100 books like What the Happiest Retirees Know

By Wes Moss,

Here are 100 books that What the Happiest Retirees Know fans have personally recommended if you like What the Happiest Retirees Know. Shepherd is a community of 10,000+ authors and super readers sharing their favorite books with the world.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

Book cover of Jane Eyre

Lynn Shurr Author Of Lady Flora's Rescue

From my list on historical novels picked by a librarian.

Why am I passionate about this?

As a reference librarian, I love doing research for myself and others. By reading a well-written historical novel, we can learn about the past and compare and contrast it to our present. All but the last of my choices have strong female characters who must overcome the customs of their time. The struggle goes on today. Let these books remind you of how far we have come and how far we have to go.

Lynn's book list on historical novels picked by a librarian

Lynn Shurr Why did Lynn love this book?

When I was fifteen, I stayed up reading the end of this book under the covers with a flashlight because I could not put it down.

A scandalous bestseller in 1847, this was the first romance to feature an antihero. Mr. Rochester is far from pure and kind. He mocks Jane, who describes herself as small and plain and stands up to him. He has an immoral secret and when Jane learns of it, she leaves him. I doubt I would have.

By Charlotte Brontë,

Why should I read it?

36 authors picked Jane Eyre as one of their favorite books, and they share why you should read it. This book is for kids age 12, 13, 14, and 15.

What is this book about?

Introduction and Notes by Dr Sally Minogue, Canterbury Christ Church University College.

Jane Eyre ranks as one of the greatest and most perennially popular works of English fiction. Although the poor but plucky heroine is outwardly of plain appearance, she possesses an indomitable spirit, a sharp wit and great courage.

She is forced to battle against the exigencies of a cruel guardian, a harsh employer and a rigid social order. All of which circumscribe her life and position when she becomes governess to the daughter of the mysterious, sardonic and attractive Mr Rochester.

However, there is great kindness and warmth…


Book cover of Predictably Irrational: The Hidden Forces That Shape Our Decisions

Emily Guy Birken Author Of Making Social Security Work for You: Advice, Strategies, and Timelines That Can Maximize Your Benefits

From my list on changing the way you look at money.

Why am I passionate about this?

When I was about 8, I remember taking all the money out of my piggy bank, counting it, and carefully putting it back in again. My sister called me Ms. Moneybags. But I wasn’t worried about accumulating money. I was fascinated by money’s pure potential. I could do anything with it! From that early interest in the potential of money, I grew to be an avid reader of financial books–and that led to a surprise career as a money writer. I still love to think about money’s potential and the best ways to allocate that potential, and I love to bring my readers with me on the fascinating journey.

Emily's book list on changing the way you look at money

Emily Guy Birken Why did Emily love this book?

As of 2023, behavioral economics is no longer a surprising new look at old economics principles–but that doesn’t change just how entertaining, surprising, and challenging you will find the experiments detailed in Predictably Irrational. 

In one notable experiment, Dr. Ariely placed six-packs of soft drinks next to plates of cash inside of communal dorm fridges–to prove we tend to be honest about cash but feel no compunction about swiping someone else’s Coke. In another memorable experiment, male volunteers were asked moral questions when they were in a state of arousal–which helped prove that morals are flexible depending on the circumstances. 

Reading this book will make you realize just how often you make decisions–especially financial decisions–that are weird, illogical, and irrational.

By Dan Ariely,

Why should I read it?

13 authors picked Predictably Irrational as one of their favorite books, and they share why you should read it.

What is this book about?

Why do smart people make irrational decisions every day? The answers will surprise you. Predictably Irrational is an intriguing, witty and utterly original look at why we all make illogical decisions.

Why can a 50p aspirin do what a 5p aspirin can't? If an item is "free" it must be a bargain, right? Why is everything relative, even when it shouldn't be? How do our expectations influence our actual opinions and decisions?

