Content lessons from Stephen Colbert
Ousted from CBS, but a living legend
Gary Bloomer | SHAKING THE TREE # 331
The single most annoying phrase in business is That’s how we’ve always done it.”
Why?
Because it’s a cop out: an entrepreneurial get-out-of-accountability-jail free card. Creating content that makes people pay attention rather than having them skim past means it being willing to do things differently.
Feathers are made to be ruffled. Difficult questions deserve to be asked and answered.
Emotions and expectations need to be expressed and addressed.
Which brings me, in a roundabout way, to Stephen Colbert.
Whether you know him from The Colbert Report, or The Late Show, or from his early days at Second City, Colbert is more than a comedian. He’s a masterclass in modern content strategy.
While most content creators were busy churning out vanilla, play-it-safe blog posts that sound like they were written by a committee, Colbert was busy building a decades-long career by breaking the very rules marketers hold sacred.
He began his show with a relevant monologue that addressed a range of topics and that poked fun at authority and the absurdity of life.
He brought in a range of guests (many of whom, granted, had a movie to promote or a book to sell), most of whom were wise enough and good enough sports to know what they were signing up for.
And he knew, respected, and acknowledged his audience (those in the studio and those watching at home).
Do you do any of this? I try to and I’m well aware that I have a long, long way to go before I can event think I’m getting close to the mark.
Stephen Colbert never did it the way it’s always been done. And for that reason, he stood out. He fostered a loyal following. And he was both admired and often feared by the people in power who were often the targets of his humor.
And in that, there’s a lesson for all of us.
As always, thanks for reading.
—Gary
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P.S. If you found this useful, share it with another creator who needs an ego check (in a nice way). Want more unfiltered takes on content creation? Join my newsletter. No fluff, just the stuff that works.
Next time on Shaking the Tree: The importance of making notes by hand
ABOUT THE AUTHOR: Originally from the U.K., Gary Bloomer is a writer, branding advocate, marketing specialist, and an award-winning graphic designer.
His design work has been included in Creative Review (one of the UK’s largest design magazines). Since 2009, he has answered over 5,000 marketing and business questions in the Know-How Exchange of MarketingProfs.com, placing him among the top 3% of contributors. He lives in Wilmington, Delaware, USA.

