Start a Paid Newsletter
Companion to "Free, Paid, and the Paywall" and "Writing Issues Worth Paying For."
One sheet per issue. Free content can be tangible but should stay general; paid content must pass both tests every time: tangible (a reader could act on it this week) and repeatable (this kind of value arrives again next week).
| Part | Rule | Your draft |
|---|---|---|
| Subject line | One promise; write five options, pick the clearest; honest (misleading subject lines are a legal violation in several countries); under forty-five characters survives most inbox truncation | |
| Opening three sentences | Establish stakes with the news, the number, or the argument; never a warm-up. "Last Tuesday the agency proposed a rule that will touch every contract you manage" is an opening; "I hope this email finds you well" is a goodbye. | |
| Body | One idea, developed with evidence, to a conclusion usable this week. Subheads every few hundred words; the skimmers are paying customers too. | |
| Close | Hand the reader the next step: what to watch, what to check, what to reply with. Endings that point somewhere generate the replies that fuel future issues. |
Fixed format skeleton (what makes weekly production survivable): the lead analysis, the quick hits, the tool or resource, the one question for readers.
| Piece planned (free preview + paid body) | Tangible (act on it this week)? | Repeatable (arrives again next week)? | Free or paid |
|---|---|---|---|
| ☐ | ☐ | ||
| ☐ | ☐ |
Anything behind the paywall that fails the test eventually shows up as churn.
| A: at the moment of insight | Free preview walks to the edge of the answer, establishes you see the problem clearly, gate lands exactly where the payoff begins. | ☐ |
| B: immediately before a tangible object | You explain an approach, then announce the asset (checklist, database, template); the reader hits the gate with their hand already out. | ☐ |
| Never: no preview / wall after one paragraph / every issue locked | Every paid issue sends a meaningful free preview to the entire list, every time. |
| Draft and edit done as separate blocks (draft ugly and fast; edit cuts a third, fixes the opening, sharpens what made you pause) | ☐ |
| Reader test: could a competent generalist with a search engine and an AI assistant have produced this issue? If yes, not done. One insider-only element is the minimum, and one is enough. | ☐ |
| Read the draft aloud once; if it could have been written about any niche, it could not have been written by you | ☐ |
| Cadence contract honored (whatever rhythm the welcome email announced) | ☐ |