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Podcast 339

339: Winning the Retirement Game: How to Avoid Uncertainty and Boredom with Joe Casey

Today, I'm thrilled to welcome Joe Casey back to the podcast. Joe is an Executive Coach at PEC and a Managing Partner at Retirement Wisdom, who helps people design their lives following their corporate careers to successfully navigate their transition to retirement.

In this new book titled, Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy, he walks retirees through the obstacles they're most likely to face in the next chapter of their lives. Tackling issues such as boredom, uncertainty, and drifting by helping them craft specific strategies to tackle these problems head-on.

In today's episode, we dig into what Joe's learned from working with people from all walks of life. We talk about the difference between left-brain financial planning and right-brain life planning and why so many advisors end up having to unwind what should have been "perfect" retirement plans.

We'll also talk about how to cast off pre-retirement mindsets that won't serve you once you've transitioned out of your primary career and much more!


Here's all you have to do...

  • Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
  • Step 2.) Text BOOK, that’s B-O-O-K to 866-482-9559 for a link to our book request page, complete the form and we will ship you the book for free. It’s that simple!

PS: If you’d like a free copy of Joe’s book, all you need to do is leave us an honest review over on Apple Podcasts, then send your email and your username to [email protected], and we’ll get it out to you!

In this podcast interview, you’ll learn:
  • Why Joe sees retirement as a game–and why most retirees don’t actually want to kick back, relax, and withdraw.
  • Why so many people find themselves in a state of shock or identity crisis when they retire–and how “soft” conversations about retirement make this transition less uncomfortable.
  • How boredom paralyzes, scares, and frustrates us as we approach retirement–and what happens when we discover newfound passions.
  • What to do in the meantime as you wait for an opportunity to recharge your energy or artistic juices between career and retirement.
  • How to get retirees out of the habit of consuming 40+ hours a week of television.
  • Why retirement communities are rarely diverse and don’t always encourage us to be at our best.
  • How to make a concrete list of your killjoys and start working through them.
Inspiring Quote
  • "It’s efficient to have routines and habits and build them, but that can blind us and keep us away from spontaneity where some of the joy is." - Joe Casey
  • "Talk to people who are involved in a particular volunteer activity before you jump in and get involved, get a sense for what they like about it, what they try, and how it makes a difference." - Joe Casey
  • "Sometimes, we’re looking for the big impact, but we fail to appreciate the impact of these small acts." - Joe Casey
Interview Resources
Offer valid in the 50 United States and the District of Columbia, to first-time requestors. During the offer period, receive one (1) in-stock book per request. Limit (1) book per week per household. Limit three (3) books total each calendar year, between January 1 and December 31. Offer valid while supplies last. Howard Bailey Financial, Inc. reserves the right to cancel, terminate or modify this offer at any time. Void where restricted or otherwise prohibited.
Read the Transcript

Casey Weade: Joe, welcome back to the podcast.

Joe Casey: Great to be back.

Casey Weade: Joe, I’m excited to have you back. I really am. And I say that with love and authenticity. I had the opportunity to get your book here. I don’t know, it was probably a couple of months ago when we initially got the book, and then we had to reschedule a couple of times. I was excited that you had a new book and it was well-written, had the opportunity to dive into the book, go through all the different chapters, all these different obstacles that we’re facing as we retire that are stealing our joy. And none of us want to have our joy stolen.

And so, I wanted to have the opportunity to dive into the book with you, but I thought what was really exciting was we sent an email out to our Weekend Reading subscribers and we had some amazing feedback. And you joined us back over a year ago for an episode, and that episode was phenomenal. We had a lot of great feedback, and I could tell that those individuals that loved you the first time, well, they wanted to come back and give you some more love because we had all kinds of great questions from those subscribers. So, today, I wanted to kick it off with a little bit about the book, and then I want to dive right into those obstacles and kind of jump around how they relate to some of the fans that actually listen to the show on a regular basis.

Joe Casey: Great. Thanks.

Casey Weade: All right. Well, with that, I have to ask, looking at the book, if you’ve seen the book, you can see it is football related. It looks like there’s some kind of sports analogy going on here with winning the retirement game. So, I wanted to ask, why is the book titled Win the Retirement Game? Some might look at that and go, retirement’s not a game. So, how is retirement a game?

Joe Casey: I think it’s one of the most important games you’ll ever play. So, the reason for the title of the book is, I’ve been a sports fanatic since the age of 10. I’m older than 10 now, but I tend to see things through that lens. And the origin of the book is I took a look at the clients I’ve worked with on the retirement coaching side over the last eight years and asked a simple question, what did they need to overcome to have the type of retirement they were really looking for?

And people that I coached come from all different walks of life, but I started to see some common themes and common trends. And as I analyzed it, it looked like the NCAA basketball tournament, meaning there were early level rounds, earlier challenges that were must-haves, you must defeat them. And then it got harder and harder, and leading up to really a championship-level type of challenge at the end. And so, it just really organically followed this pattern of a tournament.

Casey Weade: Yeah. And you say you work with people from all different walks of life and we do as well here. However, I find that there are certain types and there seems to be a line drawn between those that are open to having the softer conversation and those that aren’t, those that struggle with the softer side of retirement, and those that aren’t. And I think it’s hard to really uncover what is that commonality with these individuals that are open to the conversation and struggling with that particular topic. What have you found? And that really leads us to who is right for this book. Who did you write the book for?

