September 2021 Best of the Web

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We all tell stories. When we believe them strongly enough, they can become self-fulfilling prophecies… for better or worse. So it is wise to be aware of the stories we latch onto and those we ignore.

Stories are the theme for this month’s selections. We explore the stories that guide how we invest and how we can use stories that predict the future to our advantage, or our peril.

Resources tackle stories about security and fear. We’ll examine when we should seek to simplify a narrative and when adding a little complexity makes sense. I’ll share a resource that will help you create stories with more outdoor adventure, without sacrificing financial security.

One selection tells a powerful story that challenges narratives about what brings happiness and fulfillment as we age. I’ll close by sharing a little of my personal story and what the coming months may hold.

The Stories We Tell and Believe

Jonathan Clements notes that “humans are storytelling animals.” As such, he advises using caution before making important financial decisions based on stories that may not be true, writing Telling Tales

Meb Faber conducted a fascinating interview with William Bernstein, exploring why We Are Creatures That Seek Compelling Narratives and how these narratives can lead us to follow the herd and make irrational decisions.

From the Macro Ops newsletter, most investors “mainline the endless stream of ‘quasijournalistic BS’ because they’re on a foolish hunt for certainty.” They offer an alternative approach combining probability and payoff so that success is a statistical certainty given enough time: The Importance of Expected Value.

It Doesn’t Matter How This Story Ends

Harry Sit asks What if Congress Bans Backdoor Roth and Mega Backdoor Roth? I normally hate articles about proposed law changes. These things rarely play out the way they are originally proposed. 

I’m including this one for people currently planning Roth conversions because his conclusions don’t involve making speculative decisions. Instead, they incentivize you to accelerate actions you would eventually make regardless of any law changes. Taking them sooner simply assures you don’t miss a window of opportunity if the law changes.

This is similar to my decision process after researching IBonds earlier this year. I originally became interested based on speculation that inflation is increasing. After doing my research, I recently started buying IBonds because the decision is sound for me even if my inflation fears are incorrect.

A Story about Social Security

A story that is repeatedly told in the media is that Social Security is going to run out of money. I bought into that narrative and assumed no Social Security benefits in our retirement plans.

I only took the time to do a deep dive into how early retirement impacts future Social Security benefits and subsequently altered my projections and future strategies last year, two years AFTER leaving my career.

Ben Carlson thinks the narrative that Social Security will fail is fiction. He asks and answers with authority, Can Young People Still Count on Social Security?

Stories about Change

Kristy Shen experienced a common phenomenon. She found the transition from the security of a life and career she knew to the unknowns of early retirement challenging. She writes Why Freedom Can Be Scary.

A gradual transition from career to retirement can help alleviate these fears and lessen the challenges. Kathleen Coxwell writes The Transition to Retirement: 11 Exceptional Tips for the Average Joe or Jane

Adding a Little Complexity to the Story

The largest holding in my investment portfolio is the Vanguard Total Stock Market Index Fund. The appeal of this fund is the simplicity and effectiveness it provides ordinary investors. It delivers massive diversification, owning every publicly traded U.S. stock in a tax-efficient and low-cost manner.

Rick Ferri interviewed Gerry O’Reilly and Rich Powers on the Bogleheads on Investing Podcast. They manage the $1.3 trillion held in the various share classes of this fund. It’s a fascinating look at all of the complexity that goes on behind the scenes of this “simple” investment.

I crave simplicity in my financial life unless there are outsized rewards for taking on increased complexity. One area where I enjoy a little bit of complexity is in using credit cards for their travel rewards.

If you share this interest with me, check out Penelope Wang’s How to Manage Your Credit Cards for some helpful pointers.

On a related note, I’m publishing this post from Pennsylvania where I flew to spend some time with my parents during a challenging time for our family. It was a luxury to book a cross country flight for a total cash cost of $11.20 for the U.S. 9/11 Security Fee after applying my Southwest Rapid Rewards points.

An easy way to obtain 100,000 of these points is to sign up for the Chase Sapphire Preferred® Card. After spending $4,000 on the card in the first 3 months after opening your account, you will earn 100,000 Chase Ultimate Rewards® points. These points can be used for $1,250 of travel booked directly with the card or potentially more if you transfer them point for point to one of their travel partners including Southwest Airlines.

Money + Adventure Stories

Two topics that I’m passionate about are outdoor adventure and personal finance… in that order. I’ve been loving the new Clipping Chains podcast. The podcast explores these topics with people, including me, trying to forge their own path to a more adventurous life without sacrificing financial security and independence. I encourage you to check it out.

There’s More to the Story

Marking the 20th anniversary of the September 11 attacks, Michael McAuliff wrote ‘Luckiest Man Alive’: Why 9/11 First Responders’ Outlooks May Improve Even as Physical Health Fails. This is a fascinating story that challenges the narrative about the relationship between physical and mental health. 

The stories of the first responders emphasize the importance of having a sense of purpose, meaning, and service to others and strong social support groups. These are topics that should be given a lot of thought and attention as we contemplate having happy and fulfilling lives after retirement.

A Little Bit of My Story

I wrote this month about the advantages and challenges of investing in a business after retiring. As I noted, not needing to earn more money can make it challenging at times to find the motivation to do the work necessary to be successful. This is one of those times for me.

There is a lot going on with my family and, as noted above, I’m doing some traveling to help out when and where I can. Right now, my head and my heart aren’t into writing regularly about topics relevant to this blog.

So I’m going to take a break from creating regular new content. I’m not sure exactly what this will look like and when I’ll be getting back to my regular weekly publishing schedule. For now, things will likely be more sporadic around here.

Thanks for reading and thanks for your patience. Have a great month.

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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. Now he draws on his experience to write about wealth building, DIY investing, financial planning, early retirement, and lifestyle design at Can I Retire Yet? Chris has been featured on MarketWatch, Morningstar, U.S. News & World Report, and Business Insider. He is also the primary author of the book Choose FI: Your Blueprint to Financial Independence. You can reach him at]

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