Root Ready
A podcast for growth-minded financial advisors
Root Ready
How Great Advisors Help Clients Face the Fear of Retirement
Some clients are more than financially ready to retire, but still can’t bring themselves to do it. The real issue often isn’t the numbers. It’s the fear of losing identity, structure, and purpose after decades of work.
In this episode of Root Ready, James explores how to support clients who feel stuck at the edge of retirement—not because they can’t afford to step away, but because they’re unsure who they’ll be when they do. Drawing on Viktor Frankl’s work on meaning and Riley Moynes’ four phases of retirement, the conversation dives into the emotional and psychological side of this transition.
This isn’t about pushing clients to retire—it’s about helping them define what a meaningful next chapter looks like. From reframing the role of work to encouraging purpose-driven planning, James shares how advisors can guide clients toward a fulfilling life beyond the paycheck.
Retirement planning isn’t just about reaching a number. It’s about helping people build a life they’re excited to live.
Submit a question for James here: https://rootreadypodcast.com/
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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.
Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements
Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.
So we're going to be talking about how you, as an advisor, can help that client who is financially prepared for retirement but still brings themselves, or still has trouble bringing themselves, to actually make the decision to retire. There's a fear of the unknown, there's this sense of they don't know what they're getting themselves into, what's on the other side, and they are paralyzed by this fear, by this inability to move forward, and they need your guidance as an advisor. So how do you approach that? How do you approach it when a client has concerns about retirement but those concerns have nothing to do with the financial side of things? So this was a topic that was brought to me by Paul Layton, who's our head of planning at Root, and we thought that this would be an excellent podcast or an excellent episode to go over fully, because I think this is actually one of the core things where, even if the principles from this aren't applied exactly to the situation, these are principles that can apply to many different situations and, as I was thinking about this, I think there's three levels to this. I'm sure all of you who have had that client that you run the projections, you've looked at their ability to retire. They're good to go, but they can't bring themselves to do it. And it's not because they love their job. It's not like they love their job and can't imagine saying goodbye to their coworkers and losing their ability to do what they do for work. There's just a fear of making that decision. How do you approach that?
Speaker 1:Well, I break this down, or I think of this, in three different levels. Level one this is kind of where most of us start. We think, okay, well, maybe if I can run through this client's budget numbers again really dial in what we're looking at. Maybe if we can go through the budget a few more times. Maybe if we can go through their financial projections a few more times. Maybe if I can show them how, even if there's a significant bear market right at the beginning of retirement and they'd still have a high probability of success, maybe that's the thing that will allow them to retire. Heck, maybe even you encourage them to work for another year. You know what? If you're not comfortable today, just give it more time. Build more portfolio value, increase your probability of success. Maybe a year from now, that feeling will be different and you'll be ready to retire.
Speaker 1:That's level one thinking If you cannot get yourself out of the financial side of things because you're seeing everything as purely a financial math problem. All of us, I think, start there I know I've certainly been there of why won't this person retire? They've told me they don't like their job. The numbers work. Let's keep working and reworking the numbers until they say they're ready to retire. It doesn't work.
Speaker 1:I'm sure many of you listening to this right now are thinking, yes, I have clients, or I've had clients where that was a thing. Well, here's what you have done. You've built the financial foundation which is necessary, and it's very good that you've done that. But what you haven't done is you haven't addressed the true concern. You've purely addressed the financial side of things, and what we have to start to realize is this is a deeper concern, more psychological concern. So that's level one.
Speaker 1:Level two we start to think that, oh, this is a spending problem. This is a client who maybe they've been so used to saving, they've been so used to accumulating, they've been so used to living within their means that the thing that's holding them back from retiring is they have an inability to spend. There's a psychological blocker in their mind that they cannot imagine actually pulling money out of their portfolio because they're so used to, they have such a big habit of building their portfolio, saving to their portfolio. So you start to think through this and say, okay, how do you help my client? How do I help my client actually learn how to spend some of the money from their portfolio? And as you do this, you'll realize this is an absolutely necessary thing for people to fully be able to live out and enjoy their retirement years.
