Stoic philosophy sounds impressive in theory. Reading about Marcus Aurelius handling betrayal or James Stockdale surviving imprisonment is inspiring. But what about your actual life? How does ancient wisdom help when you’re dealing with a difficult boss, a failing startup, a career plateau, or the everyday obstacles of modern existence?
In “The Obstacle is the Way,” Ryan Holiday bridges the gap between philosophical principles and practical application. He demonstrates that Stoicism isn’t just for emperors and war heroes—it’s a operating system for navigating the specific challenges you face right now. Let’s explore how to apply Stoic principles to the real obstacles in your career, business, and daily life.
Applying Stoicism to Career Setbacks and Professional Obstacles
Your career won’t follow a straight upward trajectory. You’ll face rejections, missed promotions, difficult colleagues, toxic bosses, and periods where nothing seems to work. Stoic philosophy provides a framework for navigating these challenges without losing your sanity or your trajectory.
When you face a career setback, the Stoic approach begins with perception. Strip away the emotional interpretation and look at the facts. You didn’t get the promotion—that’s a fact. “I’m not good enough and will never advance” is interpretation. The fact opens possibilities; the interpretation closes them.
Holiday shares how this played out in his own career. Early setbacks that seemed devastating at the time—projects that failed, opportunities that disappeared, relationships that ended—later proved to be redirections toward better paths. But only because he chose to see them that way and act accordingly.
The action phase means asking: what can I learn from this? What skills can I develop? What different path might open? Instead of spiraling into resentment or despair, you channel that energy into growth. The promotion you didn’t get becomes motivation to strengthen weak areas, build new skills, or explore different opportunities.
Finally, the will phase kicks in when you face obstacles genuinely beyond your control—an industry in decline, company politics, or economic forces. Here, you practice acceptance while maintaining commitment to excellence. You focus on doing outstanding work regardless of recognition, building skills regardless of immediate application, and maintaining integrity regardless of external rewards.
Navigating Business Failures and Entrepreneurial Challenges
Entrepreneurship is obstacle after obstacle. Markets shift, competitors emerge, customers disappoint, partners disagree, money runs out. The Stoic approach to business challenges is ruthlessly practical because it has to be—Stoicism was developed by people facing life-or-death obstacles, not abstract problems.
When your business faces a major obstacle, begin by separating what you control from what you don’t. You can’t control market conditions, but you control your response. You can’t control customer preferences, but you control your product development process. You can’t control the economy, but you control your cost structure and cash management.
Holiday emphasizes the importance of what the Stoics called “preferred indifferents”—outcomes you’d like but don’t need for your peace of mind or sense of purpose. You prefer to have your business succeed, but your inner peace doesn’t depend on it. This paradoxical mindset actually increases your chances of success because you make decisions from clarity rather than desperation.
Consider the story Holiday tells of Steve Jobs being fired from Apple, the company he founded. The obstacle seemed insurmountable—total rejection by the organization he built. Jobs could have become bitter and given up. Instead, he started NeXT and Pixar, experiences that taught him lessons he later brought back to Apple. His forced departure became the path to his greatest success.
When your business faces obstacles, ask yourself: what is this obstacle teaching me? What capabilities must I develop? What assumptions must I question? What new opportunities might exist that I can’t see while fixated on this problem? The obstacle becomes your business school, often teaching lessons you couldn’t learn any other way.
Dealing With Difficult People and Workplace Politics
One of the most common obstacles people face isn’t market forces or skill gaps—it’s difficult people. Toxic bosses, unethical colleagues, unreasonable clients, or dysfunctional team dynamics create daily stress and can derail careers.
The Stoic approach to difficult people starts with a radical shift in perception: others cannot harm you without your consent. They can’t make you angry, bitter, or demoralized—they can only create situations that you choose to interpret in ways that harm you. This isn’t victim-blaming; it’s recognizing where your power actually lies.
Marcus Aurelius dealt with this constantly. As emperor, he faced betrayal from trusted advisors, incompetence from officials, and challenges from enemies. His journal is full of reminders to himself about dealing with difficult people. “When you wake up in the morning, tell yourself: The people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous and surly.”
