Author Ryan Holiday
Photo courtesy of Jared Polin
If you’ve ever wanted to achieve mastery, freedom, happiness, and/or tranquility, there may be one simple method you’ve overlooked to help you attain it.
Bestselling author Ryan Holiday shows why “slowing down is the secret weapon for those charging ahead” in his latest book Stillness Is The Key.
Holiday makes ancient wisdom popular for a new generation and draws on timeless Stoic and Buddhist philosophy. More practically, he shows why “great leaders conquer tempers, avoid distractions, discover great insights, and achieve happiness through stillness.”
If you’re ready to ”be steady while the world spins around you”, check out our conversation for actionable tips on how to achieve more by doing less.
Ryan Holiday’s book, Stillness Is The Key
Image courtesy of Ryan Holiday
Making major shifts
It’s much more common to have career changes than it once was. And for Holiday, he had a similar shift himself.
The public met him through his first book Trust Me, I’m Lying, which pulled back the curtain on media manipulation. After a follow-up book on growth hacking came what some would perceive as a shift to Stoic topics in The Obstacle Is The Way and Ego Is The Enemy. So, I had to ask, how and why the shift?
Holiday explains, “Philosophy and stoicism came first, then I had this marketing career. And I won’t say that marketing career spun wildly out of control, but I just realized that wasn’t what I wanted to do or be. And so when I wrote, Trust Me, I’m Lying, it was supposed to be sort of closing that chapter in my life, which it was. It’s just, to the public, that’s the beginning of a chapter, because that’s their first sort of introduction to me. So if I’d wanted to keep doing those things and if that’s what I thought was worth one’s time, I wouldn’t have written a book about them, I would have just kept quietly doing them in the shadows. But that was the closing of a chapter of my life, and then the beginning of what I thought was a new chapter, which is me as a writer. So, I think it’s sort of a natural transition.”
Define success for yourself
Before setting out to achieve something, you first have to decide on the goal. More important, however, is doing a gut check to determine if the goal is yours, or someone else’s. So, I asked Holiday how he now defines success for himself.
He shared, “To me, success is primarily indicated by autonomy. When I see very successful people who have next-to-no freedom in their life because the success circumscribes who they’re supposed to be, to me, that isn’t success. What is more alarming is that the nature of the success circumscribes what they’re able to do because it takes up so much of their time. So, to me, success is waking up and being in control of my day. Of course, this requires some financial freedom, but it’s primarily about the ability to make your own decisions, live your life the way that you want it to be, and be in control of your career.”
Saying no makes space for the right yes’
“We think success is having more and more responsibilities and having more and more projects on your plate. It can be, but again, I think that can be very limiting. We think that life is about taking on opportunities, however, success might be more about knowing which opportunities to reject. So that’s something that I have to think about a lot in my own life. Let’s say I agree to do 50 podcasts today. I could do that: I could record them back-to-back-to-back, and that would seem as if it were good for my writing career. However, what’s being pushed aside is the most important thing that I do, which is sitting down to write.
The problem is you get the ROI from doing the press, you put in an hour of your time, you sell X amount of copies. You spend an hour sitting alone writing, you actually don’t know what the ROI is on that, because it’s measured so far off in the distance. I have to remind myself constantly that when I’m scheduling things, or when I’m saying yes to things, I’m saying no to the most important thing professionally, which is my work. And then, personally, you’re also probably saying no to your kids or your spouse, or even just taking care of yourself. When people over-commit, they don’t think about things like, ‘Oh, I’m going to the gym now less because I don’t have time.’ But those costs are very real.”
How to decide when to say which
“Jonathan Fader, who is a sports psychologist, talks about how in professional baseball, you become a professional baseball player by your ability to swing at pitches, but you stay in the professional leagues based on your ability not to swing at pitches, to be able to discern a good pitch from a bad pitch.
Your framework for deciding when to say yes or no… should be no most of the time. The irony is that when you’re starting in your career, you have to say yes to everything, because that’s how you get momentum. And then, as soon as you have that momentum, it totally flips, and now you’re about saying no to everything.
There are a couple of frameworks out there. There’s, ‘Hell, yes’, or ‘Hell, no’ which I think is too simple. A lot of the things that I’ve said yes to, that changed my life, I was not sure were a great idea. So, to me, what I try to think about is, ‘Is this going to be something I’m proud of? Am I going to be glad that I spent time on this project?’ The answer to most things is no, right? You wouldn’t. Even if it pays well, you’re not gonna be so glad that you did that. And so, flashing forward to the future a little bit I think is one way to do it.”
Simplifying stillness for the active
“I think one of the problems with the idea of stillness is it feels very abstract, and it feels very cerebral. Or it feels like, ‘Oh, I’m just supposed to meditate?’ They think, ‘I’m not gonna do that, so it’s not for me.’ Right? And I think there are a couple of really practical things you can do to add more stillness to your life.
Number one would be just to get up early. When you get up early, there are fewer things going on, you can start the day off with quiet reflective time. I think that’s really important. Not only do I get up early, but doing so leads into the second thing, which is not touching my phone. This is a new thing I picked up in the last six months or so. I don’t touch my phone for the first hour of the day, and I now push that often to as many as two or three hours. I want to do as much of what Cal Newport calls ‘deep work’ in the morning before any interruptions have happened.
Number three, I would say, do some sort of physical activity. It seems paradoxical that movement would produce stillness, but it does. Every morning, I go for a long walk, or a bike ride with my son, and then in the afternoon I swim or run. Obviously, I have some freedom being able to make my own schedule to do this, but the idea to take time where you are just being present in a physical activity is really important.
