24 Best Books on Planning for (and Enjoying) Retirement


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Planning for your retirement is far more than just a financial endeavor. Of course, it’s important to arrange your finances for the years you’ll be without employment.

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But that’s only one part of retirement. You’ll have a lot of time on your hands. It can be hard to decide what you’ll do with yourself. You’ll finally have time to pursue your passions. Planning for retirement involves thinking about how you’d like to spend your time.

Consider these books when you’re planning your retirement. Some of these are broad overviews on the subject of retirement. Others deal specifically with one aspect of it. But they all offer unique and useful information. 

Books on Retirement Planning

Not every book about retirement planning is about financial planning. But most of them incorporate some discussion about finances. It’s impossible to talk about your plans for retirement without including some discussion of your financial activity. It’s an important thing to consider especially if you’ve got a big retirement bucket list. 

The good news is that most books offer a mix of tips and tricks. So you can determine how in-depth you want to get on most retirement topics. Here are just a few books to consider when you’re starting your planning.

1. The Retirement Maze by Robert Pascale

The Retirement Maze includes a comprehensive explanation of what you need to prepare for retirement. It outlines the common challenges that people face in retirement.

And it explains how to avoid them. This is a great big-picture read for getting started with all aspects of retirement.

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2. Get What's Yours: The Secrets to Maxing Out Your Social Security by Laurence J. Kotlikoff, Philip Moeller, et al.

Get What's Yours is a how-to book focused on when you should retire. It helps you figure out the best age to retire to maximize your Social Security payout.

It also talks about further maximizing your payout based on your retirement circumstances. When figuring out how much money you’ll need, this book is a helpful resource. Especially for those who have been working and living in the United States.

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3. Retire Inspired by Chris Hogan

Chris Hogan is a financial wellness guru whose books offer practical advice. If you feel overwhelmed every time you think about retiring, give Retire Inspired a go. It addresses that feeling and keeps things positive.

Rather than encouraging the reader to save as much money as possible, it asks you to think critically. This book can help you decide what you want from your retirement. Figuring out what your retirement might look like can help you feel excited to save for it.

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4. How to Make Your Money Last by Jane Bryant Quinn

While saving for retirement can be a challenge, it shouldn’t be your only focus. It’s also important to consider how you’ll spend your money after you retire.

If you want to be able to travel the world, your plans will look different than someone who just wants to stay home. In How to Make Your Money Last, Quinn guides you through the process of creating a plan that will allow you to retire on your terms. 

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5. The Simple Path to Wealth by J L Collins

Like many money books, The Simple Path to Wealth aims to give you practical steps to live off your savings. It offers advice that can help you pick ways to invest and prepare for retirement. Collins covers how to use different financial tools to maximize your retirement funds.

The financial aspects of retirement can seem less interesting, but this is a good book to start with. Even if you've got other pressing retirement concerns, don’t ignore this detail. Thinking about money before you start retirement will make everything easier. 

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

Eisenberg helps people who are working toward financial independence during retirement. The Number will help you create a goal "number."

That is the amount of money you need to live off your passive investment income. Even if your number feels large, it can give you a concrete thing to aim for with your savings efforts.

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7. How to Retire Happy, Wild, and Free by Ernie J. Zelinski

Zelinski’s fun advice focuses less on money and more on freedom.

How to Retire Happy, Wild, and Free asks you to think about this important question: what do you not want to worry about during retirement? Answering this question can help you work backward and figure out how you can prepare for the life you want.

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8. The Retiring Mind by Robert P. Delamontagne

The Retiring Mind focuses on an often overlooked aspect of retirement: the changing psychology of your new life.

You’re no longer working a job or raising children or whatever else you did before retirement. This transition can be more jarring than some people expect, so focusing on how to do it well is a smart effort.

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9. How to Retire with Enough Money: And How to Know What Enough Is by Teresa Ghilarducci

Many of these books focus on this same idea of being prepared for retirement. But How to Retire with Enough Money takes it a step farther to interrogate "enough."

She helps you focus on what you deem important for your retirement. She encourages you to avoid worrying about what others might consider important. And she helps you calculate a reasonable savings rate by working backward from what "enough" means for you. 

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10. AgeProof: Living Longer Without Running Out of Money Or Breaking a Hip by Jean Chatzky, Michael Roizen, and Ted Spiker

AgeProof moves beyond just the financial parts of retirement. It encourages you to take a practical look at the impacts of aging on one’s body, mind, and bank account.

With suggestions backed by research, this book gives you practical ways to plan. And will help you take great care of your body and mind.

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Best Books on Enjoying Retirement

Not all your planning needs to be focused on health and financial wellness. Here are some of the other books that can help you put your best foot forward into an enjoyable retirement.

11. 65 Things to Do When You Retire by Many Authors

65 Things to Do When You Retire offers you a wide variety of things to ignite your imagination. While you don’t have to commit to doing anything immediately it’s good to have some plans.

A meaningful retirement should include some new activities or goals. You could decide to travel, volunteer, join an organization, or try a new hobby. There is no limit to what you can explore once you’ve retired. 

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12. Just Move! by James P. Owen

Owen’s inspiring book reminds the reader that retirement-time exercise isn’t the same for every retiree. Some retirees will be running marathons.