Speaker 1:But this alone is still not quite the answer. Simply being able to flip that switch and go from that saving mindset to the spending mindset, actually giving oneself permission to spend what they work so hard for, that's good. And then it's going to enable spending. But that alone is not going to lead to a meaningful, purposeful, joyful retirement, one that's going to help a client alleviate some of those fears that they have about the unknown as they're thinking about their retirement years. So that is a very important skill set to master. I talk about that in other podcasts of how do you actually help clients who are very stuck in that mindset I need to save, save, save and cannot spend any of it Very important mindset.
Speaker 1:But that alone is not going to make the difference. And that makes sense. Because, again, the goal here, when we're going back to that client who has these blockers of they're fearful of retirement really what we're trying to help them do is guide them into a very meaningful, purposeful, enjoyable retirement. I'm not trying to force the issue, say go retire and be miserable. No, we're saying let's retire and let's do some amazing things, let's get the most out of life with our money. So how do we do that?
Speaker 1:Well, spending is one aspect. But I know lots of people that spend tons of money. They have no problem spending. They're not enjoying their lives. And on the flip side, I know lots of people who do have trouble spending. They live well, within their means, but they have very happy lives. So that alone is not the core blocker which brings us to level three. So if level one is building the financial foundation, level two is starting to dig into some of the psychological barriers, which is going to be helpful in many cases, of helping clients to learn how to spend, to build those habits of actually spending their money to align with what they want to spend money on.
Speaker 1:But what we haven't done yet is addressed the issue of purpose and meaning, and that's what you do with level three thinking here and level three thinking comes from the standpoint of what you start to realize is it says nothing to do with retirement. If all of life can simply be broken down into pre-retirement and post-retirement, we've missed the script. We're not born, we're not alive. We're not doing what we're doing simply so that one day maybe at 60 or 65, we can retire. But unfortunately that's how too many people live.
Speaker 1:There's this sense that maybe retirement is the promised land. That's where there's happiness, that's where I'll finally enjoy, that's where things will actually start to become easier. But then, once people get there, they have these blockers that we're talking about. They can't actually bring themselves to retire because what they start to realize is maybe it's not everything they'd hoped for. And they're realizing that because they start thinking through what am I actually going to do when I retire? Am I going to be happy when I retire? I don't even know who I am. I don't even know what I like to do.
Speaker 1:I spent so many years of my life working and sacrificing and raising a family and being responsible and putting money away, all those maybe sparks I used to have, all those hobbies I used to have, all those things I used to pursue. I don't do any of those things anymore. Work is all I have, and even if I don't like it, there's at least a sense of purpose and meaning to it, and I think that this is really well illustrated in Viktor Frankl's book. Viktor Frankl, who's a Holocaust survivor, wrote Man's Search for Meaning, and one of the key findings, the observations he had there, was that, as a result of his experiences in multiple concentration camps and then his work as a psychologist after, what he determined or what he saw is man's search, people's search, is not just for pleasure, it's for meaning and it's for purpose. And that's what I think we have to start realizing as advisors is that when you're running these Monte Carlo simulations and when you're running these analyses and you're saying, why won't my client retire? They've got such a high probability of success. We've gone through their budget, we've gone through their numbers, we've gone through their investments. They're good, but they won't do it there's a deeper thing going on here, and that's what we need to be able to address as advisors, and that's what we're going to be discussing in today's podcast episode.
