Winning at Retirement


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Winning at Retirement should be one of the first books a person picks up when thinking about their future and retirement.


Winning at Retirement is a step-by-step guide to ending up among the many Americans who describe retirement as the best years of their life.

Beyond addressing practical considerations like money, health, and where to live, Winning challenges you to ask “who am I going to be in retirement?” Retirement is an opportunity for reinvention, or as a popular quotation from the book says “a blank sheet of paper”. But far too many people plan for the financial aspects without recognizing the importance of seeking a meaningful, impactful identity. A purposeful life is a happy life!

Today’s retirees are plugged-in. They have smart phones, are internet savvy, and follow their grandchildren on Facebook. Winning takes a thoroughly modern look at the subject, describing web tools, apps, TED talks, and the vast world of resources that are at your fingertips in your quest for financial stability, health, and purpose. In the end you will learn about the Retirement Happiness Map, a simple but powerful way to organize your retirement decisions.

Step inside, you won’t be disappointed.

“There is a strong chance that retirement will represent the best time in your life.”


We will all get older and will eventually need to figure out what life in the retirement years will look like. There are many areas that need to be thought about and researched: finances, health, lifestyle, location and estate planning. Thinking about these topics ahead of time can help people not just enjoy retirement, but win at retirement.

Winning at Retirement: A Guide to Health, Wealth & Purpose in the Best Years of Your Life is not a complete guide to retirement; however, it goes over all the important topics and gives an overview of the most important information for that topic. It then gives lists of other resources to dive deeper into topics like TED talks and in-depth retirement books. 

In 11 chapters, the author covers social security, Medicare and insurance, estate planning, retirement accounts, living locations, current technology tools available for retirement planning, healthy living. There is even a chapter on money maxims that goes over key ideas on how to view investments. It really is a whole-person approach to retirement in this book. One chapter focuses on exercising and eating healthy to not just prolong life, but to have a richer and fuller life as you get older. Retirement is not just about having enough money. It is about enjoying life, which is why the book is titled Winning at Retirement.

This book is a must-read for anyone who has entered the work force. Knowing the information in this book can help them think about and plan for the future a long time before it happens. While reading this close to retirement could still be helpful for the topics of insurance and social security, the topic of investments is better to read about in your 20s or 30s. Knowing about the different types of investment accounts is key so you can start saving in your younger years. This should be one of the first books a person picks up when thinking about their future. It doesn’t have all the answers, but it has an overview of all the topics and mentions a lot of other great resources to dig deeper.

Reviewed by

I love to read and my friends and family seek me out for book suggestions. I have a blog with more than 300 book reviews now. I am also a freelance writer and am working on a novel.


Winning at Retirement is a step-by-step guide to ending up among the many Americans who describe retirement as the best years of their life.

Beyond addressing practical considerations like money, health, and where to live, Winning challenges you to ask “who am I going to be in retirement?” Retirement is an opportunity for reinvention, or as a popular quotation from the book says “a blank sheet of paper”. But far too many people plan for the financial aspects without recognizing the importance of seeking a meaningful, impactful identity. A purposeful life is a happy life!

Today’s retirees are plugged-in. They have smart phones, are internet savvy, and follow their grandchildren on Facebook. Winning takes a thoroughly modern look at the subject, describing web tools, apps, TED talks, and the vast world of resources that are at your fingertips in your quest for financial stability, health, and purpose. In the end you will learn about the Retirement Happiness Map, a simple but powerful way to organize your retirement decisions.

Step inside, you won’t be disappointed.


If you are in retirement, or are starting to look forward to it, we have some good news for you: turns out the peak ages for happiness are later in life. In fact, people are more likely to describe themselves as “very happy” at 69 than at any other age.1 One study2 found that just under half of retirees describe themselves as “very satisfied” in retirement. Not bad odds—although the number was above 60% back in 1998, so the trend is not looking good. If about half of retirees describe themselves as very satisfied and half do not, the question is . . . how do you end up in the “winning” half?