In this astounding book, behavioural economist Dan Ariely cuts to the heart of our strange behaviour, demonstrating how irrationality often supplants rational thought and that the reason for…


Book cover of What Retirees Want: A Holistic View of Life's Third Age

Jan Cullinane Author Of The New Retirement: The Ultimate Guide to the Rest of Your Life, 3rd edition

From my list on comprehensive retirement to make you happy.

Why am I passionate about this?

I’ve lived in four states because of corporate transfers. My background is college teaching/administration, and for each relocation, I found a new job, house, and social groups. This is what retirement is about, the opportunity to learn, re-invent, re-define yourself, and pursue new opportunities and passions. My biology/psychology/relocation background prepared me to address the non-financial aspects of retirement, and I know CPAs/CFPs willing to share their financial expertise. I’ve authored five retirement books, I’m the “Healthy Living” columnist for a magazine, and I’ve been speaking/writing about retirement for the past 22 years. I have a B.S., an M.Ed., and I’m ABD for my doctorate. I can also speak backwards fluently!

Jan's book list on comprehensive retirement to make you happy

Jan Cullinane Why did Jan love this book?

I like authors who back up statements with research. Ken Dychtwald, CEO of Age Wave, has been studying the Boomer generation for more than three decades, and uses his research to not only demonstrate how this generation has transformed retirement, but also provides important insights for those who work with, sell to, or are Boomers themselves. Virtually every page has a nugget of useful and applicable information.

By Ken Dychtwald,

Why should I read it?

1 author picked What Retirees Want as one of their favorite books, and they share why you should read it.

What is this book about?

"Dychtwald and Morison offer a brilliant and convincing perspective: an essential re-think of what 'aging' and 'retirement' mean today and an invitation to help mobilize the best in the tidal wave of Boomer Third Agers."
-Daniel Goleman, PhD, Author, Emotional Intelligence: Why It Can Matter More Than IQ

Throughout 99 percent of human history, life expectancy at birth was less than 18 years. Few people had a chance to age. Today, thanks to extraordinary medical, demographic, and economic shifts, most of us expect to live long lives. Consequently, the world is witnessing a powerful new version of retirement, driven by…


Book cover of Your Erroneous Zones: Step-By-Step Advice for Escaping the Trap of Negative Thinking and Taking Control of Your Life

Jan Cullinane Author Of The New Retirement: The Ultimate Guide to the Rest of Your Life, 3rd edition

From my list on comprehensive retirement to make you happy.

Why am I passionate about this?

I’ve lived in four states because of corporate transfers. My background is college teaching/administration, and for each relocation, I found a new job, house, and social groups. This is what retirement is about, the opportunity to learn, re-invent, re-define yourself, and pursue new opportunities and passions. My biology/psychology/relocation background prepared me to address the non-financial aspects of retirement, and I know CPAs/CFPs willing to share their financial expertise. I’ve authored five retirement books, I’m the “Healthy Living” columnist for a magazine, and I’ve been speaking/writing about retirement for the past 22 years. I have a B.S., an M.Ed., and I’m ABD for my doctorate. I can also speak backwards fluently!

Jan's book list on comprehensive retirement to make you happy

Jan Cullinane Why did Jan love this book?

This book was originally published in 1976. It was the first time I internalized the concept that we may not be able to control what happens to us, but we can control how we react to things. This simple thought was – and is – transformational. It’s something that guides my actions to this day. Dyer provides readers with the tools to identify faulty thinking and to change our behavior to become happier and more successful. 

By Wayne W. Dyer,

Why should I read it?

1 author picked Your Erroneous Zones as one of their favorite books, and they share why you should read it.

What is this book about?

THE RECORD-BREAKING, #1 NEW YORK TIMES BESTSELLER – OVER 35 MILLION COPIES SOLD

The first book by Wayne Dyer, author of the multimillion-copy bestseller Pulling Your Own Strings and national bestsellers There’s a Spiritual Solution to Every Problem and Wisdom of the Ages, a positive and practical guide to breaking free from the trap of negative thinking and enjoying life to the fullest.

