13 Best Books After Early Retirement
Most books about how to obtain financial independence, how to retire early, or what to do after an unexpected early retirement focus on the financial aspects—and these books usually serve as marketing material to get you signed up with a specific financial advisor or institution.
We didn’t read any books on FIRE until we learned that we might have enough saved to leave our W2 lives in our early 40s (that is, if we continued to keep our expenses relatively low). However, after leaving the conventional workforce, we’ve done a lot of digging and found several books that have helped us navigate the waters of early retirement as GenXers.
Not too many people write about life after retirement, and if they do it is often about taxes, budgeting, and planning your final expenses. But after a few months of digging through books, we’ve found a few gems.
In this blog, we share our favorites and what we enjoyed about each. Note that the links to the recommended books are Amazon affiliate links. We make a small affiliate commission whenever you use these links at no additional cost for you. Thanks for supporting our little blog!
Best Book to Read Your First Week of Early Retirement
Keys to a Successful Retirement
Fritz Gilbert blogs at The Retirement Manifesto and released a book in 2020 covering what to expect in the first weeks, months and years of retirement. It covers especially well the psychological shift into self-directed living after 30, 40, 50, or 60 years of being told what to do by other adults.
Fritz spent over 30 years at the same company, climbed the ranks, and retired in his mid 50s. In this book, he offers a window into what to expect in those first days after W2 employment ends. Fritz studied retirement as a hobby years before he left traditional employment, and his depth and breadth of research on this topic shows.
Folks who are younger Baby Boomers and GenXers who spent 15+ years in a corporate environment will find a lot of value in this book. Fritz first tells his own story and the proceeds with giving a nice framework to map out your next 10 - 40 years.
Sometimes it is available for free with a Kindle unlimited subscription.
Best Book to Read If You are Bored in Early Retirement
How to Retire Happy, Wild, and Free: Retirement Wisdom That You Won't Get from Your Financial Advisor
Ernie’s writing feels like talking to the outlaw uncle you may or may not have had while sipping a margarita in a salty dive bar as he shares years of experience on how to not be bored in retirement. It’s really a book about enjoying life.
This is a great read if you have put enjoying life on the “back burner” and feel lost or bored with a planned (or unplanned) exit from the workforce. The book is full of stories and quotes to inspire you, shake you out of a rut, and become reconnected with your inner free spirit.
The book can get a little repetitive, and a few lines are a little dated or targeted to an older audience, but hey, that’s what’s great about your outlaw uncle, too.
Best Book to Read if You Are A Recovering Work Addict
The Pathless Path: Imagining a New Story For Work and Life
If you’ve found the conventional working path a disappointment early on or mid-career, I highly recommend this book about how work permeates so much of our culture and how to not make the same mistakes if your definition of retirement means “next career.” If friends, family or colleagues have said “but you are throwing away a good job” or “but you’re a high potential employee,” then this book is for you.
Paul worked for about a decade in corporate consulting and was steadily climbing the ladder when an illness and discontent prompted him to reflect on his life and work.
Paul’s The Pathless Path podcast is a great supplement to the book.
Best Poetry Book for Early Retirement
Devotions: The Selected Poems of Mary Oliver
One thread that runs through the financial independence community is the famous Mary Oliver quote, “Tell Me What It Is You Plan To Do With Your One Wild And Precious Life” from her poem, “The Summer Day.”
Treat yourself (or an early retired friend) to this collection of 200 poems by Oliver. These are great poems for slowing down, enjoying life, and reading before bed or getting up in the morning. If you have abruptly left a busy career, mindful reading of works by authors like Mary Oliver can help your mind adapt to a different pace of living.
Best Book on Understanding the Phases of Transitions
Life is in the Transitions: Mastering Change at Any Age
Many of us, especially in the US, have a lot of our identity tied up in the world of work. In a big transition such as early retirement, one needs to write a new script.