Joe Casey: I wrote the book for people who are planning to retire or are just retired, but they’re not done yet. They don’t want to just kick back, relax, and withdraw. They really want to engage, maybe in something new and maybe in some type of purpose-driven activity usually. So, it’s people who feel like they’ve got a lot left in the tank, so to speak, from a life side. In terms of who benefits, I find that if you think about what you do and you’re absolutely someone I always talk about, you get both sides of this equation. But on the financial side, it’s really a left-brain-dominated thing. It’s quantitative, it’s logical, it’s linear. And that’s a comfort zone for a lot of people.

But there’s this other side of retirement. What are you going to do with your time? How are you going to invest that? And that’s totally different. It’s more of a right-brain thing. It’s not as logical, it’s more intuitive. And it takes some adjusting. You have to shift gears to get into that space. But it means while they may not be someone’s comfort zone early, I find that that’s where there’s a lot of upside for them. And I always tell people the really simple version of it. You want to bring your whole brain through retirement. It’s well worth it.

Casey Weade: Well, we think about this right side of the brain is the softer side of retirement, right? And yet, when I look at your book, or even just look at the cover and think about it being a game and thinking about, if it’s a game, that means there is strategy involved, that means we need to be leveraging our right brain and our left brain. And I think quite often, we’re just thinking with our right brain when it comes to these softer sides.

How do you think we leverage our left brain and the softer side of retirement planning? And you might say it the other way. How do we leverage that right brain and the left side, side of the planning? I think too often, we’re thinking of these as two separate things. We keep them separate rather than bringing the power of both sides together.

Joe Casey: It’s a great point. You really want to combine them and you want to have the right balance from the left brain side. You want to really have a plan. You want to have an organization. You want to have a clear sense of what are the things that are most important to you financially and non-financially. So, what are your priorities?

That sounds like an easy question, but it actually takes some thought to step back and talk about it and engage others because other people in your life may have a different perspective, get your thinking in a different direction. So, I think having the foundation of the realities, the priorities are important, left brain place to start. But you also want to bring some imagination. And that’s sometimes where I think people can struggle because if you think about 30 years in the workplace, some professions require imagination, but sometimes that gets drilled out of us a little bit and you need some time to adjust, to reengage in that more creative thing about what could be, what do I want this next phase of life which could last decades, really wants to be? And how to then start to go back to left brain and how do I get there?

But I think it starts with really thinking about the possibilities and being willing to experiment and explore. And the biggest thing is to step outside of your comfort zone. I always tell my clients that, and for me, writing the book was a step out of my comfort zone. So, I had that experience as well. If you’ve written books, it’s a different type of endeavor.

Casey Weade: You’ve worked with a lot of clients over the years, and I wonder if you’ve seen this before, or maybe you can just speak to this in particular, and that would be a lot of financial advisors I found, as we onboard and train advisors, they’re a little uncomfortable having the softer conversation. What happens and what maybe has happened to individuals that you’ve seen that have only really focused on that left brand, that have only really focused on the harder side of I’m going to go maybe with a financial advisor, I want to retire and I want them to put together a retirement plan and they don’t have the softer conversation? Where does that lead them?

Joe Casey: So, I think it leads them to really come to the starting line, so to speak, in a better position because you’ve done the preparation, the planning, so you’ve got that side set and clear. But what it does is it sets them up for some realizations, often surprises of, okay, what’s life going to be like now? Because you lose a lot when you move away from the world to full-time work and there’s a long list of things, but there are things like structure. All of sudden, your time is your own, which sounds great, but you’ve got to really add some structure that works for you with a balance and flexibility in there as well.

You also lose a lot of status, meaning that, in the US anyway, we can note a lot of status with titles and positions and those types of things. And sometimes, people struggle with all of a sudden, who am I now, which might then have worked with a lot of physicians since COVID? And that’s one that they find challenging, is they’re still a doctor, but it’s a little different. So, who am I now? The identity part comes in pretty quickly.

And then connectivity, particularly for us, men-type people, we tend to have sometimes more of our social connectivity connected professionally, and so. there’s a need to find a new tribe. And so, that can be disorienting because all of a sudden, people find those calls or texts or emails aren’t really being returned by your pals at work as quickly as they were a few weeks ago because now you’re out of the loop. So, I think sometimes that’s a little bit of a surprise. People sometimes show a complete shock. But the good news is still that our opportunity to redefine it, to make it what you want, and that’s different for everybody.

Casey Weade: And that’s why I’ve tried to educate advisors. You could be doing someone an injustice by getting them into retirement if that’s not exactly where they want to be. I have put together this retirement plan. You put them in this place financially they said they wanted to be. We didn’t ask the right questions to really understand that’s truly what they want to be or what they actually want it to look like in the first place. And then, that can cause not just psychological issues for the client, but also, it can cause financial issues as well. You put together a plan that was designed to do one thing, and then six months, six years later, that’s well, I never really thought it was going to be like this. And we have to unwind this plan.

You mentioned identity, and this is one that I feel like I’ve been challenged with, especially over the last 12 months. I feel like I’ve been going through some personal identity shifts, and maybe even over the last couple of years. And I feel like, as I go through changes in identity, and I went back through my life and I have uncovered this seems to happen around every 10 years roughly, I’ll go through some type of major identity change, which is an improvement. I’m evolving. I’m improving. However, throughout that process, I often found I’m often regressing back to a previous identity. And then I’m growing, and I’m regressing back to a previous identity.

You talk about physicians often having struggles with making this transition from an identity perspective. I’m wondering if that ever ends. Does that ever end? We just go in, we meet with Joe, we work with him for 6, 12 months, and hey, we’re good. Yeah, we resolved the identity crisis. Or is this something that we’re going to have to continue to work on the rest of our lives? And what does that look like?

