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The Bad-Decade Case Study Every FI Investor Needs: Understanding Sequence of Returns Risk
Let’s talk about the single meanest trick the stock market can play on new retirees. It’s not that stocks go down. Everybody who’s held an index fund for more than five minutes knows stocks go down sometimes. The mean trick is when they go down. Because in retirement, timing isn’t just a detail. Timing is…
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I Make Good Money, But I Have Nothing to Show for It: A Diagnostic Checklist
You check your bank account after payday and there’s a nice, healthy number staring back at you. Then you check it again two weeks later, right before the next payday, and that number has quietly evaporated. You make six figures. Your friends probably think you’re doing great. And yet you couldn’t tell someone where the…
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Your Budget Has a Blind Spot, and It Shows Up Every December
You did it. You built a budget. You know exactly what you spend on groceries, gas, streaming services, and that one recurring $4.99 charge for an app you forgot you downloaded. You feel like a financial genius. Then September rolls around and your car registration is due. October brings your homeowner’s insurance renewal. November hits…
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Market Time vs. Timing the Market: My Neighbor Is Living Proof
Last weekend I moved. Don’t get impressed. I’m still moving every day this week, too. (Why do I have so much stuff?!?) On Saturday, my neighbor showed up at my door with a home cooked meal and I nearly cried into the casserole dish. We sat down to dinner and of course, started talking about…
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Every Retired Person I Know Says the Same Thing (And It’s Not “I Wish I’d Saved More”)
I’ve talked to a lot of early-retired people. It’s basically my job, but also, there is a steady stream of early retirees coming through Longmont. And I’ve noticed a pattern that’s remarkably consistent. Ask a retiree what they’d change and nearly every single one says some version of the same sentence. “I wish I would…
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Coast FI Math: The Real Formula and When It Stops Working
If you’ve spent any time in the FI corners of the internet, you’ve heard someone proudly announce “I’m Coast FI.” It sounds impressive, but half the time the person saying it hasn’t actually done the math. Coast FI is a great concept. It’s also one of the most misunderstood numbers in the entire FI vocabulary,…
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When Your Life Is the Research: How Watching the World Turned Into Our Best Investments
There’s an old saying that luck is what happens when preparation meets opportunity. I used to think that was just a nice thing people said to make hard work sound more romantic. Now I think it might be the most accurate description of my husband Carl’s investment portfolio that exists. Carl and I have a…
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The Spending Experiment That Taught Us Frugal Isn’t the Same as Smart
When Carl and I went on the I Will Teach You To Be Rich podcast with Ramit Sethi, we thought we were going in for a fun conversation about money. What we walked away with instead was a full audit of our own frugality, and honestly, it stung a little. For years, we told ourselves…
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Mega-Cap Tech: Individually, Each Giant Makes Sense… Collectively, They Don’t (Is it an AI Bubble?)
Eleven interconnected AI/Tech companies are valued at a combined $27T as of July 2026. While each company individually has a plausible path to success, what you have to believe for the collection as a whole should give you real pause. I think the hardest challenge for investors in 2026 is the discomfort so many of…
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The Tax Trap Waiting at Age 73 (and How to Get Out of It)
After Carl and I chatted with The Money Guys, we’ve had a LOT of conversations surrounding where our money is currently located, and how to optimize for less overall taxes paid. (And this article is for those of you who ARE NOT yet 73 and taking RMDs. So please keep reading for tips for our…
