Introducing Humbled and Grateful

Humbled and Grateful started the same way many bad leadership posts do. With a pause. A deep breath. And the quiet realization that something had gone terribly wrong.

For years, my LinkedIn feed has been flooded with a very specific genre of writing. The anguished executive LinkedIn confession. The founder who “didn’t sleep” before making a decision that somehow only improved their own life. The leader who couches every act of power in vulnerability language, hoping empathy might dull the edge. And now, even worse, these "deep thoughts" aren't even original - they are 100% AI generated.

After a while, it stopped feeling accidental.

I kept seeing the same patterns. The same tropes. The same humblebrags dressed up as wisdom. The same moral theater performed by people who never actually risk anything when the curtain falls.

Humbled and Grateful exists because there was too much of that and not enough people pointing at it and laughing.

Satire, Not Parody

This site is not about dunking on individuals. It is about holding up a mirror to a culture that has learned how to aestheticize authority.

The CEO who “anguishes” over layoffs, only to be rewarded with a staggering bonus hours later. That is not fiction. It is just the emotional framing turned up enough that the absurdity becomes undeniable.

If you missed it, The Burden of Leadership: Navigating Choppy Waters captures that exact moment of executive self reflection and gratitude.

Or the startup founder explaining why his kids will not be getting Christmas presents this year because “the real gift is the grind.” A masterpiece of rationalization, sacrifice theater, and misplaced virtue signaling.

Or Morgan, Security Whisperer, dispensing Die Hard inspired wisdom to the cybersecurity trenches with complete sincerity and zero self awareness.

None of these are exaggerations. They are compressions. The joke works because the original material already lives one step from parody.

Why Satire Works Here

Modern leadership culture has learned how to be unfalsifiable. Any criticism can be reframed as a lack of empathy. Any pushback can be dismissed as negativity. Satire cuts through that because it refuses to argue on the same terms.

Instead of saying “this is wrong,” it says “this is exactly what you sound like.”

If you laugh and feel uncomfortable at the same time, good. That tension is the point.

Not Just Writing, Also Building

Part of the joy of this project has been that it is not just editorial. It is also technical.

I used this as an excuse to build a fresh content and video pipeline from scratch. Automations powered by n8n. Audio transcription using OpenAI Whisper. Templates and text generation stitched together ffmpeg, which turned out to be far more pleasant than expected.

Search is handled by Meilisearch, which has been a refreshing reminder that software does not have to be complicated to be powerful. It just has to be honest about what it is trying to do.

Building the stack has been as much fun as writing the posts. There is something deeply satisfying about pairing cultural critique with clean, simple systems.

Where Else to Find Us

The satire is not confined to the site.

We are actively posting short form video on TikTok and on Instagram.

YouTube and other platforms are coming soon. The tone will remain the same. Earnest delivery. Straight face. Just enough sincerity to let the content indict itself.

Why This Exists

Humbled and Grateful is for anyone who has ever read a leadership post and thought, “This can’t be serious,” only to realize it absolutely was.

It is for people who build things and are tired of the performance layer wrapped around power. For people who recognize the language. For people who have learned to spot “grateful for the journey” as a warning sign.

If you see yourself reflected here and feel defensive, that might be worth sitting with. If you laugh, you are probably already in on the joke.

More coming soon. Always humbled. Always grateful.