Joe Casey: I think you hit on one of the key things that people often forget or fail to realize about our time, and that’s we don’t stop growing once we leave the world of full-time work. We keep growing personally. We keep learning. And then sometimes people, again, fall into the trap of thinking retirement is the end of the line, and now, it’s just all about kicking back and relaxing. But you actually still keep growing, and I think the identity thing, you can keep evolving.

If you think about how often we update the software in our phones, you can’t run that software, your iPhone back on iOS 3.2. So, every once in a while, we’ve got to update it, as you said, the identity, not as frequently, you’re going to be changing that too quickly and that would be jarring. But every so often, that’s something back. And I think you also had a key in terms of your own personal experience of it’s not all linear, it’s not all straight upward or forward. Sometimes you step back and add dimensions.

And sometimes, this can be one of the biggest challenges. Sometimes there are things we have to let go of in order to grow, and some of those things from the world of full-time work fall into that category. But I think it’s shedding certain parts of identity, getting more in touch with who we really are at our core. And then what are some of the other dimensions we want to expand and grow into and learn?

Casey Weade: It’s great. Joe, I’m excited to get into these nine obstacles. Let’s kick it off, all right. I don’t know that we’re going to get in every single one. I’ve thought about this quite a bit. I said, I don’t know that we can dive in deep to each one of these. If you would like to dive in deeper, then get a copy of Joe’s book, and we’re going to give it away here today. So, stick around. We’ll give it away to you, and you’ll be able to dive in deeper to these.

But there are a few that stood out to me that I said, I think we can add some more color around this. I have some questions for myself. And then we had some of our Weekend Reading subscribers that had submitted their own questions as well over the last several days. And as I think each one of these questions, we can kind of assign to one of these obstacles, and that first one being, as I see it, it’s boredom, so one of the obstacles that I see in it.

When I look at each one of the obstacles, I don’t see them necessarily as very defined nine obstacles, I see them all very intertwined and building on top of one another. And I think that’s what you’re trying to explain, right? That it’s going from prep to maybe the championship game?

Joe Casey: Yes, absolutely.

Casey Weade: And when I look at that first one, boredom, we had a question that came in from Jane. And feel free to tie this into some of these other obstacles. And I think Jane has a question that really relates well to filling time and retirement. So, Jane says, “I’m 10 years from retirement.” So, Jane is 10 years out from retirement. She says, “What can I do to prepare for the nonfinancial side of things?” General question, however, she goes on to say, “I feel I have a good grasp on the financial side, but with limited free time, I feel like I can’t adopt new hobbies or interests.” So, she has limited free time, and I think a lot of individuals are going through this. I’m in the peak of my earning years. I don’t have time to take away and figure out what my new hobbies or interests are. So, what can somebody do with that limited free time to start creating some of those new hobbies or interests? So, it’s not just like throwing a fish in cold water.

Joe Casey: Great question. First of all, Jane will have the game to be thinking a decade ahead. That is great to hear. And I’m sure she’ll do well by starting the preparation now. I think the biggest thing is to think of things in terms of an experimental mindset, meaning the good news is, you don’t have to have it all figured out in advance. You can learn, evolve, try out things, and experiment as you go through.

And so, I think as it relates to new interests, new hobbies, take an experimental approach. What’s one thing I want to try or learn more about next year? Just one. And it could be starting very small, but let’s say it’s a particular thing, well, I’d like to learn more about this particular hobby. Just find a group that’s involved in it or even do some research, but start to get engaged in it in a way that you can handle. Not all in, not jumping in with both feet, but just dipping your toe in the water a bit and seeing what it’s like.

There’s a couple of things that come from that. You’ll discover some things that turn into a passion later. You’ll discover some things that really aren’t when you thought there. And then you also meet some new people. So, I think just focus on one. Don’t try to make it all wrong. Don’t try to do everything. Just start.

But keep a list of the things that catch your attention that in boredom, boredom came up for me because so many of my clients in the first conversation, particularly men, say I’m afraid of retirement. That surprised me. What are you concerned about? I’m afraid I’ll be bored. And so, I started to look into it and I was just surprised, discovered there’s a ton of academic research on boredom. Who knew? Although we all became experts in the early phases of the pandemic on boredom a little bit, too.

But there are some things that can be used as a catalyst, that can give you a signal that it’s time to do something else or to add something in there. So, we need to be patient with it, pay attention to it, and use it as a catalyst to get going on some other areas, but great to hear Jane’s planning 10 years out.

Casey Weade: I think we can feel that we need to dive all in if we want to start a new interest or a hobby, but Dean Niewolny from the Halftime Institute, he often talks about low-cost probes. We don’t have to dive that deep. And I saw my mother-in-law really embrace that. She wanted to try some new things. She didn’t know she’d like woodworking, but she tried it. I think the class was one day a week from 6 to 8 o’clock at night.

And she ended up meeting some new friends and really building out her social circle, I mean, some guys and gals. And it was really good in a lot of ways. And it didn’t take but a couple of hours a week in the evening, right? It doesn’t have to take away from that much. And she continued to do more and more woodworking into the future because she found out it was something that she is loving. And as she is working less year after year, she’s doing more of the things and diving in deeper with these interests and hobbies.

Now, talking about boredom, when I think about our kids, I think in, today, raising children, we feel that we need to keep them engaged all the time. It’s not good to be bored. They need to have this to do or that to do. We need to run here. We need around there. But when our kids are bored, that’s when I see the growth happen, right? That’s the best opportunity for them.

