Looking for the best books on retirement planning to guide your next chapter? Whether you’re preparing to retire, already navigating life after work, or simply want to make smarter choices with your money and time, the right book can change everything. In this curated list of 100+ of the best books on retirement planning, living in retirement, aging, and making the most of your money and time in 2025 and beyond, you’ll find practical guidance, inspiring stories, and fresh perspectives to help you plan wisely, live fully, and thrive through every stage of retirement.
Below you’ll find all kinds of books: contemporary fiction titles, nonfiction on investing and other personal finance topics, plus self help, with many books on finding meaning in life and living long and healthfully. This is truly the ultimate list of the best books on retirement planning and for making the most of your money and time.
Email us other suggestions! (And, if you want to put this literary wisdom into practice, use the Boldin Retirement Planner to run scenarios and ensure you live the life you want!)
Best Books on Retirement Planning, Work, Investing, and Personal Finance
Here are a few of Boldin’s and Boldin users’ favorite and best books on retirement planning, financial planning, personal finance, investing, work, and retirement:
The Simple Path to Wealth: Your road map to financial independence and a rich, free life by J L Collins: If you ask knowledgeable people about the best book on retirement planning and personal finance, more often than not they will recommend A Simple Path to Wealth. The book grew out of a series of letters to Collins’s daughter concerning various things—mostly about money and investing. It is a clear, accessible guide to achieving financial independence and creating a life of freedom.
Collins emphasizes the importance of saving and investing wisely, particularly through low-cost index funds. The book breaks down complex financial concepts into straightforward advice, making it easy to understand how to grow wealth over time.
How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement by Christine Benz: These lessons range from nitty gritty financial matters to quality-of-life considerations that help pre-retirees and retirees maximize their “time on earth” allocations.
How Not to Invest by Barry Ritholtz with foreword by Morgan Housel: We all make mistakes. The goal with this book is to help you make fewer of them, and to have the mistakes you do make be less expensive.
Retire Before Mom and Dad: The Simple Numbers Behind A Lifetime of Financial Freedom by Rob Berger: Forbes contributor and DougRoller founder Rob Berger, has written an extremely accessible and enjoyable book on the investing principles that will lay the foundation of your financial independence.
I Will Teach You to Be Rich: No Guilt. No Excuses. Just a 6-Week Program That Works by Ramit Sethi: Personal finance expert Ramit Sethi has been called a “wealth wizard” by Forbes and the “new guru on the block” by Fortune. Now he’s updated and expanded his modern money classic for a new age, delivering a simple, powerful, no-BS 6-week program that just works.
The Bogleheads Guide to Investing by Taylor Larimore, Mel Lindauer, and Michael LeBoeuf, with foreword by John C. Bogle: The fundamentals of sophisticated and smart retirement investing, kept simple.
The Bogle Effect: How John Bogle and Vanguard Turned Wall Street Inside Out and Saved Investors Trillions by Eric Balchunas: Today, nearly every dollar invested in America goes to either Vanguard funds or Vanguard-influenced funds. But Bogle’s impact and this “great cost migration” reaches well beyond index funds into many other areas, such as active management, ETFs, the advisory world, quantitative investing, ESG, behavioral finance and even trading platforms. The Bogle Effect takes readers through each of these worlds to show how they—and the investors they serve—are being reshaped and reformed.
The Wealth Money Can’t Buy: The 8 Hidden Habits to Live Your Richest Life by Robin Sharma: Real wealth is so much more than cash in the bank, flashy cars in the driveway and luxury vacations on exotic islands. Too many financially prosperous people are surprisingly poor when it comes to the things that truly matter for a life of happiness, vitality, and serenity.
Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad One by James Clear: While this book isn’t strictly about money, the lessons found herein can be incredibly impactful on your financial situation. No matter your goals, Atomic Habits offers a proven framework for improving – every day. James Clear, one of the world’s leading experts on habit formation, reveals practical strategies that will teach you exactly how to form good habits, break bad ones, and master the tiny behaviors that lead to remarkable results.
The Algebra of Wealth: A Simple Formula for Financial Security by Scott Galloway: In The Algebra of Wealth, Scott Galloway lays bare the rules of financial success in today’s economy. In his characteristic unvarnished, no-BS style, he explains what you need to know in order to better your chances for economic security no matter what.
Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence by Vicki Robin, Joe Dominguez, Mr. Money Mustache: For more than twenty-five years, Your Money or Your Life has been considered the go-to book fortaking back your life by changing your relationship with money. Hundreds of thousands of people have followed this nine-step program, learning to live more deliberately and meaningfully with Vicki Robin’s guidance.
Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins: Bill Perkins wants to rescue you from over-saving and under-living. Regardless of your age, Die with Zero will teach you Perkins’s plan for optimizing your life, stage by stage, so you’re fully engaged and enjoying what you’ve worked and saved for. Many Boldin users rank this as the best book on retirement planning.
Finance for the People: Getting a Grip on Your Finances by Paco de Leon: Unlike most personal finance books that focus on skills and behaviors, FINANCE FOR THE PEOPLE asks you to examine your beliefs and experiences around money—blending extremely practical exercises with mindfulness, and including more than 50 illustrations and diagrams to make the concepts accessible (and even fun). With deep insider expertise from years spent in many different corners of the financial industry, Paco de Leon is a friendly, approachable, and wise guide who invites readers to change their relationship with money.
You Deserve to Be Rich by Rashad Bilal and Troy Millings: This book is full of tips, insights, and stories about real people, just like you, who have used the tools of wealth building to overcome barriers and build the life they want.
Find Your Why: A Practical Guide for Discovering Purpose for You and Your Team by Simon Sinek, David Mead, and Peter Docker: As Start With Why has spread around the world, countless readers have asked me the same question: How can I apply Start With Why to my career, team, company or nonprofit? Along with two of my colleagues, Peter Docker and David Mead, I created this hands-on, step-by-step guide to help you find your WHY.
Principles by Ray Dalio: This book is part memoir, part how-to guide for crafting the life you want based on the principles that matter to you.
The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss: This book has been the guide to thousands who want to retire early, very early.
Get What’s Yours – Revised & Updated: The Secrets to Maxing Out Your Social Security by Laurence J. Kotlikoff, Philip Moeller, and Paul Solman: This is considered to be the definitive book on getting the most out of Social Security.
A Random Walk down Wall Street: The Time-tested Strategy for Successful Investing by Burton G. Malkiel: This is considered the one book you really need to read if you want to manage your own investments.
The Automatic Millionaire, Expanded and Updated: A Powerful One-Step Plan to Live and Finish Rich by David Bach: Straight forward achievable advice for personal finance and retirement readiness.
How to Make Your Money Last: The Indispensable Retirement Guide by Jane Bryant Quinn: Author Jane Bryant Quinn shows you how to make sure you don’t run out of money in retirement.
The Intelligent Investor by Benjamin Graham: This is a classic that focuses on a strategy of loss minimization over profit maximization.
The Dhandho Investor by Mohnish Pabrai: The low risk value method to high returns.
Big Mistakes: The Best Investors and Their Worst Investments by Michael Batnick: Learn from the big mistakes of the world’s best investors.
The Millionaire Next Door by Thomas J. Stanley and William D. Danko: The bestselling The Millionaire Next Door identifies seven common traits that show up again and again among those who have accumulated wealth. Most of the truly wealthy in this country don’t live in Beverly Hills or on Park Avenue-they live next door.
How to Retire Happy, Wild and Free by Ernie J. Zelinski: 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.
Start Your F.I.R.E. (Financial Independence Retire Early): A Modern Guide to Early Retirement by Dylin Redling and Allison Tom: Authors Dylin and Allison Tom relate their journey to financial independence and give you several FIRE strategies for saving and budgeting. They even include sample spreadsheets (they call it “kindling”) to get you going!
Income on Demand: Master Your Retirement Portfolio, Ignore the Market, and Leave the IRS Weeping by Jonathan D. Bird: Jonathan D. Bird, CFP’s book takes a bold stance on investing for retirement. Forget about creating a “retirement paycheck.” Instead, think about growing your stock portfolio from a young age.
Don’t Go Broke in Retirement: A Simple Plan to Build Lifetime Retirement Income by Steve Vernon: Steve Vernon, who worked for 35 years as a actuary consultant, gives you a simple blueprint for creating your own “pension” in retirement.
The Psychology Behind Money
Emotions play a bigger part – a much bigger part – in money management than most people realize.
The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness by Morgan Housel: Doing well doesn’t actually have much to do with what you know. People who are good with money have better habits, which are hard to teach, even to really, really smart people.
