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

[Píaras Cíonnaoíth]

A Practical Guide to Retirement Readiness...

Most of us drag our feet on retirement planning, treating it like a form to fill out rather than a life to think through. Randy Thurman sees it differently. His question-and-answer format doesn't stand at a podium and lecture. It pulls up a chair. One decision at a time, it walks beside you through Social Security timing, Medicare enrollment, tax planning, and the quieter question of what you'll leave behind for the people you love. Nothing here is rushed. The book seems to understand that your circumstances aren't identical to anyone else's, so it lets you move at your own pace instead of handing you the same tired advice everyone gets.

That kind of patience is rare, and it's exactly what makes this book so useful for advisors, and for adult children trying to help a parent find their footing in an unfamiliar and often disorienting chapter. It reads like something you could hand to someone and say, come on, let's figure this out together. There's no performance in the tone, no reaching for impressive words. Just plain language doing honest work, quietly turning what usually feels like a maze into something you can actually walk through.

[Sarah Jensen]

Book Review: Retire With Confidence: 52 Questions to Ask Before You Retire—With Expert Answers
By Randy L. Thurman

Rating: ★★★★½ (4.44 out of 5 stars)

Full review available here: https://prairiefoxreads.blogspot.com/...

Publication and Context

Title: Retire With Confidence: 52 Questions to Ask Before You Retire—With Expert Answers
Author: Randy L. Thurman
Publication Date: May 12, 2026
Publisher: Advantage Books
Page Count: 250 pages
Format: Kindle Edition (ASIN: B0GN9XHXG6 / ISBN: 9798891883901)
Genres: Self-Help / Nonfiction / Personal Finance

Disclaimer: I was provided a complimentary copy of this book from the publisher for review purposes. This has not affected the content, objectivity, or analytical stance of this review.

Contextual Backdrop:
Navigating retirement in 2026 requires more than just a pension and a savings account. With shifting inflation rates, complex tax code updates, and the ever-evolving landscapes of Medicare and Social Security, pre-retirees face a daunting financial puzzle. Randy L. Thurman, a nationally recognized retirement advisor, steps into this environment with a highly structured, pragmatic guide designed to cut through the anxiety and replace it with actionable data.

Purpose and Themes of the Work

The fundamental purpose of this book is to bridge the gap between “hoping for the best” and possessing a bulletproof retirement strategy. The premise is built on a simple but alarming truth: most people spend more time planning a week-long vacation than they do planning the last three decades of their lives.

The core themes are financial literacy, proactive risk management, and personalized planning. Thurman dismantles the myth of the “one-size-fits-all” retirement, pushing readers instead to evaluate their unique life circumstances through a series of targeted inquiries.
Summary of the Work

Clocking in at an accessible 250 pages, Retire With Confidence is structured around 52 essential questions—conveniently allowing a reader to tackle one question a week for a year, or to devour the book over a weekend.

Thurman guides the reader through several critical phases of retirement planning. He begins with foundational calculations—determining what your true retirement needs actually are—before moving into the labyrinth of government benefits, offering strategies to optimize Social Security and Medicare. The book also tackles the heavier, often-avoided topics: navigating tax implications to avoid losing a chunk of your nest egg, protecting your legacy for loved ones, and identifying the costliest mistakes that derail otherwise solid retirement plans.
Analysis and Evaluation
Format, Pacing, and Structure

The Q&A format is the book’s greatest asset. Financial planning can easily become a dry, impenetrable wall of text, but dividing the journey into 52 distinct questions makes the process feel incredibly manageable. Each question gets straight to the point, usually taking up just 4 to 5 pages of clear, focused advice. This structure allows readers to easily skip around to the sections most relevant to their immediate concerns (e.g., jumping straight to Medicare if that is their current hurdle).
Subjects and Voices

Thurman writes with the calm, reassuring authority of a seasoned fiduciary. He successfully avoids overly dense financial jargon, acting as a translator for complex economic concepts. His tone is pragmatic but encouraging, shifting the reader’s mindset from fear of the unknown to empowerment through knowledge.
Strengths and Limitations

Strengths: The organization of the book is superb. It acts as both a comprehensive overview and a practical workbook. It is especially strong in pointing out “blind spots” that everyday workers might miss, such as specific tax traps or the nuances of timing Social Security claims.
Limitations: Because the book covers 52 massive topics in just 250 pages, it serves as a high-level guide rather than a granular, deep-dive textbook. Readers with highly complex estates or unique business-owner transitions will still need to consult a CPA or financial planner. Additionally, as with all financial books, specific tax and Medicare figures are subject to legislative changes over time.
Suitability and Audience Guidance

Content Considerations: Purely educational and financial. No sensitive content.
Target Audience: This book hits the bullseye for adults aged 50 and older, specifically those within a 10-year countdown to leaving the workforce. It is also a fantastic resource for adult children who are trying to help their aging parents organize their finances, or for younger, highly proactive investors wanting a roadmap for their “FIRE” (Financial Independence, Retire Early) goals.

