How to Retire – Book Review

The book consists of twenty chapters. Each chapter is an interview with a different expert covering topics relevant to retirement planning.

Read on to get my biggest takeaways and get a chance to win a copy of the book for yourself.

Retirement Planning Is Hard

For those unfamiliar with Christine Benz, she is the director of personal finance and retirement planning for Morningstar, co-hosts the Morningstar Longview Podcast, and is active with the Bogleheads. Most people would consider her a retirement expert.

Yet Benz admits in the conclusion that “this book is a bit of a ‘me-search’ project” as she considers her pending retirement. I appreciate her humility in seeking other experts to contribute to the book. Her curiosity and the respect she has for each individual she interviewed are evident.

The fact is, retirement planning is hard. No one can possibly know everything. Retirement planning requires making our best guesses at various unknowable variables over potentially long periods. 

Those variables are both financial and personal. Each is given fair treatment in this book.

Given Benz’s history with Morningstar and the Bogleheads, I expected most of the focus of this book to be on the technical financial topics. To be sure, she didn’t shortchange those topics.

Chapters topics include:

• Allocating your retirement portfolio,
• Structuring your retirement portfolio for cash flows,
• Different retirement income styles,
• Thoughtful approaches for claiming Social Security benefits,
• Creating a spending plan,
• Understanding how expenses will likely change over time,
• Planning for taxes, and
• Creating an estate plan.

Interesting Places to Start and End the Book

However, the book starts with a foreword by Jonathan Clements. He wrote, “When I started thinking about retirement in my 20’s and early 30’s, I viewed it as a simple financial endeavor… I (now) see retirement as not just a practical financial issue but also a topic chock-full of intellectually fascinating questions about risk, purpose, happiness, family, peace of mind, legacy, and more.”

The book then opens with chapters titled:

• Visualizing your in-retirement lifestyle, 
• Laying the groundwork, and 
• Nurturing relationships. 

The book ends with an interview with hospice doctor Jordan Grumet titled Leave No Regrets.

Related: My review of Grumet’s book Taking Stock

Even within the technical chapters, Benz’s interviews tend to take holistic approaches. For example, healthcare expert Carolyn McClanahan covers Medigap vs. Medicare Advantage Plans, IRMAA, and long-term care planning. 

However, her interview also discussed the importance of lifestyle decisions that help avoid chronic disease. These conditions destroy quality of life and drive healthcare spending for many people. She labeled her proposed better alternative the “live long, die quickly” plan.

Related: How To Live Long and Live Well in Retirement

For some readers, this holistic approach may be a turn-off. Like the young version of Clements, some of you may think retirement is simply a math problem to be solved and everything else is navel gazing.

However, I see Benz’s approach as a feature and not a bug. Based on the popularity of certain “softer” topics on this blog, I think most of you reading this will as well.

Related: Confessions of an Early Retiree

New (to me) Experts and Resources

I was familiar with many of the experts interviewed in the book. Three of my favorite chapters were interviews with people I had never heard of before reading it. 

In Chapter 3 Benz interviewed Laura Carstensen, a researcher at the Stanford Center on Longevity. The chapter focused on the role relationships play in life expectancy and quality of life.

I particularly appreciated her idea of “diversifying” your close friend group. She advocates for developing a few close relationships so you are not as vulnerable to the loss of a spouse, partner, or best friend to serious illness or death. 

In Chapter 12, Benz interviewed journalist Mark Miller about housing choices in retirement. There was a fair bit of overlap between Miller’s recommendations and my writing about three key considerations when deciding where to retire.

However, this chapter made me ponder how different this process is when planning early vs. traditional retirement. Miller also focused on factors like whether physical characteristics of the home are conducive to aging and access to healthcare.

I gave zero consideration to those factors when choosing where to live after leaving my career. However, as I helped care for my mom through the end of her life and continue to help my dad navigate housing decisions since her passing, I recognize how important and underappreciated Miller’s insights are.

In Chapter 19, Benz interviewed estate planning attorney Jennifer Rozelle about the importance of and practical steps to take in developing an estate plan. They also address elder care issues. This chapter was a treasure trove of practical and actionable information.

