August 2022 Best of the Web

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This month, I have some fantastic resources to help you save more, invest smarter and retire sooner. More importantly, they include valuable wisdom to use those tools to live your best life.

The Best

We’ll learn from the mistakes of others, examine the surprising spending patterns of early retirees, and explore important strategies to avoid a bad sequence of market returns early in your retirement.

Resources will help you with the technical and emotional aspects of creating an estate plan and managing an investment portfolio. We’ll also explore strategies for choosing the right Medicare options.

Voices of Wisdom

I recently reviewed Jordan Grummet’s new book. A few year’s ago, early retiree Mark Trautman wrote a guest post for the blog. Each resonated with blog readers, with good reason. These are two of the most thoughtful and wise people I’ve met in the FIRE community.

I highly encourage anyone reading this blog to listen to their important conversation on the Earn & Invest Podcast: Does Your Money Serve You?

Learning From Mistakes

Allan Roth writes Wrong! My Mistakes Over a 20-Year Advisory Career.

Ben Carlson examines Why People Make Dumb Financial Decisions on Purpose.

Retirement Spending

Nick Maggiulli asks and answers How Do Retirees Actually Spend Their Money?

Wade Pfau provides 4 Ways to Manage Sequence of Returns Risk in Retirement.

Doing the Hard Stuff

When starting down the road of educating myself about personal finance, the finance part was intimidating. The more I learn, the more convinced I become that dealing with the personal aspect is the far greater challenge.

John Stoj bravely shared a personal example. Financial Advisor Friday Confessional: My dad died 4 years ago. I’m the executor. I still haven’t closed the estate. Why? And what can you do to prevent the same thing from happening to you.

That one resonated way too much. One year ago, my friend Emily shared the lessons learned after losing her husband to an aggressive brain tumor. I encouraged you to make sure you learned from her generously sharing her story and use it as impetus to get your affairs in order.

I committed to do the same myself, writing: “I will personally hold myself publicly accountable by committing to writing a blog post by the end of this year. I’ll share steps we took and what I learned in the process.”

One year later, like Jon, I continue to avoid doing these things I know I should. I will try to do better and I encourage you to do the same.

John Yeigh did update his estate planning documents. He shares important lessons he learned in the process: Where There’s a Will.

Keeping It Simple

While there is some complexity to estate planning, with investing simple is almost always better.

Mike Piper answers the obvious follow-up question to that statement. Why Do Advisors Recommend Complex Portfolios?

Figuring Out Medicare

Darrow and then I have written this blog to document our journeys into and through early retirement. As such, we’ve written extensively about the challenge of bridging the gap from getting health care through a job to qualifying for Medicare, including last week’s post that shared how recent legislation impacts this.

While that is a great challenge, it may imply that once you reach Medicare eligibility the challenges end. Unfortunately that is not the case.

John Greaney writes What I’m doing for Medicare insurance at age 65.

Hat tip to a reader who shared this excellent resource with me. This audience is incredibly knowledgable and wise. I’m grateful to all of you who choose to read this blog and especially those of you who generously share ideas and resources with me and the community through your private emails and public comments. 

Thank you for reading and being part of this community! Have a great month.

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Valuable Resources

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  • Our Books

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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 Financial planning inquiries can be sent to]

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  1. Hi Chris,
    Thank you for the great resources. I noticed a couple things in the article you included from John Greaney that I want to clarify.

    He mentions: “Both Plan F and Plan G [Medigap Plans] offer a high deductible version at a much lower premium where you are responsible for the FIRST $2,340 per year….” I just want to clarify, Original Medicare + Medigap (high deductible plan) work differently than the high deductible health insurance plans we had in the past through my employer. This is because with a high deductible Medigap Plan, Original Medicare still covers 80%. So, when he says “you are responsible for the FIRST $2,340…” that only applies to the 20% that is covered by the Medigap plan. As an example, for a $100 medical bill, $80 is paid by Original Medicare and $20 would go toward the Medigap high deductible plan until you reach the $2,340 and then it would cover all the costs.

    Also, he mentions the lowest premium for a High Deductible Plan G (in Washington State) is $44/month which is true. However, there is a $50/month plan that includes a Silver Sneakers gym plan that the $44/month plan does not. I just mention this because you hear some people say it does not matter which Medigap plan you select because they are all required by law to provide the same medical coverage and so you should go with the one with the lowest premium. However, some plans offer other perks like the gym membership. So, I think it is prudent to read the descriptions of the Medigap plans and not just go by the one with the lowest listed premium just in case there are perks like the gym membership to consider.

    I hope these clarifications are helpful.

  2. The medicare costs article was eye-popping. I’m mid 60s getting bombarded with medicare advantage mailings. It was great to have such clear-cut numbers to cut thru the marketing speak baloney.
    I’ll take the author’s wise advice into consideration when I eventually have to go to medicare.

    1. As someone who turned 65 two years ago and opted for a Medicare Advantage plan, I’m highly skeptical of the author’s “wise” advice. For one thing, he places far too much emphasis on “skimming,” as if a CEO’s salary should be the main criterion for selecting or rejecting a health insurance plan. Second, he ignores the the fact that MA plans typically come with dental, vision, and hearing coverage, and dismisses the value of Silver Sneakers (which saves me the $95/month I would otherwise pay for my gym membership) as a pre-Covid relic. His ignorance in this regard causes him to think that the only reason a third of all Medicare beneficiaries choose MA is because they’ve been duped by slick marketing.

      I’ve read many articles like the one from this author; they generally assume that everyone has the same values, interests, and healthcare needs as the author. This article was no exception.

      1. The dental, vision and hearing coverage offered by most Medicare Advantage plans (particularly the $0 monthly premiums) is the absolutely bare minimum service.

        From over 7 years of first hand experience helping people select plans as a certified Medicate SHIIP counselor, too many people select their plans based on these minimal services and Silver Sneakers. They ignore the most critical factors: co-pays, co-insurance, annual deductible, and maximum out of pocket limits.

        Many, many people are indeed “duped” by the “slick” marketing and relentless advertising which emphasizes the $0 premiums while failing to mention that the maximum out of pocket costs can exceed $7000 each year.

        AARP is the biggest and slimiest marketer of all. AARP collects more than $1 billion each year in endorsement fees for insurance companies. But people trust AARP.

  3. I have been a state certified Medicare counselor under the Senior Health Insurance Information Program (SHIIP) for over 7 years. I have done extensive analysis of all the Medicare options and have helped hundreds of individuals choose their Medicare Supplement, Medicare Part D Prescription drug plan or Part C Medicare Advantage plan.

    I concur 100% with John Greaney’s analysis and choices for his Medicare options.

    Unfortunately, the vast majority of people do not do any analysis and instead rely on the suggestions of family and friends, or worse, buy into the misinformation of the insurance companies sales reps. DON’T chose the same insurance options as your friends and family- they are NOT you!

    I have been asked by many individuals with Medicare Advantage plans who have developed serious illnesses and now cannot afford the co-pays and co-insurance charges to switch to a Medicare Supplement. Unfortunately, it’s too late once they have gotten ill. But I rarely get asked by individuals with Medicare Supplements to switch to Medicare Advantage.

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