That’s the question we set out to answer, and our findings are described in this book. The title is tongue-in-cheek, of course. Retirement is not a game to be played, nor a contest. But we want  you to get fired up about it. You should be excited about retirement; you should view it as a great opportunity and a grand adventure. Our search for answers about retirement happiness was enlightening and filled us with optimism. We discovered common elements that seem to put people on the right path, and all should be within your grasp.

Retirement is a blank sheet of paper. It is a chance to redesign your life into something new and different. For many, that something proves to be a lifestyle characterized by freedom and happiness . . . the best of times, the golden age. We are here to provide you with advice that will maximize your chances of crafting that sort of retirement for yourself.

TED Talks

One way wisdom is shared these days is through TED Talks (and related TEDx Talks). Short for “Technology, Entertainment and Design,” these are brief presentations that allow some of the most brilliant minds in the world to share their thoughts and theories. We will discuss TED Talks in greater detail in Chapter 8: Tech Tools for Retirement Success. Until then, look for TED callout boxes throughout the book referencing presentations related to the content we will cover. You can visit and search the title of a talk to find it, or if you search for the title on Google, you should find it hosted on YouTube.

Turning Points

There are several natural turning points that happen in life. Not every person experiences every one of them, and life has a way of throwing unexpected changes at us—good and bad—that do not fit into these neat little boxes. But there are some common transitions that most people encounter. Each is an opportunity for reinvention.

There is the transition from grade school to high school, and (for some) from high school to college. When you switch schools, especially if it involves moving or being surrounded by a different group of kids, it is a chance to become a new person to a certain extent. You could end up with different friends, develop new interests, maybe change your hair or style of dress. Going to a new school can represent a major identity shift. Most of the time we carry over a good deal of our prior persona, but there is at least the option of a fresh start.

After school the next big change is finding a “real” job. The career choice. For some this will be the first step down a fairly straight path. For others, the beginning of a winding road. In any case, choosing a career is a defining moment. After all, so much of who we are in life is based on the work that we do.

Marriage is another momentous life change. Choose right, and it might be the most positive decision you ever make. The life turn that will shape everything that follows for the better. Choose wrong, and all manner of mayhem can ensue. There is a vast spectrum of marriage outcomes ranging from something out of a romance novel to the John and Lorena Bobbitt story. No matter what happens, marriage represents a big-time life transition.

And then, for some people, there are children. Wow, there’s a transition! This is the change that you have the least amount of control over. It is no longer just you (and your spouse) calling the shots. Oh no, your life is now dictated by one or several part-time maniacs called children. Of course, for many, this is the most fulfilling of life’s transitions. Parenthood can provide meaning to your life. For a hectic period of years, and in some ways forever, your existence will be shaped dramatically by your role as a parent if you end up on that path.

The Golden Years

The last common turning point is retirement. This change often comes less encumbered than those that came before it. It can be, as we said, a blank sheet of paper. It is our intent to give you some ideas that will help you navigate that blank sheet. But first, let’s start with some great news: there is a strong chance that retirement will represent the best time of your life. Yes, that is the incredible, surprising, uplifting reality of retirement. According to the data we’ve seen, for a large number of people, retirement rocks.

A variety of studies and surveys depict happiness trends at different ages as being U-shaped. On average, happiness is high in our late teens and early twenties, then trends down until it hits a low point between the ages of 50 and 53. But then there is a shift and happiness begins to rise into retirement and beyond, eventually hitting the highest levels in our 70s and beyond. Shocker, right? Well, perhaps not if you are already there, and have experienced this phenomenon for yourself.

Figure I.1: The Happiness Curve

From The Happiness Curve, © Jonathan Rauch.

Reprinted by permission.

Let’s consider the happiness curve in light of the big life transitions we just talked about. Although then we’ll talk about the fact that biology may play a role as well.

Youth is a time for infinite optimism. Every kid is going to be an astronaut, right? And in our teens and early 20s, we tend to be possessed of a sense of immortality and—hopefully—belief in a boundless future.

