Category: 📕 Tax Book

This post is the Conclusion of the book Keep More of What You Earn — a plain-English guide to US taxes. A year after the lunch that opened this book, Maria and Denise met again. Same desks, same company — but Maria had done her December checklist, fixed her withholding, funded her HSA, and claimed…

This post is Chapter 14 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. December 28th. Two freelancers, same income, same deductions — almost. Elena spends the week between Christmas and New Year’s with a checklist: she tops up her HSA, harvests a $4,000 investment loss,…

This post is Chapter 13 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. Two investors, same $50,000, same market, same decade. Chris trades actively in a taxable brokerage account — generating short-term gains taxed as ordinary income, never harvesting a loss. Pat buys a broad…

This post is Chapter 12 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. Nadia’s first year as a freelance marketing consultant went beautifully — $92,000 in client payments, working from her spare bedroom, no boss. Then April arrived. Her tax software delivered the news: $24,700…

This post is Chapter 11 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. The Alvarez family is choosing health plans at open enrollment. The PPO costs $320/month in premiums with a $1,000 deductible. The high-deductible plan (HDHP) costs $140/month with a $3,500 deductible. The benefits…

This post is Chapter 10 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. Two 25-year-olds start at the same company at the same $60,000 salary. Alex enrolls in the 401(k) on day one: 10% of pay, capturing the full employer match. Jordan means to enroll…

This post is Chapter 9 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. The envelope is unmistakable: government seal, “Department of the Treasury — Internal Revenue Service,” your full name in the window. Karen’s hands shake opening it. Inside: “CP2000 — Notice of Underreported Income.”…

This post is Chapter 8 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. On April 14th, Robert finally finishes his return. He owes $2,300. “I’ll file the extension,” he tells his wife, “so I have until October to pay.” She stares at him. “That’s… not…

This post is Chapter 7 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. Three people, three Aprils. Elena, a barista with one W-2 and the standard deduction, pays $129 for deluxe tax software she didn’t need. Marcus, a freelance photographer with $92,000 in 1099 income…

This post is Chapter 6 of 14 of the book Keep More of What You Earn — a plain-English guide to US taxes. Every filing season, someone asks me some version of: “I’m a homeowner, so I should itemize, right?” Or the reverse: “I rent, so I just take the standard deduction?” Both questions reveal…