Bruce Feiler interviewed 225 people from across the US who were going through big changes like losing or quitting jobs, changing careers, losing limbs, getting divorced, or getting sober. What is covered in the book surprised me. We’re taught that big life changes typically clump together in our 20s and 30s (education, marriage, children, etc.) However Bruce’s research found that most big life transitions happen in our 40s and 50s.
If you are a GenXer and have lived a non-linear life, you may find this book helpful in understanding what each phase of a transition is, what to expect, and how others have navigated transitions.
Best Book on Money and Death by a Hospice Doctor
Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life
Jordan Grumet (aka Doc G) is well known in the world of personal finance. Like ourselves, he had been saving and investing for years without a clear goal. Eventually, he began to question his identity as a doctor. He began blogging about this topic—especially the “Art of Subtraction,” or working to remove the parts of one’s job that no longer serve you so that you can discern if it is the career or just parts of your career that you can no longer tolerate before considering a pivot to something else.
Jordan does briefly cover some big picture aspects of personal finance. However, the crux of the book is on the topic of our finite lives and his experiences with dying and money. Jordan mentions that no one ever said on their death bed, “I wish I had worked more and made more money,” but many people work well past the point of having “enough.”
Taking Stock covers a lot of ground that most in the personal finance space don’t go: having difficult conversations, planning for the end of life, and regret. Jordan is a gifted writer, interviewer, and speaker. I’ve had the chance to see him at the EconoMe conference and was interviewed with two other guests on Jordan’s podcast Earn & Invest in 2020.
Best Book to Understand The Pull for More Than Enough
Wanting: The Power of Mimetic Desire in Everyday Life
The personal finance communities talk a lot about the hedonic treadmill, but few writers really peel back the proverbial onion to explore and understand the hedonic treadmill and all the cognitive biases at play.
In his book Wanting, Luke Burgis helps us to why we want things—things we think we should want but don’t always understand why. Luke founded a company and then walked away and was immediately relieved—even though while he was building the company there was nothing he wanted more than to see it succeed and be part of it.
The book proceeds to explain mimetic theory, or why we want things, and how to be aware of its influence in our everyday lives.
A few of my favorite quotes from the book:
“It may help you avoid waiting until middle age or later to learn that money or prestige or a comfortable life is not primarily what you want.”
“It’s decidedly difficult to figure out why you bought certain things; it’s extraordinary hard to understand why you strive toward certain achievements. So hard that few people think to ask.”
I rarely reread books, and I’ve read Luke’s book three times.
Best Book for (Second) Career Pivots
From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life
Arthur Brooks writes weekly at Atlantic magazine and in his words “tears down [his] life to the studs every 10 years.” He’s also had a couple of podcasts on the topic of happiness in midlife and beyond.
His most recent book is targeted toward the mid-career professional who is thinking of making a big change. It’s a common misconception that most people in high-tech disciplines believe that they can keep doing the same level of work well into their 50s and 60s. They plan their finances, career, and income projections based on this assumption. However, Brooks has discovered in his work at Harvard Business School that there is a natural process by which our fluid intelligence decreases and our crystallized intelligence increases.
I recommend this book if you have left the corporate world but are still interested in doing some work, especially teaching or mentoring, in your previous field.
Best Book on Activism in Early Retirement
Wallet Activism
Many people are familiar with author Tanja Hester and her popular book Work Optional on achieving financial independence from traditional employment.
Tanja’s new book would be interesting for someone who is interested in volunteering, advocating, or wanting to make a difference in the world in early retirement. She also explains how some companies and organizations are well aware of consumer interest in trending environmental and social issues, and helps you see through this to help you make mindful contributions or purchases.
If you are looking for a deeper (and not watered down!) understanding of how you can make a real difference on the earth and with people during early retirement, you’ll enjoy this book.
Best Book On Prioritizing Your Time
Die With Zero: Getting All You Can from Your Money and Your Life
“I want the last check I write to bounce.” If you’ve uttered (or loved) this phrase, then look no further for your next read by author Bill Perkins.
