Choosing a paid plan
When to upgrade, how to compare plans, and what to check in the terms and after you buy.
What it is
A paid plan makes sense when you keep running into a specific limit on the free one and you know which task the upgrade will solve. This checklist takes you from that question to a reminder before renewal. There are no prices here because they change: see the What's current page and the official sites. To compare several services side by side, use the "Compare tools before you buy" sheet.
- Plans
- Subscriptions
- Choosing
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BEFORE YOU BUY
- [ ] You've used the free plan for at least [2 weeks] and keep hitting a specific limit (message cap, a feature you need, file size), not just "I'd like better"
- [ ] You've written down which task the paid plan will solve and how much time it will save each week
- [ ] You've done the math: hours saved × the value of your hour is more than the subscription price
- [ ] You've checked whether the feature already comes with something you pay for (email, office suite, CRM)
COMPARING PLANS
- [ ] Prices and limits come from the service's official website today, not from an article or a video
- [ ] It's clear exactly what is limited: number of messages, file size, access to models, features
- [ ] Sales tax and any currency conversion fees are factored in
- [ ] You've compared monthly and yearly billing; choose yearly only after a month of real use
- [ ] For a team, look at a team plan: shared projects, access management, data terms
DATA AND TERMS
- [ ] You've read how the service handles your data on this plan and whether you can turn off its use for training
- [ ] If you work with client data, the plan fits the requirements of your contracts
- [ ] You know how to cancel and what happens to your files and history after you cancel
AFTER YOU BUY
- [ ] A reminder on your calendar 3 days before renewal: "Am I using it? Is it paying off?"
- [ ] All subscriptions are in one list with price and renewal date (see the "Cost of your AI tool stack" calculator)
- [ ] In a month: if you use it less than once a week, cancel or move to a lower planLessons that use it
More in Checklists
- Before you launch a product · 27 items: payments, analytics, legal basics, support, launch day and a review one week later.
- Data security when working with AI · What not to paste into a chat, which settings to check and how to limit AI agents.
- Onboarding an employee or contractor · What to prepare before the first day, and what to do on day 1, week 1, month 1 and day 90.
Checked: October 2026