If you're plagued by guilt or worry and find yourself unwittingly falling into the same old self-destructive patterns, then you have "erroneous zones" – whole facets of your approach to life that act as barriers to your…


Book cover of Retirement Income Redesigned: Master Plans for Distribution -- An Adviser's Guide for Funding Boomers' Best Years

Wade Pfau Author Of Retirement Planning Guidebook: Navigating the Important Decisions for Retirement Success

From my list on preparing you for retirement.

Why am I passionate about this?

I am economist who first started exploring retirement planning for my own personal situation. I became so captivated by the topic that I changed fields and was selected as the Professor of Retirement Income at the American College of Financial Services. I am a past curriculum director for the Retirement Management Analyst designation and past program director for the Retirement Income Certified Professional designation. More recently, I am the co-creator of the Retirement Income Style Awareness and co-host of the Retire with Style podcast. I enjoy learning and teaching about all topics related to retirement.

Wade's book list on preparing you for retirement

Wade Pfau Why did Wade love this book?

Harold Evensky and Deanna Katz bring together a collection of experts to explore many different facets of retirement income planning.

This book was ahead of its time in exploring retirement income as a distinct field of financial planning, and it laid important foundations in place. Readers can learn from leading experts about understanding sequence-of-return risk, spending from investments, using annuities, and much more.  

By Harold Evensky (editor), Deena B. Katz (editor),

Why should I read it?

1 author picked Retirement Income Redesigned as one of their favorite books, and they share why you should read it.

What is this book about?

Clients nearing retirement have some significant challenges to face. And so do their advisers. They can expect to live far longer after they retire. And the problems they expect their advisers to solve are far more complex. The traditional sources of retirement income may be shriveling, but boomers don't intend to downsize their plans. Instead, they're redefining what it means to be retired―as well as what they require of financial advisers. Planners who aren't prepared will be left behind. Those who are will step up to some lucrative and challenging work.

To help get the work done, Harold Evensky and…


Book cover of The Ultimate Retirement Guide for 50+: Winning Strategies to Make Your Money Last a Lifetime

Liisa Kyle Author Of Making the Most of Your Retirement: Ways to Foster Health, Happiness & Fulfillment at Any Age

From my list on if you are thinking about retirement.

Why am I passionate about this?

As a life coach and author of two dozen self-help books, I’ve spent the past twenty years helping people prepare for, plan, and go through major life changes, such as the transition to retirement. I’ve interviewed dozens of retirees about the challenges and opportunities they’ve experienced during their retirement. I’ve designed this guide so you can be strategic in choosing your path, overcome challenges, and make adjustments to make the most of this chapter of your life.

Liisa's book list on if you are thinking about retirement

Liisa Kyle Why did Liisa love this book?

Money is the biggest concern for most people thinking about retirement. Suze Orman is the queen of straight-talk about how best to manage your finances during this chapter of your life. She explains practical steps you need to take to make sure you have enough money to last your lifetime. I love that she is ruthless about making readers consider the long-term effects of their purchases and financial decisions.

By Suze Orman,

Why should I read it?

1 author picked The Ultimate Retirement Guide for 50+ as one of their favorite books, and they share why you should read it.

What is this book about?

THE PATH TO YOUR ULTIMATE RETIREMENT STARTS RIGHT HERE

When you think about planning for retirement - whether it's years in the future or just around the corner - you're bound to have questions. Can I ever afford to stop working? Will Social Security be there for me when I need it? How can I make my money last? Have I waited too long to start saving?

Suze Orman, America's most recognized expert on personal finance, answers all the questions that keep you up at night - starting with the biggest one: It is never too late to start planning…


Book cover of Work Optional: Retire Early the Non-Penny-Pinching Way

Jonathan Chevreau Author Of Findependence Day

From my list on financial independence and retirement.

Why am I passionate about this?

