The Best Retirement Planning Books of 2025
One of the biggest surprises for people approaching retirement is how unprepared they feel; not financially, but mentally. After 35 years of saving, working, and investing, you suddenly have to stop putting money into your retirement, and start taking money out of your retirement.
And most people tell me the same thing:
“Jeremy, I’ve never done this before. I don’t know what I don’t know, and I don’t want to make a mistake I can’t fix.”
That’s exactly why the right book can make such a difference. A good retirement book doesn’t just give you information, it shows you what to do.
Here are my top retirement books of 2025.
What Are the Best Retirement Books to Read in 2025?
The Art of Spending Money by Morgan Housel
It’s somewhat easy to be a retirement saver; just spend less than you make and invest the difference. And when you’re great at retirement saving you often dread retirement spending.
While saving for retirement got you there, how you spend in retirement will determine whether all your sacrifice was worth it.
Morgan Housel’s The Art of Spending Money will show you how to spend money on what makes you happy, not what others expect you to spend money on.
Another title Morgan Housel could have chosen would be, “The Joy of Contentment, and the Scourge of Expectations.”
Housel’s writing is simple, honest, and incredibly relatable. He explains:
- Why we anchor our money habits to old, outdated fears
- Why spending is emotional and how to understand those emotions
- How to spend money in ways that genuinely improve your life
My favorite quote comes from page 179, “The highest use of money is to use it to control your time, granting freedom and independence to live life the way you choose.”
If you want a healthier relationship with your money; not reckless spending or penny-pinching fear, but confidence, then start with The Art of Spending Money.
My Mother’s Money by Beth Pinsker
Most families have a financial story tucked away somewhere. And many retirees find themselves in the middle of two storylines at once: launching their own retirement while also managing their parents’ final years.
My Mother’s Money hits right at that crossroads.
She combines personal storytelling with practical guidance to help families navigate:
- A parent’s financial truth; sometimes messy, sometimes surprising
- The emotional work of stepping into a caregiving role
- Mistakes that can derail a parent’s financial stability
- How inheritance, long-term care, and family decisions really play out
What I appreciate most is how honest the book is. It doesn’t sugarcoat the difficult conversations. Instead, it gives you a roadmap to handle them with respect, clarity, and compassion.
If you’re balancing your retirement dreams with your parents’ financial reality, then My Mother’s Money by Beth Pinsker belongs on your list.
Retirement Bites by Kerry Hannon
Retirement isn’t a long vacation. It’s a major identity shift. And Kerry Hannon does a great job explaining why so many new retirees are surprised by the emotional challenges like boredom, loss of routine, changes in relationships, and unexpected anxieties.
While the subtitle is A Gen X Guide to Securing Your Financial Future, Retirement Bites does a great job preparing anyone for retirement by showing you that planning your finances is tough, but doable, and that you are more than your money and more than your job title.
This book reads like a conversation with someone who knows retirement isn’t always easy but also knows the path forward.
If you want your retirement to feel good, not just look good on paper, then Retirement Bites will help you get there.
Retire Often by Jillian Johnsrud
This is a refreshing book because it challenges the old idea that retirement is a one-time event at age 65. Johnsrud suggests something different: retiring in phases, taking breaks throughout life, and building flexibility into your future.
Her ideas fit especially well for retirees who don’t want to go from 100% work to 0% overnight.
In Retire Often, you’ll learn:
- How to build seasons of work and rest
- How to design your next chapter with intention
- How to think about purpose in shorter, more meaningful cycles
- Why retirement should evolve as your life evolves
If you’re considering part-time work, consulting, travel, or frequent lifestyle shifts, Retire Often offers a helpful blueprint for designing a retirement that’s active, flexible, and personal.
Retire Today: Create Your Retirement Master Plan in 5 Simple Steps by Jeremy Keil
Yes, my book is on this list, and here’s why: people need a simple structure for one of the most complicated transitions of their lives. That’s why I wrote Retire Today; to give people the clear, understandable framework they’ve been missing.
The book walks you through the five steps of your Retirement Master Plan:
- Spend: Understand what retirement will really cost
- Make: Create reliable retirement income
- Keep: Lower your taxes so you keep more of your money
- Invest: Invest your retirement savings thoughtfully and efficiently
- Leave: Pass money on intentionally, not accidentally
The goal is simple: help you retire confidently by giving you clarity and direction, without complex jargon or endless charts.
If you’re a detail-oriented person who likes checklists, real numbers, examples, and step-by-step planning, you’ll find this book helpful as you build your retirement strategy.
What Makes These the Top Retirement Books for 2025?
If you look closely, these five books each answer a different part of the same question:
“How do I retire well both financially and emotionally?”
Here’s how they fit together:
- The Art of Spending Money helps you build a healthy mindset around spending in retirement.
- My Mother’s Money prepares you for the family realities that often show up at the same time.
- Retirement Bites guides you through the emotional transition of leaving work.
- Retire Often encourages you to design a flexible, intentional lifestyle.
- Retire Today gives you the full financial framework to put it all into practice.
Together, they cover the real retirement experience, not just the math or the theory, but the life you’re trying to build.
Make 2025 the Year You Get Confident About Retirement
You don’t need to read a stack of complicated financial textbooks to feel prepared. A few good books can give you the clarity, confidence, and perspective you need.
Start with one or two from this list. Pick the one that speaks most to where you are right now:
- The Art of Spending Money will help you feel confident spending in retirement.
- My Mother’s Money will help you balancing your retirement and your parent’s aging journey.
- Retirement Bites will help with the emotional transition into retirement.
- Retire Often will help you create a phased retirement or try retirement out before you commit to a full retirement.
- Retire Today will help you give you step-by-step plan to retire with confidence.
Retirement is a big transition, but these books can help you make it a great one—clear, intentional, and aligned with the life you want to live.
About the Author
Jeremy Keil, CFP®, CFA® is a financial advisor in Milwaukee, WI, author of the bestseller Retire Today: Create Your Retirement Master Plan in 5 Simple Steps and host of both the Retire Today Podcast and Mr. Retirement YouTube channel
Additional Links:
- Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
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Connect With Jeremy Keil
- Keil Financial Partners
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