Reading about Stoic philosophy is inspiring. Understanding the principles intellectually is valuable. But the true power of Stoicism comes from daily practice—from actually doing the exercises that train your mind to handle obstacles differently. In “The Obstacle is the Way,” Ryan Holiday doesn’t just explain Stoic principles; he shows how to practice them.
The Stoics weren’t theorists—they were practitioners. Marcus Aurelius wrote his Meditations as a daily practice of reminding himself how to think and act. Seneca practiced voluntary discomfort regularly to prove he could handle hardship. Epictetus taught specific exercises to his students. These weren’t optional add-ons to philosophy; they were the philosophy itself.
Let’s explore the practical exercises and daily practices that can transform how you face obstacles, building the mental strength and resilience that characterize Stoic practitioners throughout history.
Morning Premeditatio: Preparing for the Day’s Obstacles
The Stoics began each day with a practice called “premeditatio malorum”—the premeditation of evils. This isn’t about being pessimistic; it’s about being prepared. Before the day begins, you mentally rehearse potential obstacles and decide how you’ll respond.
Marcus Aurelius practiced this every morning, writing in his journal: “When you wake up in the morning, tell yourself: The people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous and surly.” He wasn’t being cynical—he was preparing himself mentally so these behaviors wouldn’t surprise or disturb him.
Holiday suggests a practical morning exercise: spend five minutes considering what obstacles might arise today. Your meeting might go poorly. Traffic might make you late. Someone might criticize your work. A project might fail. Don’t dwell on these pessimistically—simply acknowledge them as possibilities and decide now how you’ll respond.
The power of this practice is that it removes the element of surprise from obstacles. You’re not caught flat-footed when difficulty arises; you’ve already considered it and chosen your response. Your prefrontal cortex makes decisions in the morning rather than your amygdala making reactions in the heat of the moment.
The View From Above: Gaining Cosmic Perspective
Another powerful Stoic exercise is the “view from above”—imagining yourself from increasingly distant perspectives to gain clarity about what truly matters. Marcus Aurelius practiced this regularly, describing it in his Meditations.
Start with your immediate situation. Then zoom out to see your city, your country, your continent. Continue zooming: see Earth from space, the solar system, the galaxy. From this cosmic perspective, how significant is your current obstacle? Not in a way that dismisses it, but in a way that right-sizes it relative to the vastness of existence.
Holiday explains that this exercise accomplishes two things. First, it reduces anxiety about obstacles by providing appropriate perspective—your career setback matters, but it’s not the center of the universe. Second, it connects you to something larger than yourself, providing meaning and resilience when personal obstacles feel overwhelming.
Practice this weekly, or whenever an obstacle feels unbearable. Take ten minutes to imagine your situation from increasing distances. What would aliens observing Earth see? What would future historians note about this moment? The practice cultivates what the Stoics called “the long view”—seeing temporary obstacles within the context of deep time and vast space.
Negative Visualization: Appreciating What You Have
One of the most counterintuitive but powerful Stoic practices is regularly imagining losing what you value most. This negative visualization isn’t about manifesting negativity; it’s about deepening appreciation and reducing vulnerability to loss.
Seneca practiced this regularly, periodically living as if he’d lost everything—eating simple food, wearing plain clothes, sleeping on the floor. He wasn’t being masochistic; he was proving to himself that he could survive and even thrive without his wealth and comfort. This removed the fear of loss, which he believed was often worse than actual loss.
Holiday suggests starting small with this practice. Before going to work, imagine losing your job. How would you handle it? What would you do? Recognize that while you’d prefer to keep your job, you could survive and even find new opportunities if you lost it. This removes the desperate fear that makes you tolerate abuse or prevents you from taking necessary risks.
Before seeing loved ones, imagine this might be the last time. Not to be morbid, but to be present and appreciative. Notice how this shifts your attention from petty grievances to genuine connection. The Stoics believed that everything we have is on loan from fortune—recognizing this doesn’t make us sad; it makes us grateful and present.
Voluntary Discomfort: Building Resilience Through Practice
The Stoics regularly practiced voluntary discomfort—choosing to experience hardship when they didn’t have to. This wasn’t about suffering for its own sake; it was about proving to themselves that discomfort wouldn’t destroy them and building resilience before they needed it.
Seneca took this seriously, writing: “Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: ‘Is this the condition that I feared?'”
