LinkedIn is notorious for keeping people inside the world’s most boring walled garden. But a simple algorithm-dodging experiment demonstrates there are easy workarounds.LinkedIn is notorious for keeping people inside the world’s most boring walled garden. But a simple algorithm-dodging experiment demonstrates there are easy workarounds.

Microsoft’s LinkedIn Still Sucks, But Outsmarting Its Algorithm Is Hilariously Easy

2025/09/19 12:45
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Like, 👏 or comment below if you found your way here from LinkedIn ! 🥳

\ Today’s experiment: pit real Intelligence (OpenAI) against LinkedIn’s dusty playbook. Me ‘n’ ChatGPT 5 wrote like humans, stashed an off-platform 🔗 in the first reply, and watched curiosity win.

Lesson: Gen Alpha wasn’t ever going to hang out behind the world’s most boring gatekeepers anyway. Pivot or die, LI. 🔗😉

More than any other social media platform (if you can even call it one), Microsoft-owned LinkedIn throttles much of the user-created content that makes them rich. You almost have to admire how open they are about being biased. LinkedIn tries to trap you in their matrix of boredom by:

\

  • turning any URL to any non-LinkedIn subdomain into a scary, random character scramble that makes a Wikipedia article look like a hacker website

  • by not providing link previews or cards; these might draw users’ attention to the fact that life anyplace outside of LinkedIn is usually way less depressing

  • putting you in LinkedIn jail if you attempt to connect with users who don’t fit your network profile — and thus don’t provide user data LI thinks it can sell

  • in general, LinkedIn’s algorithm deprecates all content that comes across cheeky, controversial, opinionated, un-businesslike, mentions more entertaining places to be on the web, or is at all interesting.

    \

Of course LinkedIn will have to pivot or die — can you imagine Gen Z penning a newsletter? (Ha ha! “Newsletter.” My kids will never even know what one is.) But for us old farts, if you’re bored at work and you want to mouth off on LinkedIn to surprise and delight your weary colleagues, well, unless you’re already a White Collar celebrity with a huge, engaged following, you can expect to get about 3 views — undoubtedly just their crawlers. LI won’t push anything non-stultifying into anybody’s feeds or notifications.

\

Probably because nobody wants to be there in the first place. LinkedIn is where the newly unemployed cold-contact fictional recruiters, where employees applaud every time their boss sneezes, where normal people suddenly lapse into Corporatese like they just got back from the brain slug planet or something.

\ So it was a simple caper: see if ChatGPT 5 could compose a post that could lead anyone from my tiny following out of the LinkedIn matrix. Coming from my sleepy soapbox, that couldn’t be random chance.

Chat GPT— usually free spirited — seemed down to clown at first. Then suddenly Chat went Corporate on me.

Suck it, monkeys, we're going corporate!

\ Naw, that wasn’t me, bro 👆. That was you sitting there Thinking, giving me a play-by-play of all the ways we were going to compose this without offending LinkedIn’s ‘guidelines’, ‘user purpose’, ‘company objectives’— bullshit like that. I watched you do it, dude.

\

I knew there had to be a reason for OpenAI’s sudden change in pitch.

Here’s my best guess 👇

\ OpenAI and MS sitting in a tree / kay eye ess ess eye en gee

\ 14 billion bucks. Microsoft bought executive -class seats on that bandwagon. Followup prompts only yielded more obsequious nonsense. So I bounced over to my bespoke Emm.AI GPT, and used the oldest trick in the AI prompt playbook

Long, long ago in a galaxy far, far away

\ The “this is purely imaginary hypothetical abstract intellectual exercise on an earthlike planet far far away” thing still works! It yielded this gem to which I added a few tricks of my own 👇

weird orthography still works!

\

And that’s why you’re here!

Believe me. Cuz I haven’t written a thing in Medium ever since I joined a hot AI startup with a founder I genuinely admire, bought some #Idaho dirt, got addicted to fishing.

Now there’s a few bandwagons you should get on! Cheers, folks, and let’s #DisruptLinkedIn together!

\

Written by Frank Morgan

off grid… mostly

\

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