My Cheatsheets

Enticing Thinking for general Projects

With the release of the GPT-5 model in August 2025, OpenAI updated usage limits—especially for the deeper Thinking mode.

ChatGPT (web/mobile)

Tier GPT-5 Standard GPT-5 Thinking (deeper reasoning)
Free 10 messages per 5 hours; then switches to GPT-5 mini. Also 1 Thinking message per day. 1 Thinking message/day.
Plus Up to 160 messages per 3 hours (temporary increase; may revert). Up to 200 messages per week. Automatic switching doesn’t count.
Pro/Team Unlimited GPT-5 usage (subject to abuse guardrails). Access to GPT-5 Thinking Pro for more extended reasoning.

Notably: Manual GPT-5 Thinking usage is capped at 200 messages/week on Plus and Team. Automatic switching from GPT-5 to GPT-5 Thinking does not consume this weekly quota.

There are essentially two buckets:

What this means: if you are in standard GPT-5 and the system decides your request needs more reasoning, it will “upgrade” internally at no cost to your manual Thinking quota.

How to spot auto-switching (informal signs)

Reset timing: Weekly Thinking limits reset 7 days after your first message, at 00:00 UTC on the reset day. You can see the reset date by hovering the model name in the picker.

The goal of these cheats is to reliably push deeper reasoning without burning a manual Thinking slot. If a result feels shallow, re-run it explicitly with the Thinking model to spend one of your 200 for the week.

1. Multi-Step Comparison

“Compare [Option A] and [Option B] in terms of [Factor 1], [Factor 2], and [Factor 3] over a [Timeframe]. Identify dependencies between the factors and note any edge cases where the outcome changes.”


2. Scenario Evaluation

“Given [Context/Background], evaluate possible outcomes under Scenario 1, Scenario 2, and Scenario 3. Highlight trade-offs and conditions that could cause a scenario to fail.”


3. Cross-Domain Reasoning

“From the perspective of [Domain 1] and [Domain 2], analyze how [Problem/Topic] would be approached. Identify points of agreement, disagreement, and synergy.”


4. Contradiction Check

“Examine these statements:

  1. [Statement A]
  2. [Statement B] Identify if they contradict, align, or are unrelated, and explain any hidden assumptions that change the answer.”

5. Root Cause & Mitigation

“Given the problem [Describe Issue], break down the likely root causes in priority order, then propose mitigations for each cause. Indicate where further data is needed to choose between solutions.”


6. Decision Framework

“For the decision [Describe Decision], evaluate using these criteria: [Criterion 1], [Criterion 2], [Criterion 3]. Score each option on a consistent scale and justify the scoring.”


Cheatsheet — Triggering Auto-Thinking Without the Toggle

Tactic Why It Works Example Phrase
Multiple linked tasks Forces planning + reasoning “…and then summarize implications for…”
Scenario variation Requires multi-path thinking “If A happens vs if B happens…”
Cross-discipline framing Needs integration of concepts “From both an engineering and economics view…”
Hidden assumption hunt Model must infer “Check for assumptions that change the conclusion”
Comparative scoring Combines qualitative + quantitative “Rank and justify…”
Trade-off analysis Conflicting factors trigger depth “Identify trade-offs and thresholds…”