Numerous Boldin subscribers have called The Psychology of Money among the best books on retirement planning they have ever read. (And Boldin users are a knowledgeable bunch!)
Nudge: Improving Decisions About Health, Wealthy and Happiness by Richard H. Thaler and Cass R. Sunstein: Every day we make choices—about what to buy or eat, about financial investments or our children’s health and education, even about the causes we champion or the planet itself. Unfortunately, we often choose poorly. Nudge is about how we make these choices and how we can make better ones.
The Power of Habit: Why We Do What We Do in Life and Business by Charles Duhigg: This instant classic explores how we can change our lives by changing our habits.
The 7 Habits of Highly Effective People by Stephen R. Covey: Stephen R. Covey’s book, The 7 Habits of Highly Effective People, has been a top seller for the simple reason that it ignores trends and pop psychology for proven principles of fairness, integrity, honesty, and human dignity.
Outliers: The Story of Success by Malcolm Gladwell: In this stunning new book, Malcolm Gladwell takes us on an intellectual journey through the world of “outliers” — the best and the brightest, the most famous and the most successful. He asks the question: what makes high-achievers different?
Mindset: The New Psycology of Success by Carol S. Dweck, Ph.D.: After decades of research, world-renowned Stanford University psychologist Carol S. Dweck, Ph.D., discovered a simple but groundbreaking idea: the power of mindset. In this brilliant book, she shows how success in school, work, sports, the arts, and almost every area of human endeavor can be dramatically influenced by how we think about our talents and abilities.
Thinking, Fast and Slow by Daniel Kahneman: Engaging the reader in a lively conversation about how we think, Kahneman reveals where we can and cannot trust our intuitions and how we can tap into the benefits of slow thinking. He offers practical and enlightening insights into how choices are made in both our business and our personal lives―and how we can use different techniques to guard against the mental glitches that often get us into trouble.
Think and Grow Rich by Napoleon Hill: Think and Grow Rich has been called the “Granddaddy of All Motivational Literature.” It was the first book to boldly ask, “What makes a winner?”
Scarcity: The New Science of Having Less and How it Defines Our Lives by Sendhil Mullainathan: In this provocative book based on cutting-edge research, Sendhil Mullainathan and Eldar Shafir show that scarcity creates a distinct psychology for everyone struggling to manage with less than they need.
Books About Healthy Aging
Retirement isn’t all about money. Many of the best books on retirement planning illustrate how to live healthfully. Here are some of the best:
Outlive: The Science and Art of Longevity by Peter Attia: Wouldn’t you like to live longer? And better? In this operating manual for longevity, Dr. Peter Attia draws on the latest science to deliver innovative nutritional interventions, techniques for optimizing exercise and sleep, and tools for addressing emotional and mental health.
This book has sold over one million copies and is highly recommended.
Successful Aging: A Neuroscientist Explores the Power and Potential of Our Lives by Daniel J. Levitin: This book argues that aging isn’t a process of decay but a third stage of development (much like Dychtwald’s “third age.”) He backs up his arguments with neuroscience, and says changes in mental states after 60 aren’t all negative. Though older people may not learn in the same intuitive, absorptive way children do, their brains are not incapable of learning, as many people still believe.
Keep Sharp: Build a Better Brain at Any Age by Sanjay Gupta: Keep Sharp debunks common myths about aging and cognitive decline, explores whether there’s a “best” diet or exercise regimen for the brain, and explains whether it’s healthier to play video games that test memory and processing speed, or to engage in more social interaction. Discover what we can learn from “super-brained” people who are in their eighties and nineties with no signs of slowing down—and whether there are truly any benefits to drugs, supplements, and vitamins.”
Build the Life You Want: The Art and Science of Getting Happier by Arthur C. Brookes and Oprah Winfrey: This book invites you to begin a journey toward greater happiness no matter how challenging your circumstances. Drawing on cutting-edge science and their years of helping people translate ideas into action, they show you how to improve your life right now instead of waiting for the outside world to change.
Life in the Transitions: Mastering Change at Any Age by Bruce Feiler: Feiler introduces a powerful new tool kit for navigating transitions. He lays out specific strategies each of us can use to re-imagine and rebuild our lives.
