Fans pick 100 books like Work Optional

By Tanja Hester,

Here are 100 books that Work Optional fans have personally recommended if you like Work Optional. Shepherd is a community of 12,000+ authors and super readers sharing their favorite books with the world.

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Book cover of How to Retire Happy, Wild, and Free: Retirement Wisdom That You Won't Get from Your Financial Advisor

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?

Edmonton-based author Ernie Zelinski is probably best known for this self-published international bestseller.

Zelinski semi-retired at 30 after being fired from an engineering job. One of his first books was called The Joy of Not Working, and he later published The Joy of Being Retired: 365 Reasons Why Retirement Rocks—and Work Sucks!. But the one that really struck a nerve for FIRE proponents was How to Retire Happy, Wild and Free, subtitled “Retirement wisdom that you won’t get from your financial advisor”.

Zelinski sugar-coats the content with pull-out quotes and a few cartoons. As the back-cover blurb of my 2014 edition proclaims, “Retirement is the beginning of life, not the end.” It follows that Zelinski believes that the earlier you take Early Retirement, the better, and encourages readers to pluck up the courage to do just that.

To that end, his focus on frugality allows him to…

By Ernie J. Zelinski,

Why should I read it?

2 authors picked How to Retire Happy, Wild, and Free as one of their favorite books, and they share why you should read it.

What is this book about?

How to Retire Happy, Wild, and Free offers inspirational advice on how to enjoy life to its fullest. The key to achieving an active and satisfying retirement involves a great deal more than having adequate financial resources; it also encompasses all other aspects of life -- interesting leisure activities, creative pursuits, physical well-being, mental well-being, and solid social support.

World-class author and innovator Ernie J. Zelinski guides you to:

Gain courage to take early retirement; in fact, the earlier the better. Put money in proper perspective so that you don't need a million dollars to retire. Generate purpose in your…


Book cover of Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence

Holly Trantham Author Of Beyond Getting By: The Financial Diet's Guide to Abundant and Intentional Living

From my list on rethinking your relationship with work and money.

Why am I passionate about this?

At The Financial Diet, I’ve written and produced videos about money, productivity, and work/life balance for the better part of a decade. I’ve come to the conclusion that most of our commonly held beliefs about money and work are incorrect: your job shouldn’t be your main purpose, and money shouldn’t be the end goal in and of itself. I’ve also been a longtime nonfiction reader, and I lead a monthly book club for our Patreon members. This list is composed of my favorite selections from those meetings (a few of which I’d read previously), and I hope they invite you to question your own relationship with work and money!

Holly's book list on rethinking your relationship with work and money

Holly Trantham Why did Holly love this book?

To me, this book is a classic in the realm of personal finance for a reason. It is the clearest explanation of how money is not actually about money; if you’re actually living by your values and seeking a life that makes you feel truly fulfilled, the point of working is to earn enough money to live on and take care of your future with, while being able to spend the majority of your time doing what you actually enjoy.

I love that this book is centered around finding a purpose without tying that purpose to how you earn a living. It also gives really clear suggestions for long-term investing, and I was happy to see that updated for our current times in the newest edition. 

By Vicki Robin, Joe Dominguez,

Why should I read it?

6 authors picked Your Money or Your Life as one of their favorite books, and they share why you should read it.

What is this book about?

Have Enough Money for a Rich Life-Without Winning the Lottery
How much money is enough? Vicki Robin has made it her life's work to explore this question. Her remarkable discovery: money is energy-and conscious awareness is the key to finding its real value. On Your Money or Your Life Robin shares the nine-step program originally created with her teaching partner Joe Dominguez, which has helped nearly three quarters of a million people worldwide reach new levels of comfort, competence, and consciousness around their personal finances. Updated for the 21st century, this two-CD program offers hands-on tools and practical insights to…


Book cover of Enough: True Measures of Money, Business, and Life

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?

The late Jack Bogle, founder of Vanguard Group, published this excellent book in 2009.

Consider the following apophyrical tale related in Chapter 10 of Enough: “Too Much Success, Not Enough Character.” It concerns an old greyhound who spent his days at a race track chasing a mechanical rabbit. Over the years, the dog had won over a million dollars for his owner but ultimately decided to quit: not because he was mistreated or had become disabled but because “I found out that the rabbit I was chasing wasn’t even real.”

Those who accumulate more money than they need in life and end up as the richest denizen in the cemetery would do well to reflect on the main premises of Enough. Remember, financial independence is about having income exceed expenses, no matter how modest those expenses might be. It’s about working only because you want to, not because you…

By John C. Bogle,

Why should I read it?