And then I think the fourth one would be what we were talking about earlier, which is why don’t we find some things to eliminate? Possessions, obligations, impositions: what can we eliminate? And when we eliminate those things, stillness has the ability to ensue.”
Be like Napoleon
Well, maybe just in this one way. Holiday writes about a practice Napoleon had of not responding to mail for three weeks. When he did, most of the issues were then resolved.
So we talked about any practical application for this with e-mail. He shared, “I think inbox zero is a great concept that tortures a lot of people. I practice what we might call a Napoleonic version of inbox zero. I don’t want to have a thousand unread emails, because then it’s this looming thing that I have to take care of. But, what I do is when an email comes in, if it’s clearly an email from a fan or a random person asking for a favor, or a media request, or whatever, I mark it as a star in Gmail, and then I mark it as read. And I don’t get to those until a couple weeks or months later. Usually, when I’m flying, I open up my laptop instead of watching a movie and get through all those emails.
What happens is that a huge number of those things I wasn’t going to do anyway. Or, the problem has solved itself, as Napoleon said. Or someone will be asking for personal advice and I’ll reply sometimes two months later, and they’ll respond the next day and they’ll say, ‘I never thought you would respond. Thank you so much.’ And I realize, ‘Oh, they sent this email not expecting a response.’
So, this pressure that I felt to respond right away was totally made up. And so by putting a bit of a pause in there, it helps me sort things, and I don’t get overwhelmed. Even if someone sends me something nasty, if I’m not reading it for a while, it sort of takes the edge off of it. Then, what that leaves is the stuff that actually is timely, to which I do have to respond. Most of the email that we get is not time-sensitive at all, and it’s about being able to separate urgent from important.”
Three separate journaling practices
There is much evidence that points to the power of writing down our thoughts, goals, and dreams. Holiday is a believer in this to help instill stillness, so much so that he has three different journaling practices.
He shares, “I have one that’s a one-line-a-day journal, and it has spots for five years. I’m three years into the journal, where I write about what happened yesterday, so I can see what’s been going on for three years. Every year I go through it; it’s great.
Then, I write in a standard Moleskin about what’s been going on, what I’ve been working on, what I’m struggling with, that sort of thing.
And then, the third one is The Daily Stoic Journal, which gives you a prompt to think about in the morning, and you prepare for the day ahead, and then you reflect in the evening.
What journaling is about is taking some quiet time where you’re not in front of a screen, where you’re sitting down, and you’re just processing your thoughts. So many of the thoughts that we have, when they’re verbalized or they’re written down, they just prove to be quite silly, and so much of what we’re upset about, we’re upset about because we’re alone with it. And when we put it down on paper, it lessens. Anne Frank, who’s probably the most famous diarist of all time, she wrote in her diary that paper is more patient than people, and I think that’s a great line. To me, that’s why journaling is so important.”
Hold your goal loosely
“One of the things you realize as an author, or anyone in business, is that outcomes are ultimately outside of your control, or most of them are. And if you decide that success is selling a lot of copies, or getting a lot of page views, or winning an award, you’ve now taken your happiness and handed it over to someone else. What you want to focus on is what’s in your control. What I’m talking about in the book, and what I try to practice in my own life, is really scaling back my goals to be away from these external things and to be rooted in things that I control. So, my goal is to write the best book that I possibly can.”
“Truly great people whom I admire have always been one half of a relationship that was greater than the sum of its parts. Winston Churchill talks about how his greatest accomplishment was convincing his wife to marry him. You look at all sorts of artistic relationships. You think of the artist as this solitary figure, but often, there’s an unsung hero, a man or a woman that is making the trains run on time that allows them to live in this more ethereal world. And so, I really wanted to strike back against this idea that success requires you to forgo relationships. I would argue that relationships are what make success more attainable. The whole point of success is to have someone to share it with. You can’t take it with you when you die. It doesn’t mean anything if no one’s there to celebrate it with you. And so, I think relationships and stillness and success are all critical ingredients to the good life.”
Confidence vs ego
“One of the things I talked about in the book is the distinction between confidence and ego, and ego is often based on these external things. Ego could be, ‘Look how famous I am, look how successful I am.’ It could be, ‘Look how beautiful my wife is, or look how powerful my husband is.’ And so people take these external things as the source of their validation, their worth as a person, which is good as long as things are good. But what happens when you find out that person doesn’t love you anymore, or you find out that the audience has moved on, or you find out somebody stole all your money. If your sense of worth has been tied up in these external things, you are in for a very rude, unpleasant surprise. And so, the importance of focusing on this inner scorecard is about what intrinsic part of yourself, or your work, are you drawing confidence from? That is what is going to prevent you from being insufferable in good times, and then I think it’s what is going to prevent you from suffering in bad times.”
Hobbies provide needed rest
“We think hobbies are this sort of distraction from our work, but the hobby might give your brain much-needed rest or a different perspective to have some massive breakthrough personally or professionally. It’s important for people to realize that taking time off, taking time to yourself, not doing things is not irresponsible. It may be the most responsible thing you can do. You can pay someone to take out the trash, but you can’t pay someone to think about the big picture for you. If you are not doing that, if you’re not delegating in such a way that you have room to go off and think, you’re not going to get the results you want that come from that.”
Want more success and fulfillment in your life? Then check out this free masterclass with Deepak Chopra and me. In it, we share the 5 key things you need to know to create a more meaningful life!