The Lines We Never Asked About
AI exposed boundaries that creatives never bothered to understand.
Put yourself in the shoes of a painter who’s spent decades mastering your craft.
You’ve studied composition, light, and shadow for years. You’ve paced in front of countless blank canvases, sketched through millions of pages. You’ve agonized over painting a single blade of grass, willing the light to bounce off it just right.
Then one day, someone builds a tool that mimics paintings like yours. What took you a lifetime to master now takes a middle schooler a few keyboard strokes.
Untrained eyes look at this AI-generated “artwork” and think it’s amazing.
But you see every flaw.
And so it goes with every creative endeavor that’s getting displaced with AI—including writing.
When the average person uses AI to write, they feel empowered. They can now produce highly convincing content without all the toil of learning the craft.
Meanwhile, writers look at it the way a Michelin chef tastes a frozen dinner. Sure, it might satisfy hunger. But we can spot every shortcut, every place where depth got replaced with pattern-matching.
But the part that really stings?
For most business purposes, AI content is good enough.
Good Enough Is Good Enough
Like it or not, AI-generated writing gets engagement. It gets clicks and shares. Most people haven’t studied the craft like writers have, so they just see interesting ideas arranged in familiar patterns.
It’s convincing enough to pass muster with the masses.
Writers dunk on AI because—from our perspective—it’s mediocre at best. But to the majority of the business world, it works just fine. Plus it’s faster and cheaper than hiring a writer with talent.
It’s infuriating to watch your life’s work reduced to a commodity. To see the nuance and care you bring to every sentence get dismissed as unnecessary cost.
If you’re an artist, you’re likely outraged. But don’t make the mistake of blaming AI.
AI didn’t create the problem. It’s a scapegoat. The real problem is that AI has exposed what was always true.
Companies Don’t Value Creativity
Companies have never truly valued the art behind creative work. They only value the outputs. Technology just removed the need to pretend otherwise.
Here’s what I mean:
Artists value the mastery of their craft. The hours spent mastering rhythm and emotional resonance. The process of wrestling with old ideas until something new appears. The connection that forms between our work and other people. For us, the creative process is the reward—not the output.
Business leaders value entirely different things. Efficiency and predictable outcomes. The ability to scale without increasing costs. Metrics that fit neatly into spreadsheets. To them, creative work is a means to an end—and that end is always money.
This is why CEOs and CFOs can’t see what creatives see.
Artists aren’t better or smarter than them. People just lack the exposure and experience and expertise. To them, content is a lever to pull to make money. Humans are resources, listed alongside copy machines and computers in their ERP. And when you compare the cost of people to AI—people lose every time.
Look, I’m not saying every business is the enemy of art. That’s not what this is about. Business leaders can value creativity. But there’s a reason it’s so rare.
The Audience Problem
Think about the B2B companies people celebrate for bold, creative marketing. A few that come to mind are Vector, KlientBoost, and Klue.
Who celebrates them? Marketers. Who do they market to? Marketers.
They get to be creative because their audience permits it and wants it.
But if you’re marketing finance tools to CFOs, forget creativity.
If your buyers work in conservative industries—finance, healthcare, industrial—executives will tell you they “just want the facts.” That creativity will turn them off. That you need to play it safe.
But here’s what I can’t figure out: Do B2B audiences really prefer boring, safe marketing? Or have executives just convinced themselves they do?
What I do know is, B2B business leaders are risk-averse. It’s easier to play it safe than take the risk by coloring outside the lines. And when leadership won’t let you test creative ideas, their belief becomes your reality.
AI didn’t kill creativity in B2B. Risk-averse leadership did. AI just made it cheaper to stay comfortable.
The Lines We Never Asked About
Have you ever created something with personality—something more human—only to hear that it’s “not professional enough”? That it’s “too edgy for our audience”?
