Best Books on Retirement

There are a lot books out there on retirement.  Here are our reviews of what we consider to be the best reads on re-defining retirement.


Second Act Careers with Purpose

Purpose and a Paycheck

by Chris Farrell (2019 – HarperCollins Leadership)   Subtitle: Finding Meaning, Money, and Happiness in the Second Half of Life   Books on retirement tend to focus primarily on financial planning.  Economist and journalist Chris Farrell covers the financial side of the road, but he also goes beyond that in this inspiring book. He tells the captivating story of how baby boomers are re-inventing themselves – and retirement – through self-employment and entrepreneurship. The idea of working in retirement seems like an oxymoron to some.  But Farrell provides an accessible tour through the research on the benefits of working longer.  […]
Do you love your work? Transitioning to retirement may be hard.

Retirement and Its Discontents

(Subtitle: Why We Won’t Stop Working Even If We Can)   by Michelle Pannor Silver (2018 – Columbia University Press)   “Retirement’s freedom can create challenges for people who’s life’s work was closely associated with their sense of self-worth.”   Michelle Pannor Silver delves deeply into the experience of retirement for people whose identities are closely linked with their work. She provides a window into the lived experiences of different people’s transitions to retirement and the challenges and opportunities that emerge. The book paints a portrait of retirement that is complex and emotionally nuanced, at both an individual and societal […]
One of the best books to prepare for life in retirement is The Second Mountain by David Brooks. It highlights the shift toward meaning and purpose in the second half of life.

The Second Mountain

by David Brooks (2019 – Penguin Random House)   Two books I’ve read in the last five years offered different perspectives on a central theme that profoundly changed how I view the life course and retirement. The Shift by the late Wayne Dyer and Falling Upward by Richard Rohr both taught me that the agenda for the second half of life is quite different than the first half. What drives and fulfills us in the first half of life is important, but fulfillment in the later phases of life will come from a deeper place and higher aspirations. As Dyer puts […]
Encore Adulthood by Phyllis Moen provides enlightening research and stories about Baby Boomers taking charge in the second half of life

Encore Adulthood

by Phyllis Moen (2016, Oxford University Press) The one job career is history. Most baby boomers are interested in second act careers or other creative ways to reinvent . themselves in mid to later life. Yet, the vast majority of books on retirement focus on financial planning. Some attempt to provide a comprehensive manual on how to retire. This book is quite different. Phyllis Moen, a professor at the University of Minnesota, offers a tour of the big picture issues around retirement and provides smart prescriptions for individuals, families, and institutions on how to navigate and improve the future.   […]
How to retire

Generation Cherry: Powerful Strategies to Give You a Second Bite of the Cherry

by Tim Drake (2017 – RedDoor Publishing) You may be checking your 401(k) and IRA regularly these days, but how about your mindset? In Short Tim Drake’s book is about cultivating the proper mindset, resilience, and creativity to create a ‘second bite of the cherry’ in mid-life and beyond. It’s not a theoretical piece. It’s based on his personal experiences. After having built a successful business, being forced to sell it during a recession at 50 in the 1990s, he needed to create new opportunities for himself. Unfortunately, many Baby Boomers today are forced away from traditional employment and shift toward alternative working […]
successful aging

Better with Age: The Psychology of Successful Aging

by Alan Castel (2018 – Oxford University Press)   We are all aging. Are you up to date on successful aging in retirement? In Short   There are many misconceptions about aging and they can paint an overly negative picture. Alan Castel’s book Better with Age dispels many of them, along with ageist stereotypes, evidence-based recommendations on how to age successfully. Castel is a Professor of Psychology at UCLA and he has a knack for translating research on aging into easy-to-understand practical takeaways. One interesting aspect of this book is that it’s targeted at a wide range of ages. The […]

From Working To Wisdom

The Adventures and Dreams of Older Americans by Brendan Hare  (2015 -Joppa Flats Publishing ) In Short You will find this book is less about retirement than it is about the experiences of growing older. The author, Brendan Hare, like many of us was anxious about his own retirement and was unable to picture what his retirement life would be like.  Brendan’s journey of discovery took him to interview over 40 people from all walks of life as he listened to and learned from their experiences of growing older and it helped him answer many questions for himself as it will […]

Breaking Up with Busy

By Yvonne Tally (2018 – New World Library) Doesn’t it seem like we’re really busy? It’s become a status symbol in our society.  But why are we so busy today? In Short Yvonne Tally explains that it doesn’t happen overnight. It starts with good intentions. We get things done and that’s rewarded. We have professional success – and we’re given more to do. (More is good, right?) We start a family. We get involved in our community. All of these good things start stacking up until we feel like we’re in a real-life version of Jenga. So we carefully figure out […]

