20 Books That Will Change Your Life and How You Think About Retirement

If you are a part of what is considered Generation X, you know that you probably have anywhere from 25-35 years until retirement — or at least that’s what the government and most pension plans suggest as a retirement age. Since we’re currently focused on other aspects of our lives such as building careers, starting families, and trying to accumulate wealth, why would I bring up a topic that is seemingly more appropriate for someone closing in on retirement?

To answer this, all you have to do is ask yourself if you plan on retiring at 65-67 or later just because that is what is expected of you. I’m guessing that you would rather “retire” earlier and then have the freedom to pursue your dreams before reaching this predetermined age. For some, this may be starting a second career, others may want to travel the world, and some of you may simply want to have the flexibility of working on your own terms. Whatever your dreams are, it doesn’t make any sense to begin to seriously plan for them in the ten or so years before you plan on retiring. There are plenty of steps you can take today that will position yourself for making the moves necessary to achieve your goals plenty of time in advance.

As a retirement planning counselor, I am often asked what kinds of books or resources are available to help people begin planning for the rest of their lives. I’m not just talking about money and investing for retirement, we do enough of that already. Many people are looking for much more — they are already maxing out their retirement accounts, they have paid off all of their debt, so there has to be some greater goal. Luckily, there are a lot of resources available to help you put things into perspective and begin thinking about what matters most in your life. So, I have compiled a list of 20 of the top books in this category that can, and probably will change your life and how you view retirement.

Don’t Retire, REWIREDon’t Retire, REWIRE: 5 Steps to Fulfilling Work that Fuels Your Passion, Suits Your Personality, or Fills Your Pocket by Jeri Sedlar and Rick Miners.

These authors provide an alternative to traditional retirement that recognizes the varied needs of individuals. Thanks to modern medicine, many people are living longer than ever and are able to continue working to otherwise contribute to society for years after what most people would consider retirement. This book is full of information, quizzes, and discussion to help you identify what your own personal drivers are and provides tips for creating your own optimum situation. Don’t Retire, REWIRE will force you to think about what you want to do with the rest of your life in a completely new way.

The NumberThe Number: What Do You Need for the Rest of Your Life and What Will It Cost? by Lee Eisenberg.

We all know that money is an important part of life, and even more important if you want to live a comfortable retirement. Eisenberg, the former editor of Esquire magazine, bridges the gap between preparing financially for retirement and the importance of creating a life plan that identifies where the money will actually be spent. We always hear numbers and rules of thumb that allow you to estimate how much money you’ll need to have in retirement, and while a good start, they are only estimates. This book attempts to go beyond the money basics and emphasizes the importance of life planning alongside financial planning.

Life LaunchLife Launch: A Passionate Guide to the Rest of Your Life by Frederic M. Hudson and Pamela D. McLean.

Life Launch is a book for any age as it provides insight and road maps of all life stages from twenty to ninety. Stephen Covey, author of The Seven Habits of Highly Effective People gives this book high marks and says it “provides the tools for productivity approaching change during our adult years with confidence, vigor and excitement.” This book presents planning with a unique use of maps, or visual concepts that guide you through the various stages of your life. Life Launch will give your life passion and purpose.

TransitionsTransitions: Making Sense of Life’s Changes, Revised 25th Anniversary Edition by William Bridges.

Life is full of change, and this book has been in print for over 25 years helping readers cope with the change and transitions in their lives. Bridges describes the three stages of transition as: endings, the neutral zone, and the new beginning. Regardless of your age or financial position, you will experience transitions in your life, and this book can help provide the road map that allows you to navigate them.

Second ActsSecond Acts: Creating the Life You Really Want, Building the Career You Truly Desire by Stephen M. Pollan and Mark Levine.

Second Acts is another great book that is geared towards all ages. It doesn’t matter if you’re just starting out your career, or you’re winding down and look forward to retirement, this guide to reinventing your life talks about how to pursue your dreams. This book features many success stories from not only the authors, but from those of their clients as well. If you’re looking to reinvent yourself and create the life you really want, this book will be very motivational.

