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The Boring Newsletter, 3/25/2023

Hello Friendos! What with all the recent excitement around Silicon Valley Bank, a couple of other bank collapses, and the Federal Reserve raising rates this week, I thought this was the perfect time to really go deep on paystubs (from a W-2 job). That’s right, I’m giving you my sizzling hot take on paystubs and […]

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The Boring Newsletter, 3/18/2023 🍀

Hello Friendos! Today we’re talking tax write-offs. Have you ever heard someone talk about tax-write offs like they were getting something for free, as if the government was handing them a big bag of money? It might go like: Or maybe it sounds like this: I just smile and nod, smile and nod, but what […]

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The Boring Newsletter, 3/11/2023

Hello Friendos! This week we have…a pop quiz! It’s a math quiz and a word problem…nnnnooooooooooo. Don’t worry, I think you’ll pass even if you didn’t study. Ok, here it is. Imagine you are getting ready for a road trip and want to buy a deluxe first aid kit ($40) and a couple tubes of […]

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The Boring Newsletter, 3/4/2023

Hello Friendos! Last week I waxed rhapsodic about investing in low-cost index funds. I promised in a future newsletter I would explain exactly what I meant by “low-cost.” The day has arrived! Now, this is usually when a financial writer would launch into a mathematical example to demonstrate that if you invest for decades and […]

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The Boring Newsletter, 2/26/2023

Hi Friendos! In honor of the newly released 50th anniversary edition of Burton Malkiel’s book, A Random Walk Down Wall Street, this week’s topic is index funds. It’s a bit longer than usual due to the paramount importance of the topic. I prefer investing in stocks and bonds using low-cost index funds, not expensive actively […]

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The Boring Newsletter, 2/18/2023

Hello Friendos! I hope you are having a nice holiday weekend. This week I’d like to sing the praises of a boring and often overlooked component of financial strength: maintenance (of your things). I once had a colleague who was maybe 22 years old at the time, and somehow we got to chatting about shoes. […]

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The Boring Newsletter, Love Edition ❤️

Hello Friendos! Valentine’s Day is next week, so I wanted to take this opportunity to remind you that…one day, we’ll all be dead! (Too dark? Eh, let’s press on.) Have you ever known someone with strife in their family around inheritance? The deceased may not have done a great job with the estate planning. If […]

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Pay As You Go, or You Will Owe

Or…why do I have to pay more money in April when I’ve been paying all year long? The U.S. income tax system is pay-as-you-go, meaning, the IRS expects you to pay taxes on your income as you earn it throughout the year. In fact, if you owe too much at tax time (relative to your […]

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File Your Taxes For Free If You Can

Did you know there are a number of ways to file your taxes for free? By “free” I mean where you don’t have to pay a tax preparer, you don’t have to pay for tax software, and you don’t pay for any other out of pocket costs. “Free” probably does mean using some of your […]

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Why Charitable Donations Are Not Tax Deductions For Most People

(aka: explaining the Standard Deduction and Itemized Deductions in Three Easy Steps) “Everybody knows” that charitable donations are tax-deductible. “Everybody knows” that you get a tax break on your home mortgage. Everybody is mostly wrong. Here’s why: Step 1: In the U.S., it basically works like this:  Step 2: You have two options for that […]