September 2019 Best of the Web

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We have a collection of great articles and exciting blog news to share this month.

There is a lot of angst about market bubbles and pending recessions, so we kick things off there. We also share some great resources for those grappling with complex investment decisions.

We go to a place that we usually try to avoid on this blog, exploring the intersection of politics and personal finance. One area where this intersection is impossible to ignore for Americans is dealing with our medical insurance marketplace. This month’s articles provide important information whether you are considering short-term policies, navigating ACA open enrollment, or utilizing Medicare.

We close with inspiration and practical ideas for those who feel stuck because you’re late to the game with saving, investing and planning for retirement or because you don’t think early retirement is realistic. . .

Blog News

Before we dive into this month’s articles, I have two exciting pieces of blog news to share.

Earlier this month, Can I Retire Yet? won the Plutus Award for Best Retirement Blog. The Plutus Awards celebrate excellence in independent financial media. Darrow and I are honored for the recognition and wanted to share the news. You can see all of the winners here.

The other writing project I’ve been working on is the book Choose FI: Your Blueprint to Financial Independence. It will be released Tuesday, October 1. I’ll be doing a few events in support of the book, and I’d love to meet any readers of the blog in person.

I’ll be in the Detroit area for a live event with Joe Saul-Sehy of Stacking Benjamins on Thursday, October 3. You can find more information about the event by clicking here.

On Saturday, October 12 I’ll give a talk and sign books at the Sugarhouse Barnes & Noble in Salt Lake City. You can find more information about that event by clicking here.

Finally, my co-authors Brad Barrett and Jonathan Mendonsa, hosts of the popular Choose FI podcast, will be at the Richmond Public Library on Wednesday October 23. You can find more information about that event by clicking here.

With that, let’s get to this month’s articles. . .

Recessions and Bubbles

Darrow’s post about Preparing for the Next Recession was very popular this month as angst grows among investors. We start with a few other perspectives on this topic.

Karsten “Big ERN” Jeske writes My Thoughts on the Upcoming Recession.

Michael Burry became well known as one of the memorable contrarian characters in “The Big Short.” He placed massive bets against the sub-prime mortgages that led to the 2008 housing bubble that none of the “experts” recognized was forming. So he created quite a buzz when he suggested a bubble is now forming in index funds. Ben Carlson addresses this with Debunking the Silly “Passive is a Bubble” Myth.

Investing is Simple?

There is a saying that investing is simple, but not easy. But it’s not always simple.

Mike Piper gives a good framework for thinking about risk, writing Risk Adjusted Returns: What’s the Point?

Investing can be fairly simple if you start with a coherent strategy. Unfortunately, many of us didn’t. This can create unnecessary taxation in taxable investment accounts. Christine Benz addresses this with Stop the Mutual Fund Capital Gains Distribution Madness!

An annuity may be the right decision for some retirees. But, it can be difficult to sort through annuity products. The worst products for consumers are often the most aggressively sold products due to high commissions they create for salespeople. Penelope Wang writes Why Indexed Annuities May Promise More Than They Deliver.

More Politics in Personal Finance?

Earlier this month, I attended FinCon in Washington D.C. The Washington Post’s Helaine Olin was there as well, following which she wrote Why the world of personal finance needs more politics.

JD Roth countered by asking Does the world of personal finance need more politics?

Our policy has always been similar to Roth’s, emphasizing empowering readers to learn the rules as they are rather than discussing how we wish they were.

A perfect example is sharing the next article from Bloomberg Businessweek: Health Insurance That Doesn’t Cover the Bills Has Flooded the Market Under Trump. Anyone considering short-term medical insurance to bridge the gap between early retirement and medicare eligibility needs to understand the risks involved with these policies.

Open Enrollment

Continuing on the theme of health insurance, we have about one month until the annual open enrollment period begins.

Clint Proctor writes Choosing Your Health Insurance: A Guide for Open Enrollment.

For those who have bridged the gap to Medicare, Eleanor Laise writes Navigate 2020 Medicare Changes During Open Enrollment.

Getting Unstuck

Making the changes to do what it takes to achieve FIRE, or even reach financial independence and retire securely at any age, can be much harder once you are entrenched in a particular way of life. Seth Godin writes Being Stuck is Reasonable.