The Age-Proof Brain: New Strategies to Improve Memory, Protect Immunity, and Fight Off Dementia by Marc Millstein: In The Age-Proof Brain, scientist and popular speaker Dr. Marc Milstein reveals the secrets to improving brain function, which lie in the brain’s surprising connection with the rest of the body. Debunking common misinformation, he offers science-driven strategies in an entertaining, motivating, and easy-to-follow guide to stave dementia and live better.
Somehow: Thoughts on Love by Anne Lamott: “Love is our only hope,” Anne Lamott writes in this perceptive new book. “It is not always the easiest choice, but it is always the right one, the noble path, the way home to safety, no matter how bleak the future looks.” The book also touches on aging.
I Feel Bad About My Neck: And Other Thoughts About Being a Woman by Nora Ephron: From the writer of some of our most beloved romantic comedies and numerous books comes an uproarious tale about life as a woman of a certain age.
The End of Old Age: Living a Longer, More Purposeful Life by Marc E. Agronin: As one of America’s leading geriatric psychiatrists, Dr. Marc Agronin sees both the sickest and the healthiest of seniors. He observes what works to make their lives better and more purposeful and what doesn’t.
Better with Age: The Psychology of Successful Aging by Alan D. Castel: Better with Age addresses the many myths and paradoxes about the aging process. Although most people think of their later years in terms of decline, they can be one of the best times in life. This book presents the latest scientific research about the psychology of aging, coupled with insights from those who have succeeded in doing it well.
Happiness Is a Choice You Make: Lessons from a Year Among the Oldest Old by John Leland: Happiness Is a Choice You Make is an enduring collection of lessons that emphasizes, above all, the extraordinary influence we wield over the quality of our lives.
Healthy Aging: A Lifelong Guide to Your Well Being by Andrew Weil: Two of the world’s leading experts explain the vital link between health and wealth that could add years to your life and dollars to your retirement savings.
Age Proof: Living Longer Without Running Out of Money or Breaking a Hip by Jean Chatzky and Michael Roizen: Two of the world’s leading experts explain the vital link between health and wealth that could add years to your life and dollars to your retirement savings.
Women Rowing North: Navigating Life’s Currents and Flourishing as We Age by Mary Pipher: Drawing on her own experience as daughter, sister, mother, grandmother, caregiver, clinical psychologist, and cultural anthropologist, Pipher explores ways women can cultivate resilient responses to the challenges they face.
Borrowed Time: The Science of How and Why We Age by Sue Armstrong: Borrowed Time investigates such mind-boggling experiments as transfusing young blood into old rodents, and research into transplanting the first human head, among many others. It will explore where science is taking us and what issues are being raised from a psychological, philosophical and ethical perspective, through interviews with, and profiles of, key scientists in the field and the people who represent interesting and important aspects of aging.
The Blue Zones Kitchen: 100 Recipes to Live to 100 by Dan Buettner: Building on decades of research, longevity expert Dan Buettner has gathered 100 recipes inspired by the Blue Zones, home to the healthiest and happiest communities in the world.
Lifespan: Why We Age — and Why We Don’t Have To by David A. Sinclair: Through a page-turning narrative, Dr. Sinclair invites you into the process of scientific discovery and reveals the emerging technologies and simple lifestyle changes—such as intermittent fasting, cold exposure, exercising with the right intensity, and eating less meat—that have been shown to help us live younger and healthier for longer.
The Telomere Effect: A Revolutionary Approach to Living Younger, Healthier, Longer by Dr. Elizabeth Blackburn and Dr. Elissa Epel: This book will make you reassess how you live your life on a day-to-day basis. It is the first book to explain how we age at a cellular level and how we can make simple changes to keep our chromosomes and cells healthy, allowing us to stay disease-free longer and live more vital and meaningful lives.
Better Than Before: What I Learned About Making and Breaking Habits–to Sleep More, Quit Sugar, Procrastinate Less, and Generally Build a Happier Life by Gretchen Rubin: The author of the blockbuster New York Times bestsellers, The Happiness Project and Happier at Home, tackles the critical question: How do we change?
Choosing Your Place, Rethinking Home as You Age by Amanda Lambert and Leslie Eckford: Get insights from real people about creative retirement housing options: retirement abroad, co housing, senior living communities and more.
Making the Best of What’s Left by Judith Viorst: In a career that has spanned more than fifty years, Judith Viorst has captivated readers with her bestselling children’s books and collections of poetry reflecting on each decade of life. Now in her nineties, Viorst writes about life’s “Final Fifth,” those who are eighty to one hundred years old. Her signature blend of humor and vulnerability infuses personal anecdotes and observations, drawing you into her world of memories and candid conversations.