One of the main reasons I left the 9-5 grind was an awakening during the early weeks of the pandemic, a realization that we are not promised tomorrow, and that if you or a colleague were to pass away, your job is likely to get reposted days after your passing. While many Americans will struggle to save enough for retirement, there’s a little discussed segment of the population that over-save and under-use their resources and die with more than enough.
My favorite portion of the book is where Bill has you bucket things you want to do in five year segments. It really opens your eyes! For example, you realize that there are some things that you need to do in your 40s or 50s because you may not be physically able to do them in your 60s or 70s. Alternatively, there are some more costly and sedentary activities that you might want to postpone to later in your “slow-go” years so that you can budget in the active goals earlier in your life.
If you are looking for a very provocative book on spending in retirement or semi-retirement, this is it. Everyone I’ve met who has read it has been simultaneously stimulated to take some action, especially on shifting spending to activities with friends and family instead of accumulating more things.
Best Book on Finding Your True Self in Retirement
Transcend: The New Science of Self-Actualization
Scott Barry Kaufman has been podcasting at The Psychology Podcast for years. Scott has written several books on humanistic psychology. His best to date is Transcend. I read over 60 books after I left W2 employment in 2020, and this one was my favorite of the year.
Our culture puts a lot of emphasis on work and the idea that self-actualization can be easily achieved in the workplace. However, I’ve come to believe that this is not the case. In order to have moments of self-actualization, one needs to have integration of everything that is within you. Traditional workplaces often require walling off of portions of ourselves during working hours to achieve business goals or to fit in, so the whole self is not often present.
If you’ve a passion for psychology and want to understand more about Maslow was really getting at in the hierarchy of needs, you will like this book. In the appendix there’s plenty of exercises to practice getting in touch with parts of yourself that you may have shut away during your corporate years.
Best Book for Testing Post-Retirement Business Ideas
Will It Fly?: How to Test Your Next Business Idea So You Don't Waste Your Time and Money
Early retirement or semi-retirement often means working in a different way: in a new field, on a passion project, volunteering, or caring for family members or friends. If running a small business is something you have always wanted to do, this great book by entrepreneur Pat Flynn is a great place to start.
Too often, those leaving a corporate work environment think too much about setting up the same type of infrastructure for a business before testing ideas and just seeing what works. Pat walks through testing different business ideas step by step before investing in ideas that simply won’t work. This is great because you may not want to spend too much time or money on chasing after bad business ideas in retirement.
One of the best kept secrets about retirement or semi-retirement is that you can often take time and test several ideas without pressure to perform or meet a deadline. If you get bored with an idea, or you simply don’t like the work after doing it for a little bit, no problem! Try the next idea and incorporate what you learn in your next venture.
Best Book on Mindfulness in Retirement
Stop Missing Your Life: How to be Deeply Present in an Un-Present World
I first heard of Cory Muscara in 2018 or 2019. I was having difficulty sleeping. Darren and I had heard of mindfulness meditation and started searching for a person’s voice and style we both liked. He even has a meditation on coffee! These days we listen to Cory’s meditations on the Mindfulness App. A couple of years ago Cory wrote a book on the benefits of meditation in the modern age. I highly recommend the audio version of this book as Cory narrates the Audible version himself. The book also includes meditations related to most chapters.
This is a great book for those who are looking for a better relationship between mind and body, to slow down and become more present, or to process any trauma in transitioning from work to retirement or semi-retirement. It’s also a great resource for anyone wanting to become more curious in this new phase of life, and become more focused.
Wrapping Up
And there we have it, 13 books on how to navigate the challenges of early retirement, and with minimal emphasis on finances!
We hope you enjoy one or more of these books either in Kindle, Audible, or traditional book format. When you are finished with your book, check with your local library to see if they would like your gently used copy. Or pass it on to a friend!
Do you have any favorite non-financial retirement books? If so, let us know in the comments!
