Should Writers Start Branding Themselves “Content Entrepreneurs” To Escape Freelancing Suckydom?

There’s a distinct possibility that this photograph was taken ten seconds before a prospective client asked this guy: “lovely draft. Could we see a V8?” Photo by Ron Lach from Pexels

As an active Medium publisher, I also read a fair amount of writing on this network also.

I’m also beginning to try to engage more with other writers here. This is what makes Medium such a cool idea in my opinion: it’s a writing community that’s also a social network. (Why are the italics there: I will make my best effort never to refer to another author’s writing as “content”; nor them as a “content creator”)

If you enjoyed a piece — or disagreed with it — you can pop into the comments section and let the author know. Even a relationship borne from differences of opinion can become something fruitful.

This afternoon, a piece popped up on my news feed that instantly caught my attention.

It didn’t hold back with the headline either: “Fuck Writing Jobs” K.B. Hubbard proudly intoned.

My initial response to this was “K.B., I’d be happy to get a drink with you any time, buddy”

I’ve been writing ever since I first started hemming words into one of those clunky old digital typewriters that were the stopgap between real typewriter and word processors (probable age: about 10).

I hold what typically feels like a pretty useless degree in journalism; covered a historic state visit with a press pool and got to look like I knew how to react when presented with the sight of the Queen of England visiting my hometown (no that’s not a metaphor); and have written everything from clickbait articles about how to microwave burgers to speeches for city mayors commemorating honors on authors and advertorials trying to get Irish Americans to visit Irish islands (they’re a heavenly patch of the Emerald Isle didn’t you hear?). (I guess you could say I’m a failed journalist that ended up in corporate comms).

But I recently explained why I’ve decided to drop the ‘writer’ branding altogether. Because it’s sucky. And because a friend of a friend once told me about the sunk cost fallacy and I’ve finally accepted that that applies to more than throwing out old electrical appliances because “making shawarma at home with this thing would be cool. Besides, we’ve been storing it for a year.”

But if you want me to compact a long and emotional read into a single paragraph and dig in further: I realized, some time last year, that writers are being chronically short-changed by companies who assume that writers can only write and thus deserve to be compensated merely for the (short) amount of time they imagine it takes them to do that.

When a company that had just raised $10 million dollars asked me if I could do better on a $400 quote for a piece of writing, I knew that we writers were all (yes, collectively) doomed.

They needed writers with niche experience and a portfolio of pieces. Both of which I had (I hesitate to say “in spades” but … I’ve been doing this for a while). With $10M in the bank they shouldn’t have had to be scrimping. And yet here they were doing just that. Again. This was the niche B2B tech space that the money is apparently aflush in (it is; just don’t sell yourself as a writer).

So there I was asking myself if I should drop the price by $100 or send back a simple but ill-advised one sentence email I feel like K.B. might have appreciated: “f**k you you miserly p**k!”

(Here’s a sanitized formulation if you need one: “Thanks for that transparency about your budget! I think we’re going to have a hard time meeting in the middle here. Perhaps I can suggest instead my nephew Dave. He’s living in a shed somewhere out rural and I don’t think he’s eaten in weeks so I’m sure he’d be happy to just do this for exposure and then potentially we can talk about his usual rate, which is $0.00001 per word”).

Oh yes — and my career micro-pivot.

After knocking together brain cells with a brand strategist who lives locally to me, I determined that I was dealing with the right clients but approaching them all wrong by grossly underselling what I could do for them. He was selling consulting services for (at least) four figure retains. I was trying to knock down quotes on blog posts by $100. Something gave.

The game plan I cooked up for myself:

By simply widening out my service offering to re-position what I used to do for businesses — marketing communications — I could make more money and not be treated like the literary equivalent of a code monkey. Fun, no? Ironically this sometimes simply involves finding different ways to describe the mechanisms through which I can bring value in different ways. I de-niched a little and played some Scrabble. A literary pursuit after all.

So even though I think that “content” is frankly the dumbest word the marketing universe has ever cooked up that fails to really distinguish between the words on the back of a cereal box and an Oscar-winning piece of cinematography, I’m with the thrust of the argument.

But then K.B.’s piece took a turn that I found less agreeable. Or rather one that I thought was worth opening for discussion.

“Take Your Skill And Make A Skill Baby With It “

So let’s get back to K.B.’s piece:

After dropping a few F-bombs in the direction of “writing jobs” (I’m a bit more old fashioned than K.B.; I try not to swear online but I share his disdain), K.B. finally lays out his plan for writers who want to escape the sinking cesspool that is today’s “content writing” industry.”

Here it is in full:

Here’s my (repeatable, easily stolen) plan:

What skill can you mate with writing? I don’t mean mate like glue together. I mean actually mate. Take your writing skill and find another thing in your life that you’re passionate about. Make babies.

