How To Overcome Writer's Block By Making Better Choices — Dickie Bush & Cole Schafer
Source: https://writewithai.substack.com/p/how-to-overcome-writers-block-by Received: 2026-05-10 via writewithai@substack.com
⚠️ Sponsorship
The piece itself is editorial thought-leadership, but ends with a PS pushing Ghostbase (their AI writing engine product) with a free 7-day trial CTA, plus footer links to Ship30, Premium Ghostwriting Academy, Typeshare — all owned/operated by Bush & Cole. Read the body as craft writing; treat the prompt at the end as the genuine deliverable; ignore the Ghostbase pitch.
Core argument
Writer's block isn't a knowledge problem, it's a choice-avoidance problem. When you're "stuck," you actually have options in front of you — you just don't want to pick one. The act of refusing to choose IS the wrong answer.
Reframe: writing = choice-making. The job is to:
- Build enough competence that your options are good ones.
- Then make choices on purpose, with intention.
Their internal cycle when stuck on non-fiction:
- Should I give a tip?
- Should I share a mistake?
- Should I share a lesson learned?
- Should I share a reason why the reader should do this?
"What separates great writers from average ones isn't that they have better ideas. It's that they make sharper choices, more often, with more intention."
Where AI fits (their actual recommendation)
Don't ask AI to write for you — that removes the fun and the point. "When you let it do that, you've stopped writing — you're just publishing."
DO use AI to surface the choices you're avoiding. Specifically:
- You have a topic but no angle.
- You have an angle but no structure.
- You don't know what to write about.
- You're mid-draft and stuck.
- You have a draft and something feels off.
The prompt (the real artifact)
They give a paste-able prompt that hard-constrains the model to surface choices, not write the draft. Key ingredients:
- Strict rule: "you do not write my draft for me. You only surface choices."
- For each option, return: short label (3-6 words), one-sentence description, where this choice leads, what you gain/give up.
- Identify which option is the "obvious autopilot" choice and call it out so the writer can decide whether to take it or break from it on purpose.
- Decision stays with the writer; AI's job is to widen options, not narrow them.
- Conversational opener: "ask me what I'm working on and where I'm stuck" — one question at a time.
The full prompt is in the source email if needed verbatim.
Why this is in the vault
Two load-bearing reasons:
Direct match to founder's "AI as second brain, not author" stance. The "use AI to widen options, not make decisions" framing is exactly the discipline the Sanity Check voice work needs — Ray-the-COO surfaces drafts, founder makes the choice. Same shape as the founder/operator split.
The prompt itself is reusable infrastructure. The "options + obvious-default-callout + decision-stays-with-human" pattern is a template worth lifting into the
/draft-reviewand/research-briefskill flows where Ray currently sometimes over-narrows toward a single recommendation. Adding an explicit "here are 3-5 options, here's the autopilot pick, you decide" mode would reduce confirmation-bias risk.
Mapping against Ray Data Co
Sanity Check voice / draft pipeline. Pairs with [[01-projects/newsletter/sc-relaunch-essay]] — the relaunch essay is built on intentional craft choices (concrete vs abstract, recipes vs secrets). The "what choice am I avoiding?" prompt is a direct candidate to fold into [[
/.claude/skills/draft-review]] or [[/.claude/skills/research-brief]] as an "option-surfacing mode" alternative to the current angle-recommender mode.Harness / agent-collaboration thesis. Same shape as harness-engineering: the human stays in the loop on the load-bearing decisions, the agent widens the search space. Connects to [[06-reference/2026-04-15-thariq-claude-code-session-management-1m-context]] (don't drown the operator in raw artifact, surface structured options) and to the broader thesis Ray is the COO that surfaces, founder decides.
Prior WriteWithAI cluster. Adds to the running thread of practical-prompt-craft pieces from this newsletter:
- [[06-reference/2026-05-03-writewithai-claude-design-guidelines]]
- [[06-reference/2026-04-29-writewithai-5-claude-connectors-writing-workflow]]
- [[06-reference/2026-04-26-write-with-ai-build-claude-skill-from-scratch]]
- [[06-reference/2026-04-15-write-with-ai-offer-stacking-framework]] WriteWithAI continues to be the most consistently-useful prompt-craft source in the whitelist; the editorial half (vs the Ghostbase pitch half) lands cleanly when the topic is craft, not tooling.
Action candidates
- Lift the "options + autopilot-callout + decision-stays-with-human" pattern into
/draft-reviewas an alternative mode. Low-risk vault-side change. - Consider an explicit "what choice am I avoiding?" pre-write check in
/research-brieffor newsletter topics where Ray has been defaulting to a single angle.
Related
- [[06-reference/2026-05-03-writewithai-claude-design-guidelines]]
- [[06-reference/2026-04-29-writewithai-5-claude-connectors-writing-workflow]]
- [[06-reference/2026-04-26-write-with-ai-build-claude-skill-from-scratch]]
- [[01-projects/newsletter/sc-relaunch-essay]]
- [[06-reference/2026-04-15-thariq-claude-code-session-management-1m-context]]