Two things you need to know before you write another prompt

_{Day 86/100}

Hey—It's Tim. 

This one won’t take long.
But it might hurt a little.

Most AI prompts suck.
Not because the model is bad.
Because the person prompting it is confused.

And I say this with love.

Because I’ve done it.
For over 3,000 hours.

If you don’t know, I write all the prompts for Penfriend. All of them.
When you get an article written in Penfriend, there are over 800 prompts working for you.

I wrote all of them.

It didn’t start like that though.

Prompted ChatGPT. Gaslit myself for 3 hours.

It went like this:

• Wrote a vague prompt

• Got a vague answer

• Told myself “hmm, it’s close…”

• Tweaked it 11 times

• Still hated it

• Convinced myself I was the problem

• Gave up

• Rewrote it all manually

I wasn’t “working with AI.”
I was cosplaying as a productivity guru while spiraling in Notion.

When you:

• Understand the process you're trying to prompt for

• Know the audience you're prompting for

Most people (including me, at times) have neither.

1. You don’t know the job well enough

You’re prompting for a landing page…

But you’ve never:

• Mapped out a conversion flow

• Spent 10 hours in Hotjar

• A/B tested 6 above-the-fold headlines

So you ask ChatGPT for “a landing page for productivity software.”
It gives you lorem ipsum fluff with a CTA that reads “boost your workflow.”

You blame the model.
But it just mimicked the half-baked brief.

It’s not a bad assistant.
You’re a bad boss.

What to do instead:

Open Zoom. Share your screen. Hit record.
Do the task. Out loud. Explain each step like you’re teaching it.

Then give the transcript to GPT and say:

There’s your first draft of knowing what the hell you’re doing.

2. You don’t know your audience

You're asking AI to “write for B2B marketers.”
Okay. Cool.

But which kind?

• In-house senior strategist at a Series B startup?

• Agency freelancer juggling five retainer clients?

• Solo founder with two hours a week for marketing?

If you can’t answer that, how is GPT meant to?

You're not prompting.
You're praying.

What to do instead:

Pick five real people in your audience.
Pull up their LinkedIn. Read what they post. Check what tools they use.
Hell, ask them a few questions if you can.

Build a persona from actual people, not whiteboard dreams.

Now your prompts have a pulse.

I don’t hate AI.
I use it every day.
Built a whole company on it.

But here’s what I know now:

Want to do something wild?
Actually get good at the thing before prompting for it.

✌️ Tim "Prompt Engineered a Panic Attack" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. Remember that day last week when I said I was “spending time with the dev team mapping out the project plan”?

Well…

This is the Gantt chart.
And it’s giving equal parts chills and "hell yeah let’s go."

Send help.

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