Ageism and Second Careers
This Chair Rocks: A Manifesto Against Ageism by Ashton Applewhite: It’s time to create a world of age equality by making discrimination on the basis of age as unacceptable as any other kind of bias. Whether you’re older or hoping to get there, this book will shake you by the shoulders, cheer you up, make you mad, and change the way you see the rest of your life. Age pride!
Bolder: Making the Most of Our Longer Lives by Carl Honoré: Carl Honoré has travelled the globe speaking to influential figures who are bucking preconceived notions of age, whether at work or in their personal lives. He looks at the cultural, medical, and technological developments that are opening new possibilities for us all. Bolder is a radical re-think of our approach to everything from education, healthcare and work, to design, relationships and politics. An essential and inspiring read for everyone interested in our collective future.
You Are a Badass, How to Stop Doubting Your Greatness and Start Living an Awesome Life by Jen Sincero: Twenty seven quick chapters with funny stories, sage advice, easy exercises, and the occasional swear word, helping you to create a life you totally love.
Retirement Reinvention: Make Your Next Act Your Best Act by Robin Ryan: Retirement has changed, and America’s most trusted career counselor is here to guide you through your own Retirement Reinvention.
Over the Hill But Not the Cliff: 5 Strategies for 50+ Job Seekers by Lori B. Rassas: Over the Hill But Not the Cliff is a straightforward and practical guide that job seekers 50+ can use to not only survive in the modern workplace, but thrive.
What Retirees Want: A Holistic View of Life’s Third Age by Ken Dychtwald: Dychtwald. is a psychologist and educator. Some of the fascinating topics in his book are, how likely it is you’ll outlive your retirement savings, the tech that will lengthen our lives, and how third-agers can capitalize on the upsides of aging.
Finding Meaning and Purpose in Retirement
From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life by Arthur C. Brooks: how to transform his future from one of disappointment over waning abilities into an opportunity for progress. From Strength to Strength is the result, a practical roadmap for the rest of your life.
Drawing on social science, philosophy, biography, theology, and eastern wisdom, as well as dozens of interviews with everyday men and women, Brooks shows us that true life success is well within our reach. By refocusing on certain priorities and habits that anyone can learn, such as deep wisdom, detachment from empty rewards, connection and service to others, and spiritual progress, we can set ourselves up for increased happiness.
The Second Mountain: How People Move from the Prison of Self to the Joy of Commitment by David Brooks: n The Second Mountain, David Brooks explores the four commitments that define a life of meaning and purpose: to a spouse and family, to a vocation, to a philosophy or faith, and to a community. Our personal fulfillment depends on how well we choose and execute these commitments. Brooks looks at a range of people who have lived joyous, committed lives, and who have embraced the necessity and beauty of dependence. He gathers their wisdom on how to choose a partner, how to pick a vocation, how to live out a philosophy, and how we can begin to integrate our commitments into one overriding purpose.
The Happiness Curve: Why Life Gets Better After 50 by Jonathan Rauch: Research suggests that happiness slumps in midlife. Full of insight and data, The Happiness Curve features many ways to endure the slump and avoid its perils and traps.
Purposeful Retirement: How to Bring Happiness and Meaning to Your Retirement by Hyrum W. Smith: Leaving the professional world doesn’t mean losing your purpose: A guide to aging well and moving on to a fulfilling second act.
Awe: The New Science of Everyday Wonder and How It Can Transform Your Life by Dacher Keltner: Keltner defines awe as “the feeling of being in the presence of something vast that transcends your current understanding of the world.” And, he argues that this feeling has huge impact on our overall well being.
10% Happier Revised Edition: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works–A True Story by Dan Harris: The science supporting the health benefits of meditation continues to grow as does the number of Americans who count themselves as practitioners but, it took reading 10% HAPPIER to make me actually want to give it a try.
Man’s Search for Meaning by Viktor E. Frankl: If you read lists about the books successful people most often credited with being inspirational, it is a good bet that this will be a top contender.
The Art of Happiness by Dalai Lama: This book is the cornerstone of positive psychology.