But others will reap big wellness benefits just from subtle movements each day. Just Move! will inspire you to make movement part of your retirement plan from the beginning.

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13. Purposeful Retirement: How to Bring Happiness and Meaning to Your Retirement by Hyrum W. Smith

Smith focuses on how retirement isn’t "time off" but rather "time on." Purposeful Retirement can help you find your new activity or a new source of joy. It’s a helpful guide to creating your routine for retired life.

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14. The Single Woman's Guide to Retirement by Jan Cullinane

Retirement is just as fulfilling for those who enter it single. But it doesn’t hurt to have a book about the topic to help you. Cullinane writes about the approach a single woman can take to plan for retirement.

The Single Woman's Guide to Retirement speaks to anyone who is planning their retirement without a partner. The steps will be similar but not quite the same. After reading this book, you’ll be able to plan more efficiently. You won’t need to stop to think about how advice geared to couples could be applied to a single person. 

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15. Roadmap for the Rest of Your Life: Smart Choices About Money, Health, Work, Lifestyle...and Pursuing Your Dreams by Bart Astor

This AARP-published text offers a wide variety of advice. It can contribute to finding and pursuing your dreams in retirement.

Roadmap for the Rest of Your Life advises you on the little stuff, like taking advantage of senior discounts. And on the big stuff too, like making an end-of-life plan.

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16. The Bucket List: 1000 Adventures Big & Small edited by Kath Stathers

While few people will do all 1,000 adventures, The Bucket List can be inspiring. It might encourage you to add one or two extra goals to your list. You can get creative about achieving your bucket list items.

Think about who you want to accomplish these adventures with. Sometimes a big part of the adventure is who you share it with. 

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17. Being a Grandparent by Ray Guarendi

Guarendi’s practical guide is a great starting place, especially if you don’t have grandchildren yet.

Even if you won’t have a major caretaking role in the lives of your grandchildren, give Being a Grandparent a look. It might inspire you to spend time with them. Doing so will allow you to reap the benefits of their companionship.

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18. Ultimate Vacation: The Definitive Guide to Living Well Today and Retiring Well Tomorrow by Randy Carver

Ultimate Vacation focuses on vacation/living well before retirement, but Carver’s point about balancing pleasures is an important one.

It can help you figure out how to have special moments in your first year of retirement as well as in your tenth or twentieth year. If you’re thinking about how retirement luxuries might impact your budget give it a go. 

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19. Being Mortal by Atul Gawande

Gawande’s sage insight into living a life full of purpose and meaning is important for everyone.

Add in his practical advice on getting things accomplished, and you have a great guide. Being Mortal a good reminder to acknowledge and celebrate every moment you have on Earth. You can read our full Being Mortal review if you're thinking about picking it up. 

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Best Funny Books on Retirement

These books might be good gifts for your friends who are retiring. They’re all casual and easy-going while poking a little fun at the reader.

Not really about preparing, they're more focused on adopting an attitude of good humor. You'll enjoy each day more if you can laugh about the occasional inconveniences.

20. Living Together After Retirement, Or: There's a Spouse in the House! by Graham Harrop

Harrop’s silly book features cartoons and anecdotes about what it’s like for couples to be together all day. After years of partnership, this might be the first time you’re spending significant time with your partner.

That can be a big shift from your usual routine. The cartoons in Living Together After Retirement can be a reminder that this transition isn’t just unique to you. 

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21. How to Survive Retirement by Clive Whichelow and Mike Haskins

This tongue-in-cheek mini-book has cartoons and goofy advice for retirees.

While not a book with long-form writing, How to Survive Retirement can be a nice bonus to tuck into a gift for a retiree. You could also leave it on your coffee table during a retirement party.

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22. Becoming Better Grownups: Rediscovering What Matters and Remembering How to Fly by Brad Montague

Becoming Better Grownups is a beautiful book that reminds us of the most important priorities. It argues that senior citizens and children are the ones who have their priorities in order.

And that everyone else could learn something from observing them. Montague manages to deliver this message and make you laugh, too.

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23. You’re Only Old Once! A Book for Obsolete Children by Dr. Seuss

Dr. Seuss’s zany humor might not be for everyone. But You're Only Old Once! will make some giggle because of its funny insights and silly rhymes.

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24. Last Laughs: Cartoons About Aging, Retirement...and the Great Beyond by Mort Gerberg

If you or your friends like a little gallows humor or humor about the downside of getting older, try this collection.

This series of cartoons is sure to send you into peals of laughter. Many of these cartoons, by a variety of famous cartoonists, have appeared in other places. Last Laughs is an anthology that puts them all together for your enjoyment.

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Retirement Books for Exploring and Enjoying Life After a Career

Give these books a try. It could be you want some funny jokes to share at a retirement party. Or you’re looking for practical advice about retiring with enough money saved. Whatever the reason, these retirement books will deliver. You also might consider subscribing to a magazine for retirees. A lot of them deliver practical and interesting advice relevant to the current world. Try reading books on finding happiness, as well, to enrich your retired life even more. 

Regardless of which book you read, or how you prepare, you’ve already taken an important step. Preparing ahead of time and considering what you want from retirement is key. Doing so will reduce your stress as your time to retire approaches. And it will help you start your retirement off on the right foot.

Looking for more ways to be prepared in old age? Read our guide on how to prepare for old age and being childless.


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