And as we transition to retirement, we can see boredom as a negative thing, but it can be a real opportunity as well. You stated that retirees have roughly 2,500 hours or more each year to fill. So, why is it that some do view this as an opportunity and others view this as a problem? Do you see a difference between the mindset these two individuals have?

Joe Casey: Yes. And I think it goes back to your point earlier about blending the two, the left brain approach and the right brain approach. The left brain approach to this is I’ve got all these hours. It’s an investment decision. How can I step back, look at the options? Where do I want to really place my bets in terms of how I want to invest my time?

And then the right brain comes in with the imagination. What could be? What can I try? What can I do? What do I really wish I had done going back? Sometimes, I see people returning to something they love to do when they were younger. And then as they got more involved in their career, family, raising kids, etc., they put it aside. Now, you can bring it back.

My main character in the book picks up a guitar which he hadn’t played since college. I do not have any musical building, but we do have a guitarist in the house, our 21-year-old son. But he picked it back up again and started to do it. So, I think sometimes it’s looking back and saying, is this something I missed? I really love that I can bring it back, or something new that I want to learn but use both sides of the brain to look at that investment decision of all the extra time.

Casey Weade: Well, maybe one of these two things relates to that. So, in your same chapter around boredom, there are a couple of things in Chapter 2 there that you mentioned. So, maybe you hit on both of these. Maybe you go to the one that gives you the most energy. You refer to a couple of different things. You talk about the mental and physical positive outcomes of openness to experience, and then you also talk about something called belief window. So, openness to experience, belief window, go.

Joe Casey: So, openness to experience is from the big five factors theory of personality. My goal is not to bore people who are watching and listening while we go through this, but it’s a personality trait. So, it’s something that, as you age, you can look at how open am I. And can I just try something? Again, same principle, start small one thing at a time.

The belief window is a personal experience I had in my corporate days. I had a quick story. I’ll try to make it quick and not boring. I was called into the office of my boss and my boss’s boss one day, and she had the president of Franklin Planner, now FranklinCovey, Hyrum Smith in the room.

So, he’s got this great concept. We were a big client of theirs. We had the financial and the Franklin Planners for all our financial advisors and used that system. And he’s got this great idea and he’d like to just preview with you and see what you think. Would it be good for our managers? And he walked me through, he said, “Look, we all have this belief window. It’s like a plexiglass force field, if you will, in front of us. And we see the world through that lens. But sometimes, it gets cloudy. There are things in their beliefs that aren’t really of service anymore. And we can’t really see the true reality.” And I said, “Well, thanks, appreciate that. I don’t think it would really fit.” I thought it was a daft idea. It took me quite some time that they couldn’t care less about my opinion. They were actually trying to get me to learn a lesson, that I had some incorrect principles in my belief window.

So, once that dawned on me, it was a great principle to have. And I thought, wow, now I can see more clearly if I look at those different things. And it’s a great metaphor for retirement because there are some beliefs we had during the working years that we can now put aside and we could see the future more clearly about what’s possible for us.

Casey Weade: It’s good. We have a window of opportunity. And we certainly do. In Chapter 4, you go into loneliness. One of those opportunities we have a window of is social connection. And I do think and when I look at individuals that maybe they waited, they retired at 70, and now, at 80, they’re finding, okay, this is an issue. I’m going to cultivate some more social connections. It can be much more challenging, right? We had a window of opportunity to really accelerate in that area and ensure that we built a tribe.

So let’s talk a little bit about building a tribe. You cited some research from Pew Research on how Americans in their 60s are almost alone twice as much every day as those in their 40s and 50s. So, it’s a huge loss of social structure, right? What are some ways to build that new tribe? Give us some tactics, give us some strategies. What can we do to start building that tribe?

Joe Casey: Sure. So, you’re going to find new connections and new friendships through doing things with others. That sounds obvious, but you got to really go where the fish are, so to speak, if you want to fish. So, look at activities you can get involved in. Some are fun things, hobbies, etc. I know everyone listening is thinking of pickleball. Which side of that? That controversy you’re on.

But it could be volunteering for things. Again, start small, but you could get involved in something. It could be as simple as a new book club for those who are so inclined to that type of thing. It could be, again, as you pointed out, with your mother, one class, whether it’s virtual or in person, can open up new connections.

So, think about where are the people congregating who you think might be good candidates for your new tribe, and then try to get involved because you really bring a lot to the table there. I also mentioned later in the book there’s research by an academic in Canada by the name of Robert Stebbins. And he talks about, basically, things that become serious interest. And that’s another way to get involved in terms of if there’s something you’re interested in, then you want to master to take on.

Even if you’re a beginner, getting involved, people know more about it. You can learn and develop a lot of common relationships that way, but get involved in something. Don’t go to 10 things. Don’t take on too much. Go to one or two to meet some new people.

Casey Weade: I see a challenge here. You’re talking about building a retirement portfolio and how we also need to build a kind of friend or a social portfolio. And just like your financial portfolio, it needs to be diversified. We need to have a diversification among our friends and acquaintances. And I want you to speak to why that is.

However, I think there’s also a challenge for most in this. And you mentioned pickleball, right? It goes, well, who’s going to be playing pickleball at 2 o’clock on a Tuesday? I mean, you’re not going to find a lot of diversity in that crowd, the same thing with golf, the same thing with the book club.

And I’ve seen this with younger individuals. I’ve got a group of friends that I play golf with on Friday and it’s like, well, there’s not a lot of diversity in the group that’s playing golf on Friday afternoon when most people are still working. So, what do we do about that? And talk a little bit about the benefits of that diversification.

