Pricing and free trial: the two hardest decisions I made building WorkBuddy

WorkBuddy is an AI-powered work journal for the self-employed and solo workers. You journal your workday in five prompts, plan for tomorrow, and every Sunday night you get an AI-generated summary of your week. Patterns you missed, wins worth celebrating, honest reflection on what was hard. I'm building it solo alongside client work and launching mid-August.

Pricing a product you built alone is uncomfortable in a specific way. There is no one to sanity-check you. No team to pressure-test the number. Just you, a blank doc, and the quiet suspicion that whatever you pick will be wrong.

I landed on $12/month or $120/year. One plan. Everything included. I'm happy with it now. Getting there took longer than I'd like to admit.

The free trial decision was harder.

I started with 7 days. It felt standard. Enough time to try the product, form an opinion, decide if it's worth paying for. Except WorkBuddy has a problem with 7 days.

The flagship feature is a weekly AI summary, generated every Sunday from your journal entries. It's the whole point. It's what makes the journaling worth doing. And with a 7-day trial, a user who signs up on a Saturday sees nothing on Sunday. Then, if they don't convert before the next Sunday, they never see it at all before getting locked out.

I was asking people to pay for a feature they'd never experienced. That's not a trial. That's just hoping they trust me.

So I moved to 14 days. Two Sundays guaranteed. At least one full week of journaling with a summary waiting at the end of it. That's what the product actually needs to make its case.

The trade-off is obvious: longer trial, slower conversion signal, higher chance someone journals for two weeks and decides it's not for them. I made peace with that. A user who experiences the summary and still doesn't convert is useful information. A user who churns before they ever see it is just a gap in the funnel.

No credit card required. Data preserved even after lockout. If someone pays a month later, they pick up exactly where they left off.

Launching mid-August. Beta access closes soon. Check it out.