Brad Feld

Tag: stoicism

I no longer subscribe to many daily email newsletters, but I’ve kept a few. My favorite to wake up to is Ryan Holiday’s The Daily Stoic.

Today’s headline was It’s Possible to Tune These Things Out but it linked to an older post titled The True Power Behind Stoic “Indifference”.

At morning coffee a while ago, Amy and I had a long conversation about the phrase “I don’t care.” I struggled to explain what I was trying to say and how it was often misunderstood when I said it. Through her reaction and feedback, she helped me better understand what people heard when I said “I don’t care.”

I tried shifting to the phrase “I’m indifferent” instead of “I don’t care.” I continued to feel that I was being misunderstood when I said this. I’d often provide strengths and weaknesses of each option presented but then end with “I’m indifferent.” I knew that this was confusing to some, but I didn’t know why until I read The True Power Behind Stoic “Indifference”.

Of all the loaded words in Stoic philosophy, “indifferent” is one of the most provocative. Marcus AureliusSeneca, and Epictetus each tell us that the Stoic is indifferent to external things, indifferent to wealth, indifferent to pain, indifferent to winning, indifferent to hope and dreams and everything else. You hear it enough times and it starts to sound like these people don’t care about anything. Especially since the modern definition of the word means precisely that. But this is a dangerous misreading.

Recently, I got feedback from several people that I was profoundly unhelpful in a particular situation by saying, “I’m indifferent.” I thought about it on a run, which is unusual for me as I rarely focus on one thing during a run but prefer to let my brain go all over the place. In this particular situation, my brain seemed to lock down on the dissonance around this phrase.

The situation in question had two paths: A and B. I had a modest preference for A, but I was good with either A and B. I had explained this, but when asked which I preferred, I said, “I’m indifferent.”

After my run, I explained this more clearly, reiterating that I had a modest preference for A but was good with either A or B. Instead of “indifference,” I stated that I was “tranquil.” After even more reflection, I think a better concept would have been “equanimity.”

Back to the The True Power Behind Stoic “Indifference”.

The Stoics were not indifferent in that sense at all, it’s that they were good either way. It’s not that they didn’t care, it’s that they were good either way. Does that make sense? The point was to be strong enough that there wasn’t a need to need things to go in a particular direction. Seneca for his part would say that obviously it’s better to be rich than poor, tall than short, but the Stoic was indifferent when fate actually dealt out its hand on the matter. Because the Stoic was strong enough to make good of it—whatever it was.

Boom. After reading this, I got the disconnect people were having, which was reinforced by the contemporary view of equating “I’m indifferent” to “I don’t care,” which is very different from “I’m good either way.”

Think of that today, that it’s not about apathy or even a lack of expectation. It’s simply the quiet strength of not needing a preference, because you’re that strong.

Ryan – thanks again for helping me understand myself a little better.


Ryan Holiday’s newest book, Stillness Is The Key, came out at the beginning of October. I ended up with two copies and thought I’d read it over the weekend after they showed up at my house. The weekend slipped by and I didn’t pick it up until mid-day on Thanksgiving.

It was pouring rain in San Diego all day so it was a perfect laying on the couch reading afternoon. I just finished and, once again, Ryan delivered with this book.

Ryan divided the book into three sections: Mind, Spirit, and Body. He has a thorough exploration, broken up into about a dozen chapters, for each category. As is his style, there are many detailed and powerful examples.

He leads with Seneca, a friend of all Stoics and a frequent visitor in Ryan’s writing. He tells a short story around apatheia, or upekkha, or aslama, or hishtavut, or samatvam, or euthymia, or hesychia, or ataraxia, or aequanimitas – a word that finally comes closer to translation into English.

That word is stillness. In the intro to the book, Ryan says,

To be steady while the world spins around you. To act without frenzy. To hear only what needs to be heard. To possess quietude—exterior and interior—on command.

Buddhism. Stoicism. Epicureanism. Christianity. Hinduism. It’s all but impossible to find a philosophical school or religion that does not venerate this inner peace—this stillness—as the highest good and as the key to elite performance and a happy life.

And when basically all of the widom of the ancient world agrees on something, only a fool would decline to listen.

I thought the chapters in each section were extremely well-titled and are listed below. Like reading a poem, slow yourself down and, instead of skimming the next three paragraphs, read them aloud.

Mind: The domain of the mind, Become present, Limit your inputs, Empty the mind, Slow down think deeply, Start journaling, Cultivate silence, Seek wisdom, Find confidence avoid ego, Let go.

Spirit: The domain of the soul, Choose virtue, Heal the inner child, Beware desire, Enough, Bathe in beauty, Accept a higher power, Enter relationships, Conquer your anger, All is one.

Body: The domain of the body, Say no, Take a walk, Build a routine, Get rid of your stuff, Seek solitude, Be a human being, Go to sleep, Find a hobby, Beware escapism, Act bravely.

If even one chapter in each section strikes a chord with you, I encourage you to grab a copy of Stillness Is The Key.

Ryan – thanks for adding another phenomenal book to my bookshelf.


Ryan Holiday’s new book Stillness Is The Key is out. I have a copy on the top of my infinite pile of books at home along with a copy on my Kindle. I’ll be reading it this weekend.

For a moment of inspiration today, take a look at his launch video.

I’ve read every one of Ryan’s books. I’ve loved them all, learned from them, and gotten ideas and inspiration about how to adapt and adjust my behavior.

I look forward to some time this weekend with Stillness is the Key.


This book was a delight. I started reading it earlier this year, caught up quickly (I started in July), and then mostly read a page each day when I was in the bathroom in the morning. I let it unfold slowly, reading the daily quote and Ryan Holiday’s (and Stephen Hanselman’s) thoughts on the quote, and then rereading the quote.

I was near the end so I finished it off last night. I smiled when after I read the December 31 meditation.

Stoicism is fascinating to me. While I don’t categorize myself as anything and try to resist being put in boxes, I like to take elements of different philosophies, religions, approaches, and styles and weave them into the fabric of me. As I was reading The Daily Stoic I found many ideas that spoke to me.

I’ve known Ryan from a distance for a while. We ended up at a dinner together at either SXSW or CES a number of years together and I remember an interesting and engaged conversation. For a while, I subscribed to his monthly Reading List email but in a fit of unsubscribing from everything, I unsubscribed.

I just re-subscribed.

Several times a year, I send a book (or two) to all the CEOs in our portfolio. I sent this one out this fall. I’ve heard back from a few that they enjoyed it, and I’m hoping that most of the CEOs are at least dipping into it.

If you’ve heard any of the names Zeno of CitiumChrysippusCato the YoungerSenecaEpictetusHierocles, or Marcus Aurelius, then you’ve heard of at least one of the famous Stoic philosophers. If you’ve studied any of them, you are in for a treat with this book as it presents Stoicism in a unique and very accessible way.

For a taste of the kind of quotes Holiday and Hanselman riff off of in the book, take a look at the fun Brain Quotes pages for Marcus Aurelius and Seneca.

The book starts with a quote every day on January 1st. You’ve still got a few days to grab a copy from Amazon and start the year out with a daily dose of Stoicism.