Here’s the deal. Every time I think I’m past all the self-doubt, it comes back strong with a moment there, a random meeting, or the quiet corner in the office. And suddenly, the head trash is back.

HEYYYYYYY KYLE!!! I’M HERRREEEEEE.

It happened twice this week. Actually, I was reminded of it twice this week.

First, rewatching The Darkest Hour, when Clementine reminds Churchill that strength comes from imperfection and wisdom comes from doubt. I wrote about that line weeks ago, but it keeps circling back because it’s true in ways we don’t like to acknowledge.

Then Kady Srivivasan dropped one of the clearest explanations I’ve read about why leaders freeze or stay quiet long after we’ve “earned” our seat. She calls it Imperfection Syndrome. Not the fear of belonging but the fear of looking foolish.

So, we will dive into dealing with our own head trash, imposter syndrome, and imperfection syndrome. And I pulled up an oldie but a goodie: the content brief template. I rebuilt it late last year, but it is an excellent example of planning, so you don’t fear foolishness. 

So this week’s entry is about that tension, the doubt that never fully goes away, the planning that keeps us honest, and the simple routines that help us ship when our brains try to talk us out of it.

Let’s get into it. 

♥️ kyle

On Imposter Syndrome, Imperfection Syndrome, and the Head Trash We All Carry

I keep coming back to a line from The Darkest Hour. Clementine tells Churchill:
“You are strong because you are imperfect. You are wise because you have doubts.”

I wrote about it a couple of weeks ago in entry 52, because it captures something most leaders know but rarely admit. Doubt and imperfection are not weaknesses if used correctly. 

And this week, another tickled my head trash, and imposter syndrome writing fancy. A good follow and brilliant marketer, Kady Srivivasan wrote about the difference between Imposter Syndrome and what she calls Imperfection Syndrome. It is one of the clearest explanations I have seen for why we (seasoned leaders) still freeze, hesitate, or stay quiet at the tables we worked so hard to get to. Below is Kady’s post in full.

Is it Imposter Syndrome or Imperfection Syndrome?

by Kady Srivivasan

Recently, I had a conversation with a woman exec that I admire, about the idea of Imposter Syndrome. For some reason that term has never quite fit me. If imposter syndrome is about feeling like you don’t belong, well, that is true for every situation I have been in.

But I placed myself in those rooms deliberately, often far outside my comfort zone, so the feeling never carried much shame.

But what I struggle with is what I call the Imperfection Syndrome - the insecurity and anxiety of not knowing whether I am making a fool of myself by doing something, or speaking up, or suggesting a new approach.

A friend gave me feedback that brought this into sharp focus. He mentioned that I was not visible enough on Slack or email, that I was not contributing publicly in the way a leader should. That landed harder than I expected. In my head, I had framed my silence as efficiency. I told myself I would contribute when needed. The truth was simpler. I was afraid of looking foolish, especially in the early days of a new role.

This raised a question I needed to confront: How do I show up with credibility when credibility is built only by showing up?

I have realised that the only path is to shift my focus away from perception and toward learning. I have to focus on the act of shipping. Not perfecting or performing or pleasing (as Brene Brown would put it). In short, being ok with being imperfect.

Of course I should not wander into every conversation with unfinished thinking. Discernment still matters. But in most situations the risk of imperfection is far lower than the cost of silence. So I am adopting what I call the Reverse Pareto Principle:
20 percent: plan and think
80 percent: ship and learn

I am going to let go of calculations of risk to reputation vs value of contribution, and instead focus on what I am learning that will make the most contribution to the collective good.

I am reminded of something David Foster Wallace said years ago:
“If you are never confused, you are not paying attention.”

If you have battled your own version of Imperfection Syndrome, I would love to hear how you have learned to show up anyway.

How Her Post Connects to Head Trash

What I love about Kady’s framing is that it avoids the silly version of imposter syndrome. This is not about belonging because most of us placed ourselves in the room. The tension you feel is more about performance than deep identity.

It is the same thing I call head trash. The quiet second-guessing before a decision. The hesitation before hitting publish. The instinct to stay silent in meetings stems from calculating the reputational downside of looking foolish.

I’ve typed this multiple times over the years, and I’ll type it again: I don’t ever fully believe I am doing enough. Or the right thing. I know the operators who read this understand exactly what I mean.

And the reason why I read and then reread Kady’s post is because silence can feel safe, but it usually costs you credibility. You have to contribute to succeed. 

Which is why I keep returning to that Churchill quote. Strength comes from imperfection. Wisdom comes from doubt.

Because we work in a world that rewards the illusion of certainty, leaders always feel the pressure to show command of every number and answer every question. 

Except none of that is real. 

The more senior you get, the more your job becomes navigating ambiguity and running experiments. The more you pretend you know everything, the more your head trash spirals.

When you remove the performance layer, your work gets simpler:

• Ask better questions.

• Ship the work sooner.

• Narrate what you know, what you are testing, and what could fail.

• Build a few peers who tell you the truth.

This is how you build credibility without performing confidence.

Imperfection Is the Only Way Forward

When Kady talks about shipping at 80 percent, it matches a pattern I see across every strong leader I know. They get reps and take feedback as a way to change, not as judgment. It’s a big difference. Some points to remember, or rules to live by.

• When you ship more often, you think more clearly.

• When you share before you're ready, you eliminate the fuel driving anxiety.

• When you define “done” by behaviors instead of fantasy, you trust yourself.

 Different labels. Same truth. If you are dealing with your own version of this, remember the simple ritual I shared in entry 52:

• Name the fear. One sentence.

• Pull three receipts that contradict it.

• Pick the smallest next step and take it.

Ask yourself who gets the final vote in your f’ed up head: the evidence or the fear. Because all the of us deal with it in one way or another, it’s the beauty of being human. 

We are imperfect, but we are wise because we have doubts. And your credibility will only grow when you consistently show us.

On The Only Content Brief I Actually Use

I have spent most of my career pretending I don’t need a plan. That’s not entirely true, but it feels true. :) 

Much to my team’s pain at times, I like to move fast. I want to ship. I NEED to get the idea out of my head before it disappears. And for a long time, I believed planning slowed everything down. 

Then you wake up one day to find yourself with a team of over thirty, a nine-figure pipeline target, and a blocked calendar. The work is absolute chaos. 

And the only way to move fast at scale is to plan better.

I was reminded of that this week when I revisited a content brief template I created late last year. It’s a Frankenstein of every planning doc I have used over the last decade. It borrows from agencies, PMM teams, brand strategists, old bosses, new bosses, and a few expensive consultants. It has been broken and rebuilt more times than I want to admit.

But here’s the real reason the template exists:
It saves you from pretending.

It forces clarity on seven things marketers love to skip:

1. The purpose.

2. The customer.

3. The story.

4. The outcome.

5. The channels.

6. The owners.

7. The sales enablement.

Because the moment you skip any one of them, the whole thing collapses (believe me). You. This template was my way out of that mess, and it includes all the basics:

• Project overview

• Goals and KPIs

• Audience

• Key messaging

• Deliverables

• Distribution

• Sales enablement

But the part I care about most is the messaging section, because that is where most marketers lose it. The uploaded version of the template has two things I always come back to: the “main story” and the “operational or relational theme.” They came directly from work I have been doing this year on narrative building and content frameworks. 

A good brief tells the team this is the hill we are climbing and why they should follow.

You can find the template here. Just make a copy!