But he didn’t stop at expecting difficulty—he prepared his response. He would remind himself that these people were acting from ignorance, that getting angry with them was like getting angry at a fig tree for producing figs, and that his job was to maintain his own excellence regardless of their behavior.
Holiday suggests practical applications of this wisdom. When a colleague undermines you, resist the temptation to respond in kind. Instead, focus on doing excellent work that speaks for itself. When a boss is unreasonable, accept that this is part of your current reality and ask what capabilities you can develop in response. When politics threaten your position, recognize what you can and cannot control, and direct your energy accordingly.
The action phase with difficult people often involves indirect approaches. You can’t change them directly, but you can change your relationship with them, change your situation, or change how their behavior affects you. Sometimes the right action is setting boundaries. Sometimes it’s finding allies. Sometimes it’s documenting issues for HR. And sometimes it’s realizing this obstacle is redirecting you toward better opportunities elsewhere.
Overcoming Analysis Paralysis and Decision-Making Obstacles
Modern life presents endless choices and information, often leading to analysis paralysis. You can’t decide whether to change careers, start a business, take a promotion, or make a major life change. The Stoic approach to decision-making cuts through this paralysis.
First, recognize that not deciding is a decision. Every day you don’t move forward is a choice to stay where you are. The Stoics were action-oriented—they believed in making decisions with the best available information and then adjusting course as needed.
Holiday emphasizes the importance of focusing on what the Stoics called “the dichotomy of control.” In any decision, identify what you control (your effort, your choices, your response) and what you don’t (outcomes, other people’s reactions, external results). Make your decision based on what you control, and accept uncertainty about the rest.
When facing a major decision, ask yourself: what’s the worst realistic outcome? Can I handle that? Usually, you can. The catastrophic scenarios we imagine are far worse than realistic worst cases. This isn’t about being reckless—it’s about being realistic rather than paralyzed by imagined disasters.
The Stoic approach also means accepting that there’s rarely one perfect choice. Most decisions aren’t between good and bad; they’re between different goods or different challenges. Commit to a choice, act on it with full effort, and trust that you’ll learn what you need to learn regardless of the outcome.
Managing Work-Life Balance and Competing Priorities
One of the most persistent obstacles people face is the challenge of competing priorities—career, family, health, personal growth, relationships. The Stoic approach doesn’t promise easy answers but provides a framework for navigating these tensions.
Begin with clarity about your values. What actually matters most to you? Not what you think should matter or what others expect, but what genuinely aligns with your deepest values? The Stoics believed in living according to nature—your nature, your purpose, your authentic priorities.
Holiday points out that the Stoics didn’t try to “balance” everything equally. Instead, they focused on excellence in what mattered most while accepting good-enough in other areas. Marcus Aurelius was simultaneously emperor, philosopher, husband, and father—roles that constantly conflicted. He navigated this by being clear about his priorities and accepting that perfection in all areas was impossible.
The action phase means making concrete choices that reflect your priorities. If family matters most, your career decisions should support that value, even when it means passing up opportunities. If building something meaningful drives you, relationships and personal time may need to accommodate that priority.
The will phase recognizes that you’ll never have perfect balance, and beating yourself up about it only creates additional suffering. Accept the trade-offs inherent in your choices, commit fully to what you’ve prioritized, and refuse to waste energy on guilt about what you’re not doing.
Handling Financial Stress and Economic Obstacles
Financial problems create unique stress because they affect every area of life. Job loss, debt, failed investments, or insufficient income are obstacles that feel overwhelming and inescapable. The Stoic approach to financial obstacles is particularly relevant because most Stoics understood poverty firsthand.
Epictetus was enslaved—he literally owned nothing. Seneca, though wealthy, regularly practiced voluntary poverty to prove he could survive without his wealth. These weren’t just theoretical exercises; they were preparing for the reality that external circumstances could strip away their resources at any moment.
The perception shift starts with recognizing the difference between needs and wants. What do you actually need versus what you prefer? Modern culture conflates these constantly, creating perpetual dissatisfaction. The Stoics practiced differentiating luxury from necessity, not to live in deprivation but to reduce vulnerability to external circumstances.
Holiday shares examples of people who faced financial ruin and rebuilt. The common thread wasn’t just hard work or luck—it was the ability to see opportunity in the obstacle. Bankruptcy forced some to develop new skills. Job loss pushed others toward better careers. Financial pressure motivated innovation they wouldn’t have attempted from comfort.