How to Retire HappyHow to Retire Happy, Wild, and Free: Retirement Wisdom That You Won’t Get from Your Financial Advisor by Ernie J. Zelinski.

Do you want to retire in your 30s? Well, this is the book for you. The author of this book did retire at age 30, even while still in debt. It doesn’t matter how old you are, you can retire at almost any age. The trick is finding what is more important to you and taking the plunge. It is up to you to make the most of your life, and this book provides a lot of motivation to steer you towards your goals and provide the inspiration necessary to take that next step.

The Art of PossibilityThe Art of Possibility: Transforming Professional and Personal Life by Rosamund Stone Zander and Benjamin Zander.

Anything is possible, and this book aims to change your entire outlook on life through illustrating possibility as an art. This national bestseller is written so that it is very easy to read and anyone can relate to the illustrations and situations that are presented. Not only does the book address making positive changes in your personal life, but it goes beyond that to describe changes that can be made in your professional life as well.

Too Young to RetireToo Young to Retire: 101 Ways To Start The Rest of Your Life by Howard and Marika Stone.

Everyone likes a good list, and this book delivers 101 ways to start the rest of your life. While these ideas are great, the book goes beyond just providing ideas for what to do with the rest of your life and discusses stories, exercises, and resources covering everything from money to wellness. One unique feature is the “try this” section at the end of each chapter. These small activities allow you to make progress towards your larger overall goals.

The Creative AgeThe Creative Age: Awakening Human Potential in the Second Half of Life by Gene Cohen, MD, Ph.D.

The Creative Age is chocked full of inspiring stories backed by medical and scientific evidence that illustrates the stages of life. There are many forms of creativity, and the book argues this basic human attribute increases with age. Dr. Cohen was also the director of the National Institute on Aging and founded the Washington DC Center on Aging. This book will help you develop your creativity and put it to good use as you continue to age.

The Mature MindThe Mature Mind: The Positive Power of the Aging Brain by Gene Cohen, MD, Ph.D.

The Mature Mind is another book by Dr. Cohen that discusses the aging mind, but this one is more technical in nature and discusses scientific research on brain functionality and structure. Dr. Cohen also goes on to expand on famous research by Erickson and introduces developmental intelligence. This book brings good news if you’re worried that you will lose some of your cognitive abilities as you age since his studies show that older brains are even more flexible.

Now What?Now What?: 90 Days to a New Life Direction by Laura Berman Fortgang.

Laura is a life coach that has been successful in teaching people how to make major changes in their lives. The book is full of exercises that allows you to define your life and what inspires and motivates you. By identifying your talents, values, and needs, you can begin your journey to take your life in a new and positive direction in as little as 90 days. Each chapter contains more anecdotes and specific exercises, which help make the goals practical and tangible and the idea of change seem possible.

Repacking Your BagsRepacking Your Bags: Lighten Your Load for the Rest of Your Life by Richard Leider and David Shapiro.

Repacking Your Bags focuses on achieving purpose, balance, and change. If you’ve ever packed your bags for a long trip, you know that in order to maximize space and limit wrinkles, you need to pack in a specific way. This book uses this metaphor to illustrate how you may have to unpack and then repack the bags of your life in order to maximize your life’s purpose. Repacking Your Bags will help you identify your own personal vision of the good life and design your life in order to live it.

Aging WellAging Well: Surprising Guideposts to a Happier Life from the Landmark Harvard Study of Adult Development by George E. Vaillant, M.D.

This book is a culmination of a Harvard study that spanned over 50 years and followed over 800 subjects. Aging is a complicated process that takes into account many social and physiological factors and this book discusses findings from the study so that you can age well. Aging Well is recommended for readers who are interested in learning about the quality-of-life issues of aging from the people who have the most to teach. A respected researcher, psychiatrist, professor at Harvard Medical School, and author of several books, Vaillant uses individual life histories to illustrate how social and emotional development is an ongoing process.

How to Create the Life You Want After 50How to Create the Life You Want After 50 by Sara Brown Ph.D. and Joan Malling.