Joe Casey: Sure. No, it’s a great point. And by the way, on the pickleball point, I do not play, but you’d be surprised at that 2 o’clock afternoon, it’s actually more people than anything than you might imagine. But the diversity is important. That’s why I think looking at different avenues.

So, you might find more diversity in terms of thinking, gender, ethnicity, etc., in some of the learning-type activities and/or some of the volunteer-type activities. So, you can certainly meet different sets of people in those different endeavors. I think the classes, in particular, are very good ones.

When I went back to school and did a third master’s at 60, I had just a range of people, many of whom I’m still in contact with, from all over. It was virtual primarily but met a number of people in person at times. And you can meet a lot of people coming around with a common interest. So, I think classes are a good one. Volunteer is another, the exposure to different types of people in terms of thought and other factors.

Casey Weade: Yeah, I see that in the volunteering space for sure. Definitely, it seems like, I mean, for one, we pay our team members to go out and volunteer during the week. So, you’re going to have the opportunity to create some diversification there. But I like what you said that it’s not all about age diversification, but there’s also diversification in thought, diversification in political beliefs, diversification in gender. There are a lot of different ways to achieve that diversification.

Joe Casey: And one example, I’m part of a group that’s been going on, starting its third year now. We’re spun off from the Encore Network, which spun off from And this group of 12 people that were invited to look at multigenerational issues. And so, we have people, the oldest members in their 90s. We have a couple of people in their late 20s or early 30s. And it’s a group that gets together about every six weeks to talk about specific issues, groups, written articles together, and people really like the connectivity. And it’s a diverse group in many ways, not just in terms of age. And it really is eye-opening when you hear different perspectives on similar topics.

Casey Weade: Well, you’ve written on articles around dementia. I have dementia that runs in my family. So, I always go, okay. So, what can I do to try to avoid this at all costs? And you hear a lot of things about physical activity, engaging the mind, etc., but when I think about this, having diversity in our circle for always around the same people that know the same things and are not going to challenge our way of thinking, that means we’re not going to get those neurons firing as much as we could if we are around different kinds of perspective. So, there are also some serious health benefits there.

Joe Casey: Absolutely. And literally, as you know, you learn so much from hosting a podcast. I interviewed a psychologist, I said Dr. Mike Rucker has a book coming out January 3rd called The Fun Habit. And he talked about the positive impact of having more fun on cognitive reserve and in cognitive health because it gets you out of linear thinking or just thinking in a habitual way, but being more open to spontaneity and in doing things in different ways. So, I think that’s a great point.

Casey Weade: Well, let’s talk a little bit about inertia here, Joe. So, I want to get to inertia, again, with a question. And this question comes from another one of our fans, Nancy, a Weekend Reading subscriber. And the question goes on a little bit, so bear with me. However, sometimes, I’ll shorten up these questions, get straight to the point, but I think the color here does add some good value. And you might see this as something that relates to a previous question. However, I think the color can help broaden the perspective here.

So, Nancy says, “As someone working at a high-stress, more than full-time tech job and caregiving a loved one, my time for preparing for my imminent retirement is very limited. I barely have the wherewithal to get the financial side sorted out. Even so, I have a very good sense of what I want to do. I want to return to my creative life that I had before getting involved in software development. And I feel particularly drawn to conceptual art and art activism. Even so, I feel unprepared for the nonfinancial transition. My initial plan is to take time to relax, work on some creative projects, and let my direction grow. When I do have spare time, I do little bits of some of the art projects waiting for me. But are there other things I can do now during the very few spare moments that I have available to better prepare?” So, answer this any way you want. And I thought it was interesting that she had a really strong interest in the arts. And you mentioned in your book a lot about creativity and retirement, the benefits of that. Maybe we can tie it to that.

Joe Casey: Sure. Great to hear, again, what Nancy is thinking about in advance. And we can all relate to the stress of a full-time career. And it seems like it’s impossible to dedicate time for a parent.

So, I think similar principles, first of all, I rely a lot in the book on Gene Cohen’s research, the late Gene Cohen of George Washington University, who really did a landmark study on the benefits of engaging consistently in the arts on all kinds of health and wellness dimensions. So, I think that that’s a great thing for her to be involved in.

But I think she raised the thing about our point that’s broader, which is sometimes, we think we have to wait for the perfect time to have that time to recharge. So, it’s great that she’s thinking about let me dedicate some time to recharge, get re-engaged in the art, great to hear. But what can you do in the meantime? How can you shift the allocation of some of your time to that along the way? I know it seems impossible, but one thing I do with my executive coaching clients, we do a time audit, and very simply take a look at, print the calendar for the last couple of months, and just analyze where did time go.

Highlight the ones where you had some more control. It was more discretionary. There were meetings you didn’t really have to be at, but you did, or things you did that you really didn’t have to do or some windows and this includes weekends. Or you can just dedicate a little bit of time to that recharging, that re-engaging the arts to get a running start, again, get one thing at a time, start small, but take a look at how you’re investing your time today, and can you find a winner, too?

I find usually people can spend 10% to 15% of their time differently by getting a clear picture of analyzing it back to left brain, and then being willing to try doing some new things with it. So, you can see if they can carve out some now. It seems impossible, but if you look at it in a way, I think you can find some pockets of things that are less important that are taking up some time now.

