_{Day 197/100}

Hey—It's Tim. 

If you are done with the launch, then just scroll a bit. This is for people that want in.
I promise after this it’s a normal newsletter.

Ok. Now that I’ve paid the bills, let’s do the fun thing.

I started drawing you.

Not metaphorically. Pencil on paper.
Three tiny characters who sit beside my screen and stare me down while I write.

It’s the cheapest copy upgrade I’ve ever shipped.

Draw your reader (literally)

I’ve always loved character drawing, so this came naturally during the rebuild.

It’s the specificity. When I sketch “you,” my writing stops trying to please the internet and starts helping a person.

And all these people I’ve been at some point in my life.
I’m writing to versions of me in the past that would love to know what I know now.

Everything tightens: fewer hedges, cleaner verbs, more “here’s what to do next.”

Three tiny sketches I write to

The Solo Operator

MacBook open to three Google Docs titled V2_final_FINAL, Toggl ticking, invoice draft sitting in Wave.
Afternoon “deep work” happens at the café table by the only outlet.
Your AirPods live on Transparency because clients love surprise Loom links.
You keep a Notion page of client voices (“Tom use long paragraphs to seem smart, hates exclamation marks”), a folder of swipe files called “hooks lol,” and four Upwork invites you’ll never accept.
he day oscillates between “quick tweak?” DMs and praying a client extends the retainer before rent hits.

Tell-tale habits: saves links to read at midnight, edits in Grammarly but trusts gut, writes the first line three times.

The In-House Island

You live in a WeWork with a coffee you got for free when you walked in.

Calendar Tetris says Campaign > Webinar > Email > Maybe Blog?
Legal sits on v4 (“circling back next week”).
Sales pings: “Got a one-pager we can send today?”

Your doc titles are CaseStudy_Draft_v7_FINAL_final and your KPI is “make pipeline move,” not “get 10k views.”
You’re allergic to meetings that create tasks for you.
You want content that doubles as a deck for the AE, a post for LinkedIn, and a nurture email - without begging an SME for quotes.

Tell-tale habits: keeps a stash of approved phrases, writes in bullet points first, measures success in “things sales actually sent.”

The Team Lead / Head of Content

You manage two writers, one designer, and thirty opinions. Margin dies in round-three edits. Clients ask for “more thought leadership” and you translate that into briefs at 10:47pm.
Your superpower is voice QA; your curse is being the bottleneck. Asana boards look green until you open the doc and… nope.
You want drafts that pass QA first time, sources that withstand a skeptical CMO, and an output curve that bends up without adding headcount.

Tell-tale habits: color-codes briefs, leaves timestamped edit notes, keeps a “never again” list of banned phrases.

Sorry, not sorry if any of these are you.

Vague avatars make beige copy. Make them uncomfortably specific:

• Give them a setting (corner table by the outlet, booth #3, desk by the ficus).

• Give them a constraint (45 minutes before the 2pm stand-up).

• Give them one obsession (reply-worthy emails > traffic at all costs).

• Give them a tell (saves three competing headlines into Apple Notes named “lol”).

The more real they feel, the braver your sentences get.

The twelve-minute exercise

Minute 0–3: Draw three stick figures. Add one prop each (laptop sticker, lanyard, invoice PDF).
Minute 3–6: Write a single “unlock line” for each (see above). Tape them above your camera.
Minute 6–9: Pick today’s reader. Write a 30-word promise they actually want.
Minute 9–12: Draft the opening paragraph addressing them by their world, not their title.

Steal my mini-card template:

Name: __________
Where they are right now: ______________________
Time constraint: _______________________________
One obsession: ________________________________
One fear: ____________________________________
Unlock line: _________________________________
What I will help them do today: _______________

See you tomorrow for the big day :D

✌️ Tim "I drew the rest of the owl" Hanson
CMO @Penfriend.ai

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

P.S. This is the last you’ll hear of the founder tier. I’m done after this. It goes away in less than 10 hours anyway, so I literally would have nothing to say.

Back to the regular show tomorrow.
Thanks for sticking around.

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