Cool (Unexpected) Things I’ve Learned from Ryan Holiday | Tim Denning

Stoicism was dead before Ryan Holiday.

I shouldn’t admit this but I had no clue what it was until I read Ryan’s work. The names Marcus Aurelius, Seneca, and Epictetus could have been Peppa Pig characters for I knew.

Opening my mind to stoicism made me see wisdom hasn’t changed at all. It’s been the same for thousands of years.

Here’s what else I learned from Ryan Holiday (gotta love his lucky last name).

The secret most people don’t know about Ryan Holiday

Major success is rarely accidental.

It’s typically manufactured behind the scenes so the public may think it’s an accident. The secret most people don’t know is Ryan was a researcher for three New York Times Bestselling authors:

1. Tim Ferriss
2. Tucker Max
3. Robert Greene

By being around these heavy hitters it would be near-impossible for him not to have succeeded in following in their footsteps.

Rather than waiting for the magical phone call from the unicorn princess waiting up in the stars to grant wishes to budding writers, Ryan got his hands dirty and did the grunt work of research for the pros (probably for free).

It took courage and no doubt would have been hard. He did it in his downtime outside of his normal career working in marketing for American Apparel (read his book about the job and you’ll see it was more like chaos…haha).

Ryan didn’t just become a great author. He learned to build relationships — not network — with the best writers in the world.

He’s not the only one.

A friend of mine, Jack Raines, has gone from unknown writer to a superstar everyone is talking about in only 6 months. One article called “F You Money” is what I suspect started it all. (I loved it so much I put it in my newsletter.)

Since writing this article he has been featured by Tim Ferriss, Sahil Bloom, Nassim Taleb, and Money with Katie.

His success looks random until you see how he operates. He doesn’t network either. Nope. Like Ryan he builds smart relationships and writes words for big-name brands/people.

I, too, didn’t accidentally learn writing either. I wrote for free on a popular self-help website in return for mentoring from the well-known blogger who started it.

Become an apprentice.

You can hold two opposing opinions in your gorgeous brain at the same time

While doing research for this story I learned something unexpected about Ryan. In 2016 he wrote a letter to his father begging him not to vote for a certain reality tv star president.

In 2020 he wrote another letter begging his father not to vote again for the man with the bad wig.

What’s bizarre is this same clown of an ex-president oddly offered him a role in his administration as a communications director. It’s as if the former president couldn’t read the room (wouldn’t be the first time).

Ryan identifies as a conservative republican. He’s a Texan that owns guns, raises cows to eat, prefers a low-tax place to live, flies an American flag for all to see, and prefers to be left the hell alone.

Despite all of that he joined Joe Biden on his 2020 campaign trail to ensure “the opposing crazy guy” didn’t stand a chance of victory. (He even hung the Biden sign back at his Texas ranch).

The lesson here is simple: You can support a cause you don’t believe in, to protect the world from a madman, because it’s the right thing to do.

Use the power of zooming in on one thing

The cliche advice is to go broad and try and be fancy.

Ryan did the opposite. For the last ten years he’s done nothing else but write about stoicism and his admiration for the lessons we can learn from Marcus Aurelius. Most smart people would have told him beforehand not to do it.

It’s an unsexy subject that has been covered millions of times for thousands of years. “There’s nothing new about it” they’d say. Well, they’d be wrong.

Ryan reinvented stoicism because he made it relevant again.

He took the stories and reworked them, which made them new. Most of all, he was doing work he was deeply passionate about. I suspect he would have done it for free and not blinked twice.

Perhaps even starved to do it.

(Now that’s real work.)

Writing wisdom from Ryan that applies to life

1. No such thing as writer’s block (just insufficient research)

Writer’s block is when you’re staring at a blank page and nothing will come out. You blame your brain for a lack of ideas. Stupid.

Ryan taught me that ideas aren’t the problem. It’s a lack of research.

More broadly, failure in life isn’t the problem either. It’s a lack of preparation. If you want to sit down and achieve a big goal like writing, the work starts months and even years before.

Fake psychological conditions like writer’s block aren’t the problem — preparation is.

2. “Remember: it’s all material”

I once wrote years ago, “The best writing ideas come from actually living life and going outside.”

Ryan taught me everything in life is material. The best writers aren’t great with spelling or grammar, and don’t have literary degrees. Nope.

The best writers have interesting stories to tell because they leave the comfort of their office covered in walls of pillows and go out and have interesting experiences.

In some way it’s why I quit my job, walked away from a startup I loved, overcame mental illness, became desperate and dateless, fell in love again, got married, got my wife pregnant, and now make money online while waiting for my baby girl to arrive.

Change adds variety to life. It gives us experiences we can learn from and teach to others through our stories.

If you want to be better at telling stories then have more experiences.

And if you don’t think storytelling matters then you’ll never persuade 99% of people to do anything. As I always say, life is one big game of sales.

Stories close more sales opportunities in life.

3. “Write what you can’t NOT write”

There are some things I have to write about. Not everyone cares about them and many won’t get read widely, but if I don’t write them then I have regrets and wonder “what if?”

Despite what’s good for our careers and our bank balances there are times we need to make art for the hell of it. Ryan’s quote applies more broadly…

Do what you can’t NOT do.

For me that’s writing. For you it could be painting or starting a business or trying to marry someone who’s in love with someone else.

If you don’t do what you feel you can’t do, you’ll one day have enormous regrets. And regrets rot your soul until you become a bitter, twisted, son of a gun no one has a kind word to say about.

Just do it.

Decide between alive time and dead

Let’s end with an inspirational story to leave you speechless.

Earlier in Ryan’s career he said yes to a 12-month consulting gig. It turned out to be the gig from hell. Chaos everywhere. A Wall Street hedge fund trying to rip apart and take over a company for profit.

There was no point trying to do his consulting gig properly and making progress at work. Ryan sat in his office chair frozen.

Shortly after a piece of advice came to him from his writing mentor Robert Greene. He told Ryan there are two types of time: Alive time and dead time.

Dead time is when you’re not in control and wait for things to happen to you. You’re the puppet waiting for the puppet master to pull your strings and bring you to life.

Alive time is when you’re in full control and don’t waste a single minute on BS. In this state you are endlessly learning, growing, and improving.

Robert learned about dead time in his former life. Before he became a world-famous author he worked, according to Ryan, something like 80 random jobs for moronic bosses over 20 years. He had no control in these jobs.

Rather than sit around lifeless in a dead-end job, Robert chose to use his downtime to learn, grow, read, and research pretty much anything.

Those 20 years gave Robert the material he needed to write his breakout book 48 Laws of Power.

Ryan decided to follow in Robert’s footsteps. He started reading everything he could. (See photos below that he took of the mammoth pile of books.)

Ryan filled two boxes of notecards by reading all these books.

The second box of notecards became his breakout bestselling book Ego is the Enemy. Robert says if you’re going to work a job you hate, that sucks away all your energy, that destroys your creativity, you may as well be dead.

When you think of life like that you’ve got nothing to lose. May as well explore your curiosity and see what’s possible.

That’s the best lesson Ryan Holiday taught me. (Thanks mate.)