Speaker 1:One other piece of information to add on top of that is just an understanding how different demographics work today. So in the US population millennials today as this recording, I believe are in their late 20s to mid 40s, somewhere thereabouts. You start to see what motivates millennials versus what motivates Gen X versus what motivates baby boomers, and you can start to see how each demographic is different. Millennials, for example my guess is most of you watching this are millennials very much driven by impact, driven by something they want to be part of, something that's bigger than themselves creativity, all these other things. Well, baby boomers and of course, none of these are universal, everyone's an individual and everyone's different, but as a whole, baby boomers are very much driven by work as their purpose. They tend to have a very strong work ethic. To them, it's very important to have been loyal and to have stuck with a company for a very long period of time. So you take these things and you start to also understand cultural and even family influences of who were baby boomers' parents.
Speaker 1:Well, their parents were typically part of the greatest generation. The greatest generation didn't have the luxury, a lot of times, of retirement and self-actualization, all these things that we talk about. It was survival, it was providing for your family, it was taking care of others, it was sacrifice. And so you have these baby boomers who saw that as their example. And there's sometimes this feeling of guilt. I remember talking to a family member who was retiring and he was talking about how difficult it was for him to retire at a relatively early age I think it was about 62 or so and I asked him why. And he said well, I saw my dad work well beyond that age so that he could continue to provide for our family. And so, even though this individual was financially ready, was financially secure, was good to go, there's still this sense of obligation and responsibility. If I saw what my parents did to provide for me, I almost feel guilty doing some of these things.
Speaker 1:And so we start to see that there's something much deeper than a Monte Carlo simulation. There's something much deeper than your portfolio balance or your ability to create income. There's this search for meaning and purpose. And even if that person, even if that client you're talking to, isn't totally in love with work, that work, if nothing else, is filling that void for purpose, that thing for meaning. That work is going to serve as that. That job is going to serve that role. So let's go back to the original prompt how do you help that person.
Speaker 1:It's not enough just to understand what some of the blockers are for some of your clients going into retirement. Ideally, if we want to be the best advisors we can be, we're expanding our skill set. We're expanding our tool set, the things that we can bring to the client relationship beyond just a you know what? I'll take care of your financial stuff. You go figure out the other stuff on your own. Now, meaning and purpose is something that is very unique to you as an individual, to each person as an individual. You cannot find someone's meaning and purpose for them, but what you can do as an advisor is you can offer your wisdom, your experience, the lessons you have learned, whether in your own life or even from other clients' lives, and you can share this with your clients. The unique thing about being an advisor is you're having conversations, you're talking about deeper things with your client, just due to the nature of your work, than maybe anyone else in your client's life.
Speaker 1:So just because we have that ability, just because we have that opportunity, does not automatically make us good at it. This is something we need to work at. Just because we have that opportunity, don't say, oh, I must be doing a good job. These conversations are coming up. No, we have to work at this. This is something that we have to strive to be excellent at, because it's our job that opens up that opportunity. But it's our responsibility. We want to be the best we can, to improve in that area, to be excellent in that area so that we can guide our clients the best we possibly can.
Speaker 1:Okay, so what do we do about it? Like I said, you cannot give someone meaning. You cannot give someone purpose. You can't just tell them what it is and expect that it's going to be okay. And to take it even a step further with things like asset allocation, things like the tax strategy, things like some of the financial aspects, you can do that for the person, and that's part of the fun is we get to help design the stuff. With what the client's goals are, we actually have control over. How are we shaping the construction of their financial strategy to optimize for that?
Speaker 1:This is different. This is something that you can only help a client to remove himself from the noise, help them take a big step back, and you can provide some guidance, you can provide some recommendations. You can provide a way of looking at things, a way of organizing their thinking, and that's what we're going to talk about right now, because there's two things that I think are pretty simple but can be difficult to do. As you try to help a client explore some of these things. The first thing you can help a client to do, or at least encourage a client to do, is simply reflect.
Speaker 1:Now the way that I do this reflection that's so broad. What does that mean? I journal almost every single day, even if it's just five minutes, 10 minutes, 15 minutes, asking myself the question what am I doing? What am I working on? Where do I want to be? And is the thing that I'm doing today, or the things I'm focused on today, moving me closer to where I want to be in the future? In fact, where do I even want to be in the future? Why do I want that for my future? Is that really my desire, or is that just something I think that I want, because I've seen other people with that?
