Author and media strategist Ryan Holiday believes that a question asked at the right time can change the course of a life, can still a turbulent mind, or heal an angry heart. “While every situation can generate its own,” Holiday writes, “there are twelve questions that deserve to be asked not just once but many times over the course of a lifetime, some even many times over the course of the day.” Though the instinct is to look for answers, the questions teach us the most, Holiday maintains.
Start now by asking:
Who Do You Spend Time With?
“Goethe would say “Tell me who you spend time with and I will tell you who you are.” It’s who we know and what we do that influences who we will become. What you do puts you around people, and the people you’re around affects what you do,” Holiday writes.
Take a moment to think about your friends and colleagues: do they inspire you, validate you, or drag you down? Contemplate on this: adult who spends time with other adults who tolerate crappy jobs, or unhappy lifestyles is going to find themselves making similar choices.
“Same goes for what you read, what you watch, what you think about,” Holiday continues. “Your life comes to resemble its environment (Ben Hardy calls this the proximity effect). So choose your surroundings wisely.”
If you recall, this ties in to our recent Dadly Daily Declaration from James Clear’s book, Atomic Habits:
One of the most effective things you can do to build better habits is to join a culture where your desired behavior is the normal behavior. New habits seem achievable when you see others doing them every day. If you are surrounded by fit people, you’re more likely to consider working out to be a common habit. Your culture sets your expectation for what is “normal.” Surround yourself with people who have the habits you want to have yourself. You’ll rise together.
To make your habits more attractive, take this strategy one step further. Join a culture where (1) your desired behavior is the normal behavior and (2) you already have something in common with the group. If you already similar to the other members of the group in some way, change becomes more appealing because it feels like something people like you already do.
Is This In My Control?
“Epictetus says that the chief task of the philosopher is to make the distinction between what is in their control and what is not — what is up to us and what is not up to us?” Holiday posits. “We waste incredible amounts of time on the latter and leave so many opportunities on the table by mislabeling the former.”
Our actions, our thoughts, our feelings are all up to us. Other people, the weather, external events are not. Know what is in our control: our responses to other people, the weather, and external events. “Making this distinction will make you happier, make you stronger and make you more successful if only because it concentrates your resources in the places where they matter,” Holiday writes.
What Does Your Ideal Day Look Like?
Holiday maintains that we should take an inventory of the most enjoyable and satisfying days of our life. “If you don’t know what your ideal day looks like, how are you ever going to make decisions or plans for ensuring that you actually get to experience them on a regular basis?” Holiday asks.
What did you do?
Why did you like them?
This next bit is quite important. Holiday believes you must be sure that “your job, personal life, even the place you’ve chosen to live takes you towards these, not away from them. If you don’t want an office, don’t set up an office. If you enjoy being in harness and that’s what makes you feel good, then you’ll probably need something that has a lot of responsibilities and set requirements.”
“If you enjoy influence more than material success, then make sure you pick something that allows for that. If you’re a quiet person, then you need a lifestyle that will let you be quiet — not one that forces you to be constantly not yourself,” Holiday writes. “If you thrive on attention and collaboration, then pick accordingly. If you want to live in the same place for a long time, maybe buy a house. If you don’t — God, please don’t. And on and on and on.”
To Be Or To Do?
John Boyd, one of the best strategists of the last century, asked the promising young acolytes under him: “To be or to do? Which way will you go?”
Meaning, will you choose to fall in love with the image of how success looks like or you focus on a higher purpose?
Holiday continues, “Will you pick obsessing over your title, number of fans, size of paycheck or on real, tangible accomplishment?” Boyd posited life presents a roll call and that roll call sorts people by their answer to this question: the doers and those who simply pretend.
Which will you be?
Which have you been?
If I Am Not For Me, Who Is? If I Am Only For Me, Who Am I?
The alternative translation of that last part, according to Holiday, is “If I am only only for me, what am I?” The answer is “the worst.” It doesn’t make you a bad person to want to be remembered, Holiday posits. Or to want to make it to the top. Or to provide for yourself and your family.
If this is all you want, it is a problem, Holiday believes.
There is a balance.
What Am I Missing By Choosing To Worry or Be Afraid?
Gavin de Becker writes in The Gift of Fear, “When you worry, ask yourself, ‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom?” Another way of putting it, according to Holiday is: Does getting upset provide you with more options?
“Obstacles in life make us emotional, but the only way we’ll survive or overcome them is by keeping those distracting emotions in check — if we can keep steady no matter what happens, no matter how much external events may fluctuate,” Holiday writes.
Holiday continues, “When you find yourself indulging in those emotions, one way to get yourself back on track is simply by reminding yourself of the cost they incur: That you’re missing something by being nervous, scared, or anxious. That you’re taking your eye off the ball to do it.”
Can you afford that?
Probably not.
