our local community. So that's what I'm working on next.
That is, that's an amazing project, right? Because, you know, retirees have time. They also have wisdom. And they have the ability to make an impact on the next generation. And just like you're doing within your family, you also can do it in schools and where people need help, where they need mentorship.
Exactly.
And a lot of times retirees don't have the physical strength to go to Habitat Humanity and build homes or rebuild homes or go volunteer at the Red Cross in disaster areas when they occur. But boy, the mental strength that retirees have and the wisdom they have to give back is something that most people don't embrace, but they really should.
Well, this is an effort that combines, as you say, some of those, the expertise, the experience, the knowledge with the needs in the community. And I'm just not aware of another nonprofit that attempts to do that in quite, in quite the same way. I think it can be very powerful, and I would, I would love to see if, if we could do something like that in our, in our local community.
That is absolutely great. Riley, thank you for joining us today. Our, our listeners are going to be thrilled that they've listened to today's podcast today. They're going to, they're going to reach out, and I mean, I would expect your your viewership on YouTube to go up by tens and tens of people because of your coming here today.
Oh, thank you.
But the clients who listen to our podcast will have heard a lot of what you've said today, not in the detail that you said it, but through our conversation in the past. And the prospects that are looking at our firm will know that vision for retirement is an important element. To me. And, um, so, so thank you for joining us today. Uh, and guys, thank you for listening. Uh, if you'll, if you'll subscribe, um, if you'll hit like and share this podcast, uh, we would, we would appreciate that. And until next time, we'll see you.
Thank you, Mike.
Thank you for joining us today on the Ideas by Mike podcast. This has been Mike Milligan, your host. Where I look to bring real-world conversations with you of people changing the game in the financial planning, investment, and retirement income space. If you want to reach out to our firm to learn more, you can go to oneoakfinancial.com. That's the number one oak financial.com. One Oak Financial is a nationwide firm here to help you build a one-of-a-kind financial plan for your one-of-a-kind life. CFP Board owns the marks CFP®, Certified Financial Planner, and CFP® in the United States. As a reminder, Mike Milligan, Certified Financial Planner, is an investment advisor representative of Advisory Alpha LLC, an SEC-registered investment advisory firm. All opinions expressed by me or our guests are solely our own opinions and do not reflect the opinions of Advisory Alpha. This recording is for informational purposes only. It should not be relied on for investment, tax, or legal decisions, and it's in no way intended to communicate or guarantee specific performance or suitability of any security instrument or product as we may have discussed. Investment advisory and financial planning services offered through Advisory Alpha LLC, a registered investment advisor. Insurance is offered through Ideas by Mike, a Virginia-based LLC. Here to serve you in all 50 states and the District of Columbia. Ideas by Mike is a separate and unaffiliated entity of Advisory Alpha, LLC. While tax and legal issues may be discussed in the general course of financial and investment planning, Advisory Alpha does not provide tax or legal services. Please consult with your tax or legal professional prior to making a decision relative to those decisions. Any and all statements of purported or observed general practices of non-affiliated firms and advisors or conditions of the broad financial services industry are solely the opinions of Mike and are not intended to be offered as factual. The validity of these statements has not been verified, and as such, no representation of their validity are made. An annuity is a long-term financial product designed largely for asset accumulation and retirement needs. All guarantees are backed by the claims-paying ability of the issuing insurance company. This podcast is produced in conjunction with Mike Milligan. LLC. Thank you again for joining us today. We'll see you on the next podcast.
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