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The rule was a useful first draft when Elizabeth Warren wrote it down in 2005. Two recessions, one pandemic, and a 41% rent increase later, the percentages quietly stopped working. Here is what I keep on a sticky note above my desk instead.
Dividend investing has a beginner trap that the introductory articles tend to skip: the highest-yielding stocks are usually high-yielding for a reason, and that reason is rarely good. Here is the short version of how to read a yield without falling for the headline.
Twelve months. Three platforms. 2,840 designs uploaded. $11,260 in gross revenue. After fees, ads, and the design subscriptions I forgot to cancel, I cleared less than my old part-time bookstore job. Here are the numbers, and the parts I would do differently.
I have looked at my own credit report at least twenty times. I have looked at other people's, with permission, about as many. Here is the small list of things actually worth fixing, and the longer list of things people waste a Saturday worrying about.
From 2018 to 2024 I held both a small REIT portfolio and a one-bedroom rental in a small US city. Here is the actual six-year P&L of both — fees, vacancies, repairs, taxes — and which one was genuinely passive.
Twelve working freelance writers shared the last two years of their invoices with me. The spread between the bottom and top of the market is wider than I expected. So is the gap between what platforms pay and what direct clients pay for identical work.
The classic advice — keep three to six months of expenses in cash — was written for a labor market that no longer exists. I ran the actual numbers on how long it takes to find a new job in my industry. The answer surprised me.
A mutual fund tracking the S&P 500 and an ETF tracking the S&P 500 own the same companies. They behave differently in three small ways that, over a decade, add up to a non-trivial gap. Here is the short version.
Every quitting-your-job story leaves out the same line: how the writer paid for health insurance in month four. Here is the dry, unromantic math of replacing W-2 income with self-employed income, run against my own situation when I made the move.
The textbook answer is to compare interest rates. The textbook answer is also incomplete. Here is the seven-column spreadsheet I ran for my own student loans, and what it told me to do.
I have held the same twelve dividend stocks for at least three years. Last year I logged every payment to the cent and ran the math against what the marketing of dividend investing promises. Five things were surprising.
My first year of freelance income I owed $7,800 in taxes I had not set aside. Four mistakes did most of the damage. None of them were complicated. All of them were the kind of thing a 20-minute conversation with a CPA would have caught.
Car insurance is not a surprise. Christmas is not a surprise. The annual Amazon Prime charge is, somehow, always a surprise. Sinking funds are the small trick that solves this entire category of problem.
For most of my adult life, US Treasury bonds yielded less than inflation. That stopped being true in 2022 and is still mostly true today. Here is what I actually do with the part of my portfolio that is not in stocks.
I had a 2019 Subaru Outback sitting in a parking spot for most of the workweek. Turo's pitch was that the spot could be earning me $400 a month. After six months I had $1,840 of gross revenue, two minor damages, and one stress-induced decision to stop. Here are the numbers.
A 4% APY sounds like meaningful money. After inflation, federal tax, and the small print most marketing pages skip, it is also exactly that — but smaller than you think. Here is the math on a $20,000 balance over a year.
It was 2019. I had heard of the backdoor Roth. I had read three blog posts about it. I did the steps in the wrong order. The IRS was reasonable about it. It still cost me, by my accounting, $4,200 in compounding I will never get back.
It was profitable. Modestly. It was also the most demoralizing thing I have ever run. I closed it in October. Here is what the dashboards do not show you about what selling on Etsy in 2025 is actually like.
Klarna, Afterpay, Affirm. They look free. The good ones, sometimes, technically are. The reason I do not use any of them is more boring than the standard 'they trap you in debt' argument — and harder to argue against.
Over twelve months in 2024 I wrote covered calls against three of my long-term equity positions. The income was real. The cost — in capped upside, in cognitive bandwidth, in one specific blow-up — was higher than the spreadsheet suggested.
Online tutoring was the side hustle I had the least patience for until I realized I had been picking the wrong platforms. Here is what eight different platforms actually paid, what they took, and the two I still use.
I do not write much about my own financial mistakes, but this one I have come back to often enough that the rebuild is more useful to share than the original failure. The short version: it is mostly time, mostly utilization, and almost never the things people focus on.
Health Savings Accounts are sold as a medical-bills wrapper. The much more interesting use of one is as a triple-tax-advantaged retirement account that nobody seems to talk about. Here is the math, and the small list of conditions under which it works.
I started a paid newsletter about budgeting for freelance writers in mid-2024. Twenty months later it crosses $1,000 a month on a list of about 410 paying readers. Here is what I actually did, week by week, including the months that did not work.
For eight months I paid $98 a year for a budgeting app with a great interface and a clever onboarding. Then I went back to a Google Sheet I built in an afternoon. The reasons are smaller than 'it saved me money' — but also weirder.
Eight years ago I split a small portfolio into two halves and let one of them run on autopilot. The autopilot half is now meaningfully ahead. The reasons are mundane and worth writing down.
Most affiliate content online is bad — overly enthusiastic, lazy with disclosures, padded for word count, written by someone who has never actually used the product. The working version of affiliate marketing looks nothing like that. Here is what I actually do.