Twelve Stoic questions to redirect your focus and values

Executive overview

Most people seek answers, but the right question at the right moment changes more than any answer. Ryan Holiday presents twelve Stoic-derived questions designed to cut through distraction and surface what actually matters.

Ask them repeatedly. Let them work on you.

The questions you choose to sit with shape the person you become.

Who and what are shaping you

• The people you spend time with are averaging you toward or away from who you want to be
• "Show me who you spend time with and I'll tell you who you are" — Gertrude/Seneca
• Applies equally to who you read, watch, and talk to
• Hard decisions follow: some people get less of your time

What's actually in your control

• Dichotomy of control (Epictetus): the chief task of the philosopher — separate what's up to you from what isn't
• Most time and energy goes to things outside our control
• What is in control: actions, thoughts, opinions
• Throwing energy at unmovable walls is waste, not effort

What does your ideal day look like

• If you can't describe a good day, you'll default to chasing money, fame, or power
• Each new opportunity needs one test: does it move me closer or further from the life I want?
• Design the day first; everything else gets filtered against it

To be or to do

• John Boyd's question: do you want to look important, or quietly get things done?
• "It's amazing how much you can accomplish if you don't care who gets the credit" — Truman
• Do you care about credit or impact?
• George Marshall turned down command at Normandy because the mission mattered more than his legacy

If I am not for me — and if I am only for me

• Fight for yourself, or you get walked over
• If all you care about is credit and attention, who are you?
• "If you play for the name on the front of the jersey, they'll remember the name on the back"

What am I missing by choosing to worry or be afraid

• Cognitive resources are finite — anxiety consumes them
• Worry doesn't just feel bad; it actively narrows what you can see
• Emotions compound the original problem when acted on

Are you doing your job

• Everyone has a job in every moment — sometimes small, sometimes large
• We focus on others' jobs because it's easier than doing our own
• Ask it plainly: are you doing it? If not, why not?

What is the most important thing to you

• All other life questions are downstream of this one
• Euthymia (Seneca): knowing your path and ignoring the paths of those who've crisscrossed yours — especially the hopelessly lost
• When you know what matters, ignoring what doesn't becomes easy

Who is this for

• Every piece of work needs a specific audience, not a vague hope
• Empathy requires knowing who they are, where they are, what they want
• Scrap your hunches; name the person

Does this actually matter

• Marcus Aurelius: "Ask yourself at every moment, is this essential?"
• Eliminating the inessential makes you better at the essential — a double benefit
• Colbert's mother after a family tragedy: "Can you look at this in the light of eternity?"
• People matter. Doing your best matters. Most of the rest doesn't.

Will this be live time or dead time

• Live time vs dead time (Robert Greene): are you using the moment or waiting it out?
• "It's not that life is short. It's that we waste a lot of it." — Seneca
• You always have the ability to make the most of this moment; usually we choose not to

Is this who I want to be

• Every action either reflects or erodes the person you're becoming
• "You're becoming who you're going to be. So you might as well not be an asshole." — Cheryl Strayed
• How you do anything is how you do everything
• Small moments add up in ways nothing else can