The Confessions of a Content Marketer

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Hey—It's Tim. 

The weekend has gone by much too fast and that familiar Sunday night knot is tightening in my gut.

So I figured I’d un-tie it the only way I know how: blurt out a few sins.

Confession Booth

Five jobs.
Five oh-god-why-did-I-do-that moments.
One marketer who should’ve known better.

The Rookie Drafter

Structural-engineering office, 2012. I was meant to draw beams, not blog posts, but I volunteered to “do some SEO.” I stuffed “3D visualisation tool” into a footer 42 times and wondered why Google laughed.
Lesson: Ranking ≠ repetition. It’s relevance (and maybe humility).

The Moonlight Freelancer

Evenings in a tiny flat in London, emailing 200 local businesses because someone said cold outreach builds grit.

Underpriced every proposal, spent most of it on courses that taught me nothing, still felt guilty raising rates 10 %.
Lesson: Charge what fixes the client’s problem and your rent -anything less is charity dressed as hustle.

The Agency Guy

Fancy office (WeWork), fancy deck , zero clue why the 87-slide “content roadmap” didn’t land. The client wanted three articles, not a novel.
Lesson: Strategy isn’t impressive - outcomes are. Shove the surplus slides in the archive and get typing.

The In-House Lead

I treated every blog like a Broadway show: intricate stage directions, costume changes, closing-night panic.

Burnt half the budget chasing “thought leadership” that converted… nobody.
Lesson: Thought leadership without a thought-through funnel is just a diary on Medium.

The Founder & CMO

Penfriend.ai, present day.

I still overthink copy. I still rename a CTA five times. But now I ship, measure, and move on - because the company’s survival > my ego.
Lesson: Perfectionism is a tax you pay with growth potential. File that return quarterly, max.

Your Turn

Pick your three biggest marketing misfires.
Jot the bruise, jot the lesson, pin it above your laptop.

Tomorrow morning you’ll know exactly what not to repeat - and that’s half the Monday battle.

✌️ Tim "Wordpress Dashboard Confessional" Hanson
CMO @Penfriend.ai

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

P.S. If we ever share a pint, remind me to tell you the story of how a typo in a meta title ranked #1 - and why I didn’t fix it for six months. Our little secret till then.

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