Some folks decided to be unreasonable and in the process changed the trajectory of their lives. Jill Confield writes Think time isn’t on your side? These late savers are all on track to hit financial independence.

What Do We Really Want?

It is much easier to get unstuck when you have a goal. Let’s close with two awesome articles that give perspective on finding the right goals.

Chuck Jaffe writes Make ‘gaining choice’ — and not early retirement — your real goal.

Dawn Baker writes A Slowly Spreading FIRE.

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[Contributing Editor 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' writing has been featured in MarketWatch, Doughroller, Business Insider and RockStar Finance. He is also the primary author of the forthcoming book Choose FI: Your Blueprint to Financial Independence. You can reach him at]

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  1. Mary Cameron says

    Congratulations on the award. I enjoy your emails.

  2. The distributions madness article really resonated with me. I bought actively managed funds a couple of decades ago and have been “suffering” ever since. As assets grow, distributions increase due to increase in the asset base. But I don’t want to sell as I want to keep the money invested and don’t want a big tax hit from capital appreciation. So I continue to pay capital gains taxes on these distributions year-over-year. So when investing using the buy and hold strategy for the very long term, the article rightly suggests you factor in the anticipated distributions of the funds you buy. All my new money now goes into more tax efficient, low cost ETFs or low distribution, low cast funds (Vanguard has some good ones).

    Side note to Chris. It can be irritating to reference an article that requires you to be a member in order to access. I already have free membership to Morningstar but don’t like listing my email with a bunch of sites.

    • Pay taxes now, or pay later. Eventually those gains will get taxed, unless you can find the opportunity to offset them along the way.

      • Chris Mamula says

        That is kind of true. But if you are a high earner, you may be paying unnecessary short-term capital gains taxes at your marginal tax rate if your investments are creating taxable events by selling securities inside of a fund, even if you hold the fund and don’t sell any shares. If you use tax efficient index funds or ETFs you will rarely if ever pay short term capital gains taxes, and you may be able to “pay” at a rate of 0% on long term capital gains if selling funds to create income in retirement when you have little or no earned income. Understanding how your investments are taxed and locating them in the most tax efficient accounts can allow you to boost your after tax returns without taking any additional risk.

    • Chris Mamula says

      I appreciate that feedback. A number of publications are putting their content behind paywalls or at least require you to create a membership to access them.

      I also had a substantial amount of money invested in actively managed funds in taxable accounts. I elected to sell them off gradually over several years, trying to set off some of my gains with losses and taking care to create too much taxable income in a given year that I couldn’t contribute to my Roth IRA. I’m honestly not sure if it was the optimal financial decision, but it eventually allowed me to start over with a strategy I was comfortable with for the long term. I now exclusively use broad based index funds with little turnover and thus minimal to no capital gains when investing in taxable accounts.

      • This is the same strategy I plan to execute once we “semi retire” and are not in our peak earning years anymore. Our marginal tax rate will be lower and the tax impact should be less when we sell these high distribution, taxable holdings.

        • Chris Mamula says

          Sounds smart. We knew we were at least 5 years away from this when we started the process, so we didn’t want to wait, though we still sold off our portfolio in pieces taking care to not produce too much taxable income in any particular year as noted. Here is a summary from my original blog. Ugly stuff.

  3. Gentlemen, congratulations on your Plutus Award! Due to your dedicated efforts to produce informative, well-researched posts that educate your readers on the many facets of retirement, the honor is, without a doubt, well-deserved. Humbly accepted, too, I might add. Good for you!

    • Chris Mamula says

      Thanks for the kind words Mary! Knowing we have people like you as a reader and regular contributor in the comments keeps us doing this.

  4. SLC on the 12th. Nice!

  5. With regards to politics, there is definitely a big political possibility that will affect every market participant. Elizabeth Warren has a serious chance of becoming president and she will not be as “market friendly” as Trump to put it euphemistically.

    • Chris Mamula says

      I think any president’s impact on the economy and stock market is vastly overestimated. Our economic system is incredibly complex and dynamic.

  6. Solid round up! Looks like I have some more reading to go do now…