2 authors picked Enough as one of their favorite books, and they share why you should read it.

What is this book about?

John Bogle puts our obsession with financial success in perspective Throughout his legendary career, John C. Bogle-founder of the Vanguard Mutual Fund Group and creator of the first index mutual fund-has helped investors build wealth the right way and led a tireless campaign to restore common sense to the investment world. Along the way, he's seen how destructive an obsession with financial success can be. Now, with Enough., he puts this dilemma in perspective. Inspired in large measure by the hundreds of lectures Bogle has delivered to professional groups and college students in recent years, Enough. seeks, paraphrasing Kurt Vonnegut,…


Book cover of Pensionize Your Nest Egg: How to Use Product Allocation to Create a Guaranteed Income for Life

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?

Pensionize Your Nest Egg, or PYNE as some readers call it, is a classic Canadian financial book by famed finance professor Moshe Milevsky and certified financial planner Alexandra Macqueen.

Its audience is primarily anxious would-be retirees who do not have the luxury of having an inflation-indexed, guaranteed-for-life Defined Benefit pension plan offered by an employer. In fact, the headline when I first reviewed the book, was “A Cure for Pension Envy.” Instead, its core reader may have lots of money in group RRSPs, Defined Contribution plans or 401(k)s that rise and fall with financial markets. Hence the subtitle of the second edition, published in 2015, is How to Use Product Allocation to Create a Guaranteed Income for Life.

In practice, this involves using a particular product – the life annuity – to make your nest egg more like a true DB pension. The authors go into some…

By Moshe A. Milevsky, Alexandra C. Macqueen,

Why should I read it?

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

What is this book about?

Pensionize Verb. 1. To convert money into income you can't outlive. 2. To create your own personal pension, a monthly income that lasts for the rest of your natural life. With the subpar performance of the markets, record-high personal debt levels, and shockingly low savings rates, it's clear that many Canadians expecting to retire in the next decade simply don't have a sufficient nest egg to ensure a worry-free retirement. Making matters worse, only about one-third of Canadians currently belong to a formal, or registered, pension plan; and even a large number of that "lucky third" will not retire with…


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 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 What the Happiest Retirees Know: 10 Habits for a Healthy, Secure, and Joyful 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 gem of a book translates the results of Wes Moss’s survey of more than 2,000 happy retirees into ten actionable habits that help you achieve your best “second act.” I love the author’s easy, breezy writing style. Find out how many “core pursuits” are needed to make you a happier retiree!

By Wes Moss,

Why should I read it?

2 authors picked What the Happiest Retirees Know as one of their favorite books, and they share why you should read it.

What is this book about?

The bestselling author of You Can Retire Sooner Than You Think and host of Money Matters reveals the 10 essential habits for a rich, rewarding, and blissful retirement.

What does it take to have a truly happy retirement? Is it money? A mortgage-free home? An active social life? A long-lasting marriage-or maybe a new one? Finance expert, author, and radio host Wes Moss asked more than 2,000 of the nation's happiest retirees to find out-and their answers may surprise you. Through a series of revealing surveys, Moss noticed a pattern of distinct, recognizable habits that the happiest retirees shared, from…


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 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 Mind Your Money: Insightful Stories and Strategies to Help You Reach Your #MoneyGoals

Jannese Torres Author Of Financially Lit!: The Modern Latina's Guide to Level Up Your Dinero & Become Financially Poderosa

From my list on books about money written by Latina authors.

Why am I passionate about this?

I’m a 5x award-winning personal finance educator and money expert who specializes in helping Latinas reach financial freedom through entrepreneurship and investing. I have been fascinated by personal finance since 2016 when I realized that I hadn’t learned anything important about money after discovering personal finance podcasts. I’m a firm believer that financial literacy is the gateway to freedom, so my work involves educating women of color on how to use money to exercise their power. 

Jannese's book list on books about money written by Latina authors

Jannese Torres Why did Jannese love this book?

Yanely’s book is a must-read no matter where you are in your financial journey. She’s engaging throughout the entire book, whether she is sharing an anecdote or a savings strategy. She is a great storyteller and uses her personal experiences to inspire others to make better choices and be financially free.

This easy-to-read book is full of practical information that can be understood by teens and young adults, as well as older consumers who are searching for ways to get ahead financially. She’s practical with her advice and empowering with her knowledge, and she makes you believe your financial goals are achievable with patience and planning.

By Yanely Espinal,

Why should I read it?

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


Book cover of How to Retire Happy, Wild, and Free: Retirement Wisdom That You Won't Get from Your Financial Advisor
Book cover of Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence
Book cover of Enough: True Measures of Money, Business, and Life

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