While the title of the book is discussing life after 50, you certainly don’t want to wait until then to read it. This book provides tips and resources for anyone who is willing to learn how to identify opportunities, needs, and desires in their lives and then create a plan to reach them by retirement. This book will help you create a step-by-step process that allows you to construct a plan now that will guide you into your later years and beyond.

The Second Half of LifeThe Second Half of Life: Opening the Eight Gates of Wisdom by Angeles Arrien.

As we approach midlife, many people begin to ponder what comes next. After years of establishing a career, starting a family, and finding stability in life, you begin to question what is in store for the second half of your life. This book provides a collection of teachings and stories from various cultures to help you navigate the “great crossing” that occurs at midlife. Angeles Arrien, Ph.D. is a cultural anthropologist, award-winning author, educator, and consultant to many organizations and businesses.

Looking ForwardLooking Forward: An Optimist’s Guide to Retirement by Ellen Freudenheim.

Thanks to increased life expectancy, Americans are living longer. Most people can happily anticipate many healthy years to come, yet they’re often at a loss about what to do in this new phase of life. And many of them may have an unfulfilled dream or two they’ve never quite been able to shake. Author Ellen Freudenheim, a baby boomer, shares her generation’s uncertainty and excitement. In an engaging, encouraging tone, she tells readers how to successfully pursue everything from second careers to additional academic degrees to volunteer work.

The Power YearsThe Power Years: A User’s Guide to the Rest of Your Life by Ken Dychtwald.

Ken Dychtwald is a well-known psychologist and gerontologist made famous by Age Wave, published in 1989. The Power Years is your step-by-step guide to “repowerment” and personal reinvention after forty. In this unique guidebook, the leading authority on aging Ken Dychtwald and award-winning journalist Daniel J. Kadlec combine their decades of cutting-edge research and reporting to reveal how you can make the Power Years the best years of your life. The Power Years helps readers envision and embrace this new chapter of life as they develop a carefully thought-out plan for personal fulfillment.

Retirement for TwoRetirement for Two: Everything You Need to Know to Thrive Together as Long as You Both Shall Live by Maryanne Vandervelde, Ph.D.

Many of us will head into retirement with a partner, so there is much more to planning for the future than simply trying to get what you want. Vandervelde discusses topics such as how to manage money within the relationship, dealing with different wants and desires, and even important medical and legal matters. There’s more to retirement than money – much more – and Vandervelde’s book can help you and your spouse understand just how different — and how much fun — life can be in retirement. –Ric Edelman, author of Ordinary People, Extraordinary Wealth.

My TimeMy Time: Making the Most of the Bonus Decades After 50 by Abigail Trafford.

I know that many readers here still have many years until age 50, but don’t dismiss this book too soon. We are constantly developing as human beings, and Abigail guides readers through various obstacles that occur as we approach this age so that we can make the most of the years beyond 50. Thanks to the longevity revolution of recent decades, today’s 55- to75-year-olds are living and working longer and healthier than ever before. This generation is the first to experience the period of personal renaissance in between middle and old age-what Trafford calls “My Time.”

The Third AgeThe Third Age: Six Principles for Personal Growth and Rejuvenation after Forty by William Sadler.

In the Third Age, Sadler conducted over a decade of research on people between the ages of 40-80 and summarizes the findings which identifies six principles of growth and renewal. Practically instructive and powerfully inspiring, The Third Age expertly guides us toward and through the second half of our lives. Sadler’s theoretical framework makes his advice more thought provoking than prescriptive, so this gracefully written volume is more challenging than many self-help guides.

Author: Jeremy Vohwinkle

My name is Jeremy Vohwinkle, and I’ve spent a number of years working in the finance industry providing financial advice to regular investors and those participating in employer-sponsored retirement plans.

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Adam Reggie
Adam Reggie

The Art of War by Asia General.It's give insight in how handle life fast balls.

Stephen Dollins
Stephen Dollins

Financial Peace by Dave Ramsey and what I'm reading now, The Real Crash by Peter Schiff.