Top 500 Ryan Holiday Quotes (2025 Update)
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401. “Let’s make one thing clear: we never earn the right to be greedy or to pursue our interests at the expense of everyone else. To think otherwise is not only egotistical, it’s counterproductive.”

— Ryan Holiday

402. “For nothing outside my reasoned choice can hinder or harm it – my reasoned choice alone can do this to itself.”

— Ryan Holiday

403. “Attach yourself to people and organizations who are already successful and subsume your identity into theirs and move both forward simultaneously.”

— Ryan Holiday

404. “So much of the distress we feel comes from reacting instinctually instead of acting with conscientious deliberation.”

— Ryan Holiday

405. “To be great, one must make great work, and making great work is incredibly hard. It must be our primary focus. We must set out, from the beginning, with complete and total commitment to the idea that our best chance of success starts during the creative process.”

— Ryan Holiday

406. “There’s nothing to feel guilty about for being idle. It’s not reckless. It’s an investment. There is nourishment in pursuits that have no purpose – that is their purpose.”

— Ryan Holiday

407. “We talk to fill the void and the uncertainty.”

— Ryan Holiday

408. “Most successful people are people you’ve never heard of. They want it that way. It keeps them sober. It helps them do their jobs.”

— Ryan Holiday

409. “A crowded world thinks that aloneness is always loneliness and that to seek it is perversion. – JOHN GRAVES.”

— Ryan Holiday

410. “Attempting to destroy something out of hate or ego often ensures that it will be preserved and disseminated forever.”

— Ryan Holiday

411. “Philosophy’s true use – “An operating system for life’s difficulties and hardships”.”

— Ryan Holiday

412. “If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.”

— Ryan Holiday

413. “Listen and connect with people, don’t perform for them.”

— Ryan Holiday

414. “One day is as all days, as the Stoics liked to say.”

— Ryan Holiday

415. “The old way – where product development and marketing were two distinct and separate processes – has been replaced.”

— Ryan Holiday

416. “Facts are better than dreams, as Churchill put it.”

— Ryan Holiday

417. “Stoicism as the ideal “personal operating system.”

— Ryan Holiday

418. “Very few go astray who comport themselves with restraint. – CONFUCIUS.”

— Ryan Holiday

419. “So we ask ourselves: Why are things the way they are? What practices should be questioned and which should remain sound? This allows us to be both exotic and accessible, shocking but not gratuitous, fresh without sacrificing timelessness.”

— Ryan Holiday

420. “From sacrifice comes meaning. From struggle comes purpose. If you’re to create something powerful and important, you must at the very least be driven by an equally powerful inner force. If.”

— Ryan Holiday

421. “We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods.”

— Ryan Holiday

422. “In the way that a good wine must be aged, or that we let meat marinate for hours in spices and sauce, an idea must be given space to develop. Rushing into things eliminates that space.”

— Ryan Holiday

423. “A great destiny, Seneca reminds us, is great slavery.”

— Ryan Holiday

424. “How often does that happen to us? We comfort a friend during a breakup, only to be surprised when our own relationship ends. We must prepare in our minds for the possibility of extreme reversals of fate. The next time you make a donation to charity, don’t just think about the good turn you’re doing, but take a moment to consider that one day you may need to receive charity yourself.”

— Ryan Holiday

425. “As a young basketball player, Bill Bradley would remind himself, “When you are not practicing, remember, someone somewhere is practicing, and when you meet him he will win.”

— Ryan Holiday

426. “I always prefer to start from a place of reality, not from my own projections and preferences. Humility is clearer-eyed than ego – and that’s important because humility always works harder than ego.”

— Ryan Holiday

427. “Our perceptions are the thing that we’re in complete control of.”

— Ryan Holiday

428. “What happened yesterday – what happened five minutes ago – is the past. We can reignite and restart whenever we like. Why not do it right now?”

— Ryan Holiday

429. “Compassion is always due,” he said to him, “to an enraged imbecile, who lays about him in blows which hurt only himself.”

— Ryan Holiday

430. “Today, you could try to increase your wealth, or you could take a shortcut and just want less.”

— Ryan Holiday

431. “Be natural and yourself and this glittering flattery will be as the passing breeze of the sea on a warm summer day.”

— Ryan Holiday

432. “Sometimes, staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path.”

— Ryan Holiday

433. “If solitude is the school of genius, as the historian Edward Gibbon put it, then the crowded, busy world is the purgatory of the idiot.”

— Ryan Holiday

434. “Remember, if there is one core teaching at the heart of this philosophy, it’s that we’re not as smart and as wise as we’d like to think we are. If we ever do want to become wise, it comes from the questioning and from humility – not, as many would like to think, from certainty, mistrust, and arrogance.”

— Ryan Holiday

435. “Is there anything sadder than the immense lengths we’ll go to impress someone? The things we’ll do to earn someone’s approval can seem, when examined in retrospect, like the result of some temporary form of insanity.”

— Ryan Holiday

436. “Fix your attention on your intelligence. Let it do its thing.”

— Ryan Holiday

437. “It’s much easier to control our perceptions and emotions than it is to give up our desire to control other people and events.”

— Ryan Holiday

438. “To be or to do – life is a constant roll call.”

— Ryan Holiday

439. “Remember that this moment is not your life, it’s just a moment in your life. Focus on what is in front of you, right now. Ignore what it “represents” or it “means” or “why it happened to you.” There is plenty else going on right here to care about any of that.”

— Ryan Holiday

440. “If we can focus on making clear what parts of our day are within our control and what parts are not, we will not only be happier, we will have a distinct advantage over other people who fail to realize they are fighting an unwinnable battle.”

— Ryan Holiday

441. “What thrives online is not the writing that reflects anything close to the reality in which you and I live. Nor does it allow for the kind of change that will create the world we wish to live in.”

— Ryan Holiday

442. “Use this knowledge to be gentle and gracious.”

— Ryan Holiday

443. “If the definition of insanity is trying the same thing over and over and expecting different results, then passion is a form of mental retardation- deliberately blunting our most critical cognitive functions.”

— Ryan Holiday

444. “An entrepreneur is someone with faith in their ability to make something where there was nothing before. To them, the idea that no one has ever done this or that is a good thing. When given an unfair task, some rightly see it as a chance to test what they’re made of – to give it all they’ve got, knowing full well how difficult it will be to win. They see it as an opportunity because it is often in that desperate nothing-to-lose state that we are our most creative.”

— Ryan Holiday

445. “Michael Arrington, the loudmouth founder and former editor in chief of TechCrunch, is famous for investing in the start-ups that his blogs would then cover. Although he no longer runs TechCrunch, he was a partner in two investment funds during his tenure and now manages his own, CrunchFund. In other words, even when he is not a direct investor he has connections or interests in dozens of companies on his beat, and his insider knowledge helps turn profits for the firm.”

— Ryan Holiday

446. “The best men are not those who have waited for chances but who have taken them; besieged chance, conquered the chance, and made chance the servitor. – E. H. CHAPIN.”

— Ryan Holiday

447. “It’s supposed to be hard. Your first attempts aren’t going to work. It’s going to take a lot out of you – but energy is an asset we can always find more of. It’s a renewable resource. Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.”

— Ryan Holiday

448. “Advertising can add fuel to a fire, but rarely is it sufficient to start one.”

— Ryan Holiday

449. “Focusing exclusively on what is in our power magnifies and enhances our power. But every ounce of energy directed at things we can’t actually influence is wasted, self-indulgent, and self-destructive.”

— Ryan Holiday

450. “With accomplishment comes a growing pressure to pretend that we know more than we do. To pretend we already know everything.”

— Ryan Holiday