PDF Summary:The Obstacle Is The Way, by Ryan Holiday

A cult classic among professional athletes, The Obstacle Is the Way is a guidebook to solving any problem preventing you from achieving ambitious goals. It’s based on the tenets of Stoicism—an ancient Greek philosophy promoting calm rationality in any situation. Ryan Holiday argues that by choosing to view your obstacles in an empowering way, you can turn them into your greatest assets.

Holiday is a marketing mogul turned Stoic guru whom the New York Times credits for the modern movement of ancient Stoicism as self-help. In this guide, we’ll provide specific strategies to help you exert Stoic discipline over both your internal world and the external world. We’ll also compare and contrast Holiday’s “life hack” Stoicism with the original philosophical texts that inspired it, as well as connect it to relevant contemporary self-help such as Grit by Angela Duckworth and Thinking in Bets by Annie Duke.

(continued)...

The lucky subjects who approached life with this positive attitude thrived because they took more risks, sought out more unfamiliar situations, and were more receptive to positive opportunities than their unlucky counterparts. These characteristics made them more likely to stumble into romantic success and promotions at work. As Holiday would predict, their optimistic perceptions determined how they responded to life events, making their lives demonstrably “luckier.”

The Internal Fight: Master Your Emotions

So far, we’ve outlined two truths from Stoicism that Holiday asserts will help you fulfill your wildest ambitions. For the rest of this guide, we’ll be discussing specific strategies to help you live according to these truths: ways to reorient your thinking and overcome any problem. First, let’s look at Holiday’s internal, emotional strategies for success.

Holiday emphasizes the importance of emotional regulation—intentionally deciding which emotions you will allow to influence your behavior. It’s a simple fact of life: You will frequently feel emotions (such as fear and anger) that work against you and push you away from your goals. If you don’t exert control over these unhelpful emotions, you won’t be able to take advantage of the opportunities within your obstacles.

(Shortform note: Holiday’s stance on emotion regulation is less extreme than the original Stoic teachings. Holiday sees negative feelings as more or less an inevitable part of life, defining emotional discipline as the ability to act despite your unhelpful emotions. On the other hand, traditional Stoics believed that by exerting your rationality, you can learn to completely cleanse yourself of harmful emotions.)

Strategy #1: Use Logic to Defuse Your Unhelpful Emotions

Holiday claims that by slowing down and analyzing your situation logically, you can soothe unhelpful, impulsive emotions like panic or anger. Whenever you feel yourself being tugged around by your emotions, stop and interview yourself to discover why you feel the way you do. Ask yourself questions, then answer them logically. You can overcome negative emotions by clarifying what irrational beliefs are making you feel this way and replacing them with a logical counterargument.

(Shortform note: In Emotional Intelligence, Daniel Goleman offers a caveat to this advice, noting that thinking over an emotion for too long may extend and intensify your negative feelings. Mental exercises such as Holiday’s self-interview may make you sadder by forcing you to dwell on whatever is making you sad. Instead, Goleman recommends intentionally planning pleasant distractions such as comforting TV or exercise to combat sadness.)

Strategy #2: Redirect Your Emotions Into Helpful Contexts

When you’re unable to fully rid yourself of negative emotions, Holiday recommends you transform them into a form that serves you. In particular, when unfair circumstances or pointless constraints frustrate you, Holiday suggests you use that anger as fuel instead of allowing it to make you reckless. Use your calm, rational mind to decide where to commit your energy, then allow yourself to act wildly and impulsively within that context.

(Shortform note: The process Holiday describes here—using your unhelpful emotions to motivate constructive action—is known in psychology as sublimation. Sigmund Freud introduced this concept into the public vocabulary. Although the majority of Freud’s hypotheses have been discredited, the concepts of sublimation and similar psychological defense mechanisms have endured.)

Strategy #3: Prepare for Long-Term Hardship

Holiday argues that to achieve your goals, you need resilience woven into your DNA as a permanent feature of your character. He asserts that it’s possible to build this kind of emotional strength with practice over time. Decide where you need to go and resolve that you will do anything it takes to get there, no matter what obstacles get in your way—then do it again. To a certain degree, it’s worth your while to intentionally seek out adversity to train yourself for the greater troubles that lie ahead.

(Shortform note: Holiday’s advice on how to cultivate perseverance can be boiled down to “Toughen up and do it.” On the other hand, in Grit, Angela Duckworth advocates for a gentler path to resilience, one that doesn’t require as much sheer willpower. Duckworth asserts that you can develop grit in stages, initially pursuing something fun that interests and gratifies you, then practicing to achieve superiority, and finally merging your skill with an altruistic purpose. In other words, resilience develops naturally as you pursue satisfying goals.)

Strategy #4: Take Things Step-by-Step

Holiday argues that the best way to tackle any fearsome problem or obstacle is to break it down and just focus on finishing one step at a time. Do the first step well, then move on to the next step and the next. Don’t think about the end goal, just what you have to do now. When you have a plan to follow, problems feel less daunting—each step is a psychologically manageable task that you can work up the courage to complete.

(Shortform note: In Eat That Frog!, Brian Tracy notes that when a task reaches a certain size, it becomes impossible to plan out the entire process ahead of time in the way Holiday describes. When your plan involves unknown variables or complex moving parts, the only thing you can do is take the first step and have faith that the next step will reveal itself to you. If you can become comfortable with this uncertainty, taking the task one step at a time will still help you feel less intimidated.)