Your skill-baby is your new content niche.

Register an LLC.

Don’t be scared to build relationships with businesses. Cold-call, cold-email, invite them on a lunch date, send them a hand-written follow-up letter.

Hubbard then suggests that those following his plan reframe themselves as “content entrepreneurs.”

Content entrepreneurs are a group of individuals with a unique talent; the ability to generate exceptional content. Not “okay” or “passing” content, but truly exceptional content that readers actually enjoy and find useful.

And he suggests as possible examples of that four formats that to me sound extremely … commonplace:

Unique, in-demand eBooks

Press releases

Content marketing

SEO rewriting

Here’s My Recommendation For What To Do Instead

I didn’t sit down at my keyboard to write a hatched job about a man known as K.B. Hubbard.

K.B. might be a great guy, but I had never heard of him today. I doubt extremely much that he’d ever heard of me. But now we’ve had the pleasure of crossing paths digitally. An amazing this, this internet, eh?

I fundamentally disagree with most of Hubbard’s argument even if I can get on bored with the basic premise that “the writing market sucks and rather than get stuck doing gigs we need to start thinking about ways to do stuff that’s a lot better.”

I like the idea of rebranding what we do for two reasons:

  • For writers to survive in this increasingly brutal marketplace, we need to hold our heads up high. However, I also think that calling ourselves “entrepreneurs” if we’re not actually doing something unique is delusional. As a freelance writer that has gone through bouts of mild depression when the market was at its bleakest and a long succession of prospects were asking whether I could make $300 $200 or $100, I’m in favor of better self-labels even if they just make us feel a little more optimistic about what we do. Being chronically devalued is more than sucky. It’s erosive to self-esteem. I venture the following assertion: most of us doing this for a living are so much more than just “writers.”
  • “Content” is such a stupid word that almost any appellation is better. Ditto “content creator” which just emphasizes that you make something incredibly vague and undefined. What are most “content marketers” doing? A modern version of brand journalism that involves some version of weaving organic keywords into texts or video or audio (or an admixture thereof). That’s enormously commonplace. Fortunately there are ways to distinguish yourself from the crowd just a little.

K.B. insists that finding a “skill baby” (to me that just sounds like a niche) and creating (subjectively) content make you eminently unique.

But I’m pretty sure that many businesses would think otherwise. Sorry. That just makes you another freelance writer. What’s your hourly rate?

A Remix on K.B.’s Plan

So as much as I disagree with constituent elements of it, I like K.B.’s plan because — fundamentally — it’s a call for writers to do something different and to start branding themselves as more than just people who can move their fingers over a keyboard to put text on the internet.

Because as the rise of writing bots like bears out (I try to take a dig at them once every few articles), by marketing ourselves thusly we now find ourselves competing with robots to stay relevant. Surely a low point for the writing profession if there ever was one.

So because I see value in K.B.’s argument but think it doesn’t go far enough, here’s a remix on it. (A derivative work of the KBH (K.B. Hubbard). OK now I’m just trolling this guy by trying to be deliberately creepy. )

  1. Expunge the word ‘writer’, ‘content’ and ‘content creator’ from your brand presence and find more descriptive and unique ways to describe what you do.
  2. Find that extra skill that Hubbard talks about. But either: a) don’t position it as content creation. Or b:) make it subject matter experience in a damn obscure industry that not many people are competing in. Now put THAT front and center and the writing/content stuff second.

For instance change:

“I’m a freelance content writer who writes about AI and is very passionate about it. I have a wide reaching portfolio of previous blog posts”


“I spent 3 months learning how to build my own computer model and actually understand how algorithms work. I specialize in building out branding and communications strategies that will drive home what your company does to help people actually get it. My previous clients say it helped them double their inbound leads”

Writer 1 is a generic freelance writer. A chump clutching to an online portfolio and hoping that somebody will rustle up a few dollars to pay them to write their blog. I have spent far too much of my career being that chump. Only a chump changing their colors knows the true pain of chumpdom.

Writer 2 is something a bit different animal. He’s not a writer.

I like to throw down some predictions on Medium so that in two years’ time I can write a bragging article that says “I predicted the future so please hire me.” I kid (mostly).

Writers are screwed. And writers are only going to get more screwed as the content drumbeat keeps getting louder and we’re increasingly seen as just the people who feed ideas into AI bots that create as much of it as fast as algorithms can.

A great way out of that future of bleakness and $100 discounting is to reframe what we do and how we add value. Emphasizing unique skillsets and industries is a great start. Feel free to weave in the content angle. Naturally always focus on the value you can bring, quantify it wherever possible, and leverage social proof to show that others can affirm your greatness. But do what you can to get away from the masses.




Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things.

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Daniel Rosehill

Daniel Rosehill

Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things.

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