Purposeful Retirement: How to Bring Happiness and Meaning to Your Retirement

By Hyrum W. Smith (2017-Mango Publishing Group)  In Short This is not a book on theory. Hyrum Smith, the former Chairman CEO of FranklinCovey and a renowned expert on time management, shares his experience and wisdom on what really matters most in retirement. It is a book filled with insights and humor. He challenges the conventional views of retirement and offers useful ideas on how to shift your mindset towards it, embrace the transition and live life fully in retirement. People often advise others to “Stay busy” in retirement. This book shows you how to that, but in a way […]

The Gig is Up: Thrive in the Gig Economy, Where Old Jobs are Obsolete and Freelancing is the Future

By Olga Mizrahi (2018 – Greenleaf Book Group Press) In Short If you’re following along, you’ll be familiar with a few central facts of life today. The first is that people are working longer. In fact, many want to work longer, not just for financial reasons, but for the benefits of continued engagement and satisfaction. In fact, for most people, retirement today will include work of some kind. The second fact of life is that the nature of work has changed and continues to evolve. Perhaps the biggest shifts are the decline of the traditional employment arrangement and the explosive […]

IKIGAI: The Japanese Secret to a Long and Happy Life

By Héctor García and Francesc Miralles (2016-Penguin Books). I first learned the word Ikigai from Susan Williams of @Booming Encore. It means reason for being and it is associated with a feeling of well-being. The authors refer to it as “the art of staying young while growing old.” In Short When I saw this book in the bookstore (I still try and do that when and where I can), I was eager to learn more. This book was born in curiosity. The co-authors are two writers, one lives in Japan and the other in Spain, who wondered what is behind the […]

The New Senior Man – Our Review

By Thelma Reese and Barbara M. Fleisher  (2017 – Roman & Littlefield Publishers). In Short Following their 2013 book, The New Senior Woman, Reese and Fleisher, two retired college professors, tackled the sometimes thorny issue of how men successfully transition to life in retirement. There are many things to love about this book. First, there are thoughtful conversations with many men, from all walks of life, at various stages of their retirement journey woven into the book. These provide snippets of real-life case studies that paint a rich portrait of lived experience and wisdom. The reader comes away with a […]

The Couple’s Retirement Puzzle

10 Must-Have Conversations for Creating an Amazing New Life Together by Roberta K. Taylor, RNCS, MEd and Dorian Mintzer, MSW, PhD  (2014 – Sourcebooks) In Short Retirement is a time of potential challenge for couples. While there are many conversations that you (as couples) should be having, perhaps you haven’t thought about how to have them. If that is the case – The Couple’s Retirement Puzzle is for you! Combining real-life stories with their own personal experiences, the authors offer sound advice and recommendations on some of the most complex problems couples can face when thinking about retirement.   Each conversation […]

Thriving in Retirement: Lessons from Baby Boomer Women

By Anne C. Coon and Judith Ann Feuerherm (2017-Praeger) Women face some unique headwinds that can have a cumulative and lasting effect beyond the workplace and into retirement. The authors tell stories of 25 women across their careers and life course into their retirement years. It’s a timely book, as it includes frank recollections of the toll that discrimination and harassment played in the careers and lives of these women. This book is primarily about resilience and creativity through the compelling stories of women who overcame multiple obstacles and are living satisfying lives in retirement – on their own terms. […]

The Power of Meaning * Crafting a Life That Matters

by Emily Esfahani Smith (2017 – Crown Publishing Group) At Retirement Wisdom, we’re big on of purpose. In fact, studies have found that your longevity may even depend on it. Yet, purpose is one of those subjects that I sometimes find hard to get my arms around. I wonder about how someone discovers their purpose – particularly when they transition from their primary career to their next chapter. I always feel like it requires a lengthy trip to mountains and extensive navel-gazing. That will need to wait for another day. Someday. Maybe. It turns out that the mountains are optional. […]

A New Purpose

Redefining Money, Family, Work, Retirement, and Success By Ken Dychtwald, PhD and Daniel J. Kadlec (2009 – Harper)   In Short This is an enjoyable and thought-provoking book on what sometimes can feel like an elusive topic – finding Purpose in our lives. The authors help the reader connect with the concept of purpose by taking us through a journey of discovery, covering key topics including: what success really is, the importance of relationships, the power of giving, how we are using our lives to make a real difference. They offer a refreshing view of philanthropy and ways to make […]

Entrepreneurial You: Monetize Your Expertise, Create Multiple Income Streams, and Thrive

By Dorie Clark (2017 – Harvard Business Review Press) In Short The gig economy is real. Over the past 12 years there has been a notable growth in alternative work arrangements  especially among older workers. And we’re not talking about Uber drivers. More and more people who are mid-career or beyond are concluding that moving on from corporate life offers greater flexibility and interesting, rewarding work. Many are deciding that it’s time to become their own boss. The ranks of silver entrepreneurs continues to grow. Food for Thought While the gig economy offers opportunities for Second Acts, it’s quite competitive. […]

