Retire With Confidence: 52 Questions to Ask Before You Retire—With Expert Answers

by Randy L. Thurman

Are you truly ready for retirement, or just hoping for the best?

Most Americans spend more time planning a vacation than planning their retirement. If you’re among the millions approaching this life-changing transition, you can’t afford to wing it.

Retire With Confidence eliminates the guesswork with answers to 52 essential questions every pre-retiree should be asking. This comprehensive guide leads you through the critical decisions that will make or break your retirement—from Social Security and Medicare to investments and tax strategy.

Perfect for:
• Adults 50+ considering retirement
• Anyone within 10 years of leaving the workforce
• Financial advisors seeking client resources
• Adult children helping aging parents

Inside, you’ll discover how to:
• Calculate your true retirement needs
• Optimize Social Security and Medicare decisions
• Navigate complex tax implications
• Protect your legacy and loved ones
• Avoid the costliest retirement mistakes

Written by a nationally recognized retirement advisor with decades of experience, this isn’t another generic retirement book filled with one-size-fits-all advice. Each question is designed to address your unique situation and guide you toward personalized solutions. Don’t let uncertainty rob you of the retirement you’ve earned. Get the clarity and confidence you need to retire successfully.

Genres: Self Help, Nonfiction

250 pages, Kindle Edition

Published May 12, 2026

About the author

I started out in banking in the mid 80s in Oklahoma City. I had saved up $6500 from college and had a stock broker call me up. He had a stock that was "poised to move." Silly me, I thought he meant up. I told him to send me the financials to analyze, which he did. It looked pretty good. I invested half my life savings ($3000) in a stock called Kelly-Johnsons. In 6 months, I lost it all. He called and apologized and said he "wanted to make it up to me." What a guy. He said he had an oil stock, they just hit a well, and we got to move fast. I invested the other half of my life savings in Plano petroleum. In 2 weeks it went from 40 to 6.

It was then, I became obsessed with financial planning and investing. Reading everything I could, taking classes, etc. I acquired a passion for financial planning and became and advisor, in 1987.

I have 4 degrees, two from Oklahoma State. A BS in Electrical Engineering, and an MBA. I have two associates degrees from Oklahoma City Community College, in Accounting and Real Estate Investing. Since the start of my sophomore year I paid my way through college.

I'm a CPA and CFP and run a fee-only investment advisory firm for conservative investors.

Pati, Levi and I live in South Oklahoma City and have a place in Stillwater. We enjoy Oklahoma State University sports and spending time in Stillwater.

Reviews

[Susan Hamann · Rating 5 out of 5]

The author has 40 years of experience guiding people into retirement. He realized that in the seminars he taught, most people asked the same questions, so he decided to write a book to answer the most important and common questions.

The first chapter covers 2 questions. The first may seem easy to answer until you become retired and wonder how to fill your time. “Am I ready to Retire?” He explains emotional readiness and financial readiness.

The next chapter is the chapter that everyone has – “How Much Money Do I Need? He spells out that things that you’ll need money for. He provides several different categories to consider when you put together your spending plan. Worksheets are provided to help you identify where your money will be coming from and what you’re likely to spend it on. What is your life expectancy and how to plan for inflation.

Chapter 3 is “Social Security Income.” I personally thought I had a good idea of what Social Security was all about, but when I retired, I realized how little I knew. This chapter not only explains a lot, it provides some good strategies.

Chapter 4 explains “Pension Plans.” If you’re lucky enough to be covered by one, there are potentially more options for how you’d like it distributed than you may have thought.

Chapter 5 covers “Retirement Accounts.” You know, the places where you have stashed money for retirement? You might want a plan on how to withdraw your savings to optimize what you’ve saved.

Chapter 6, “Other Sources of Income” explores exactly that.

Chater 7 discusses “Investment Strategies.” After you’re retired, your investment goals and strategies will probably need to be adjusted because your needs and income will change. The author explains a number of options and strategies with excellent explanations.

Chapter 8 is all about “Tax Strategies.” This is an area that many of us forget about. Do you know when you are required to withdraw from your tax-sheltered retirement accounts? How will that affect your taxes? I found his advice to be very useful.