The Subtle Art of Not Giving a F*ck by Mark Manson: Maybe try the millenial self help guide from a superstar blogger who shows how to stop trying to be positive all the time so that we can truly become better, happier people.
The Good Life: Lessons from the World’s Longest Scientific Study of Happiness by Robert Waldinger and Marc Schulz: This book documents the findings from the longest scientific study of happiness ever conducted. Authors Robert Waldinger, MD and Marc Schulz, PhD currently lead the Harvard Study of Adult Development , a research project started in 1938 with the aim to find out what makes for a good life, what makes people thrive, and how to achieve happiness. The study has been running for 8 decades and have had four generations of participants. The research has produced 200 scientific papers and 9 books.
Jonathan Livingston Seagull by Richard Bach: Maybe go a bit retro with this 1970s classic.
A New Earth: Awakening to Your Life’s Purpose by Eckhart Tolle: The spiritual teacher and author describes ancient truths and applies them to life in the 21st century; encouraging readers to live in the present moment. First published in 2005, the book sold five million copies in North America by 2009.
Gratitude by Oliver Sacks: The book chronicles the famous neurologist and author’s thoughts, wishes, regrets, and, above all, feelings of love, happiness, and gratitude even as he faced the cancer that ended his life last year at 82.
The Five Minute Journal: A Happier You in 5 Minutes a Day by Intelligent Change: Using the science of positive psychology to improve happiness, The Five Minute Journal focuses your attention on the good in your life. Improve your mental well-being and feel better every day.
The Alchemist by Paulo Coelho: Although set as a novel following the journey of a shepherd traveling to discover the meaning of a recurring dream, the New York Times called this book “more self-help than literature.” The journey teaches the reader about listening to our hearts, recognizing opportunity, and following our dreams. Originally published in Portuguese in 1988, it has been translated into more than 67 languages and is an international bestseller.
The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life by Chris Guillebeau: American entrepreneur Chris Guillebeau set out to visit every country on planet Earth by the time he turned 35. Everywhere he went, he found people pursuing extraordinary goals. These conversations compelled Guillebeau to study the link between questing and long-term happiness.
You Learn by Living by Eleanor Roosevelt: The former First Lady penned this simple guide to living a fuller life at the age of seventy-six. The book offers her own philosophy on living with compassion, confidence, maturity, and civic stewardship. The book may be more than 50 years old, but her advice is as applicable today as it was in 1960.
The Bullet Journal Method: Track the Past, Order the Present, Design the Future by Ryder Carroll: Organize your thoughts and focus on what is meaningful to you.
Life Worth Living: A Guide to What Matters Most by Miroslav Volf, Matthew Croasmun, and Ryan McAnnally-Linz: Drawing from the major world religions and from impressively truthful and courageous secular figures, Life Worth Living is a guide to life’s most pressing question, the one asked of all of us: How are we to live?
Contemporary Fiction About Retirement and Aging
When you think about the best books on retirement planning, fiction isn’t the first category that comes to mind. However, there is lots of literature that explores what this phase of life is really all about, the struggles and the triumphs. Some books are escapist, others funny and many are quite inspiring.
The Life Impossible: A Novel by Matt Haig: Filled with wonder and wild adventure, thisis a story of hope and the life-changing power of a new beginning.
Florence Adler Swims Forever by Rachel Beanland: USA Today calls Rachel Beanland’s Florence Adler Swims Forever, “The perfect summer read.” The story begins with a shocking tragedy that results in three generations of the Adler family grappling with heartbreak, romance and the weight of family secrets across the course of one summer.
The Vanishing Half by Brit Bennett: Weaving together multiple strands and generations of this family from the Deep South to California, from the 1950s to the 1990s, Brit Bennett produces a story that is at once a riveting, emotional family story and a brilliant exploration of the American history of passing.
Looking well beyond issues of race, The Vanishing Half considers the lasting influence of the past as it shapes a person’s decisions, desires, and expectations, and explores some of the multiple reasons and realms in which people sometimes feel pulled to live as something other than their origins.
Squeeze Me by Carl Hiaasen: Wealthy Palm Beach retirees star in Carl Hiaasen’s irreverent, ingenious and highly entertaining story. This is a novel of social and political intrigue, set against the glittering backdrop of Florida’s gold coast.
The Unlikely Pilgrimage of Harold Fry by Ray Dalio: One Amazon reviewer calls this book a perfect example of “boomer lit” — stories about aging boomers struggling with this phase of life. However, this book is so good that I know one 16-year-old fan of thrillers and dystopia who includes this among his favorite all-time reads.