Casey Weade: So, is this how inertia can be a really negative thing in retirement and maybe in that pre-retirement phase? We’re not really paying attention to the things we’re doing. We’re kind of defaulting into the same thing. And we’re going on about life and we’re not really focusing on how we’re spending our time. I think, for me, I like to do an activity inventory once a month and go, well, what did I do over the last 30 days? And what should I eliminate moving forward to free up more of that time so they don’t just fall in the default of doing the same things that maybe aren’t that meaningful year after year?

Joe Casey: I love the idea of stepping back and doing that analysis on a consistent basis because that gives us the ability to see the patterns because our brains are wired for efficiency. We like the shortcuts, and so, we like things that we can put on autopilot. So, that’s a good thing. But when we get too much on autopilot, we fail to see some of the patterns.

And the reason I first learned about inertia was when I did a mastery and coaching thesis where I interviewed 20 of the top coaches in the US and UK, and one in particular, Marshall Goldsmith spent a half day with me at his home in California at the time. And as we’re leaving, we’re talking about what he’s learned about helping people change. He said the biggest obstacle, the biggest enemy is inertia because it just has a weight on its opponents to keep the status quo.

So, I think being intentional about where you are and where you want to go and breaking out of that, again, like boredom, using inertia as a signal or a catalyst for something new. But I love the fact that you’re doing that activity. That’s a great practice.

Casey Weade: You’re saying the inertia is the opponent of creativity because we need to create space in order to be creative.

Joe Casey: Yes, because it blinds us to just keep doing the same things. It’s like the movie Groundhog Day, Bill Murray. And it’s efficient to have routines and habits and build them, but that can blind us and keep us away from spontaneity where some of the joy is. Again, we want to protect the joy, and it’s in the subtitle. And the inertia can keep us away from experiencing certain moments of joy that can come if we’re stepping back and looking at it differently.

Casey Weade: Well, again, this ties back to another one, right? This ties back to boredom. We want to create some time to be bored so that we have the opportunity to eliminate the– we need to eliminate the inertia to create opportunity for boredom, to create opportunity for creativity in the end. It’s like I see it with my kids, I myself, well, there’s nothing to do. They get bored and they complain. They might whine about it, but the next thing you know, they’re putting together a puzzle or they’re building a house or they’re doing some type of creative pursuit before you know it. And they would never have that opportunity if you just set them in front of a TV and let them watch TV for the next two hours instead of being bored.

Joe Casey: It’s amazing. You can look at the TV and see over 500 channels and say, boy, there’s really nothing on.

Casey Weade: Yeah, and for retirees, what are the statistics there? And I’ve seen some of this in the past, but TV can be a major detriment for retirees. Can you speak any numbers around that? Are you finding that retirees are watching a lot more TV? And how do you get them out of that habit?

Joe Casey: I think there are two things. One, there’s TV, and then now looking at screens in total. So, with the exception of YouTube and your podcast, which is a very good investment of time. There’s also the time we spend looking at screens. So, on the TV side, one that I saw was a Nielsen data was like 48 hours a week, which is a lot of time knowing when they started their retirement plan, started investing in their IRA and 401(k) thought, boy, I’ll be able to watch CNBC as much as I want.

Casey Weade: It’s 48 hours a week is the average– human or the average retiree?

Joe Casey: Average older adult.

Casey Weade: Okay.

Joe Casey: And that’s a stunning stat, but it goes back to that stat you mentioned, too, about how much time people spend alone. There’s a great chart that was published in The Wall Street Journal and Visual Capitalist had it too. I’ll send it to you. You can include it in your show notes if you want. And it really shows that mark over time.

So, I think there’s a vacuum created, there’s a time created when you move away from full-time work. And how does that get filled? Without the intentionality of getting involved in some new things, interacting with people, there’s a vacuum there, it’s easiest to start watching the different shows, Netflix. There are so many great options, some of the great things to do. People, you can get pulled into these things, but it can really be a major, major time waste, and there’s an addictive quality to it.

And I think it’s something people can really step back, like your activity review. How much time am I spending with screens? And is that really why I sacrificed and saved and invested all those years? What are some better uses of my time? Because I want to spend my TV time on sports, politics here and there, some other things, and great shows when they come up, but I want to be mindful of how much am I putting in that bucket.

Casey Weade: One of those opportunities might be to spend some money or maybe it relates to spending some money. So, I’ve got a question from a fan, and this is one that I see come up quite a bit. I didn’t necessarily see it exactly tying back to one of the specific obstacles. I didn’t see this listed as a specific obstacle, but it’s one that I see come up on a regular basis. And I think you can tie it back to some of the things that you’ve seen with the families you’ve worked with, individuals you’ve worked with, and for sure, these specific obstacles and maybe a couple of them.

We had one of our fans, Jeff, sent over a question. Jeff said, “After 35 years of financially acting, living in a thrifty, frugal, and prudent manner, my greatest challenge in retirement is overcoming a mindset of not spending money. I often see other challenging topics discussed that arise in retirement, but I have not come across how to change my save-first nature. Heck, this is why we sacrificed for so long so we could enjoy our golden years, but I can’t get past unnecessary spending. Help.”

Joe Casey: Jeff has highlighted a really common problem that I see. It’s how you change your mindset, so…

Casey Weade: Really, add a little color. I know, Jeff. I have known Jeff for a long time and Jeff is in it. He can spend all the money he wants to spend. All right. So, this is a challenge. And he knows it and he can see it and he can visualize it. He knows what he can do. It’s not a financial uncertainty issue. It is, as you’re speaking to now, it’s a psychological issue.