Strategy #5: Motivate Yourself by Helping Others

Holiday asserts that by turning your attention outward and helping others, you can tap into an unlimited source of motivation and strength that will help you overcome obstacles. Negative emotions like anxiety and self-pity fade away when you discover a way to move forward and do good. Whenever you feel stuck, find a way to help someone other than yourself.

(Shortform note: While Holiday frames the feeling of contribution to others as a source of motivation to achieve your virtuous goals, in The Courage to Be Disliked, Ichiro Kishimi and Fumitake Koga make the more extreme argument that these feelings of contribution are the essence of all happiness. Kishimi and Koga assert that happiness is based on self-worth—whether or not you think you’re a “good person”—and contribution to others is the source of all self-worth.)

Strategy #6: Accept Things for What They Are

Holiday’s final strategy to master your emotions is to accept things for what they are. Some aspects of life are impossible to change—for instance, the actions of others, or a tragedy that has already happened. Holding an emotional grudge against a reality you can’t change will only make it more difficult to achieve your goals. Instead, peaceably accept things for what they are.

(Shortform note: In The Happiness Trap, Russ Harris explains how readers can use something called “Acceptance and Commitment Therapy,” or “ACT,” to find happiness in their lives. Harris uses the same rationale as Holiday to support his advice: We should focus on what we can control and peaceably accept whatever is out of our control. Harris, however, gets more specific than Holiday, applying this logic to negative thoughts. If a negative thought pushes you toward something you can change, it’s helpful, so act on it. If it pushes you toward something you can’t change, accept it and ignore it.)

The External Fight: Do What It Takes to Succeed

We’ll conclude with a set of Holiday’s strategies to overcome obstacles in the external world, difficult yet rewarding paths to success that require you to transform obstacles into gifts at every turn.

Strategy #1: Act, Don’t Think

The core of Holiday’s overall strategy for success is to start immediately and rush toward your goal as quickly and aggressively as possible. Consistently putting in effort is how you build the momentum necessary to reach your goals, and momentum is more important than anything else. If you ever stop aggressively moving forward with as much effort as you can muster, instead of overthinking your every step, you risk becoming soft and complacent.

(Shortform note: Holiday warns of the dangers of overthinking, but in The One Thing, Gary Keller argues that if you act without first considering how to optimize your effort, underthinking can be just as harmful. Keller makes the case that even if you’re aggressively taking action toward your goal, you’re wasting your time if you’re not focusing on your “One Thing”—the task that will get you to your most ambitious goal faster than anything else. To find your One Thing, Keller suggests asking yourself “What one thing can I focus on that will have the greatest impact on my overall goal?”)

Strategy #2: Learn Something From Every Failure

Holiday acknowledges that if you follow his advice to act aggressively and persistently, you’ll inevitably fail often. However, he sees this as an unequivocally good thing. Trial and error is the most effective way to learn anything. Every failure teaches you how not to do something and forces you to come up with ideas you wouldn’t have normally thought of.

(Shortform note: In Thinking in Bets, professional poker player Annie Duke argues that the best way to learn from your mistakes is to view every decision you make as a bet—a gamble based on the idea that something might be true. This way, you recognize that every belief you have has a chance of being incorrect, and every suboptimal decision you make comes at a cost.)

Strategy #3: Set Unreasonable Goals

Holiday asserts that people who habitually fear failure—that is to say, almost everyone—generally assume that they can accomplish far less than they actually can. To avoid this mistake, he advises you to confidently set unreasonably ambitious goals and attempt to do the impossible. He advises you to seek out high-pressure situations like this because they’re most likely to inspire your best work. By focusing on the energizing effect of a big risk, you can transform it from something terrifying into something exciting.

(Shortform note: In The 10X Rule, Grant Cardone argues that most people fail because they don’t set difficult enough goals. How can this be? Most people set average, realistic goals and underestimate the effort it takes to achieve them. When it becomes obvious how much work these goals actually require, they aren’t excited enough to push through the unexpected struggle, so they quit. On the other hand, accomplishing something that seems impossible is a dream that will make you want to put in ten times the effort you normally would.)

Strategy #4: Predict What Will Go Wrong

Holiday argues that it’s important to remember that eventually, things will go wrong. People will let you down and random disasters will strike—this is the only constant in our unpredictable world. Your only defense is to anticipate what could go wrong and prevent or prepare for it. Holiday recommends making this a core step of your routine: Before taking any action, try to think up contingency plans for everything you can imagine going wrong.

(Shortform note: In The Dichotomy of Leadership, Jocko Willink and Leif Babin argue that while planning for what could go wrong (as Holiday suggests) helps avert painful disasters, overplanning—attempting to prepare a detailed response for every possible setback—can be just as harmful. Trying to predict everything that could go wrong will severely slow you down, and may even halt your progress entirely. At a certain point, this wasted time becomes more costly than it’s worth.)

Strategy #5: Do Something Unexpected

In many cases, the most successful strategy is that which is least expected. Holiday explains that the conventional strategy—the one other people in your situation use the most often—frequently has the lowest chance of success, as it’s the strategy your enemies and obstacles are the most prepared for. Using an obscure strategy to reach your goal often allows you to succeed with far less effort.

For example, if you’re trying to get your novel published, instead of sending query letters to agents or publishers and burying your pitch among thousands of others, find an unconventional way to make connections in the industry—for instance, locate a nearby writers’ conference to network at and volunteer to help run it.

(Shortform note: In The 48 Laws of Power, Robert Greene claims that even if your unexpected strategy isn’t successful in itself, acting unpredictably is still valuable. When no one understands why you’re doing something, you create an air of intrigue, attracting attention from onlookers. You may even earn their respect as people ascribe sophisticated motives to your actions that you never had.)