Many people discover that their money is better prepared for retirement than they are. Why? Because it’s easy to think of retirement planning as solely a financial matter. Financial planning is a left-brain process. It’s quantitative, linear, illogical, but deciding how to invest your time takes a different mindset. It’s a right brain process, it’s qualitative, non-linear and intuitive. It takes imagination.

Today, retirement can last decades, it’s a period of renewal, reinvention and personal growth. And it requires a whole new approach to a retirement plan. Win the Retirement Game guides you through nine obstacles people face when they retire. From boredom and uncertainty, to the disorientation of drifting, you’ll learn how to face each one with the right set of tools and craft a specific strategy to overcome it.

Are you ready to design and live a unique next life? Tap into these research-based solutions and get started today. This is The Author Hour Podcast and I’m your host, Frank Garza. Today, I’m joined by Joe Casey, author of a brand-new book, Win the Retirement Game: How to Outsmart the Nine Forces Trying to Steal Your Joy.

Joe, welcome to the show.

Joe Casey: Thanks so much Frank, great to be here.

Frank Garza: So to start, I just love to hear a little bit about your background and how that led to you writing this book.

Joe Casey: Sure. So, I’m a former HR person. Some might say a reformed HR person. And I spent 26 years in HR in Wall Street with Merrill Lynch, I was head of HR for the investment banking and sales and trading side and international in my last role, and I had an executive coach in the year 2000 for a year because it must have been a hard case. 

That led me really inside how coaching works, and I saw such an impact in not only myself as a leader but the team I led and the ripple effects in the organizations I supported, that I became curious about coaching and learned that that’s what I wanted to do after HR. So, I took early retirement at age 52 and became an executive coach 13 years ago. So I work with senior leaders, mostly in financial services but also in pharmaceutical technology, and CEOs of private equity-backed companies.

I also work with emerging leaders, high potential leaders in different companies and then seven years into it, I had an engagement where a client I was coaching, he was deemed to be the successor to the CEO, and halfway through the coaching process, he said, “I don’t want to be him, I want to retire early” and since I had done the same thing, it started to come more and more of my clients asking, “How did you do what you did? Creating something new, a new life after your first career?” and so I became curious. 

I became so curious, I went back to school for a third master’s degree, this one gerontology at USC because I want to understand the life course, how we age, and how people can really change things in second act. So I built a second coaching practice called Retirement Wisdom, where we help people design a new life after their primary career, because what’s different today is, retirement’s last a lot longer. It used to be about eight years on average. Now, it’s between 25 to 30 at times.

Frank Garza: So, your book, Win the Retirement Game, can you tell me a little bit more about who the target audience is for that? Who do you have in mind as you’re writing it?

Joe Casey: So it’s for people who are getting ready to retire, they’re probably still working or they’re early in their retirement years and they’re thinking about, “What’s next. What am I going to do after this?” and most people in that category have done the financial planning. They haven’t given as much thought to, “How am I going to invest my time?”

That’s because it’s easy to put off, you can get to it when you get to it, but preparing early makes a huge difference, and the other big thing, and this is what really led me to write the book, is the people that focus on the financial planning side, which is critical to do.

It’s a left-brain type of activity but planning for how you’re going to invest your time over the next couple of decades, that’s a right brain thing and it takes imagination. So the book helps to give people a sense of how to bring imagination, the planning really, in this next phase of their life.

Combating Retirement Boredom

Frank Garza: Yeah, I really like your angle there because I do feel like most of what I read about retirement is how to plan for it financially and it’s not how to plan for all that other stuff, and so your book really digs into that, and in the first chapter called, “Welcome to the Retirement Game” you mentioned that retirement is one of life’s most stressful events. Why is it so stressful?

Joe Casey: It’s stressful because there’s a lot of loss that comes with it and there’s a tug of war behind, between rather, some of the things that you gain when you retire and some of the things you’re losing, and so what’s stressful is working through those tensions, that tug of war, to find the new pathway forward.

For example, you lose a lot of things that we take for granted about work. We get a lot besides our paycheck. Status, our days are structured, we have driving purpose often that comes from our work in many cases, and we have a lot of collegiality, a lot of social relationships in the workplace that sometimes extend outside the workplace.

All of a sudden, when people walk away from the world of full-time work, all those things are either gone or diminished and so people describe that they feel loss and they feel lost. Some people, and many of my clients that I will have worked with, especially men, confessed to me that they’re actually afraid and when I ask, “All right, what are you afraid of?” 

They confide in me that they’re afraid of being bored and afraid of being not as relevant as they had been during their career years. So it’s working through that, there’s a lot of uncertainty and I think that’s the most stressful thing of all.