Joe Casey: And I think it’s really about taking a look, taking a step back, saying, okay, I did save and sacrifice and invest all these years. I’m now in this new phase. What are really the things that I want to use my money for? How am I going to plan that and start to experiment? Where can you loosen up a little bit? Are you investing your time and things for fun? Does it take money to have that happen? Start there. How can I use my money in the way that I envisioned going back to the beginning?

When you thought about saving for retirement, what did you envision retirement would be like in terms of activities? It wasn’t watching your portfolio 10 times a day, probably. And so, what are those things that you can use your resources for better use and try on a different mindset but start to recognize you’re a new face? And I think working with someone like yourself to get clear on what are the risks, what are some of the fears behind the continued saving, the continued frugality, and try loosening up a little bit.

Casey Weade: Yeah. It sounds easy.

Joe Casey: With proper guidance and advice from a financial professional like yourself.

Casey Weade: I’ve got to say, I feel like one of the things that I’ve seen work in the past, and maybe you’ve seen this as well, I’ve seen it work when they start integrating new individuals into their social circle, maybe bringing someone into that social circle that knows how to spend some money, maybe they have some different tastes, may they have some things that they’re interested in that they like to spend money in that you’ve never been interested in. Maybe it’s fine wine, maybe it’s cars, maybe it’s real estate, whatever it is. But getting around those individuals can help open your mind to the joys of spending those additional dollars.

Joe Casey: And I think it starts with the question of shifting your mindset from this is now something I get to do. What can I do with these resources I’ve built? What do I really want to do? And what does that open up for me, and then starting to engage in that?

Casey Weade: Oh, man, it’s coming full circle. Now, Jeff, as he moved into a retirement community, continuing care retirement community just, I don’t know, a few years ago, and I mean, he’s still young, he’s in his early 60s. So, he’s surrounded in this community by a very undiverse crowd, a crowd that’s older than he is. So, he’s surrounded by individuals that are very frugal. It’s going to be hard to change your ways until you broaden and diversify that social circle. I mean, so much of this seems to come back to social circle.

Joe Casey: Yes. And it’s the old saying you’re the sum of the five people you spend the most time with. So, I think looking at that and I’ve seen other people start to look at that in terms of who are the people you’re surrounding yourself and would like to surround yourself with more. And sometimes, that means pruning some relationships of people who tend to be more negative or toxic, and they can be some addition by subtraction, which is a hard subject and difficult thing to say.

But look at who’s really giving us the positive energy. We don’t want just hanging out with a bunch of free-spending gamblers, for example, who have great ideas to spend as money, but who are some people that really focus or they’re enjoying the activities or enjoying life, they’re savoring what they built? Maybe there are one or two people that way.

Casey Weade: Well, this is my biggest problem with the way it seems that we’ve moved, especially over the last 10, 20 years, is we’re getting more and more polarized and more concentrated in like-minded individuals. And that’s my issue with these retirement communities that have popped up all over the country is they’re not diverse. I feel like, well, that’s going to have so many different negative mental and physical impacts for individuals. Maybe you can speak to some research right now.

Joe Casey: So, there is a lot because you’re looking at– there are two sides. People do like the commonality. It does help some people in retirement communities with the social circle activities, etc., etc. But there is this kind of segregation aspect of it as opposed to, in addition to the other types of lack of diversity that tend to be there. So, I think it’s what can you get engaged in to do it?

The best thing I saw it was actually a film that was done by a young person by the name of Lance Oppenheim. And it was about the villages in Florida. And I’ve also sent your client on my podcast, he’s actually a good guest. And he went down there, and he’s literally in his early 20s when he did it and really just hung out and lived there for a period of time. It was a documentary on different people’s lives but gave you a window into some of the upsides and downsides to that. So, I think it, again, comes back to what are you really looking for out of this next phase of life. How can things help your enjoyment, looking to track from it and being mindful of that?

Casey Weade: Lance Oppenheim, I’m going to check out that documentary now. So, hey, let’s talk a little bit about volunteering and maybe just purpose in general, meaning impact and retirement. So, we have a question from Stacy that I think relates to that. I wasn’t sure where we would put this. We put in under obligations, we put in under drift. Stacy said, “Volunteering can certainly give a retiree a sense of purpose, but what do you recommend as a technique to find where you can make the biggest impact?”

And my own little two cents there, it seems like we often default into doing these charitable activities and thinking that we’re making this big impact, which is great. We’re making a good impact, but it may not be our highest and best use to make a bigger impact in the world. So, back to Stacy’s questions, she said, “Is it just signing up for every charity volunteer opportunity until you get a feeling about it?” So, I mean, I guess that speaks directly to what I just said.

Joe Casey: I think it’s really being thoughtful about it, meaning do your homework. Talk to people who are involved in a particular volunteer activity before you jump in and get involved, get a sense for what they like about it, what they try, and how it makes a difference. I think it also requires being thoughtful about the impact of small things. Sometimes, we’re looking for the big impact, but sometimes we fail to appreciate the impact of these small acts.

So, there’s research about that coming out as well, the impact of small random acts of kindness. So, I think reframing what your contribution can be, you might think it’s small relative to what you can do and your capabilities, but it actually may have a really big impact on one person or many, and look for those opportunities. But choose carefully what type of organization you get involved in because they may have a great website and a great mission, but some are more functional than others and some are more political than the corporate world you might be coming out of. So, get a chance to talk and involve in it, ask just some basic questions about whether you love about it. What are some of the challenges to deal with? Or you can get a sense for how passionate they are and how engaged they’re.

