The Call I Can't Forget

_{Day 187/100}

A Tuesday in August 2022, 9:02 a.m. Zoom.

Her camera pops on.

Kitchen table, hoodie, suitcase half-zipped on a chair behind her.
You can hear the kettle click off. Slack pings through her laptop speakers like rain on a tin roof.

She doesn’t do small talk.

Silence.
I see it - the red skin under her eyes, mascara smudge from rubbing.
She shows me her calendar: “All-hands,” “Founder sync,” “Sales demo,” and finally “Flight — LAS.”

Four weeks of conferences,
Eight people at the company,
One of them “Marketing.” Her.

We had done the upfront graft.

Competitor tear-downs. Keyword map. Ten outlines sitting there, ready - good ones.
And yet in the seven weeks together, zero new live articles.

Not because she didn’t care.
Because she has a thousand other things to do first.

I ask her what’s on the list for today, she starts listing.
Tell me if this doesn’t sound familiar…

finish the homepage rewrite,
build a whitepaper,
draft nurture emails,
slice last week’s webinar into shorts,
chase a customer quote,
fix UTMs,
update pricing tables,
QA forms,
get quotes for graphics,
brief a freelancer,
rewrite what the freelancer sent back,
fire that freelancer,
jump on a sales call “just for context,”
prep booth swag,
book the flight,
send the agenda,
answer “quick” questions in three threads,
and - somewhere in there - “make a world-class blog.”

Her voice drops.

“I can’t get the founder for a quote. I can’t keep the voice straight. If I publish something half-baked, it’ll haunt me. If I wait for perfect, I’ll never ship.”

I ask one question: “What would make this week winnable?”

She doesn’t hesitate.

That was it.
That was the moment.

Not a lightning bolt.
A slow, heavy click.
She didn’t need a bigger strategy doc.
She needed oxygen. She needed the jobs behind the job handled.

The interview she didn’t have time to run, the first draft she didn’t have time to hate, the confidence she couldn’t borrow from a dashboard.

If you’re reading this and it feels uncomfortably familiar

Yeah. It’s you. It’s me. It was her.

This is why I’m making Penfriend

That Tuesday call was the click. Not fireworks - just the quiet certainty that we keep losing weeks to jobs-behind-the-job.

She didn’t need “more strategy.” She needed a way to breathe: get a quote without playing calendar Tetris, turn an outline into a draft that actually sounded like them, and know - honestly - when “good enough” is good enough.

I’ve been her at every rung.

Freelancer waiting on a founder’s voice note.
Agency lead rewriting v7 at midnight.
CMO trying to ship while the plane boards.

That call wasn’t unique. It was the pattern. So I stopped trying to be everyone’s extra pair of hands and started building the tool that gives you yours back.

It all kicks off tomorrow…

✌️ Tim "final_final_v7_really_the_last_one_this_time_I_swear_to_god" Hanson
CMO @Penfriend.ai

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

P.S. That site? We pulled it back after she got back from the 4 weeks of shepherding a booth.

Earnt me one of these :D

Penfriend.ai
Made by content marketers. Used by better ones.