Frank Garza: Yeah, the boredom thing, I can really see that. So somebody who has retired, maybe they’ve been in it for I don’t know, six months, a year, and let’s say they find themselves absolutely bored, what are some things they can do to combat that?

Joe Casey: I find that it’s taking on some new things, and the best quote, and I have it in the book, is from Dorothy Parker, that the antidote to boredom is curiosity. Get engaged and thinking about new things, exploring things that you never had time to do that now you do, it can lead to some interesting things. 

You don’t want to be overwhelmed, you don’t want to be jumping around from thing A to thing B to thing C to thing D but you want to really have an opportunity to get involved in something different, something new, something you’ve always wanted to explore and really being curious about the world around you. 

Being curious about some of the people in your world and in your life that maybe have not been front and center as you would have liked during your working years.

Frank Garza: You spend another chapter talking about loneliness and how you need to enhance your social connectivity, and you go over law of statistics about how much less time people spend with others, often times after they retire. Can you just elaborate on that, on how loneliness is a problem once you retire, and what are some ideas for combatting loneliness?

Joe Casey: Sure, and I think that’s another source of the stress where people are surrounded by others at work, and a lot of people will mention that I don’t miss work since I retired but I miss the people. They’ll quickly follow-up, well, most of them, but I think what people find is all of a sudden, the time they spend is more by themselves and it’s more reflective time that unfortunately, a lot of people end up filling with things like screen time, notably TV. 

The stats are actually astounding in terms of the amount of TV that people who are retirees actually watch, and no one had that in mind when they were slaving away, sacrificing, saving and investing over all those years to be able to watch CNBC and Morning with Joe for extensive periods of time, or whatever or Netflix show or whatever you like to do. So I think that the key thing there is to understand also the health aspects. 

Studies have shown that it’s a health risk, that we get a lot physically and emotionally from other people and connectivity, and then you really have to set about to cultivate often a new tribe, and you can’t do that all at once and the best way to do that is by doing things with others. It’s a natural way to meet people, something you’re interested in, it can build off to some new connections.

Frank Garza: Finding a new tribe, what would be some ideas for, if anyone’s going to make a list of, “Okay, hey, I’m going to go try and find a new tribe” and they were looking for ideas, what could you offer them?

Finding a New Tribe

Joe Casey: Three things. The first thing is to really look at what’s something that you have a natural interest that you’d like to do more of. Meaning, I like to play tennis, I like to run. In my case, I was a runner, so you could join a running group. I didn’t do that, I ran by myself, but if you really were serious about it, you could look for what are some people who like to do the things I would like to do more of? Something to be engaged in, kept it up but you’d like to do more of it, and you do with others.

The second is, looking for opportunities to get involved in learning. Lifelong learning is such an important thing for many reasons, but what are some classes you can take? It doesn’t have to be a full-blown program, it can just be one class. Starting small is really important, but something that you got a keen interest in and you can learn with others. Hopefully, as the pandemic gets to new phases, we’ll be able to do continually more and more in person things, that gives you a chance to get to know others. Even if it’s virtual, connections develop that way.

And then third thing, which I’ve mentioned before and will continue mentioning because I think it’s vital, what’s something new you want to take on? What’s something new you want to learn about, something new you want to do that can involve other people? It could be a sport, some people I have worked with as clients take up some type of artistic endeavor, creative endeavor or it could be something just social. 

Things that you already do, walking, running, et cetera, book clubs, all those things can be particularly useful to get to know other people.

Frank Garza: Let’s talk about art a little bit more because you did spend quite a bit of time talking about how exploring art specifically can be beneficial. What are some of the benefits of exploring art?

Joe Casey: So I’ve read a lot about the work of Gene Cohen, the late Gene Cohen, who was with George Washington University, and he did a very large study about the creative arts and the impact of arts on older people, older adults, and their health benefits. There’s, again, what I’ll call a twofer benefit, meaning, you get two for the price of one, the benefit of doing artistic, creative activities with other people.

So you get the social benefits, you get the physical and mental health and emotional health benefits but my favorite story, which I include in the book, is about Gene Cohen on a more practical level. He talked about big C creativity, classic art types of things. He talked about lower case C creativity, which is day-to-day life, and the best example of that is he was being visited by his in-laws, he lived in suburban Washington, DC. 

They were coming into Union Station DC and it was in the middle of a blizzard. He couldn’t get to them and as they looked around, they couldn’t get out, pre-Uber and no taxis to be found. So his father-in-law had a great example of lower C creativity. What we did was, he walked across the street, ordered a pizza for delivery to Gene Cohen’s residence and he and his wife joined along for the ride. 