Speaker 1:And as you do this, even if there's not a super strict structure to what you're doing, you are allowing yourself to disconnect from the noise, to disconnect from our busyness of our days, our lives, our responsibilities. Because, if you think through the standpoint of your client, or many clients and every client, of course, is different. So I'm talking specifically that client that's struggling with this. When was the last time they really thought about what they actually wanted? Anyone. You graduate college, you get a good job. You get that good job so that you can get promoted. You get married along the way, maybe you buy a home, you raise a family. You keep getting promoted. You're working 40, 50 hours a week. You have responsibilities, you send kids to school, you have direct reports, you have people that you report to. All these things start to crowd out our day so that, from the time that you wake up until the time that you go to bed at night, any non-working or non-responsible hour is typically spent watching Netflix, scrolling social media, doing something relatively mindless.
Speaker 1:And when you don't take time to step back and actually think about what do I want? Who am I? What do I want to be? That's why you have trouble, and when I'm saying you, I'm talking to anyone. This could be an advisor, this could be the client. That's why we have trouble retiring because, well, at least I have work and work's this known entity and even if I don't enjoy it. It provides structure, provides purpose, it gives me something to do. It gives me that meaning to life, even if it's not the meaning that I would like for myself, but I don't know what meaning I would like for myself. I don't know what I'd like to do for myself. And until you can disconnect, this can be journaling, this can be conversations with others, this can be prayer, this can be meditation, this can be exercise just disconnecting and allowing your mind to think and asking yourself those questions of what do I actually want to do with my life? It's that type of an approach that's actually going to allow you to be intentional with what you're doing.
Speaker 1:If you're just doing the things that you're doing because someone else is expecting it of you this could be a boss, this could be a manager, this could be society, this could be a spouse, this could be parents, this could be children chances are you're not living the life that you actually want to live and as esoteric and as out there as it seems. This is why we do financial planning. If our financial plan does not lead to better outcomes, not just financially, but for the way someone lives their life, we've limited the impact of what our work can be. Our work can be so incredibly powerful if it is connected to something deeper than just a probability of success. Even just going to that, what is probability of success that you don't run out of money? It's a pretty poor probability of success if we're defining what your life is based upon.
Speaker 1:If my definition of success for my clients is you didn't run out of money, I could justify that. That's why they're hiring me. I'm a financial advisor. I need to make sure they don't. But how much deeper could I have gone? Yes, that should be something that we keep in mind. We don't want our clients to run out of money, but hopefully we want so much more than that.
Speaker 1:And this is a tough balance, because you cannot tell your clients to do this. You can't do it for them, you can't force it upon them, but you can encourage them to do this. So how do you actually encourage your clients to do this? Well, this is a learned skill. This is something that can be very tricky. This isn't something that's just a very binary. When your client says this then do this. This needs to be something that you are able to integrate into the way you approach everything as an advisor.
Speaker 1:Some common questions that I'll even ask myself sometimes when I'm journaling and these are great questions that you can ask an advisor or ask a client, I should say is assume you're 90 years old. You're sitting on your front porch thinking about your life. If you're married, your spouse is there with you. What would have happened, what needs to have happened, over the course of your lifetime, for you to be sitting on that front porch and say that was a life well-lived? If I can go back and do it again, wouldn't change a thing, because my guess is when those clients that are struggling to retire start thinking about that, that's where some of the insights are gonna start coming from. It's not gonna be. I wish I got one more bonus. It's not gonna be. I wish I stuck around to get one more stock vesting. They're going to have to think about that.
