The 12 Best Books on Retirement Planning, Investing & Social Security

Written by Ari Parker Updated: Friday, November 14, 2025

Planning for retirement can help set you and your family up for financial security in the long term. But the process is complex and can be confusing even for the most financially savvy retiree.

Retirement planning books offer expertly tested guidance on crucial aspects of the retirement planning process, including investing, Social Security, spending, and healthcare.  

In this article, we’ll cover our top recommendations for retirement planning books that will help you plan for a stable and more enjoyable future.

Key takeaways

  • Retirement planning books can help you prepare for retirement by learning how to invest and build a retirement spending plan. 

  • Some of the best retirement planning books include The Bogleheads’ Guide to Retirement Planning and the Complete Retirement Survival Guide

  • Before choosing a retirement planning book, think about what you’re most interested to learn and whether you prefer a simplified writing style or a guide that goes into greater detail.

Best overall retirement planning books

If you’re not sure where to begin when it comes to retirement planning, consider these books that offer helpful tips on the most important aspects of making an actionable retirement plan. 

The Bogleheads’ Guide to Retirement Planning by Taylor Larimore, Mel Lindauer, Richard A Ferri and Laura Farnsworth Dogu

Published in 2009, The Bogleheads Guide to Retirement Planning offers insights on a wide variety of retirement planning topics, including the different types of savings accounts and retirement accounts, withdrawal strategies for retirement, and estate planning. 

The Complete Retirement Survival Guide by Peter J. Strauss and Nancy Lederman

Written by Peter J. Strauss, the co-director and founder of New York Law School’s Elder Law Clinic, and Nancy Lederman, this book, published in 2003, covers the legal and financial rights of the elderly and disabled. It covers topics such as planning for healthcare needs, managing and paying for healthcare, financing long-term care, taxes, and life planning for you and your family.

Top books for 401k and investment strategies

Navigating the stock market is important when planning for retirement. These guides offer tested strategies for increasing your returns over time.

The 401K Millionaire by Krute Iwaszko

This step-by-step 401 guide published in 1998 dissects 401K plans, including how their tax benefits, contribution requirements, and withdrawal limitations work.  

A Random Walk Down Wall Street by Burton Malkiel

Written by Princeton University economist Burton Malkiel, A Random Walk Down Wall Street remains one of the most popular investment guides since its original publication in 1973. Grab a copy if you want to learn more about investment management techniques, factor investing, risk parities, index funds, or ESG portfolios. 

The Simple Path to Wealth by JL Collins

The Simple Path to Wealth introduces straightforward strategies for the FIRE (Financial Independence, Retire Early) movement. 

Social Security planning books

For many seniors, Social Security is a confusing and daunting subject. These books can help to illuminate the ins and outs of the system.

Social Security For Dummies by Jonathan Peterson

Read this book for clear, simple, and actionable guidance on how to understand your social security benefits and prepare a long-term financial plan..

Get What’s Yours by Laurence Kotlikoff, Philip Moeller, and Paul Solman

A comprehensive manual written by well-known financial commentators that explains the Social Security system in detail and how to maximize your benefits.

Books for retirement withdrawal strategies

Learning how to spend in retirement is another important topic worth researching. Check out these books for tips on how to spend while protecting your financial security. 

How Much Can I Spend in Retirement? by Wade Pfau

A pragmatic guide that will help you determine a reasonable retirement spending rate based on the 4% rule of thumb for retirement spending. For additional guidance by author and professor of Retirement Income at The American College, Wade Pfau, check out the other three books in his series, The Retirement Researcher Guide (four books total). 

A Richer Retirement by William P. Bengen

Entrepreneur, researcher, and financial planner William P. Bengen explains how to maximize your withdrawals based on eight financial elements so that you can enjoy your retirement without overspending. 

Healthcare and Medicare planning books

Planning for retirement isn’t just about finances. Making the right healthcare decisions for you and your family is crucial to a safe and healthy retirement.

Medicare for Dummies by Patricia Berry

Get easy-to-follow guidance on how the Medicare system works and how to find the plan that offers the most benefits for you and your family with this accessibly written guide.

Maximizing Your Medicare by Jae Oh

Clear and concise, Oh’s informative guide helps readers discern the differences between Medicare plans and how to enroll in the right plan for your needs.

How to choose the right retirement planning book

With so many informative retirement books on the market, it’s important to consider what you’re looking for in a retirement guide. Are you looking for help with investing, planning, or healthcare? Do you want a book that will get into the complexities of retirement planning or a guide that will simplify the nuances in easy-to-understand language? Once you have a better sense of your interests and needs, you’ll be able to narrow your search accordingly.

Bottom line

Staying informed in retirement is key to ensuring that you’re taking care of your financial wellbeing. 

Learning more about retirement by reading expertly written guides can help further your retirement planning education and prepare you for a financially stable second act. 

Frequently asked questions

What is the best retirement planning book for beginners?

The Bogleheads’ Guide to Retirement Planning by Taylor Larimore, Mel Lindauer, Richard A Ferri and Laura Farnsworth Dogu is a great comprehensive guide to retirement planning that covers all of the major topics that come up when making a viable retirement plan. 

Which books cover Social Security strategies in detail?

For more insight on the Social Security system and strategies for withdrawing during retirement, check out the book Get What’s Yours by Laurence Kotlikoff, Paul Solman, and Philip Moeller.

Are older retirement planning books still relevant?

It depends on whether the book has been updated to cover changes in the market, economy, and other factors. If you’re considering reading a book that was published years or decades ago, check to see whether there is an updated version that reflects the current market.  

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