Ryan Holiday’s advice on writing a bestseller, why you should ignore douchey thinkbois, and how to be a Stoic archer

Building Blocks: Actionable insights to build an Intentional Life

Hey everybody,

Here’s another batch of actionable insights to start your week off right, so you can be more intentional with how you live, work, and create.

Let’s get started.

​Insight 1: Trust the process

How can you consistently crank out prolific, and profound, content?

Ryan Holiday is a bestselling author who’s written 12 books in ten years and sold more than 3 million copies worldwide.

He recently shared a video about the two-year process behind writing his latest book, Discipline is Destiny.

Here are three of my favorite takeaways you can apply to your own content:

1. Trust the Process

Holiday says it was easy to doubt if his hard work of researching and organizing notes would turn into a coherent book, so he wrote himself a note before he began the project:

“Trust in the process. Keep doing your notecards. When you check this in June, if you’ve done your work, there will be a book here.”

He was right.

It’s easy to get overwhelmed by a big project.

Reminding yourself to trust the process keeps you focused on the one thing you control—your effort, not the outcome.

2. Embrace Chaos

Building moment is hard, but keeping it is even harder.

Anytime you see breakdown of someone’s writing routine, that’s the ideal writing routine when everything’s going well—not their actual routine every single day.

When Holiday was “knee-deep” into writing Discipline is Destiny, he had to go on a cross-country multi-city, multi-week tour to promote the book.

“I lost weeks because of that…When you get locked into a routine as a writer, it’s amazing. And to even do one thing in the middle of the day disrupts that. And to get in an RV and drive across the country in the middle of a pandemic with kids and all this stuff, it was insanely disruptive.

But I tried to just tell myself, am I making one small contribution today? Am I doing one thing? Is it a notecard? Is it a book that I’m reading? Is it an idea that I’m having? Am I tweaking something? I just wanted to chip away at it. I didn’t want that time to be completely lost. You just have to show up.

Discipline is not being amazing all the time. It can sometimes be just average results day in and day out and not losing that rhythm.”

In psychology, we say, “rigidity leads to pathology.” It means no matter how helpful something is at first (like a routine), refusing to adapt it to your circumstances can cause catastrophic failures down the line.

Holiday adapted his system to his circumstances, and came out with a book that’s sold over 60,000 copies its first week.

3. Don’t Be Trapped by Perfectionism

Instead of endlessly tinkering in solitude, he submits a “good enough” draft to his editors so he can get distance from the ideas and start to get feedback on how to improve it.

“If you’re not getting feedback, you’re not getting better,” he says.

This iterative approach to writing allows him to focus on creating a Minimum Viable Draft to put out into the world (of his editors and beta readers) instead of over-analyzing it to death.

Each of us is too close to our own work. We need other people’s feedback to make it better. But we’ll never get that feedback if we never share it with them.

Do yourself a favor and check out the full video:

​Insight 2: Live your own life

Earlier this week, I threw out this tweet that took off:

The reason it took off, I think, is a valuable lesson…

People are tired of being told how to live their lives.

The “By age 30…” meme may’ve started out as a pithy motivational message to inspire people to level up, but it’s become a rallying cry for douchey thinkbois clout-chasing and shaming people for not hustling 24-fucking-7.

Exhibit A:

I’m 33. I spend time with millionaires, thought leaders, and best-selling authors on a regular basis, so allow me to let you in on a little secret:

No one knows what the fuck they’re doing.

We’re all just figuring it out as we go along.

Feeling ashamed because you’re not where some anon asshat thinkboi tells you you’re supposed to be in life, or because you haven’t optimized every second of every day, is bullshit.

Tons of successful people do things purely for pleasure, like watching Netflix.

Should you be financially literate and endeavor to enrich your life? Sure. But that doesn’t mean you have to become a hustle robot and never do things you enjoy.

So before you take someone else’s advice on how you should live your life, consider these questions:

  • Is this someone I want to be more like?
  • Would their strategy work for my circumstances?
  • How do I know they’re as successful as they claim to be?

Not all opinions are worth considering.

Live your own fucking life.

​Insight 3: Remember the Stoic archer

Have you heard of the concept of the Stoic archer?

The archer controls how much they practice, how well they string their bow and calibrate their arrows, and how well they account for winds and other variables that could affect the arrow’s trajectory.

But they don’t control where the arrow ultimately lands.

As soon as they release the arrow, it’s out of their control.

All they can do is optimize for everything up until that point.

I love this metaphor because it reminds us to do two things:

  • Focus on what’s within our control.
  • Accept that effort doesn’t equal outcome.

This echoes a lesson I had to relearn recently:

So whether it’s archery, business, content creation, or martial arts, remember to focus on the one thing within your control—your effort—instead of obsessing over what you can’t—the outcome.

​Question for the Week

How, specifically, can you shift your focus to the few things you do control, instead of all the outcomes you don’t control?

​Coaching Corner

This week’s question is from Jon:

“How do you know what content to put out for free vs. paid?”

It’s easy to think you need to keep your really good content behind a paywall.

But if people come across your free content and it’s lackluster, they have zero reason to give you their money.

People don’t buy information.

They buy three things:

  • Curation
  • Organization
  • Implementation

Tons of paid courses are a repackaging of free resources.

The difference you get for the paid version is everything is consolidated together in one easy to follow sequence that helps them achieve a specific transformation.

If someone has more time than money, they’ll search out all the free stuff and Frankenstein it together themselves.

If they have more money than time, they’ll happily pay you to package it all up for them.

And if you want to improve your offering more, add in a community element.

People will pay top dollar to access a community of supportive like-minded peers that can help them level up.

Take Intentional Life Design, for example. It started off as a free article, then turned into a high-ticket cohort-based course and community people love.

Got a question you want me to answer here?

Share Your Insights

Know someone who’d love this content? Share it with them!

My goal is to help people be more intentional with how they live, work, and create.

So if you enjoy Building Blocks, I’ll be forever grateful if you help me spread these insights by sharing this issue with one other person you think would find it valuable.

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Until next time—memento mori,


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