With the end of adolescence, optimism may be harder to come by. Your mid- to late 20s are a time of new personal freedom as you leave school behind and try to embark on a career path. But it can be a time of too much freedom; you might not have a sense of direction yet. Financial security is probably a distant dream at this point, and chances are you can’t really answer the question: “What do you want to do with the rest of your life?”

As you move into marriage and, especially, parenthood, the pressures of becoming a real grown-up can become acute. During these times, as we struggle with a wide variety of stresses, happiness can be elusive. And looking forward might not provide much help, as we see retirement as either something abstract, something vaguely comical (shuffleboard and early-bird specials), or something to dread.

Thankfully, we are probably looking at it all wrong. As the data referenced earlier shows, the best years may still lie ahead. This idea might run counter to what you have been thinking about retirement, and aging in general, for most of your life. In our youth-obsessed culture it is common to dread retirement. Let’s face it: no one is excited about aging. The last birthday anyone looks forward to is 21; after that we tend to view the passing of the years with some measure of concern, regret, or outright terror. It’s hard not to equate aging with death, and during the various stages of our youth, retirement is associated with physical decline and proximity to the end.

We will look at the critical subject of health and wellness later on, because warding off physical decline is key to a successful retirement. In any case, the big secret that many in retirement know is that, despite the obvious challenges presented by aging, our later years can still turn out to be our best years.

While researching this book we set out to read everything we could get our hands on related to the central idea of finding happiness in retirement. We came across a number of great books in the process, and you’ll find them all listed on the Library page3 of (the companion website for this book, which contains additional resources related to the topics we will cover). We discovered one example—The Happiness Curve: Why Life Gets Better After Midlife4 —as we were putting the finishing touches on this book.

The Happiness Curve was so compelling that it caused us to rewrite the section you are reading right now. Primarily because we got something wrong: we thought that the U-shaped curve of happiness was entirely a function of life circumstances. Instead, it turns out that we may be hardwired for a dose of misery in our 40s and 50s, followed by rising happiness into our later years. In fact, the pattern has even been detected in studies of monkeys.

The implications of this information are significant, especially for anyone in their 40s and 50s who may be feeling a gnawing sense of depression or discontent. Turns out the concept of “midlife crisis” might be missing the mark. A better description for a large number of people might be “midlife malaise.” And there may actually be some sort of biological imperative causing people to feel blue in midlife.

The good news is that the tide tends to reverse, and many of us can look forward to brighter days ahead. In fact, the research suggests that our days grow and stay brighter until much later in life (well into our 80s), when health issues often become a big factor.

Obviously the concept is all about averages, and not everyone will experience the same pattern. Also, life can throw curve balls at us that interfere with this natural uptrend in happiness. Nonetheless, it’s an optimistic and encouraging concept, and it is well supported by scientific data. We recommend The Happiness Curve enthusiastically for adults of all ages, as this seems like a critical concept for people to understand as they make their way through life’s changes and challenges.

A Vision of the Future

Throughout this book, we are going to focus on describing specific attitudes and action steps that we hope will increase your chances for happiness in retirement, but let’s take a minute to think about the world you will retire into. We have no way of knowing what the future will look like exactly. But it might be a constructive exercise to engage in a bit of futurism and imagine the good and bad that may lie ahead.

Let’s start with the bad. After all, we are so bombarded with negativity these days that it sometimes seems like there is nothing else.

Anyone old enough to be seriously contemplating retirement can remember the sense of constant looming threat that America lived with during the Cold War. Depending on your age, this may conjure images of the Vietnam War, the Cuban Missile Crisis, or drills during school where they taught you to hide under your desk in case of a nuclear attack (a plan surely dreamed up by government committee). But then, seemingly out of the blue, the Soviet Union crumbled, the Berlin Wall fell, and for an all-too-brief period there was a time of relative peace in the world.

Then came 9/11 and everything changed again. Or, in a sense, returned to the way things had been. Once again there is the looming threat, the fear that slips from our mind for a bit, but is brought back to the fore again and again by news of war, terror attacks, threats, and a world in turmoil.