Chapter 9 covers “Threats and Hazards.” This is a great chapter to read to uncover some threats to your security as you age, and how you spend your money. You may not even be considering it yet, but elder fraud is real and more common that you might think. We think we’re sophisticated enough to avoid these scams, but the fraudsters are very sophisticated.

Chapter 10, “Do I Need a Financial Advisor?” I found lots of good advice in this chapter and although I’m not an advisor, I think that I’m quite well informed. The author asks, “How can I find a trustworthy retirement advisor.” He guides you with 6 additional questions with detailed comments that are excellent. This may be the most important chapter in the book, in my own opinion.

The last section of the book provides resources, both books, and websites.
This book is an outstanding starting point. And by that, I mean that he provides the questions and discusses some of the options that you should be thinking about. The author guides you to consider your own situation. And provides a pathway for you to chart out your plan. If you would like to get more in-depth information, his references should be of great value to you.

I received an early version of this e-book. Thank you to NetGalley and the publisher.

[Paula · Rating 5 out of 5]

Retire With Confidence: 52 Questions to Ask Before You Retire—With Expert Answers by Randy L. Thurman had a lot of good information and lots to consider before retirement. I am nearing retirement, and this is a good resource to have regarding all the tax issues, tax payments, longevity and planning, etc. It's a lot to consider!

This book is an invaluable resource for anyone approaching retirement. The book addresses a critical gap in financial planning where, as the author says, many people spend more time planning vacations than considering their financial futures. What I liked most about this guide is its structured approach. The 52 essential questions serve as a roadmap, guiding readers through the complexities of retirement planning. From understanding Social Security and Medicare to making informed investment choices, each topic is clearly explained, making it accessible for those, like me, who may not have a financial background. The author offers practical advice and expert insights that help demystify the often-overwhelming world of retirement planning.

I also found it refreshing that this book is tailored for a variety of readers—whether you’re an adult over 50, someone nearing retirement, or even a financial advisor looking for client resources, there's something here for everyone. Additionally, adult children looking to assist aging parents will find this guide highly beneficial. Overall, Retire With Confidence is a must-read for anyone serious about their retirement planning.

I would recommend having this book on your shelf as a valuable resource.

#RetireWithConfidence #NetGalley @AdvantageFamily

[Alisha Self · Rating 4 out of 5]

Thank you Goodreads for the ARC giveaway. *Retire With Confidence: 52 Questions to Ask Before You Retire—With Expert Answers* by Randy L. Thurman is a practical, no-nonsense guide aimed at helping readers approach retirement with clarity instead of guesswork. Built around 52 essential questions, the book tackles the major decisions that can shape retirement success, including Social Security, Medicare, taxes, and investment strategy. Thurman’s central argument is that too many people drift into retirement unprepared, and that thoughtful planning—guided by the right questions—can make the difference between financial security and uncertainty. The structure makes the book especially approachable, breaking down complex topics into manageable, decision-focused sections.

What stands out is its emphasis on personalization and real-world application. Rather than offering generic advice, Thurman encourages readers to evaluate their own financial situation, calculate true retirement needs, and avoid common (and often costly) mistakes. The book is particularly useful for adults nearing retirement, as well as those helping family members navigate the transition. While its strong focus on financial strategy may leave out deeper lifestyle or emotional aspects of retirement, it succeeds as a clear, actionable roadmap. Overall, it delivers on its promise: helping readers replace uncertainty with informed decisions and a greater sense of confidence about their future.

[Sue · Rating 5 out of 5]

This is a terrific high level view of things to consider as you approach retirement, regardless of what age. Even difficult topics such as tax considerations and various payout options for investment and retirement accounts are explained in easy to understand language. The author is a certified financial planner who (rightly) suggests people need someone like him to navigate retirement due to the complexity of tax laws and the uncertainties of health and life span.

Don’t miss the included glossary of terms and a fantastic list of resources for more information.

I highly recommend this book for those nearing retirement or who have loved ones considering it.

Family friendly.

Thanks to NetGalley and Advantage Books. I received a complimentary copy of this book. Opinions expressed in this review are completely my own.