From the HOW TO // AI newsletter · howtoai.com
Should you pay for AI? This kit answers it for your situation in about 15 minutes: a 3-signal test, 5 copy-paste diagnostic prompts, a current comparison of the four big tools, and a monthly audit so you never pay for something you stopped using.
⚠️ Pricing note: every number below was verified on September 18, 2026 against official pages. Where a company doesn't publish a number, we say "not published" instead of guessing. AI pricing changes constantly. The official links in Part 3 are always the final word.
You need a paid plan when ANY of these is true. Not before.
☐ Signal 1: You hit limits mid-task more than once a week. Not "I saw a limit warning once." A cap that stopped real work, repeatedly. Occasional limits are free working as designed.
☐ Signal 2: A feature you need does not exist on free. Examples in 2026: scheduled tasks (ChatGPT, starting on the $8 Go plan), video generation (Gemini), image and video generation and Expert mode (Grok), higher-tier models for complex work (all of them). If your task needs the feature, no amount of patience unlocks it. (Custom GPT creation used to be on this list, but OpenAI's own pages now disagree: the pricing page lists it on Go and Plus, while the help center says new GPTs can't be created on any personal plan.)
☐ Signal 3: You bill for the output. If AI work goes to clients, your boss, or your business, the math changes completely. One saved hour covers the month.
Zero boxes checked: stay free, with pride. The free tiers in 2026 are better than most paid tiers were two years ago.
Run these on your free plan this week. Where they fail tells you exactly which ceiling you're hitting, and whether it's worth $20 to remove it.
Prompt 1: The Long Document Test (tests context limits)
I'm pasting a long document below. Read all of it, then: summarize it in 5 bullets, list any deadlines or numbers it contains, and tell me the one thing a busy person would miss on a skim.
[Paste the longest work document you have]
If the AI loses the middle of the document or refuses the paste, you found the context ceiling. Free ChatGPT holds roughly 12 pages of input; Go and Plus hold about 40 (and around 320 in thinking mode). Gemini's AI Pro tier jumps from the free 32K-token window to 1M.
Prompt 2: The Volume Test (tests message limits)
I'm going to work through a project with you in many small steps over the next hour. First step: help me outline [a real task you have]. Keep answers short. I'll say "next" after each.
Work in rapid short messages for 30 to 60 minutes. If you get throttled or downgraded mid-flow, that's Signal 1 in action. The caps work differently on each tool: Claude's and Gemini's free allowances refill every 5 hours (Gemini also has a weekly cap), ChatGPT's everyday chat is unlimited but its tools (uploads, images, voice) have their own caps, and xAI doesn't publish a number for free Grok.