Frank Garza: Sorry to interrupt, I would just say that is creative. I like that. 

Joe Casey: So it’s using the different types of things we’ve learned over the years, practical wisdom, day-to-day life types of things that you can look at situations in different ways, from a different angle, and find a creative solution. So it can be something artistic or it could be something practical. 

Retirement Expectations

Frank Garza: Okay, you have a chapter called “Embrace Acceptance to Manage Expectations.” Can you talk a little bit about how, you know, I can see when someone is getting ready to retire, they have a certain expectation of what it’s going to be, how wonderful it’s going to be, what they’re going to be doing. Can you talk about how that can lead to issues in your retirement and how to manage expectations better? 

Joe Casey: Sure, so the first thing is for most people, it is not like you see in the commercials or the brochures. There’s not a lot of bar skiing and nothing but sunsets, et cetera. It’s really getting a realistic view of it, and one of the things that I advise people to do is talk to people who they know who are retired. What’s it really like? What do they know now that they wish they knew at the beginning? 

You can learn a lot. and so I think there’s one part of it is the expectations of what are you thinking about it, what are your hopes but what are some ways to calibrate that and to test it, and there’s a great opportunity to test drive some aspects of retirement before you retire. Take some time off where you get a chance to even do a staycation, which we had enough of during COVID, but just to say, “What would be like if I wasn’t an exotic resort location but just home for a week?” 

What types of things do I like to do and not like to do? But really getting a sense, a realistic sense, of what it’s really like on the positive side of the expectations, and what are some of the challenges that other retirees have faced and how do they overcome them? 

Frank Garza: Okay, later on we have a chapter, “Boost Self-Efficacy to Defeat Uncertainty.” Can you define, what is self-efficacy and what’s important to know about that with regards to retirement? 

Joe Casey: Sure, this is based on the work of one of the greatest psychologist, Albert Bandura, who recently passed away unfortunately, but I mentioned in the beginning that one of the reasons why retirement is one of life’s most stressful events is the uncertainty you have to deal with. All of a sudden, you are in this world where you don’t have to get up every day in the morning, you don’t have to get to your home office or physical office to begin the work day. 

You’ve got the freedom but what do you really do and how do you use it? So self-efficacy very simply is really about control. Taking control that you’re the person who can chart this new course. You are the person who can structure your time in different ways. You are the one who can create this new block of time and make it really the best years of your life, and I should add that the reason why it’s so important is a lot of people have a tendency to look at some of those circumstances, some of those difficulties because they’re real in moving through retirement. 

Because we are also aging at the same time and sometimes people forget that, that how we view getting older can make a big difference in how we actually age. A guest on my podcast, Retirement Wisdom Podcast, Dr. Becca Levy from Yale, who found in her ground-breaking research that how you think about aging affects how you age at a cellular level and can influence life expectancy. In her study, people who had a positive view of aging versus those negative lived seven and a half years, on average, longer. 

Transition to Retirement

Frank Garza: You also talked about the importance of pursuing a calling and you reference a study where people, I guess the study was about folks in retirement and they asked them to describe what some of their callings were and it was things such as helping others, family and caregiving, you know investment in self, personal development. Can you tell me about what you’ve seen some—what are some examples of callings that you’ve seen retirees find that have been really beneficial for them? 

Joe Casey: Sure, and this is a great topic because I think people have different perceptions about this. The first one is that more people report having a calling than I personally expected, and the view of the work that they did or the things that get involved in retirement more as a calling than I think sometimes we think, we always think of some religious or spiritual quest that’s someone’s on. 

As a client, I was drawn to become a priest or Rabbi or a nun, et cetera but it is really more about what’s drawing you to the work? What is drawing you to this new pursuit you want to do? We mentioned before about the different pace of life and retirement and if you slow down enough, you start to hear some of the things, hear your callings, it can be very helpful. I quote one of the person who was involved in my coach training at Columbia. 

John Schuster wrote a book called, Answering Your Call, and he talked about there’s some value in reviewing your call history, meaning what types of things have been calling you over the years that you put off and let it go to voice mail, and the types of callings, to answer your question specifically, that people have gotten, a lot of them have to do with the volunteer types of activities, things that people are really involved in that they care about. 

Making a difference, so to speak, that can be a small way but it can turn out to be a big thing, and the other aspect is the creative aspect. People pursuing something that they always wanted to do, write a book, take a new form of art, et cetera and they’re drawn to it, but what that has in common is usually for most of them, whether it’s volunteering or some other way, it is about helping other people, and one version is mentoring. 