And then look for opportunities where you can grow your involvement if that’s what you want to do. A lot of people, when they start off volunteering, they want to run the charity by next Thursday and they often have the skill set to do it. But someone else is doing that and often very protective of that. So, look at where you can get involved, but be open to where you can play a bigger role if that’s what you want to do.

Casey Weade: Yeah. And I’d love to get your thoughts deeper on this particular topic. As I think about individuals who are stepping into retirement, even for myself, if I decide to retire tomorrow, I feel like I’d be giving up my highest and best use and my opportunity for biggest impact. I think, often your opportunity for biggest impact is continuing to work, but now, not doing it for the same reason. It’s not about the money anymore. It’s not about saving more. It’s not about creating more income. It’s not about growing something or achieving something. But now, you’re staying in where you can impact the most lives in the biggest way by just staying in your work. But maybe there’s some challenges to that.

Joe Casey: Well, one wise person once told me about something, job optional sounds like a good concept, but I think, again, back to the inventory concept you do with activities, taking inventory of your core skills and how might you want to repurpose them in some different ways, how can they have multiple uses, multiple benefits, and sometimes, it’s through continued work, paid or unpaid. Oftentimes, it could be taking a whole different direction. Mentoring, in particular, can be a very useful activity for people in different formats, but giving a chance to have other people benefit from the hard-earned experience and wisdom that you’ve built up over the years.

Casey Weade: Don’t overlook the skills that you put to work in your work life and how those skills can be brought into the next phase of life to make the biggest impact. We don’t need to just run around and do different things that maybe we’re terrible at. I could volunteer as a soccer coach, but I don’t know the rules. That’s probably not my highest and best use. There might be a better opportunity out there that I could leverage the skills that I have already cultivated, my unique ability in making that bigger impact.

So, going back, we’ve got these nine obstacles. Anytime I see a list like that, five obstacles, nine obstacles, ten obstacles, I want to know there had to be something that didn’t make the list, right? I mean, how did we end up at nine? And maybe there isn’t, but is there one that you– and I really wanted to put that in there, but I wasn’t quite sure.

Joe Casey: The big one that I didn’t call out specifically, although it’s mentioned is fear, and it comes up early with my comments, it’s about the boredom one, but I think fear can hold people back and you can get a lot further if you name and label the fear. What is it that you really are concerned about? Because there are both hopes and dreams and concerns and fears that we have about retirement life, this next phase of life, because we’re not only playing for time, we’re planning for getting older. How can we age well and age positively? So, I think the big one is fear and being honest with ourselves and naming what are those things we’re afraid of, and then, okay, now, what can we do about them?

Casey Weade: And what I heard you say there is naming our fears, making a list of what those fears are. I think we have fears, we can understate the value of actually writing those things down, getting some clarity around what those fears are so that we can start addressing them systematically. And it’s much like the financial planning process. You might go, I’m afraid of retirement. I’m afraid of running out of money. Well, then why? And what is this specific fear? Is it market risk? Is it emergency? Is it health care? Is it inflation? Is it long-term care? What is that specific concern? Once we identify what that specific concern is, then we can address those things systematically to alleviate or eliminate the fear altogether.

At the end of every chapter, what I love about the book, probably my favorite thing is all the different exercises that you have. Now, our listeners love to listen, and then they’re workers, right? They want to go back, they want to put in some effort, they want to go put in some work. And some of those exercises are really good opportunities to do that. Now, we can’t go through every exercise, of course, but is there one that really stands out to you, maybe one you’ve seen make the biggest impact for others?

Joe Casey: I think in day-to-day life, again, with the concept that don’t wait until you retire to do these things, you can start doing them now. A lot of the exercises about gratitude are really valuable. Just taking a minute to think about different ways and things you’re grateful for pays off, get you to look at things very differently.

There’s also an exercise in there, I know I’m going way past one, but there’s one called the Killjoy List. It’s making a list of all these things that get in the way of your joys by a designer, Isabel Fedeli, who had a great book on joy. And it’s just making a list of the things that are getting in your way and looking at which of those can I do something about. And same thing with the fears, when you make a list of the fears, don’t forget about the hopes and dreams too, always balancing.

But I find there’s always someone smarter than me who’s figured out some of these things. And a lot of the fears you might have are common and start to have conversations or look into different resources like this podcast of people who have some solutions that may work for you or may be a starting point for you. So, naming them is the first step. But the Killjoy List got my attention because what are the things that get in the way because many of them, you can change.

Casey Weade: Yeah, of course. And there are so many things in the book, I mean, that’s exactly what it is, right? It’s about putting in the work, if you’re looking for a place to put in the work, where else to do it? But when the retirement came, you have all the tools, all the resources, all the opportunities to really have great conversations with your spouse, with yourself, and with others and friends, with your financial advisor. It’s a great book and we’d love to give it in the hands of as many individuals as we possibly can. So, we partnered up with Joe today. We’re going to give it away until they’re all gone. So, we want to give away the book Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

So, if you’d like to get a free copy of the book, all you have to do is write an honest rating and review over on iTunes of the podcast. So, give us an honest review, give us an honest rating, and then just shoot us over your email, [email protected], shoot us over your email, your iTunes username, and we will get you a free copy of the book in your hands. I know it’ll make a positive impact. Joe, thank you so much for taking the opportunity to come out, have this conversation with us. I know there’s going to be more to come.

Joe Casey: Great. Thanks, Casey. Great to talk with you once again and appreciate the listener questions. People are really on top of these things and great to hear how early they’re investing in their planning for retirement.

Casey Weade: Thanks, Joe.