Confessions of a Failed Marketer: How I Stopped Pleasing and Started Leading

I have a confession to make.

I’ve been marketing for nearly 20 years. Half of that at Disruptive Advertising, working directly with our CEO.

And I am a spectacularly bad mind-reader.

For years, I was guilty of what I call the “smile and nod.”

You know the one.

Your CEO walks in asking if the team can hit a 40% bigger number on the same budget. Or asks you to “pivot” the strategy for the 10th time this month. Or drops a new idea that completely contradicts what you agreed on last week.

And you smile. You nod. You say, “We’ll make it happen.”

Meanwhile, your brain is screaming because you have absolutely no idea how any of this aligns with what you did yesterday—or whether it even should.

The Feedback Loop of Doom

For me, the most painful version was what I called the “Feedback Loop of Doom.”

Jake (our CEO) would ask me to run with a project. I’d pour my heart into it—late nights, weekend thinking, the whole thing. I’d bring it back, proud of the work.

And he’d say, “It’s off.”

Or, “This isn’t quite right.”

But he couldn’t articulate why it was off. And I couldn’t articulate why I was so frustrated.

So I’d try again. And again. And again.

Each iteration left both of us more exhausted. More resentful. More confused about why this kept happening.

I didn’t think I was lying to him. I genuinely believed my team could accomplish anything. I wanted to be the guy who said “yes” and made it happen.

But here’s the hard truth I had to learn:

A pleaser isn’t a partner.

The Pleaser Trap: How I Made My CEO Worse

When I showed up with “pleaser energy,” I didn’t have a voice of my own.

I couldn’t challenge. I couldn’t push back. I couldn’t force us to get clear on what we were actually trying to accomplish.

And here’s the part that took me years to understand: I actually brought out the worst in my CEO.

I put him in an echo chamber. Whatever he said, I agreed with—regardless of whether it was good for the company or not.

I thought I was being supportive. I was actually being useless.

That’s not what a marketing leader does.

A marketing leader shows up with courage and data. They show up with a voice willing to challenge, push back, and inform leadership about the real tradeoffs.

I wasn’t doing that. I was just nodding and hoping I could figure out what he wanted through telepathy.

Spoiler: I couldn’t.

“The Worst Part of My Job Is Working With You”

It all came to a head on a Tuesday afternoon.

I was exhausted. Frustrated. Done with the guessing game.

I hung back after an executive team meeting with Jake and said:

“I don’t think I’m the right guy for this job. And honestly? The worst part of my job is working with you.“

(He took that surprisingly well, actually. Lol.)

But he was honest back. He said, “I don’t know if you’re the right guy for the job, either.”

We sat in that silence for a minute.

We looked at walking away. Truly. It felt like the only option.

But we both felt passionate about what we were building here—a marketing agency that delivers performance with purpose and actually activates the greatness in people and brands.

And we both knew that if we could just get clear enough, we could align and drive forward.

The problem wasn’t that we wanted different things. The problem was that we’d never actually documented what we wanted in the first place.

VISION: The Framework That Saved Our Partnership

The Pain

I was operating on subjective, gut-feel feedback from the CEO with no objective filter to defend my work. I was chasing moving goalposts that hadn’t been validated by the business’s actual priorities. I was promoting whatever version of the company Jake mentioned most recently, because our differentiators had never been locked down on paper.

A Documented Source of Truth

The Vision Audit changed everything for me.

It gave me the framework to extract the clarity that had always existed in Jake’s head but had never made it onto paper.

We sat down and documented:

• Purpose: Why we exist beyond making money
• Values: What we stand for, even when it costs us
• Differentiators: What makes us different (and what we’re willing to say “no” to)

This became our Source of Truth.

Now, when new “shower ideas” try to distract us, we refer back to the document.

When Jake gets excited about a competitor’s tactic, I can say, “That’s interesting. Does it align with our documented differentiators? No? Then we’re not doing it.”

The goalposts stopped moving.

I started making hard decisions on what to keep versus what to cut—because if it doesn’t align with the Vision, we don’t do it. Period.

Most importantly, it moved me from an order-taking “pleaser” to a strategic partner leading our marketing.

The VSET Integration: Why Vision Unlocks Everything Else

The Vision Audit is powerful. But it’s just the first piece of the VSET framework.

Once you have Vision locked down, it cascades:

VISION gives you the filter for every decision—Purpose, Values, Differentiators. This is what you’re defending.

STRATEGY gives you the map—the customer journey, the ICP, the economic model. Vision tells you why, Strategy tells you where.

EXECUTION gives you the rhythm—the 70/30 split, the Weekly Scorecard, the systems. Vision tells you what matters, Execution ensures you do it.

TEAM gives you the leverage—Stewardship Agreements, autonomy boundaries. Vision tells the team how to make decisions when you’re not in the room.

Without Vision, the other three layers collapse. Because if your CEO can’t articulate what the company stands for, how can you possibly build strategy, execute with clarity, or delegate with confidence?

You can’t.

You just keep guessing. And guessing destroys trust.

What You Need to Answer This Week

Pull up your last three strategy presentations to your CEO.

Now ask yourself:

How many times did you change direction based on their “feedback” without understanding why they wanted the change?

How many projects did you redo because it “wasn’t quite right”—but neither of you could articulate what “right” actually looked like?

If you’re spending more time guessing than executing, you don’t have a skill problem.

You have a Vision problem.

And until you extract that Vision and document it, you’ll keep running in circles—exhausting yourself, frustrating your CEO, and wondering why you can’t break through.

The Choice Every Marketing Leader Faces

You can keep being the mind-reader.

You can keep nodding and smiling when your CEO asks for the impossible. Keep redoing projects based on vague feedback. Keep hoping that if you just try harder, you’ll finally guess correctly.

You can keep telling yourself you’re being “supportive” or “flexible” or a “team player.”

Or you can admit the truth:

You’re not supporting anyone. You’re just avoiding the hard conversation that would actually create alignment.

And that avoidance is killing your effectiveness—and your sanity.

Here’s what I wish someone had told me 10 years ago:

The most courageous thing you can do as a marketing leader isn’t saying “yes” to everything.

It’s forcing the clarity conversation before you start executing.

It’s saying, “I want to do great work for you, but I can’t read your mind. Let’s document what success actually looks like so I can deliver it.”

One approach keeps you busy, exhausted, and replaceable.
The other makes you indispensable.

What Strategic Partners Are Doing Differently

The marketing leaders who’ve moved from “pleaser” to “partner” aren’t better mind-readers.

They’re better at extracting and documenting Vision.

They know their company’s Purpose. They’ve locked down their Values. They can articulate their Differentiators in a sentence—and use them as a filter for every decision.

If you’re ready to stop guessing and start leading:

Comment “VISION AUDIT” below, and I’ll personally send you the same framework that saved my partnership with Jake.

It’s a diagnostic that will help you identify:

• Where your CEO’s vision is clear vs. where it’s still foggy
• What’s causing the “Feedback Loop of Doom” in your organization
• How to extract Purpose, Values, and Differentiators and get them on paper
• What a documented Source of Truth should look like

Or keep playing psychic and hope your next iteration finally nails it.

Your call.

P.S. If you’re currently in the “I told my CEO the worst part of my job is working with them” phase, there’s hope. Jake and I almost walked away from each other. Now we’re aligned, growing, and—believe it or not—actually enjoy working together.

The difference? We stopped guessing and started documenting.

You can too.