Hey there Modern Authors,

This week... a little real talk.

Simon Sinek spoke to my author class and he said something that landed like a punch to the chest:

Not “a mediocre one.”
Not “a forgettable one.”

A bad one.

The room laughed.
And then it went quiet.

Because every author in that conversation knew exactly what he meant.

If you’re writing a book right now and it feels heavy… confusing… emotionally risky…
That might not be a warning sign.

It might be the signal.

The problem is, most authors don’t know how to tell the difference between:

• a book that’s hard because it’s bad, and
• a book that’s hard because it’s worth writing

That uncertainty is where people stall. Or quit. Or talk themselves into lowering the bar.

This piece is for that moment.

Why “Hard” Is the Wrong Question

Most authors ask the wrong question too early:

That question assumes something has gone wrong.

A better question is:

Because there are two very different kinds of difficulty in book writing.

Type 1: Friction Hard

This is the hard that comes from:

• vague ideas
• borrowed frameworks
• bloated concepts
• writing what sounds good instead of what you believe

This hard feels:

• foggy
• endless
• mechanical
• strangely empty

You can grind through it, but the work doesn’t change you.

Type 2: Depth Hard

This is the hard Simon is talking about.

The hard that comes from:

• going deeper than an article
• challenging your own thinking
• realizing your opening and ending can’t be the same
• discovering gaps in your logic
• confronting the fear that maybe you’re not ready

This hard feels:

• emotionally charged
• clarifying and destabilizing
• slow but meaningful
• like something is at stake

That’s the kind of hard that produces credibility, trust, and long-term impact.

Why So Many “Books” Should Have Been Articles

Simon is blunt about this, and he’s right.

Many books, especially in the thought leadership space, shouldn’t be books at all.

They’re:

• one good idea stretched too thin
• a viral post inflated into 200 pages
• a personal brand asset disguised as insight

They sell, but they don’t last.

Simon said it plainly:

If your book:

• doesn’t force you to evolve your thinking
• doesn’t require you to confront contradictions
• doesn’t demand new language

It may be easier to write.

But it won’t do the work books are uniquely capable of doing.

The Fear No One Talks About

Here’s the part most authors don’t admit out loud.

The fear isn’t:

The deeper fear is:

That fear hit me hard with Super Mentors.

There was a moment, late in the process, where I seriously considered pausing publication.

Not because I was lazy.
Not because I was stuck.

Because I was scared.

I could feel the book pulling me into deeper water:

• It was no longer just “my framework”
• It was asking me to take a real stand
• It was forcing me to be precise about what I actually believed

And once you do that, you can’t hide behind vagueness.

I remember thinking:
​If this goes out into the world and doesn’t land… that says something about me.

That’s the moment where many people retreat.

They rewrite forever.
They “wait for clarity.”
They decide to make it safer.

But that’s also the moment where good books are decided.

Simon’s Litmus Test (That Most Authors Ignore)

Simon shared something subtle but profound in the conversation:

He doesn’t sit down and decide to write a book.

He lives with an idea for years.

• He speaks it out loud.
• He tests it in conversations.
• He watches where people lean in.
• He notices what questions keep coming back.

Only then does it earn the right to become a book.

That leads to a simple but brutal test:

Ask Yourself:

• Have I lived with this idea long enough that it has changed me?
• Can I speak it clearly without slides?
• Do people argue with me about it?
• Do they ask, “Wait, say that again?”

If the answer is no, the book will feel hard for the wrong reasons.

The Decision Tree: Is This a Bad Book or a Worthy One?

When authors ask me, “How do I know if this book is worth finishing?” I walk them through this mental checklist.

1. Does the Book Require Depth You Can’t Fake?

If this could be:

• a long blog post
• a keynote transcript
• a podcast series

…it probably isn’t a book yet.

Books demand transformation, not repetition.

2. Are You Afraid of Being Clear?

Clarity is risky.

The clearer you are:

• the more people can disagree
• the harder it is to hide behind trends
• the more exposed your thinking becomes

If your discomfort comes from being specific, that’s a good sign.

3. Would This Book Still Matter If You Had No Platform?

Simon made this point sharply.

Books written to “work the algorithm” disappear.

Books written to give people language for something they’ve felt but couldn’t articulate travel for decades.

Ask:

4. Is the Hard Part Emotional or Mechanical?

If the hard part is:

• organizing chapters
• word count
• structure

That’s solvable.

If the hard part is:

• deciding what you actually believe
• letting go of borrowed ideas
• committing to a point of view

That’s the work.

The Trap of Making It Easier

One of the most dangerous moments in writing is when you realize:

You can:

• soften the claim
• add more examples instead of sharpening the point
• turn depth into advice
• swap conviction for cleverness
• outsource thinking to ChatGPT

That’s when books become forgettable.

Simon said it best:

The second path feels harder because it is.

Worthy Rivals and Imposter Fear

Another moment from the conversation matters here.

Simon talked about “worthy rivals”... authors whose work makes you uncomfortable because it exposes your gaps.

That discomfort often shows up while writing.

You think:

• “Who am I to say this?”
• “They’ve already written something better.”
• “What if I’m not adding enough?”

That’s not imposter syndrome.

That’s aspiration.

It’s your signal that you’re playing a serious game.

Bad books don’t trigger that fear.
Good ones do.

What Got Me Through Super Mentors

What helped me push through wasn’t confidence.

It was reframing the work.

I stopped asking:

And started asking:

Am I:

• saying the thing I actually believe?
• giving people language they can use?
• creating something that invites action?
• telling my truth?

Once I answered yes to those, the fear didn’t disappear.

But it stopped being a stop sign.

The Paradox Simon Leaves Us With

Simon shared something I think every first-time author needs to hear:

You don’t lose that by writing carefully.
You lose it by trying to be impressive.

The irony is:

• The books that feel hardest often have the longest lives.
• The books that feel easiest usually fade fast.

So… What Should You Do If This Is You?

If you’re in the middle of a book and thinking:
​This shouldn’t be this hard…

Pause before you quit.

Ask:

• Is this hard because I’m avoiding depth?
• Or is it hard because I’m finally in it?

If it’s the second…

You’re probably writing the right book.

And that’s the kind of book that leads to:

• credibility
• business
• speaking
• opportunity

Not because it was easy.

But because you didn’t flinch when it got hard.

👉 Watch the full Simon Sinek conversation here:

​

If you felt seen by that line... “Anyone who says it was easy probably wrote a bad one”... you’re not alone.

You’re just doing the work.

Eric