The 8 Scariest Financial Situations You Can Find Yourself In

I love Halloween, especially seeing how much fun the kids have. But for financially aware adults, the real chills don’t come from ghosts or goblins. They come from spreadsheets, surprise bills, and market meltdowns that turn your net worth chart into a horror movie graph. After over three decades of studying, working through, and writing […]

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How to Endure Suffering to Build Greater Wealth and Resilience

Despite finally having the permission to live it up in retirement, I still find it hard to spend money on things I don’t truly need. A big part of building wealth has always been about endurance and suffering. The more we can withstand—long hours, delayed gratification, and the occasional investment blowup—the greater our odds of

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Millionaire Early Retirees Probably Shouldn’t Get Healthcare Subsidies

If healthcare in America weren’t so egregiously expensive, more people would retire earlier and live better, happier lives. We’re one of the few countries in the world where affordable healthcare is tied to employment, making financial independence that much harder to achieve. Given the high cost of coverage, before you decide to retire early by

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How Empower’s Free Financial Review Helped Me Rethink Retirement

After doing my first free Empower financial professional review back in 2014, I decided to do another investment portfolio review with them. Given the portfolio review is free for anyone with over $100,000 in investable assets, and my financial situation has changed so dramatically since then, I figured, why not spend a little time uncovering potential

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Vacations Just Aren’t As Great Anymore Once You Retire Early

On October 8, 2025, we decided to go on a family vacation I was decidedly unexcited about. That entire week was supposed to be my time to attend the Fairfield Challenger tennis tournament every day with my buddy Richard. September and October are tennis paradise months in the Bay Area, with multiple tournaments and ideal

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The Cost To Prove Your Ethnicity And Heritage: Hawaiian Edition

So you’ve read my post on the growing importance of Identity Diversification and now you’re wondering what it actually takes to prove your ethnicity and heritage. Doing so can help you better navigate the shifting socioeconomic winds of society and, in some cases, even improve your odds of getting into school, landing a job, winning

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