Conclusion and Verdict

Retire With Confidence does exactly what it says on the tin. Randy L. Thurman has provided a highly practical, easy-to-navigate roadmap that transforms the daunting mountain of retirement planning into a series of achievable steps. If you are approaching the end of your primary career and feeling overwhelmed by the financial unknown, this newly released guide is an excellent, high-value starting point to secure your peace of mind.
Supplementary Elements: Reading Companions
What to Read Next

For readers looking to round out their financial and retirement education:

The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness by Morgan Housel – A brilliant companion that focuses less on the math of retirement and more on the mindset and behavioral habits needed to build and keep wealth.
Die With Zero: Getting All You Can from Your Money and Your Life by Bill Perkins – For a contrasting, thought-provoking perspective on retirement that encourages optimizing life experiences and spending down your wealth rather than over-saving out of fear.
The Simple Path to Wealth: Your Road Map to Financial Independence and a Rich, Free Life by J.L. Collins – An absolute classic for anyone who wants to simplify the investment side of their retirement portfolio, focusing heavily on the power of index funds.



Rating: ★★★★ 4.4 / 5

- Prairie Fox 🦊📖

[Susan Hamann]

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]

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

[Patrick Conner]

Retire With Confidence offers a practical approach to one of the biggest financial and personal transitions many people face. Randy L. Thurman focuses on the questions that prospective retirees should consider before leaving the workforce, making the subject feel more manageable and organized.

The 52 question format is particularly appealing because it breaks retirement planning into individual decisions rather than presenting it as one overwhelming process. Social Security, Medicare, investments, taxes, retirement needs, and legacy planning all receive attention, giving readers a broad framework for preparation.

Another strength is the book's focus on personalized decision making. Rather than suggesting that every retiree should follow the same formula, the guide encourages readers to consider their own circumstances and make informed choices based on their particular goals and needs.

The intended audience is also quite broad. Adults over 50 and people within ten years of retirement can use it as a planning resource, while financial advisors and adult children helping aging parents may also find the question and answer structure useful.

Overall, Retire With Confidence appears to be a clear and accessible resource for anyone who wants to approach retirement with greater preparation. Its practical questions and expert answers can help readers identify important decisions, avoid common mistakes, and enter the next stage of life with greater clarity.

[Alisha Self]

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.

[Suzanne]

The most useful idea behind *Retire With Confidence* is its decision to approach retirement through questions rather than one sweeping prescription. The 52 question structure reflects the reality that preparing for retirement is a collection of interconnected decisions, from Social Security and Medicare to taxes, investments and protecting the people you leave behind.

That structure also makes the subject feel less abstract. Instead of asking whether someone is generally “ready” for retirement, the book breaks readiness into practical areas that can be examined individually and in relation to one another.

The intended audience extends naturally beyond people approaching retirement. Financial advisors can use the questions as conversation starters with clients, while adult children helping aging parents may find the framework useful when financial and family decisions begin to overlap.

Readers looking for a straightforward starting point for retirement preparation should find the question driven approach accessible. The underlying message is sensible: confidence does not come from knowing every answer in advance, but from knowing which questions need to be answered before the transition begins.

[Sue]

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.

[Lisa Varo]

Thank you goodreads for this book giveaway. This resources is written by a certified financial planner with decades of experience. It is written in a question and answer format. Topics include social security, am I financially & emotionally ready to retire, pensions, retirement accounts, healthcare, financial advisors, roboadvisors, investment strategies and tax strategies. The resources section contained a lot of information as well. Great book as you start to read about retirement topics.

[Becky]

I received a copy of Retire with Confidence in exchange for an honest review. This book is a very practical, easy to understand guide for preparing for retirement, formatted as 52 questions and answers. The author draws on his decades of experience to help readers answer the question "am I ready to retire?" both emotionally and financially. This is a valuable resource to help with understanding various aspects of retirement planning, including considerations for various income streams, taxes, and health care.

[John]

a good reference

This is nice, comprehensive guide to aid with retirement planning. Randy covers all the bases and treats each question objectively. He has definitely made me rethink some of my thoughts on retirement planning. I will be keeping this book handy as we get serious about our retirement planning.

[Irene]

Excellent Resource

Very helpful overview of the things to take into consideration before retirement. Covers Social Security, planning for Medicare and health expenses. Also covers financial and investment planning.

[Adelaide rowan]

Asking questions you didn't even know you needed to consider. The "Q&A" format makes it incredibly easy to skip around to the topics that matter most to you right now.
It acts more like a comprehensive checklist than an exhaustive manual.

[Christy]

This is a great guide. Easy to follow. I got several great tips for now and I look forward to reviewing again as I get closer to retirement.

[Susan Zolper]

Buy the print copy!

Wish I had this book in print. I want to make notes in the margins. Great advice, easy to read and understand.

[Alana Pustizzi]

Good read with basic information.