But hey, at least that stuff keeps our minds off the national debt. Having barely survived the financial crisis of 2008—a modern economic meltdown rivaled only by the Great Depression in terms of impact—we can add a sense of economic dread to our fears of war and terrorism. Faith in our politicians is plumbing new lows as the reality of the societal problems we face is matched with a feeling that our leaders lack either the ideas or the fortitude needed to solve them. The nightly news is filled with debate about the economic viability of the Social Security and healthcare systems. Our population is aging—a problem shared by much of the developed world—which strains the resources needed to support happy, healthy retirements.

On top of all that, there is growing concern about the proliferation of technology and what that might mean for the future. As more and more tasks can be automated and handled by computers or robots, where does that leave humans? Will we need to reshape our economic system to accommodate a more automated world? Will the gap between rich and poor continue to grow, and with it political instability? Or more frightening still, will technological tools of destruction—such as nuclear and biological weapons—lead to a horrific outcome at some point down the road?

On the other hand, by most metrics human beings have it far better today than at any point in history. A book called Abundance5 by  Peter  Diamandis  highlights the tremendous advantages provided by technological advancement, and describes potential benefits that may lie ahead. Diamandis quotes NYU’s Dr. Marc Siegel on our current state of relative prosperity:

“Statistically, the industrialized world has never been safer. Many of us are living longer and more uneventfully. Nevertheless, we live in worst-case fear scenarios. Over the past century, we Americans have dramatically reduced our risk in virtually every area of life, resulting in life spans 60 percent longer in 2000 than in 1900. Antibiotics have reduced the likelihood of dying from infections …. Public health measures dictate standards for drinkable water and breathable air. Our garbage is removed quickly. We live in

temperature-controlled, disease-controlled lives. And yet, we worry more than ever before. The natural dangers are no longer there, but the response mechanisms are still in place, and now they are turned on much of the time. We implode, turning our adaptive fear mechanism into a maladaptive panicked response.”

We recommend checking out Abundance because, in addition to being a smart and entertaining read, it provides a welcome dose of optimism in a world that seems beset by negativity and stress.Specifically, it describes advancements in farming, healthcare, and the availability of clean water that could lead to unprecedented improvements in living conditions in the developing world, which in turn could lessen the global want that foments problems like war and terrorism. Factfulness: Ten Reasons We’re Wrong About the World—and Why Things Are Better Than You Think6 is another book that paints an optimistic picture (with data), while explaining why we are predisposed to see more negativity than positivity in the world.

As to the problem of automation replacing jobs, economist David Autor argues that this is an age-old concern that never seems to be borne out in reality. For example, he notes that in the decades since automated teller machines came into wide use, the number of bank teller jobs has actually doubled. And while farming and manufacturing jobs have decreased, a whole slew of careers in fields like computers and healthcare have taken their place. Essentially, as technology takes away some jobs and increases productivity, new job demand is created (often in forms of work that would never have been envisioned at the time of the initial technological disruption). Autor does worry that low- paying and high-paying jobs are experiencing growth, while mid-level jobs are being displaced, but he argues that a more effective approach to education—making more of our population suited to higher wage work—could provide a solution.

Another aspect of technological development that bears watching for retirees is automated driving. At the time of this writing, a division of Google called Waymo has a fleet of driverless cabs in active testing.

Dozens of other companies, ranging from leading automakers and tech firms to startups, are competing to own a piece of this potentially transformational space. Many billions of dollars have already been invested, and it’s all moving so fast that from the time we wrote the first draft of this chapter until the time we were ready to go to print about a year and a half later, we needed to rewrite this part of it.

Currently, all major automakers have some form of automated driving technology in the works, with many pointing to 2021 for the availability of “level 5” automation . . . where the cars are fully self- driving and wouldn’t even need to be equipped with steering wheels (Waymo is at that level now on a limited basis). How quickly this technology will develop and proliferate is a matter of great debate, but it is coming. This will likely represent a huge technological disruption that will cause some job losses (cab and truck drivers), while potentially impacting where people live, where they vacation, the delivery of goods and services, the insurance industry, and much more.