Holiday recommends modern versions of this ancient practice. Take cold showers even when you could take hot ones. Skip a meal occasionally when you’re not actually hungry. Walk or bike instead of driving. Sleep on the floor occasionally. Sit with discomfort rather than immediately reaching for entertainment or distraction.
The point isn’t to make yourself miserable—it’s to prove that discomfort is manageable and temporary. When you regularly choose minor discomforts, major hardships become less frightening. You’ve built evidence for yourself that you can handle difficulty, which is itself a powerful form of resilience.
More importantly, voluntary discomfort clarifies the difference between needs and wants. When you regularly do without small comforts, you realize how little you actually need to be okay. This understanding provides tremendous security—if you can be content with little, you’re less vulnerable to circumstances that might take things away.
The Dichotomy of Control: Daily Sorting Exercise
Perhaps the most fundamental Stoic practice is regularly sorting your concerns into what you control and what you don’t. Epictetus made this the foundation of his teaching: “Make a habit of distinguishing between what depends on you and what does not depend on you.”
Holiday emphasizes that this sorting exercise should be daily, not just during crises. Each evening, review your day’s concerns and sort them explicitly. Write two columns: “Within My Control” and “Outside My Control.” Be ruthlessly honest about this sorting.
In the first column, you might list your effort, your attitude, your choices, your response to events. In the second column, you’ll list other people’s opinions, economic conditions, past events, natural disasters, and most outcomes. The key insight: pour your energy into column one and practice acceptance regarding column two.
This exercise trains your mind to automatically categorize concerns as they arise. When worry appears, you immediately ask: “Is this within my control?” If not, you practice letting it go. If yes, you identify the specific action you can take. This simple sorting dramatically reduces anxiety and focuses energy where it can actually make a difference.
Evening Review: The Stoic Examination of Conscience
Seneca practiced what he called the “examination of conscience” each evening before sleep. He would review his day, assessing how he’d handled obstacles and where he could improve. This wasn’t about self-flagellation; it was about honest evaluation and continuous improvement.
Holiday recommends establishing your own evening review practice. Spend ten minutes before bed asking yourself three questions: What did I do well today? What could I have done better? What did I learn? Be specific about obstacles you faced and how you responded to them.
Did you let emotion cloud your perception? Did you take action when you should have? Did you maintain your principles under pressure? Where did you show strength? Where did you show weakness? The goal isn’t to judge yourself harshly but to honestly assess your practice so tomorrow can be better.
This daily review creates a feedback loop that accelerates growth. You’re not just experiencing obstacles; you’re learning from them systematically. Patterns become visible. Weak areas get identified. Improvements get reinforced. Over weeks and months, this practice transforms how you handle difficulty.
Journaling: Externalizing and Processing Thoughts
Marcus Aurelius kept a journal—what we now call Meditations—where he wrote to himself about Stoic principles and how to apply them. This wasn’t a diary of events; it was a philosophical working-through of how to maintain Stoic practice under extreme pressure.
Holiday himself practices daily journaling and recommends it as one of the most powerful Stoic exercises. The act of writing externalizes your thoughts, making them visible and workable. Problems that seem overwhelming in your head often look manageable on paper.
Journal about obstacles you’re facing. Describe them objectively—just the facts. Then write about different perspectives you might take. What would a Stoic say about this situation? What would Marcus Aurelius do? What action can you take? What must you accept? What opportunity might exist within this obstacle?
The process of writing forces clarity. Vague anxieties become specific concerns you can address. Emotional reactions get separated from objective facts. Potential responses get evaluated rationally rather than impulsively. Your journal becomes both a practice space for Stoic thinking and a record of your development.
Reading and Study: Learning From the Stoics
The Stoics themselves read and studied constantly. Marcus Aurelius carried books even on military campaigns. Seneca filled his letters with references to other philosophers. They understood that maintaining Stoic practice required constant reinforcement and new perspectives.
Holiday emphasizes that reading Stoic texts isn’t academic study—it’s practical training. When you read Marcus Aurelius or Epictetus or Seneca, you’re learning from people who successfully applied these principles under extreme circumstances. Their examples provide both instruction and inspiration.
Establish a daily reading practice. Even fifteen minutes each morning with Stoic texts can dramatically impact your day. Keep a copy of Meditations or Letters from a Stoic beside your bed or on your desk. When you encounter obstacles during the day, read a passage for perspective and guidance.
