4 Inspiring Life Lessons from Ryan Holiday




This essay forms part of a series I’ve titled: Inspiring Life Lessons.

In it, I document Inspiring Life Lessons I’ve picked up from Inspiring Folk who have Inspired Me.

Today’s essay focuses on the stoic and hushed voice of Ryan Holiday.

To learn about the rest, and who else features, open this page ⇒ 

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I didn’t used to like this guy…

No idea why. I had no reason not to like him.

He didn’t do anything to hurt me. 

I hadn’t even read anything of his, at the time…

Yet for some reason, I decided I didn’t like Ryan Holiday.

Maybe I saw something of myself in him that I hadn’t come to accept yet. 

(a quieter, more reserved person)

Maybe I’m just a-too-quick-to-judge douche.

Either way, my opinion soon changed once I read ‘Obstacle is The Way’.

I decided to read it because at the time I was writing ‘The Successful Mistake’ (a book that focussed on turning failure into success). Call it market research on seeing how the pros do it… I read it for a reason, but that reason soon changed once I turned the first page.

Hooked. Line and sinker.

I went on to read most of Ryan’s other books from there: Perennial Seller, Conspiracy, The Daily Stoic, Ego is The Enemy (the next book on my reading pile, Stillness is The Key).

I’ve learned a lot from the stoic and hushed voice of Ryan Holiday. Through his words on paper, and also over the airways as he speaks to podcasters and the like. Inspiring life lessons that have had a serious impact on me.

Here are four of them…

1: Confront Your Ego

His book, ‘Ego is The Enemy’ is one of my favorites. I took a lot from it, but possibly the largest lesson I learned was to see ego in a new light.

I always associated ego with cockiness and arrogance. You know the type: the guy or gal with all the confidence in the world, is extroverted and bullies their way to the front of the line.

This is how I saw ego.

Because of this, I didn’t think I had one.

I’m quieter. Private. Reserved. Ego and I don’t seem to go hand-in-hand, but having read Ryan’s book I realize how wrong I was. Ego is within us all and is part of the conversation, always. It taints discussion, both the ones we have with others and those internal conflicts.

It gets in the way of doing the “right” thing.

Often, not out of spite… rather, protection.

It tries to keep us safe but imprisons us to rules we may no longer need.

As such, Ryan taught me to confront my ego. Accept it’s there. Embrace it and talk it down. It’s no eviler than any other emotion, thought or feeling. Yet if we allow it to govern us, the road it takes us down is often a lonely one indeed.

2: The Voice Can (and will) Evolve

As a writer, I think of voice often.

  • Is my style of writing correct?
  • Is it compelling enough?
  • Will others like it?
  • Should I push it to one side and try to be like “that” writer instead?

I don’t worry about this as much anymore. I appreciate now that your voice (be it written or any other) isn’t static. It evolves and can take on new forms, often from day-to-day; and even throughout it.

You can wear different hats, tweaking the voice at all times while staying true to the essence of it.

When I first heard of Ryan, I knew him as a marketer and PR specialist. I’ve read articles about his views on marketing. His book, ‘Perennial Seller’ is largely about it. Yet I’ve also read his books about philosophy and conspiracy.

His voice transitions between the topics, yet it always remains… his.

Unique. True. Grounded.

Like ice, water and steam, the same elements at all times but determined by their environment. This empowers me to write as I wish to write. Adapt and fine-tune, of course, as each client and project requires me to.

But those fundamental elements can remain. Indeed, they need to.

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3: Follow That Inner Voice

Following on from the previous point, one of the most inspiring life lessons Ryan has given me is to follow that inner voice and write what needs to be written.

  • Marketing
  • Conspiracy
  • Stoicism
  • Bookselling
  • Overcoming adversity

Just a few topics Ryan has written about…

Not many writers do this. They find a topic or genre and stick to it. When they deviate from it, it’s only ever so slightly. The same is true in music, art and the movies.

Most people stick to what they know and what they are known for.

Yet the best tend to take on challenging projects that push them beyond.

You can write both fiction and non-fiction. You can cross genres. You can take on new topics. Who you are isn’t who you need to remain. What you do and what you are known for… like your voice, it can evolve and transition with the seasons.

4: You Needn’t Follow The Herd 

This final inspiring life lesson is possibly the on4 I admire the most.

Remember, Ryan comes from a marketing background. He’s damn good at it, too. With the following he has, he could likely build many products, packages and services that follow on from his books.

He could create a funnel and make millions.

He doesn’t. He doesn’t seem to care about any of that. No program, course or “upsell” just because he can. He writes his books and commits to the act. He doesn’t only write, of course. He speaks. He runs workshops. He does have a few online courses, I believe.

He has other business interests…

Yet he doesn’t seem to care about what the rest of the herd do.

He goes to whichever corner of the field he wishes to go to.

Again, this has given me a strange sense of permission to create what I want to create. It isn’t that a course or program is not the right path to take. So long as it has a true purpose, it is.

Yet that’s the point… to give it purpose.

The books I write are precious to me, and whatever follows on from them should hold true to this.

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4 Inspiring life lessons from a guy I once convinced myself I didn’t like. Had I remained stubborn, I wouldn’t be who I am today. It makes me wonder about all the other people and “things” I’ve been too quick to judge.

What have I missed out on?

Who could I be right now?

What about you…?

Maybe this is the biggest and most inspiring life lesson of all… 

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