5 Must-Read Books for Men Approaching Retirement

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Many men consider their career to be a significant aspect of their identity, so it also makes sense that many men report feeling unmoored and even depressed in retirement. The good news is that a profession is not the only way to find structure, purpose, and fulfillment, and we wanted to offer what we feel are the 5 Must-Read Books for Men Approaching Retirement.

It’s important to remember that men who retire to something instead of from something are more likely to find happiness and contentment in retirement. Whether you decide to travel, spend time with family, learn something new, volunteer, or become a consultant it is important to map out your retirement pursuits. While most books about retirement focus solely on financial planning, retirement elicits many other relevant questions that deserve answers.

If you are looking for inspiration for this next chapter of your life then the motivational books are sure to give you the wisdom and direction you need to proceed into your retirement with confidence.


#1 PURPOSE AND A PAYCHECK – Finding Meaning, Money, and Happiness in the Second Half of Life

by Chris Farrell (Available via Amazon)

From advice on financial planning to seeking purpose driven work, Purpose and a Paycheck has it all. Author Chris Farrell is both an economist and journalist, and he leverages both skillsets with finessed expertise in this inspirational and informative read. For those considering a new career, a new business, or a profitable calling in retirement, the real-life stories and statistics in this book are sure to give you the clarity and perspective needed to adjust to retirement in a meaningful and profitable way.

Book quote: “People in their 50s and 60s are launching new businesses at nearly twice the rate of people in their 20s.” 

We’ve talked about ingenuity of the middle-aged business person before in our blog A Guide to Making Money In Retirement. Give it a read for more tips on staying active in your retirement.


#2 RETIRING? Your Next Chapter Is About Much More Than Money

by Ted Kaufman and Bruce Hiland (Available on Amazon)

If you have no interest in slowing down in retirement then you will love this modern take on 21st-century retirement. This book will help you map out all of the non-financial aspects of retiring with a purpose. Whether you have already retired or are about to retire, the self-reflection questions and strategies poised in this book will give you the insight needed create the retirement of your dreams.

Book quote: “For too many people approaching retirement, only financial planning has gotten the necessary attention. Whether they’ve overlooked, ignored, or avoided the nonfinancial challenges, they risk being unprepared for the profound personal and life changes that retirement brings.”

Mentally speaking, retirement is much more than about the money. We’ve outlined some ideas as well in our blog Making the Most of Your 50’s – Time for a Change?


#3 THE SUBTLE ART OF NOT GIVING A F*CK

by Mark Manson (Available on Amazon and Audible)

Do not let the crude title discourage you from reading this masterpiece. There is a reason why this book sold over a million copies and was a #1 New York Times bestseller If you are a no-nonsense, call-it-like-you-see-it man, then you will love Mark Manson’s brutally honest, hilarious, and deeply profound perspective. This book does not regurgitate any of the cliché platitudes found in other stereotypical “how to be happy” motivational books. If you are at a crossroads trying to find clear, actionable inspiration then this book will not disappoint.

Book quote: “We need some sort of existential crisis to take an objective look at how we’ve been deriving our meaning in our life, and then consider changing course.”


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#4 LIFESPAN – Why We Age and Why We Don’t Have To

by David A. Sinclair, Phd (Available on Amazon and Audible)

Heralded as a New York Times Bestseller, this life-changing book was written by Dr. David Sinclair, a globally acclaimed genetics professor and co-Director of the Paul F. Glenn Center for Biology of Aging Research at Harvard Medical School. (So he knows a thing or two healthy aging!) If becoming the healthiest and strongest version of yourself is one of your goals in retirement, then this book will forever alter the way you consider aging. By the end of the book, you will understand the top takeaways of decades worth of research that will allow you to create a roadmap for not just feeling your healthiest, but truly becoming your best.

Book quote: “Aging is a disease, and that disease is treatable.”


#5 THE SECOND MOUNTAIN – The Quest for a Moral Life

by David Brooks (Available on Amazon and Audible)

If you suspect that your sense of purpose in retirement might involve some form of philanthropy, then David Brooks’ vivid perspective is worth the read. Using the concept of two mountains, the book dives deeply into how to clarify your values and make the shift from seeking successes to pursuing significance. The compelling stories and strong analogies provide readers with thought provoking material to guide self-reflection. If you are considering applying your time and experience to a cause greater than yourself in retirement, then this powerful book is a must read.

Book quote: “If the first mountain is about building up the ego and defining the self, the second mountain is about shedding the ego and losing the self. If the first mountain is about acquisition, the second mountain is about contribution.”


Final Thoughts on the 5 Must-Read Books for Men Approaching Retirement

If you are looking for some quality retirement reading, this list is an excellent place to start. Remember that the journey of life is like an excursion up a mountain. You’ve spent a lifetime growing strong as you climbed, and now you are on top of life’s mountain. The good news is that it is NOT all downhill from here. Far from it! You have strength and experience, and both are still needed and required. Retirement is not about starting over but rather continuing on in the meaningful pursuit of other worthy endeavors.

As always, we hope that you find worthwhile information here here and can use this blog on the 5 Must-Read Books for Men Approaching Retirement in helping your decisions in making the most of your 50’s. Want us to cover other self-help topics? Spoiler alert, we are anyway! But if you want something specific, reach out to me directly through our Contact page or leave a comment below, we read each one! All the best ~ Glen.

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