I also appreciated the “Related Resources” Benz included at the end of each chapter. She makes it easy to find references to go deeper into topics discussed in the interview. The resources also highlight some of each expert’s best work.

There Is No One “Right” Way

One thing I noted reading are differences in philosophies between the experts interviewed.

In Chapter 8, retirement researcher Wade Pfau made a case for annuities to provide the security of an income floor and “permission to spend” for retirees. One chapter later, William Bernstein outlines why he is “not a fan of those at all”. Among the reasons Bernstein sites are inflation risk and credit risk of the underlying insurance companies.

Related: Annuities – The Good, The Bad, and The Ugly

Bernstein’s advice for asset allocation for a retirement portfolio includes the following: “…you should not design your portfolio for normal times. Instead, design your portfolio to survive during the worst 2% of times, to avoid interrupting compounding’s magic. That basically mandates a portfolio that most people would call ‘suboptimal’…”.

Again, this goes 180° against the advice found a chapter later from JL Collins. He says, “People talk about ‘black swans’ and scary things. But if you start investing to be protected from any black swan that can happen, you’re not investing very well for the 99% of the time when those things don’t happen. I prefer to construct a portfolio that will do well 99% of the time”

There was also a theme through a number of experts in the book favoring phased retirements and incorporating ongoing work in retirement. These are ideas I regularly advocate for on this blog for early retirees. But they may be more challenging and less desirable for older retirees.

However, in other chapters the focus was nearly entirely on traditional retirees with little thought given to early retirees. As an example, the health care chapter explored Medicare and long-term care solutions, but didn’t touch on ACA plans and other potential bridges between employer provided coverage and Medicare eligibility.

As highlighted above, the housing considerations also focused on aging considerations. While valid and important for all of us at some point in time, these considerations may be decades away for early retirees.

Related: A Tale of Two Retirements – FIRE and Traditional

You Have to Create Your Own Way

Again, depending on your perspective, you may consider these contradictions as a “bug” to this approach of gathering differing expert’s thoughts and approaches to retirement. Many people want an expert to tell them what to do and how to do it. If so, you may find this book frustrating.

I consider the differing ideas and perspectives presented in this book to be a helpful feature rather than a bug. We all have unique personalities that will dictate what we want retirement to look like. We each have unique financial circumstances to create that retirement lifestyle. 

How to Retire shares the ideas of experts from different domains of retirement planning. This allows you to benefit from each expert’s knowledge, experience, and insights. You can then pick and choose what to take from each as you design your retirement plan while ignoring those ideas that do not serve you.

If that is your approach to retirement planning, the How to Retire is a great resource. I encourage you to check it out.

Win a Copy of How to Retire

If you want a chance to win a free copy of How to Retire, leave a brief (2-3 lines) comment below by Midnight tonight (Monday 9/16).

Be sure to leave a valid email in the appropriate box which will remain confidential and will allow me to contact you. I will pick two readers at random and send you a copy.

Winners will be notified by email by 9 AM EST on Tuesday 9/17. If your comment does not show up immediately, don’t worry that I didn’t receive it. First time commenters must be manually approved. Please do not leave multiple comments.

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[Chris Mamula used principles of traditional retirement planning, combined with creative lifestyle design, to retire from a career as a physical therapist at age 41. After poor experiences with the financial industry early in his professional life, he educated himself on investing and tax planning. After achieving financial independence, Chris began writing about wealth building, DIY investing, financial planning, early retirement, and lifestyle design at Can I Retire Yet? He is also the primary author of the book Choose FI: Your Blueprint to Financial Independence. Chris also does financial planning with individuals and couples at Abundo Wealth, a low-cost, advice-only financial planning firm with the mission of making quality financial advice available to populations for whom it was previously inaccessible. Chris has been featured on MarketWatch, Morningstar, U.S. News & World Report, and Business Insider. He has spoken at events including the Bogleheads and the American Institute of Certified Public Accountants annual conferences. Blog inquiries can be sent to chris@caniretireyet.com. Financial planning inquiries can be sent to chris@abundowealth.com]

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