I am a veteran semi-retired Canadian financial journalist who has long made a distinction between the terms “Retirement” and “Financial Independence.” I  recently turned 70 and have been financially independent since my early 60s BUT I am not yet retired. I coined the term Findependence in my financial novel Findependence Day, and since 2014 have been running the Financial Independence Hub blog, with new blogs every business day.

Jonathan's book list on financial independence and retirement

Jonathan Chevreau Why did Jonathan love this book?

I’ve always like the phrase “Work Optional” to describe the state of being financially independent enough that you don’t have to work for money anymore, but nevertheless choose to for reasons like having a purpose, or structure.

Work Optional is also the title of another fine American book on Financial Independence, bearing the subtitle Retire Early the Non-Penny-Pinching Way. The author is an American woman, Tanja Hester, who “retired” early at age 38, along with her husband Mark, who was then 41. I put the word “retired” in quotes because, as is usually the case with advocates of the so-called FIRE movement (Financial Independence, Retire Early), Hester didn’t actually retire to do nothing.

Generally, I find that when FIRE proponents say they “retired” at 30 or 40, what they really mean is they quit working as salaried employees for a corporation, to launch what amounts to an encore career built…

By Tanja Hester,

Why should I read it?

1 author picked Work Optional as one of their favorite books, and they share why you should read it.

What is this book about?

A practical action guide for financial independence and early retirement from the popular Our Next Life blogger.

In today's work culture, we're expected to hustle around the clock. But what if you could escape the traditional path and get on one that doesn't require working full-time until age 65? What if you could wake up every day without an alarm clock and do the things you love most?

Tanja Hester and her husband Mark left their crazed careerist lifestyle to live their dream life in Lake Tahoe, retiring early from high-stress careers. Now Tanja will help you map out a…


Book cover of The Great 401(k) Hoax: Why Your Family's Financial Security Is at Risk, and What You Can Do about It

James W. Russell Author Of The Labor Guide to Retirement Plans: For Union Organizers and Employees

From my list on retirement plans if you don’t trust Wall Street.

Why am I passionate about this?

I became fascinated with retirement plans and policy when I realized that my 401(k)-like retirement plan with a high rate of savings and investment returns would still come up way short in terms of the retirement income needed for me and my family. That led me to initiate a winning campaign to allow those of us in that plan to switch to our employer’s pension plan. In leading that struggle, I had to learn everything possible, beyond what I already knew, about retirement plans. I have a Ph.D. in sociology from the University of Wisconsin and have studied retirement plans in Latin America and Europe as well as the United States.

James' book list on retirement plans if you don’t trust Wall Street

James W. Russell Why did James love this book?

Wolman and Colmosca, former BusinessWeek writers, were among the early writers to expose just how bad 401(k)s were for workers. They showed how Wall Street interests profited from the plans at the expense of retirement security. They knew a lot about stock market investing and doubted that, even in the best of situations, the stock market would be able to produce enough value to adequately support retirees. They came to the conclusion that the 401(k) system could not be reformed and should be abolished. I liked the book because it was coming from people within the system (BusinessWeek) who realized that it was not working. 

By William Wolman, Anne Colamosca,

Why should I read it?

1 author picked The Great 401(k) Hoax as one of their favorite books, and they share why you should read it.

What is this book about?

The American public was hoodwinked: 401(k)s were established to satisfy corporations, not the interests of working Americans. Portrayed as a perpetual wealth machine, the 401(k) was meant to satisfy the needs of every employee. Yet, it was an impossible promise to fulfill: It was the great 401(k) hoax. According to William Wolman and Anne Colamosca, this was the latest act in the gradual erosion of the nation's retirement system. Drawing from reams of historical and contemporary data as well as economic, social, and political trends, they reveal the system's troubled 100year history. Beyond exposing the hoax, the authors urge everyone…


Book cover of Your Complete Guide to a Successful and Secure Retirement

Jeff Bernier Author Of The Money and Meaning Journey: A Guide to Clarity, Financial Confidence, and Joy

From my list on financial peace in retirement.