Speaker 1:Is it relationships? Is it prioritizing time with your children, with your grandchildren? Is it engaging in meaningful and fun activities? Is it involving yourself in charities or ability to give back and do things with your time and your money that are meaningful to you and those around you? Think about that. If time and money were no constraint, what would you do with your days? This isn't something you can do for your clients, as I mentioned, but what you can start to do is help them disconnect, help remove them from the noise of the day to day, and just start asking these questions. They're probably not going to come to you right away, but the more you think about these things, the more you reflect on these things, the more you journal about these things, the more you talk with your advisor or friends about these things, the more clarity you're going to have over what do you actually want to do? So that's the first thing that you can do is just encourage reflection. For me, that's journaling, but there's a number of different ways that you can do this, and that's the only way you're actually going to ever know what do you want to do with your life? What does meaning and purpose look like for you when work is removed from the picture? The second thing that you can do with your clients is just encourage them to try Give them some perspective.
Speaker 1:I had a podcast interview I'll include it in the show notes with Dr Riley Moynes, and he has a famous TED Talk where he talks about the four phases of retirement, and phase one in his TED Talk is the vacation phase. Everyone loves it. You retire, there's no more alarm clocks, there's no more people to report to, there's no more responsibilities. You love it, but that's just a honeymoon phase that wears off relatively quickly. What comes next for a lot of people is this sense of loss, the sense of loss of identity, the loss of structure, the loss of purpose, exactly what we just talked about.
Speaker 1:Stage three is probably the most important piece here. Stage three and this is where you can at least help to set expectations for your clients on the front end is trial and error. There's no magic formula, there's no silver bullet that okay, you're feeling bored, you're feeling purposeless, do this and you're good. It's just trial and error. Trial and error meaning be okay with trying different things. Go join a cooking class, go join a pickleball club, go start volunteering, go get involved anywhere and everywhere. You're not going to love everything In fact, you might not love most things, but you are going to find that thing that you love. And then, finally, phase four is reinvest and rewire.
Speaker 1:And what Dr Riley Moyne says here is that almost always, what people report as bringing them the most amount of purpose, the most amount of meaning, is their ability to give back. This could be through work at their church. This could be through working at a local shelter. This could be through giving money to causes they care about, whatever it is. This could be through mentorship. This could be through teaching, this could be anything but taking the years of experience and wisdom and skill set and financial resources you have and saying how can I now give this to others, pass this on to others. A big part of what we're talking about I referenced this briefly with what motivates, say, millennials versus baby boomers is motivation.
Speaker 1:Now there was some famous research done You've probably all heard of it Maslow's hierarchy of needs, where it talks about our baseline needs shelter, safety, food, water and it kind of moves all the way up to this sense of self-actualization. And we hear that and it sounds all about self self-actualization Am I doing what I want to do? Am I everything I can be? And that's where it ended At least most people think that. But very close to the end of his life, I think it was about 20 years after he originally published this work on what motivates people. He said self-actualization is not actually the tip of that pyramid, it's self-transcendence. And he wrote this, I think, maybe a year or two before he died. So very few people actually know that it's part of this pyramid.
Speaker 1:But self-transcendence is very different than self-actualization. Self-actualization is this and so I'm going to be retired and I'm going to be everything I can be and do everything I want to do. That's not actually a thing that brings that ultimate sense of motivation and purpose. It's self-transcendence, which means it's something greater than myself, it's beyond myself, it's giving back to others, it's the ability to whether this is for children or grandchildren or neighbors or the world at large. How can I give of myself to go beyond myself? And that's what ultimately brings the greatest motivation and sense of purpose. That's exactly what Dr Riley Moynes found as well. Those people that found a way to give back. They were by far the happiest, the most content, the people that enjoyed retirement the most.
Speaker 1:But to get there you had to go through phase three, which was the trial and the error. There's nothing that's going to be presented for you. No one's going to say, hey, james, here's your purpose. It's going to come from deep reflection and it's going to come from trying and trying and trying again. But what you can do as an advisor? You cannot try for your client, but sometimes you're setting the expectation hey, client, it's not supposed to be easy. You're not supposed to go into retirement feeling like you have everything figured out. You're going to have a honeymoon phase, some things are going to be great, but some things are going to be quite hard. And in fact, as your advisor, what I'm going to encourage you to do is can we start doing some of these things now? There's no reason just to sit around and wait for phase two of that sense of loss. Start trying things now.