Think of automated driving from the perspective of aging, however, and the implications are exciting. Mobility is a challenge later in life. When someone should give up the car keys is a difficult question faced by many a retiree, and—often with great difficulty—their families. But what if there were no keys to give up? What if you could affordably summon an automated car anytime you’d like, with the press of a button on your phone? This is not science fiction; this will be our reality in the years ahead. For older retirees it would mean less of a struggle getting to doctor appointments or running errands. It could mean the ability to vacation farther away, or even live farther away while maintaining the ability to easily visit family. This technology could represent a tremendous, liberating boon for retirees in the years to come.

It’s impossible to predict all the challenges (and positive developments) that we will encounter in the future. But in confronting the difficulties and threats of our time, we would do well to remember that human beings have always been beset by difficulties and threats. In fact, by almost any objective measure we are blessed to live better now, on average, than in any other period in history. Humankind, and America, have faced incredible challenges in the past and have always found a way to overcome and move forward. We should remain optimistic that we will find a way to meet the challenges of the future as well . . . because it does us little good to think otherwise. In seeking a path toward retirement happiness, what benefit is there to wallowing in negative assumptions? In fact, as we will discuss in Chapter 7, taking an optimistic view of life may actually help extend it.

If you are really unhappy with the vision of the world that you perceive before you, then maybe your mission in retirement should be to find a way to change things for the better in whatever way you can (see Chapter 1: A Life of Purpose).

Purpose + Security + Wellness = Happiness

There is a ton of information available about finding happiness later in life, including great books, studies, articles, and websites. It is impossible to fully cover every subject related to retirement in a single book, so in many cases we will point you in the direction of other resources that will help you to take a deeper dive into a topic.

We will summarize all that we have learned about this vast subject, and break it down to a few key areas of focus.

Our research on retirement found that the same themes, presented in varying verbiage and data, kept coming through. Happiness in retirement is possible, even likely. To achieve it you need to do three things:

•     Live guided by a sense of purpose: We urge you to spend some time thinking about how you intend to live your life in retirement, and what your purpose will be. Have you ever pondered the question: “If I could go back in time and give my younger self advice, what would it be?” Forget that—it doesn’t do you any good. Instead, give the current you some good advice. What can you do right now that will change the rest of your days for the better? That is what we are here to talk about.

•     Maintain a degree of financial stability and security (although it is possible to find happiness with a lot of money or a little).

•     Work consistently on your physical and mental wellness.

If you pull together all three of those elements—and we are here to help you do that—you will greatly increase your chances of ending up happy or, put another way, of winning at retirement. In the remaining chapters of this book, you will be given advice on how to expand your knowledge by leveraging the internet and other modern tools that are reshaping what is possible for today’s retirees. In the end, we’ll provide a clear series of steps that can help you end up among the happy half of retired Americans.

We hope that you enjoy this book, and that you come away with answers and ideas that put you firmly on the path to that goal.











1     Is happiness just a matter of waiting for the right age? https://www. matter-of-waiting-for-the-right-age/

2     Trends in Retirement Satisfaction in the United States: Fewer Having a Great Time. pdf


4     The Happiness Curve: Why Life Gets Better After Midlife by Jonathan Rauch. ISBN-13: 978-1472960986

5     Abundance: The Future Is Better Than You Think by Peter H. Diamandis. ISBN- 13: 978-1451616835

6     Factfulness: Ten Reasons We’re Wrong About the World—and Why Things Are Better Than You Think by Hans Rosling. ISBN-13: 978-1250107817

About the author

Financial Planner Patrick Foley has been guiding Americans toward happy retirements for more than 25 years. He and his partner and co-author Kristin Hillsley have developed an innovative and holistic process that inspired the book Winning at Retirement. view profile

Published on September 21, 2018

Published by

60000 words

Genre: Self-help

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