The action phase with financial obstacles is brutally practical. You assess your situation objectively, cut unnecessary expenses, develop new income streams, acquire valuable skills, and work persistently toward improvement. No drama, no excuses—just clear-eyed assessment and relentless forward movement.
The will phase means accepting your current reality without resentment while refusing to let it define your worth or limit your future. You’re experiencing financial difficulty—that’s a fact. You’re not a failure, you’re not cursed, you’re simply facing an obstacle that many have faced and overcome.
Dealing With Health Challenges and Physical Limitations
Health obstacles—whether chronic illness, injury, disability, or the general decline of aging—test every Stoic principle. These obstacles often can’t be overcome through effort or cleverness; they must be endured and adapted to.
The Stoics were realistic about the body. Marcus Aurelius suffered from chronic stomach problems. Seneca had respiratory issues. They didn’t pretend these weren’t limitations, but they refused to let physical challenges prevent them from living meaningful lives.
The perception shift with health obstacles is recognizing what remains possible rather than fixating on what’s lost. You may not be able to do what you once did, but what can you do? How can you contribute, grow, and find meaning within your actual circumstances rather than the circumstances you wish you had?
Holiday shares the story of Randy Pausch, a professor diagnosed with terminal cancer who gave his famous “Last Lecture” about achieving childhood dreams. Pausch didn’t pretend he wasn’t dying, but he chose to focus on making his remaining time meaningful rather than being consumed by bitterness or fear.
The action phase means working within your constraints rather than against them. Adapt your goals, modify your methods, and persist in finding ways to move forward. The Stoics believed that obstacles to one path often redirect you toward better paths you wouldn’t have considered otherwise.
Building Stoic Practices Into Daily Routines
The most practical application of Stoicism is making it a daily practice rather than something you remember during crises. Holiday and other modern Stoics advocate for regular practices that strengthen your ability to face obstacles.
Morning meditation or journaling where you prepare for the day’s potential obstacles, reminding yourself of what you control and what you don’t. This was Marcus Aurelius’s practice—his Meditations were essentially his morning pages, preparing himself mentally for the day ahead.
Evening review where you assess how you responded to obstacles, what you learned, and how you can improve. Seneca practiced this, asking himself each night: “What ailment of yours have you cured today? What failing have you resisted? Where can you show improvement?”
Regular practice of voluntary discomfort—taking cold showers, skipping meals occasionally, doing hard physical work—to prove to yourself that discomfort won’t destroy you. This builds resilience before you need it.
Studying examples of people who overcame obstacles similar to yours. History is full of role models who faced worse circumstances and prevailed. Their examples provide both inspiration and practical wisdom.
Conclusion: Philosophy as an Operating System
The genius of Stoic philosophy, as Holiday presents it in “The Obstacle is the Way,” is that it’s not just inspiration—it’s a practical operating system for navigating real obstacles. Whether you’re facing career challenges, business problems, difficult people, financial stress, or health issues, the Stoic framework of perception, action, and will provides concrete guidance.
The obstacles you face right now—whatever they are—are opportunities to practice this philosophy. Not just to think about it or admire it, but to actually use it. To see your challenges clearly, act on them persistently, and endure what cannot be changed with dignity and purpose.
Start small. Choose one current obstacle and apply the Stoic framework. How can you shift your perception of it? What action can you take today? What aspect of the situation do you need to accept while maintaining your will to continue?
Over time, these practices become reflexive. You automatically separate facts from interpretations, focus on what you control, and persist through setbacks. The obstacles never stop coming, but you become someone who isn’t stopped by them.
That’s the practical power of Stoicism. Not that life becomes easy, but that you become capable. Not that obstacles disappear, but that you transform them into opportunities for growth, learning, and demonstration of character.
Your obstacles are waiting. They’re your curriculum, your training ground, your opportunity to practice philosophy in action. The question isn’t whether you’ll face them—you will. The question is whether you’ll apply the wisdom that has helped humans navigate obstacles for two millennia.
The obstacle is the way. Now you know how to walk it.
Everything You Need to Know About Ryan Holiday’s “The Obstacle Is the Way” (Complete Book Guide)