Olive Kitteridge by Elizabeth Strout: This Pulitzer Prize-winning book is really more of a collection of 13 short stories. Follow Olive Kitteridge, a retired school teacher, as she grapples with changes in her world, the people around her, and comes to a better understanding of her own life.
A Man Called Ove by Fredrik Backman: I actually found this book a bit depressing. Most everyone I know thought it was funny and inspiring. Watch Ove triumph over sadness and find a new meaning in retirement.
Major Pettigrew’s Last Stand by Helen Simonson: A charming look at another chance at love and companionship later in life.
The Sense of an Ending by Julian Barnes: Complex and intense, this novel explores what happens when a man who thinks he as achieved it all, including a secure retirement, is confronted with a mysterious legacy and is forced to revise his view of himself.
Gilead by Marilynne Robinson: This story follows three generations from the Civil War to the 20th century. It is a moving story of fathers and sons.
The 100 Year Old Man Who Climbed Out the Window and Disappeared by Jonas Jonasson: Turns out the nursing home is not actually the last stop for 100-year-old Allan Karlsson. After a lifetime of adventures and being a real part of history, he is just not ready to give up the ghost.
Water for Elephants: A Novel by Sara Gruen: This book is romantic and dramatic and reminds us that rich memories can be relived and inspire new adventures.
Can’t We Talk About Something More Pleasant by Roz Chast: This hilarious memoir by the New Yorker cartoonist is a graphic novel chronicling how the author navigated her parent’s old age. If you have experienced foibles with your aging parents, this laugh out loud book is for you.
Pieces of Happiness by Anne Ostby: A novel of five lifelong friends who, in their sixties, decide to live together on a cocoa farm in Fiji, where they not only start a chocolate business but strengthen their friendships and rediscover themselves. One review calls this “chick lit for the sixty-something crowd.”
You Are Only Old Once! A Book for Obsolete Children by Dr. Seuss: Written to celebrate Seuss’s 82nd birthday, this book makes an amazing retirement gift.
Less by Andrew Sean Greer: Arthur Less will almost fall in love in Paris, almost fall to his death in Berlin, barely escape to a Moroccan ski chalet from a Saharan sandstorm, accidentally book himself as the (only) writer-in-residence at a Christian Retreat Center in Southern India, and encounter, on a desert island in the Arabian Sea, the last person on Earth he wants to face. Somewhere in there: he will turn fifty.
Crossing to Safety by Wallace Stegner: Tracing the lives, loves, and aspirations of two couples who move between Vermont and Wisconsin, it is a work of quiet majesty, deep compassion, and powerful insight into the alchemy of friendship and marriage.
A Spool of Blue Thread by Anne Tyler: Abby and Red and their four grown children have accumulated not only tender moments, laughter, and celebrations, but also jealousies, disappointments, and carefully guarded secrets.
Lillian Boxfish Takes a Walk: A Novel by Kathleen Rooney: It’s the last night of 1984 and Lillian, 85 years old but just as sharp and savvy as ever, is on her way to a party. It’s chilly enough out for her mink coat and Manhattan is grittier now―her son keeps warning her about a subway vigilante on the prowl―but the quick-tongued poetess has never been one to scare easily.
Still Life with Bread Crumbs by Anna Quindlen: Brilliantly written, powerfully observed, Still Life with Bread Crumbs is a deeply moving and often very funny story of unexpected love, and a stunningly crafted journey into the life of a woman, her heart, her mind, her days, as she discovers that life is a story with many levels, a story that is longer and more exciting than she ever imagined.
Read and Plan Your Future
Retirement is no longer a one-size-fits-all journey—it’s a time to reimagine your future, realign your values, and reclaim your time. Whether you’re focused on optimizing your finances, staying healthy and active, or finding meaning and purpose in this new chapter, the best books on retirement planning offer wisdom, clarity, and motivation to help you succeed. We hope this list sparks new ideas, opens doors, and gives you the tools to retire with confidence and live with intention. Here’s to your next great adventure.
Whether these books have helped you discover a new financial strategy, somewhere you want to travel or have inspired you to live a very very long time, use the Boldin Retirement Planner to ensure your future is secure.
Updated: April 14, 2025 (Last published: August 8, 2024)