I’ve seen this play out more times than I can count. Marketing makes a bold play. Leadership responds with polite concern. The piece gets watered down or squashed entirely. Everyone moves on.
It happens because marketing was drawing outside the lines that no one told them about.
No one communicated the vision upfront. No guardrails to reference. We just get a vague mandate to “create compelling content” or “make us stand out,” followed by surprise and disappointment when the result doesn’t match the unstated expectation.
So whose fault is it? Leadership’s, for not communicating their vision? Or is it ours, for not asking before we started?
There’s a conversation between Dave Gerhardt and the great Mark Schaefer that’s been rattling around in my head.
Dave says: “It can’t be that we’re all just morons, right? I know a lot of smart marketers who are maybe trapped at the wrong company...I found that it’s usually some company strategy things that are flawed. Show me a company with a great strategy from a business standpoint, I’ll show you a marketing team that can be successful. Is that where you see it?”
Mark replies: “I’ve got a little video on my YouTube channel. It’s sort of like a movie trailer for the book and I start out by saying it’s not your fault. Most people, they want to create, they want to innovate, they want to do better. But we have this infrastructure of fear in our industry. There’s a scaffolding of fear holding boring in place.“
I’ll link Mark’s video below. Watch it. If you’re like me, it will resonate. You’ll get fired up about the injustice of it all. It feels so true.
But, I wonder.
I wonder if we can become so certain that we’re the good marketer stuck in the bad company that we never stop to ask whether we fully understood the job.
Maybe creative marketers confuse “creative direction” with “creative freedom.” Maybe the job was never to be an artist, but rather a creative professional within the boundaries of the business.
Learn About Your Boundaries
Yes, companies can value creativity. But creativity without constraints is just self-expression. Before we push against constraints, we need to understand what they are and why they exist.
You can bring creative excellence to work that serves business goals. You can care deeply about craft while acknowledging that not every piece needs to be art.
But you need to learn your boundaries first. Here’s how:
Ask About the Lines Before You Color Outside Them
Level-set with leadership upfront. Understand their vision before trying to execute on it. What does “professional” mean to them? What does “on-brand” look like? Where’s the boundary between safe and stale? Where can you carve out some space to experiment?
Know Which Game You’re Playing
If you’re marketing to marketers, you might get to flex creativity. If you’re marketing to other B2B buyers, understand their expectations and interests. The boundaries aren’t arbitrary. They’re either imposed by assumptions or imposed by your audience. If it’s the former and not the latter, make the case for change.
Separate Craft from Ego
You can care deeply about quality without needing every piece to be your magnum opus. Some work is meant to be functional, clear, effective. Save your creative energy for more high-impact content. Not every blog post needs to be a manifesto.
Recognize When You’re in the Wrong Environment
Some companies genuinely can’t support creative work in their market. Their audience won’t tolerate it. Their leadership is too risk-averse. Their industry is too conservative. As Mark Schaefer says, it’s not your fault—there’s a scaffolding of fear holding boring in place.
Before You Push Back
The painter will always see the flaws in AI-generated art. The untrained eye will always think “good enough” is good enough. And for most business purposes, it is.
AI didn’t change what businesses value. It just made their priorities brutally visible.
You can grieve that reality. You can rage against the scaffolding of fear. You can feel frustrated by risk-averse leadership. But you can also get clarity before you start creating.
No matter where you work, the lines are always there.
Some constraints are real. Some are just assumptions that need to be tested. But you won’t know which is which until you ask.
Napkin Notes
Here’s a link to Mark’s video I mentioned. It’s for his new book, which “sets a framework for human-centered marketing that transcends the AI pandemic of dull.” Great line.
“The longer you work at a craft or discipline, the more difficult—and rewarding—it becomes to improve. Going from zero to 80 percent is easier than going from 81 to 90 percent. Going from 91 to 95 percent is more challenging still. And going from 96 to 99 percent could be a lifelong pursuit.” – Eddie Shleyner