Frank Garza: So Joe, you’ve worked with a number of people who are about to retire or going to retirement, what are some of the most common? I know we have gone through a number of these here and I am sure each person has their own challenges they go through, but if you have to pick one or two that you see most common in retirees, what would you say those are? 

Joe Casey: One is confusing the honeymoon period with actual retirement, meaning at the very beginning it’s great. You don’t have to go to work. That boss that was annoying you, it’s in the rearview mirror but it is a cliché about, what are you really retiring to? So in 20 years, 25 years is a really long vacation where even that can be gilded. I don’t know about you but if you have been on a two-week vacation, there is a point in time where, as great as it is, you want to get back. Same thing with the early part of retirement. 

What tends to happen is sometimes people get used to that vacation mode and they drift and they find it hard to get back. So I think that’s a more—one of the common mistakes is thinking it’s always going to be like the first six months. The second thing is failing to really look at what retirement is for them individually versus what other people expect.  

One author that I read, who I interviewed for my podcast, Dr. Barbara O’Neil had a great concept of the social clock, meaning a lot of times others were surrounded by—well, I think you should be doing certain things and not be doing certain things. You’re too old for that, you’re too young to be doing that, but it really comes down to doing the soul searching about what do I want to do, what’s right for me and my family now? And really starting to work on putting those things in place. 

Then the third one is failing to prepare, meaning how can you try some things, how can you get a running start coming into retirement, so you are doing some things. And then the final mistake is jumping in too soon into too many things. Not being able to say no. Not being able to carve out the time where you can step back, try some things, experiment and find out what you really want to do, because I read a lot about the book, in the later chapter, to have purpose. 

You know, I think that I find that confuses people. “You’re telling me I need to find a new sense of purpose? I looked on Amazon, I couldn’t find one” and it’s not at Home Depot either, I checked. What I find with my clients and the work I do is they come up with creating a multi-purpose retirement through small experiments that they get engaged in certain things. Some they like, some they don’t, some take hold and those sometimes become the things that they invest their time and go forward. 

Frank Garza: Well, writing a book is such a feat, so congratulations on putting this out into the world. Before we wrap up, is there anything else about you or the book that you want to make sure our listeners know? 

Joe Casey: One, that this is something that I have done myself that there are a lot of people who will talk about retirement in terms of experiences, but what I try doing in the book is give people a look into what did I learn in working with these clients over the last seven years of the obstacles they’ve faced, many of which they were surprised by, so that you can anticipate them and get ahead of them. 

The other thing for me, is I have also made adaptations of  when I was a marathon runner. I set a goal to qualify for my hometown, the Boston marathon. It took me 12 races to finally qualify but I did, I was very proud of that, but before that race I had an injury. I made it through, I had my best day ever, but then had to get treatment for it. So getting ready for Boston two weeks before I started to sense another injury, unrelated, it was starting to crop up. 

I decided to run because I felt better by race day but I ended up breaking my left hip with a half mile to go in the Boston marathon. 

Frank Garza: Oh man. 

Joe Casey: There I was, literally reaching my dream and boom, stress reaction, I was standing there paralyzed. So I learned a lot of things from that experience because one, just how helpful people were. A doctor in the medical tent found my family, arranged to have the head of orthopedic trauma surgery do the surgery the next morning, visit me every day in the hospital for a week and then arranged to get me a finisher’s medal from the head of the Boston Athletic Association, so it was very meaningful. 

But the other thing I learned was I had to change, well, a big part of my life, which is running. When I woke after the surgery, the doctor asked me if I had any questions and I said, “Yes, when can I run again?” and my wife said, “I think you gave him the wrong surgery. A lobotomy may have been the way to go” and so I learned that I still could run but I couldn’t run outdoors much. So I have a machine called the Zero Runner that I run on indoors and was able to adopt that way. 

So the reason I am telling that story is people may have dreams in retirement or things they’re looking to do but as we age, you might have to tweak it and shift and take another path, and I think that is an important part of really building the retirement that you want. 

Frank Garza: Thank you Joe, this has been such a pleasure. The book is called, Win the Retirement Game: How to Outsmart the Nine Forces Trying to Steal Your Joy. Besides checking out the book, where can people find you? 

Joe Casey: and they can listen to our podcast, which we publish weekly, The Retirement Wisdom Podcast, where we interview a number of people who are retired or planning for retirement about the non-financial side in their stories and how you can help better prepare. 

Frank Garza: Thank you, Joe. 

Joe Casey: Thanks Frank, great talking with you.