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This months selections start off with a few perspectives on investing through challenging times. Improving investment performance by picking the best stocks or sectors or timing the market is challenging at best. A better approach to improve your financial performance is to focus on decreasing your tax burden. We have resources that will help you do this.

The Best

When planning retirement, we have to be aware of worst case scenarios that can destroy our best laid plans. A lot of attention is given to factors like future market returns, tax rates, and inflation that are ultimately out of our control. This month’s resources focus on two factors you can impact: navigating the American healthcare system and avoiding divorce.

I share a resource to prepare for retirement at this challenging pandemic time. You will also find an opportunity to chat with me about any challenges you may be facing on your path to financial independence. Finally, we close with ideas to live a simpler and more efficient life to exchange work time for more play time.

Enjoy and have a great month!

Investing Through Challenging Times

JL Collins asks if it’s Time to Sell?

From the Monevator blog, The Investor asks and answers What can investors do in the face of low returns?

Amy Arnott explains Why Portfolio Diversification Still Works.

Dana Anspach has an interesting take on a timely question, writing Should You Invest in Crypto?

Tax Alpha

With low interest rates and high stock valuations, it is especially important to control the things you can control: your behavior, investment fees, and … taxes!

A popular post on this blog is Early Retirement Tax Planning 101. Phil Demuth built on those foundational principles and took a deep dive into advanced tax planning strategies on the Bogleheads on Investing podcast. This episode will be particularly useful for higher earners and/or higher net worth retirees.

Those resources provide a framework for long-term tax planning. But Mike Piper explains that your strategy needs to be fluid as your circumstances and tax laws change, writing Predicting Tax Legislation is Harder than Timing the Market.

Understanding The Business of Healthcare

Last month, I featured a pair of videos that demonstrated both the promise and challenge of recent legislation aimed at improving price transparency in American healthcare. This month I’m sharing a pair of Freakonomics podcasts that shine more light on the business of healthcare in the United States to help you understand the system we all must navigate.

How to Fix the Hot Mess of U.S. Healthcare

Is Dialysis a Test Case of Medicare for All?

Black Swans and Gray Divorce

Retirement planning requires thinking about worst case scenarios. Too often we focus on “Black Swan” events, which by definition are exceptionally rare and that we can’t predict. In the process, we focus too little on events that are much more common and equally destructive to our plans.

Stacy Francis writes about one such risk that continues to become more common, ‘Gray Divorce’ Rates Are Exploding Due to This Perfect Storm.

Relationship expert Dr. Sue Johnson was interviewed on the Farnam Street podcast. She provided interesting insights into risk factors for ‘Gray Divorce’ including becoming empty nesters and retirement.

Avoiding Discontentment in Retirement

This month, I wrote about the idea that periods of discontentment are an inevitability for many of us in retirement. You can’t necessarily avoid periods of discontentment with good planning. Still, we should prepare as well as possible for the challenges that retirement inevitably may bring.

Sam at Financial Samurai provides a Pre-Retirement Checklist for a Post-Pandemic Life for those preparing to retire at this especially challenging time.

Let’s Talk

I enjoyed meeting more blog readers in April and have cleared a couple more spots in May. If you’d like to chat, grab one of the spots on my calendar at this link. As a reminder, I’m here to talk about anything you would like about your journey to financial independence or the transition to retirement, but I can not offer any specific investment, tax related, or other financial advice.

End of the Winter Ski Season…

This month, I concluded my third ski season in Utah. Before moving on to warmer weather activities, the next selection is a fun ski video that packs a ton of wisdom about how building a simple, frugal, efficient, and active lifestyle allows you to “trade work time for play time.” 73 year-old Utah local legend Dave “The Farmer” Van Dame is featured in the short video Steeped in Tradition.

Preparing for the Summer Travel Season

As the weather gets warmer and more vaccines are going into people’s arms, I’m anticipating a busy summer travel season. The downside of this is travel will likely be expensive due to all of the pent-up demand. Using travel credit card rewards is a great way to eliminate, or at least defray some of, these costs if you use credit cards responsibly.

The Chase Sapphire Preferred® Card is my favorite card for the valuable and flexible Chase Ultimate Rewards® you accumulate with it. This card currently has a higher than usual offer of 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. This is a value of $800 cash or $1,000 if redeemed using Chase Ultimate Rewards® points. The card has a $95 annual fee.

Since I already have that card, I took advantage of another card with an increased sign-up bonus to diversify my travel rewards points. I recently signed up for the Marriott Bonvoy Boundless™ Credit Card. I love the Marriott program because they have properties almost everywhere and I’ve never been blacked out from using points with their chain. This card is currently offering 100,000 Bonus Points after you spend $3,000 on purchases in the first 3 months from account opening, compared to the normal offer of 75,000 points. This card has a $95 annual fee.

If you prefer to avoid credit card fees completely, you can earn 50,000 Bonus Points after you spend $1,000 on purchases in the first 3 months from account opening with the Marriott Bonvoy Bold™ Credit Card. This card has no annual fee. This is also a limited-time offer, increased from the normal 30,000 point bonus.

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Valuable Resources

  • The Best Retirement Calculators can help you perform detailed retirement simulations including modeling withdrawal strategies, federal and state income taxes, healthcare expenses, and more. Can I Retire Yet? partners with two of the best.
  • Free Travel or Cash Back with credit card rewards and sign up bonuses.
  • Monitor Your Investment Portfolio
    • Sign up for a free Personal Capital account to gain access to track your asset allocation, investment performance, individual account balances, net worth, cash flow, and investment expenses.
  • 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. 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 chris@caniretireyet.com.]

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