Why am I passionate about this?

As a wealth advisor for over 37 years, I find many people reach retirement lacking clarity and confidence. Traditional financial advice often focuses on things that are unknowable, uncontrollable, and frankly don’t matter that much. While sound technical investment, estate, and tax planning are critical, the soul’s need for meaning and purpose are as important as sound financial plans. The path to true financial peace may be simpler than you think. These books can help you focus on the fewer, more critical things so that you can thrive in retirement and free yourself from financial media which is not in business to support your vision of a meaningful life.

Jeff's book list on financial peace in retirement

Jeff Bernier Why did Jeff love this book?

If you could only read one book on retirement planning (other than mine of course!), this is the one I’d recommend. 

It covers a wide range of financial planning and investment topics: life-planning, goal-setting, investment strategy, financial stress-testing, spend-down strategies, tax-management, social security, Medicare, annuities, insurance, reverse mortgages, estate planning, elder abuse, and more

However, while comprehensive, it also does not get too “deep” in the weeds and is filled with wise counsel.  

By Larry Swedroe, Kevin Grogan,

Why should I read it?

1 author picked Your Complete Guide to a Successful and Secure Retirement as one of their favorite books, and they share why you should read it.

What is this book about?

Fully revised and updated second edition.

This is your one-stop, definitive resource as you prepare for a secure and comfortable retirement.

Investment and personal finance experts Larry Swedroe and Kevin Grogan present uniquely comprehensive coverage of every important aspect you need to think about as you approach retirement, including:

Social Security, Medicare, investment planning strategy, portfolio maintenance, preparing your heirs, retirement issues faced by women, the threat of elder financial abuse, going beyond financials to think about your happiness, and much more.

These topics are explained with the help of specialists in each subject. And everything is based on the…


Book cover of Tar Baby

David Wright Faladé Author Of Black Cloud Rising

From my list on complicated Black-white relations.

Why am I passionate about this?

For me, the American story is about “mixedness”—about the ways in which people of various backgrounds and beliefs have come together, oftentimes despite themselves, to make up our modern racial stew. It has been true since the Founding and is all the more so now, even as we, as a society, continue to want to resist it. These novels achieve what I aspire to in my own writing: the white characters are as complex as the Black ones. And in their struggles to make sense of the world, they all reveal the complexity and contradictions of American identity.

David's book list on complicated Black-white relations

David Wright Faladé Why did David love this book?

I came to Toni Morrison a little late. This was in the 1980s, after she’d won the Pulitzer. I read Song of Solomon first, upon the recommendation of a friend who told me he couldn’t read the end of the novel without bursting into tears. Next, Beloved: I was so awed that I reread it five times in a row!

At that point, I realized that I needed to circle back and start with her first books. The Bluest Eye and Sula both stunned me.

Then came Tar Baby. I immediately understood it to be different from the others. The novel has significant, primary characters who are white. In the other early novels, white characters might be present, but they are few and very secondary.

Six people live in relative luxury on a Caribbean island. Yet, despite themselves, their racial assumptions inform how they view and treat one…

By Toni Morrison,

Why should I read it?

1 author picked Tar Baby as one of their favorite books, and they share why you should read it.

What is this book about?

A ravishingly beautiful and emotionally incendiary reinvention of the love story by the legendary Nobel Prize winner

Jadine Childs is a Black fashion model with a white patron, a white boyfriend, and a coat made out of ninety perfect sealskins. Son is a Black fugitive who embodies everything she loathes and desires. As Morrison follows their affair, which plays out from the Caribbean to Manhattan and the deep South, she charts all the nuances of obligation and betrayal between Blacks and whites, masters and servants, and men and women.


5 book lists we think you will like!

Interested in retirement, personal finance, and planning?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about retirement, personal finance, and planning.

Retirement Explore 27 books about retirement
Personal Finance Explore 83 books about personal finance
Planning Explore 46 books about planning