Speaker 1:In fact, some people have a wonderful transition into retirement. They love retirement. It's those people that have thriving social circles. It's those people that have activities they love doing. They have people they love doing it with. They have a sense of community, they have a sense of purpose, they have a sense of adventure. They have a sense of being able to give back. There's no reason that needs to wait until retirement.
Speaker 1:Like I said at the beginning, you should not view life through pre-retirement and post-retirement. It's just life In some and some of those years you're working and some of those years you aren't working. But what can we begin doing today? Find the hobbies, find the social circles, find the sense of your ability to give back, because the more that we can do today, the better off you're going to be in retirement. So you can do that for your client. But you can absolutely set the expectation, and sometimes that's all clients need. They just need to know.
Speaker 1:Okay, I'm not alone in this. This is very normal. I've spent my whole life working. I spent my whole life with these responsibilities, and now this is a brand new chapter in life and my advisor can help me set some of these expectations of what's to come and also help to guide me through the things I should be thinking about, so that I can then go do the work to make sure that my retirement is going to be as meaningful and purposeful as possible. So those are the two things that you as an advisor, can do, and really I'm going to add a third, and the third is this you as an advisor, should journal. You as an advisor should reflect. How can we be the best guides if we're not doing this ourselves?
Speaker 1:We have such a unique opportunity with our clients, such a unique responsibility with our clients, so they are coming to us, yes, for financial stuff. That's what people think they're coming to us for Optimize my finances, make sure I'm going to be okay, but really, what they're coming to us for is to live better lives. Their life should be materially different because of their work with you. Not because in every case they're going to have millions more dollars in their portfolio at the end of their lifetimes, but because they lived fully, because they pursued what was important to them, because you, as their advisor, who had such an intimate seat at the table, because they were talking to you about financial decisions which are so personal, which are so intimate that gives you a unique opportunity to say how can I help you with the financial stuff but go beyond that. How can I make sure that your life is going to look materially different because of the work that I'm doing with you than it otherwise would have? And so if you, as an advisor, want to be able to do that journal, reflect, live your own life well so that you can be the best possible guide to your clients.
Speaker 1:If all you're doing is talking about this and you're saying the right words but you're not embodying it yourself, there's going to be a ceiling to the effectiveness of that. It's kind of like if you see these motivational speakers Tony Robbins, mel Robbins, all these people. They have words that they say, and I'm sure you've seen on your Instagram feed or online life coaches everyone knows some life coaches saying the same exact words. Why is it that some of them have 50 followers on their Instagram and no one really cares what they're saying, whereas the Tony Robbins, the Mel Robbins of the world have millions and millions and millions of followers? It's not the words they say, it's not the message, it's the messenger. You, as the advisor, are the messenger. How can you live your own life in such a way that the message has maximum impact? Because the messenger is the one delivering it.
Speaker 1:So that's what you can do and, as you come across these conversations, recognize that this isn't a financial conversation. This is a life question. This is a life conversation. This is how can I maximize who I am and what I was put on this earth to do. What people are looking for isn't pleasure, it's not just comfort, it's purpose and it's meaning. And your ability as an advisor to pursue your own purpose and meaning will allow you to do that far more effectively for your clients as well. So that's it for this episode of the Root Ready podcast. Thank you, as always, for listening. If you have a question that you want me to answer? Go to the rootreadypodcastcom. On that you can submit a question. You can see all past episodes. This podcast is just designed to be the go-to resource for growth-minded advisors who want to be the best they can be. So if you have a question you'd like my feedback on, submit it there and I'll answer it on an upcoming episode. Thank you for listening and I'll see you next time.