Answering Your Call: A Guide for Living Your Deepest Purpose

Answering Your Call: A Guide for Living Your Deepest Purpose By John Schuster  (2003 – Berrett-Koehler Publishers, Inc.) In Short Some people discover their true purpose early in life, yet it’s not uncommon for this to unfold later in life. For some, it happens mid-career and leads to a major shift. For others, approaching retirement offers the time and space for reflection, exploration and discovery of their deepest purpose. John Schuster explains that discovering your purpose is not a linear process. It is highly individual and doesn’t just occur organically – or magically. it’s a result of thoughtful reflection and […]

Designing Your Life: How to Build a Well-Lived, Joyful Life

By Bill Burnett and Dave Evans (2016 – Knopf) In Short There aren’t many books that would make a great gift for a high school graduation, a college graduation or a retirement celebration. This is one. Bill Burnett and Dave Evans are two professors at the design school at Stanford, who have opened up the material from their long-standing course on Designing Your Life to all. The book shares how the principles of design thinking can be applied to planning your life – at any stage. The book is filled with great examples of people at later stages of their […]

Organize Your Emotions, Optimize Your Life

By Margaret Moore, MBA, Edward Phillps, MD and John Hanc.  (2016 – William Morrow). Some of the best books on retirement aren’t specifically about retirement. They focus on topics that happen to be valuable in making the transition to retirement or from one career to another. This excellent book is clearly one of the very best of them. All Life Transitions Are Emotional Any big change across our lifespan is an emotional experience. When it comes to retiring, that can be underestimated. You may be wondering, ‘What’s the problem? Every day will be Saturday! The only emotions I’m feeling are […]

The 100 Year Life: Working and Living in an Age of Longevity

Living and Working in an Age of Longevity By Lynda Gratton and Andrew Scott (2016 - London, Bloomsbury) Let’s look ahead a bit - or back a bit - and imagine. It’s your 60th Birthday Party. You receive the best gift of all time. You’re given more 30 years of life. How would you react? Psyched about all you get to experience and do? Scared about what lies ahead? Well, according to statistics the authors cite, if you are 60 today, you have a 50 percent chance of living to 90. In Short It’s very difficult to see a sea change when you’re in the […]

Refire! Don’t Retire Our Review

Make the Rest of Your Life the Best of Your Life By Ken Blanchard and Morton Shaevitz  In Short If you only read one book on transitioning to retirement, I’d urge you to read this one.  This is an exceptionally insightful and inspiring book. It’s fun, easy to read and full of practical wisdom.   Ken Blanchard and Morton Shavevitz encourage us to rethink retirement. In their view,  it all starts with or attitude and beliefs. Sometimes we don’t realize that our own beliefs may be rooted in outdated views of aging and retirement. Instead they advocate thinking differently. They define Refiring as: “Adopting an attitude of embracing the years ahead with […]

The New Retirementality

by Mitch Anthony (2014-John Wiley & Sons, Inc., 4th edition) In Short The “New Retirementality” takes the reader on an educational and thought-provoking journey combining research, real-life stories, do-it-yourself exercises and concepts to help one understand what this “new retirement” is really about. This book is a must-read for those who are looking forward to years of productive retirement and want to consider a way to re-write how they retire that can affect generations to come. There is something for every reader and way too much to do justice to in this brief review, but I will provide you with […]

Books on retirement offer insights that can inspire and inform your retirement planning and help you retire smarter. Here are brief reviews of retirement books we believe are worth your time.

Retirement is Multidimensional

You need to have your financial house in order to retire well. But the best books of retirement make a compelling case that you’ll need to do more. To have a fulfilling retirement life, you need to account for how you’ll invest your time. You’ll need to experiment with ideas to create an active lifestyle that’s centered on what’s most meaningful to you and cultivate rich social relationships and interests. There’s an emotional dimension to retirement and mid-to-later life to master. And opportunities for lifelong learning and service are more abundant than ever.

Write Your Own Script

Most retirement books have traditionally written about the financial side of planning. But an increasing number of authors are spotlighting emerging research and stories of how baby boomers and proponents of the FIRE movement are ripping up the script and transforming life in retirement. Top books about retirement can update your perspective on retirement day which is radically different than in earlier generations.

Explore Work and Entrepreneurial Options

A bevy of new retirement books delivers a view of the big picture and what’s driving change in the world of work. What does work have to do with retirement? Well, a high percentage of people are expressing interest in working longer. For some, it’s deferring retirement or choosing to never retire. For others, it’s about crafting a part-time role to downshift but stay in the game. Others still are attracted to starting a business, translating their skills to freelance work, the gig economy or self-employment. Making a savvy mid-life career shift can position you well to have more control over your future.

Acquire a Positive Aging Mindset

The aging process and retirement life go hand in hand, so we’ve including some books on retirement that emphasize the latest research on positive aging. Successful aging involves learning about what aspects are within your control and practical takeaways can help you anticipate and make wise adjustments in your retirement life.

Get A Jump Start for Retirement Planning

Why read a book on retirement? Reading selected books on retirement can give your retirement planning a jump start.  You’ll get practical ideas that can upgrade your vision for your life in retirement.

We invited a number of the authors to join us on our retirement podcast.  We invite you to listen in on the conversations.