# The Writing-Sample Checklist **From Chapter 3.3 of *The 4-Hour Side Hustle*.** What counts, what doesn't, and why five beats fifty. This is the part of the AI setup people skip, and it's the part that does the heavy lifting. The Business Brief tells the model *about* your voice. The samples show it. Those are not equivalent, and the second one is what actually works. --- ## Why five real samples beat any amount of description You can write "conversational, direct, a bit dry" and the model will produce something conversational, direct and a bit dry — in the average way the internet is conversational, direct and a bit dry. Adjectives are a low-bandwidth channel. There are only so many of them, and everyone's using the same ones. A sample is high-bandwidth. It carries your sentence length, your paragraph rhythm, whether you use semicolons, whether you open with the point or build to it, how you handle bad news, what you do instead of exclamation marks. None of that survives being described. All of it survives being shown. This is why the fix for bad output is always **add material, not adjectives.** When a draft sounds wrong, the instinct is to add an instruction. Add a sample instead. --- ## What counts as a sample The bar is lower than you think, and the reason people skip this step is that they assume it's higher. **These all count:** - A well-written email to a colleague — especially one where you were explaining something - A long Slack or Teams message where you talked someone through a problem - A reply to a customer question that you were quietly pleased with - An internal document you wrote that people actually read - A LinkedIn comment where you disagreed with someone politely - A text or WhatsApp message where you explained something to a friend - A performance review you wrote for someone on your team - Notes you sent yourself after a meeting, if they're in full sentences **These don't:** - Anything you didn't write - Anything written by committee, or edited by someone else after you - Anything in a house style that isn't yours — a corporate template, a formal report you were forced to structure a certain way - Anything you'd describe as "how I write when I have to" - Marketing copy, unless you genuinely wrote it and genuinely like it - Anything under about 100 words — too short to carry rhythm The test isn't "was this published." It's **"does this sound like me at my best."** Published work is not required and often actively worse, because it's been through an editor. --- ## The trap that catches almost everyone You will be tempted to submit samples of you being professional. Don't. Priya's first attempt produced writing that was technically accurate and read like a pharmaceutical SOP — which, given her day job, was exactly right and exactly useless. She'd loaded the brief and nothing else. What fixed it was four emails she'd written to a former colleague: the kind where she was explaining something to a friend rather than documenting it for an auditor. Nothing in her prompt changed. The output changed completely. The version of you that writes to a colleague you like is almost always the version your customers should meet. The version of you that writes for an audit is not. --- ## How many, and when to stop Start with five. Test. Then add in batches and re-test. **Re-test after every five samples you add.** You will find a point where the output stops improving — usually somewhere between ten and twenty samples, depending on how varied your writing is. That's where you stop. Past that point you're spending evenings on diminishing returns, and this whole book is an argument against doing that. Fifty samples is not five times better than ten. It's about the same, and it took a Saturday. --- ## Getting them out of your inbox without losing an evening The collection itself is the friction, so make it mechanical: 1. Search your sent mail for messages over 150 words to a single recipient. Sort by length. 2. Skim the top thirty. You're looking for the ones where you were explaining, persuading, or disagreeing — not scheduling. 3. Paste the good ones into a single plain-text file, one after another, separated by a line of dashes. 4. Strip names, company names, and anything confidential. Leave everything else, including the typos. **Leave the typos.** They're part of the rhythm, and removing them nudges the model toward a formality you don't have. Twenty minutes, one file, done. --- ## One thing to check before you upload Read your file once, start to finish, and ask a single question: *would I be happy if a customer read this?* Not "is it polished" — it isn't, and shouldn't be. But if a sample contains you being sarcastic about a client, venting about a vendor, or making a claim you couldn't stand behind, take it out. The model will learn that too, and it will surface at the worst possible moment in a draft you're skimming rather than reading. --- ## Checklist - [ ] Five samples minimum, each over 100 words - [ ] Every one written by you, unedited by anyone else - [ ] At least two are you explaining something to a person you like - [ ] None are corporate-template or house-style writing - [ ] Typos and informalities left in - [ ] Names, company names and confidential details stripped out - [ ] Nothing in there you'd be embarrassed for a customer to read - [ ] Saved as one plain-text file, samples separated by a line of dashes - [ ] Uploaded to the same Project as the Business Brief - [ ] Tested with a 100-word customer email - [ ] Re-tested after each batch of five added - [ ] Stopped when the output stopped improving — and noted the number in your ledger