Should I Spend Money on the Course? I've Bought Seven and Finished None.

I've bought seven online courses in the last three years. Seven. Writing. Marketing. A business course. A coding one I got halfway through. A "build your personal brand" one I'm to...
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Should I Rent or Buy? I've Done the Math 12 Times.

I've done the math twelve times. Twelve. I have a spreadsheet — tabs, color coding, a section for "scenarios" — that compares renting versus buying across every horizon you can ima...
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Should I Buy a Car? I've Been Researching for a Year Without Test-Driving One.

I've been researching cars for a year. A full year. I know the trims, the engine options, the fuel economy numbers, the resale-value curves. I've watched the reviews — all of them,...
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Should I Merge Finances With My Partner? We Share a Bedroom, Not a Bank Account.

We share a bedroom. We share a lease. We share a dog — his name is Biscuit, and we argue about whose turn it is to walk him with the casual intimacy of people who've already decide...
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Should I Buy the iMac? I Picked the Model Three Weeks Ago and Still Haven't.

I know the exact model. I know the specs by heart. I've read every review twice and the bad ones three times, because the bad ones give me an excuse to keep reading. I've watched u...
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Should I Cancel All My Subscriptions? I've Done This Three Times This Year.

Sunday afternoon. I'd been doing this thing I do when I'm anxious — the thing where I open my bank app and scroll through the recurring charges like I'm going to find a leak I have...
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Should I Keep Lending Money to My Friend? He's Asked Six Times.

Phone buzzes. WhatsApp.
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Should I Spend Money on Myself? I Had the Money and Closed the Tab.

It was on sale. Not "clearance rack" on sale — just enough off to make you feel like you're being smart instead of indulgent. I'd been looking at it for months. Opening the page, c...
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What Should I Do With a Windfall? Every Person I Knew Had a Plan for My Money.

Here's something weird. I built a small tool because I was annoyed about a problem and thought "surely someone's fixed this" and then realized nobody had. So I fixed it. Put it onl...
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