Am I Doing My Job?
Know what three-word command Bill Belichick, Nick Saban and Sean Payton have in common: Do Your Job. The last thing the great John Wooden would say to his players in the locker room before a game was, “Well, I’ve done my job.” So the question is: Are you doing yours?
Do you even know what that job is, Holiday asks. “It’s important to remember that we can be very busy — exhaustingly busy — and still not be doing our job,” Holiday continues. “We can be caught up in the things that don’t matter, we can be interfering and encroaching on someone else’s job, we can be just plain procrastinating. All these things keep us working — but not on the job that actually matters.”
What Is The Most Important Thing?
Ask yourself this, according to Holiday: “If you don’t know what the most important thing is to you, how do you know if you’re putting it first? How do you know if you’re taking the right steps to get it?” Since you’re reading this site, maybe the most important thing to you is your family.
“What this priority means,” Holiday writes, “is that not only do you have to start measuring yourself by family-related metrics, but you have to stop comparing yourself to people with different priorities.”
Maybe money is the most important thing to you, which is perfectly fine. Know that and own it, Holiday advises. As Michael Lewis writes, the problem is the lying to yourself. “You have to know and own whatever it is,” Holiday writes. “Only then can you understand what matters and what doesn’t. Only then can you say no — can you opt out of stupid races that don’t matter, or exist. Only then is it easy to ignore ‘successful’ people, because most of the time they aren’t — at least relative to you, and often even to themselves. Only then you can develop the quiet confidence that Seneca called euthymia — ‘the belief that you’re on the right path and not led astray by the many tracks which cross yours of people who are hopelessly lost.'”
Who Is This For?
“If you’re making something, selling something, or trying to reach people you have to be able to answer this question,” Holiday writes. I”t is shocking how many entrepreneurs, writers, salesman, even politicians never bother to stop and go: Who the hell is my audience here? The result is that the message is out of tune or the wrong group is targeted (and failure usually follows). Every creative must stop and really think about who their audience is.”
What do these people want?
What do they need?
What value am I offering them?
“Don’t try to get lucky. Don’t follow your hunch. Get it right. Ask the question, make sure the answer is clear,” Holiday maintains.
Does This Actually Matter?
The reason that wise people never let the very real fact of their mortality slip too far from their mind, Holiday posits, is because it helps them ask this question: Given the shortness of life, does this thing I’m thinking about, worrying about, fighting about, throwing myself into even fucking matter?
Sadly, the answer is usually no.
“We want to ask ourselves this question before we throw good time after bad, before we waste more life than we have to,” Holiday says. “Marcus Aurelius reminded himself, ‘You could leave life right now. Let that determine what you do and say and think.’ In light of that, does this thing you’re so worked up about actually matter?”
Will This Be Alive Time or Dead Time?
Early on in Holiday’s career, he had a pivotal conversation with author Robert Greene. Holiday was working full-time at a really good job but planning his next move, saving money and thinking about what he might do next.
Holiday writes, “I told him I wanted to write a book one day, but I wasn’t sure what, how or when or what about. He told me, Ryan, there are two types of time: Dead time — where we are just waiting and Alive time — where we are learning and active and leveraging. And then he left it there with me to decide which I would choose. Alive time or Dead Time?“
“So let that question catch you the next time you find yourself sitting on your hands or goofing off as you wait,” continues Holiday. “Let it jolt you back into line. Pick up a book, pick up a pen and get back to work. Resist the temptation to get distracted with silly politics or wanderlust. Make the most of every moment as you prepare for the next move or the next event. If you want to be productive, be fully alive.”
Is This Who I Want To Be?
Fortunately for us, our mind cunningly makes the distinction between what we do and who we are. “The problem is that this is complete nonsense,” Holiday believes. “You can’t be a good person if your actions are consistently bad. You can’t be a hardworking person if you take every shortcut you can.”
“It doesn’t matter that you say you love someone, it only matters if you show that you love them, Holiday writes. Take note of Cheryl Strayed’s line: “In your twenties you’re in the process of becoming who you are, so you might as well not be an asshole.”
This is true for life itself, posits Holiday. “You are what you do – so ask yourself whenever you’re doing something: Is this reflective of the person I want to be? That I see myself to be? How we do anything is how we do everything. It is who we are. So ask this question about every action, thought and word. Because it adds up in a way that no amount of self-image or belief ever will.”
Ryan Holiday is a writer and media strategist. When he was 19 years old, Holiday dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power. He went on to become the director of marketing for American Apparel. His creative agency, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors, including Neil Strauss, Tony Robbins and Tim Ferriss. Holiday has written six books, including The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic and Perennial Seller. The Obstacle Is the Way has been translated into more than twenty languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Holiday lives on a ranch outside Austin, Texas where he writes and works in between raising cattle, donkeys and goats.