But don’t limit yourself to ancient texts. Holiday’s own books and others like Donald Robertson’s work make Stoicism accessible and relevant. Read biographies of people who embodied Stoic principles. Study examples of how others turned obstacles into advantages. Your reading creates a community of practitioners across time, all working on the same fundamental challenges.
Physical Training: Mind-Body Integration
The Stoics recognized the connection between physical and mental strength. Marcus Aurelius trained with wrestlers. Epictetus was a former slave who understood the importance of physical resilience. They knew that training your body trains your mind—particularly your ability to endure discomfort and push through difficulty.
Holiday recommends regular physical training as a Stoic practice. This doesn’t mean you need to become an athlete; it means consistently challenging your body in ways that build resilience and mental strength. Exercise that’s genuinely difficult—that requires you to push through discomfort—trains the same mental muscles you need for facing life’s obstacles.
Running when you want to stop. Lifting weights that are actually heavy. Holding a plank when every muscle is screaming. These physical practices teach you that discomfort is temporary, that you’re capable of more than you think, and that pushing through difficulty leads to growth and capability.
More broadly, treating your body as something to be trained and cared for rather than simply indulged builds the discipline that applies to every area of life. The person who can maintain a workout routine despite not feeling like it can maintain their principles despite temptation. Physical discipline and mental discipline reinforce each other.
The Obstacle Inventory: Reframing Current Challenges
Holiday suggests a powerful exercise specifically focused on current obstacles: create an inventory of your challenges and systematically reframe each one. This makes the abstract Stoic principle of “the obstacle is the way” concrete and actionable.
List every significant obstacle you’re currently facing. Don’t sugarcoat or minimize—acknowledge genuine difficulties. Then, for each obstacle, write answers to these questions: What is objectively true about this situation (facts only, no interpretation)? What unhelpful story am I telling myself about this obstacle? What opportunity might exist within this challenge? What can I learn? What action can I take? What must I accept?
This exercise forces you to systematically apply Stoic principles to your actual life rather than just reading about them abstractly. It transforms philosophy from interesting ideas to practical tools you’re actually using on real problems. Revisit this inventory weekly, updating it as obstacles change or as your perspective shifts.
Teaching and Discussion: Solidifying Understanding
The Stoics believed that teaching philosophy solidified your own understanding. Seneca wrote letters to friends partly to clarify his own thinking. Marcus Aurelius wrote his Meditations to teach himself. The act of explaining principles to others forces you to understand them more deeply.
Holiday recommends finding ways to teach what you’re learning about Stoicism. This doesn’t mean you need to become a formal teacher—just share insights with friends, discuss principles with family, or write about ideas online. When you have to explain how to apply Stoic principles to someone else’s obstacle, you understand those principles better yourself.
Join or create a community of practice. This could be a book club discussing Stoic texts, an online community, or regular conversations with friends interested in philosophy. The Stoics learned from each other; Seneca’s letters were part of a dialogue, and Epictetus taught students. Having a community provides accountability, fresh perspectives, and shared support in maintaining practice.
Conclusion: From Exercises to Lifestyle
The power of these Stoic exercises isn’t that they’re magic—it’s that they’re consistent training. Just as you can’t go to the gym once and expect to be fit, you can’t do these exercises once and expect to be resilient. The transformation comes through daily practice, building neural pathways and mental habits that eventually become automatic.
Ryan Holiday makes clear in “The Obstacle is the Way” that the goal isn’t perfection—even Marcus Aurelius struggled and had to constantly remind himself of Stoic principles. The goal is progress. Each day’s practice, each small improvement in how you handle obstacles, each instance of choosing Stoic perception over emotional reaction—these accumulate into real transformation.
Start with one or two practices that resonate most. Maybe morning premeditatio and evening review. Or journaling and physical training. Establish these as genuine habits before adding more. The consistency matters more than the number of practices.
Over time, these exercises become less like separate practices and more like a way of life. You naturally see obstacles through a Stoic lens. Your default responses become more philosophical. The discipline that required effort becomes your character. That’s when the obstacle truly becomes the way—not just as a nice idea but as your lived experience.
Everything You Need to Know About Ryan Holiday’s “The Obstacle Is the Way” (Complete Book Guide)