The Obstacle Is the Way

Summary Written by Dianne Coppola
"All great victories, be they in politics, business, art or seduction, involved resolving vexing problems with a potent cocktail of creativity, focus and daring."

- The Obstacle is the Way, page 8

The Big Idea

Be Response-Able

"We decide what we will make of every situation… Our perceptions are the thing we are in complete control of."- The Obstacle is the Way, page 21

I am a fan of the late Dr. Stephen Covey which is where I first came across the wisdom of this The Big Idea. In his work on time management, notably in reference to deciding between what is urgent and what is important, Dr. Covey emphasized the importance of a concept he coined ‘response-ability’; the ability to control how we respond to a given situation. He advised one should always pause, even if briefly, to separate fact from fiction (fiction being our emotional, knee-jerk response to a situation), before making a decision. This is sound advice that is not always easy to execute.

Do you see the glass as half-full or half-empty? Did a door close or open? Did you fail or did you learn one way that didn’t work? The way we label and talk about our challenges has a definite impact on our ability to deal effectively with those curveballs. Don’t make mountains out of molehills and definitely don’t stick your head in the sand hoping the problem will disappear. Give yourself permission to call a thirty second ‘time out’ so you can objectively assess the situation and choose a more thoughtful and proactive way forward. Practice being ‘Response-Able’.

Insight #1

Think Progress Not Perfection

"Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started."- The Obstacle is the Way, page 75

As a self-acknowledged perfectionist, this is one insight that I have to work hard at implementing. In the tech world, this insight would be known as ‘Beta-Mode’ – a term that describes a product that is reasonably functional (and so is released) yet has room for fine-tuning and debugging. In baseball, it’s called getting on base, not hitting the home run. In the world of facilitation and training (where I work), we refer to it as GEPO – Good Enough, Push On. When it comes to tackling obstacles, it means trying something, anything so that you aren’t defeated before you begin.

Holiday reminds us that everyone you or I admire, everyone who has accomplished great things, did so because they started! They didn’t wait to craft the perfect action plan. They said to themselves, ‘yes I want to ____________’ (fill in the blank with an appropriate goal) and they took the first step, seizing opportunities that came up along the way.

What are you putting off doing because the ‘time just isn’t right?’ Where do you need to generate some momentum in your life? What’s holding you back? Think about how you can make progress, however small the attempt might be, rather than striving for perfection right out of the gate. Take that first step!

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Insight #2

Focus on the Process!

"The process is order, it keeps our perceptions in check and our actions in sync."- The Obstacle is the Way, page 89

In a world fixated on delivering outcomes and products for an ‘I needed this yesterday’ crowd, this insight might seem counterintuitive. However, when pursuing a big goal or tackling a nasty problem, focusing on the process helps to lessen the self-inflicted pressure we often feel and lets us channel our energy towards what needs to be done in the moment. In essence, focusing on the process combines the wisdom of our The Big Idea and insight #1 and enables us to kill those two proverbial birds with one stone (my apologies to all bird lovers reading this summary).

Process is about the routines we set up that support our efforts to accomplish a goal or overcome a seemingly insurmountable obstacle. Process automates our decision-making and eliminates guesswork and procrastination. Process narrows our focus to the task at hand rather than the end result. In Holiday’s words: “The process is about finishing. Finishing games. Finishing workouts. Finishing film sessions. Finishing drives. Finishing reps. Finishing plays. Finishing blocks. Finishing the smallest task you have right in front of you and finishing it well. And when you’ve finished one task, process guides you to move on to the next one – like the chocolates moving along the conveyor belt in that classic I Love Lucy episode!

Where might you rely more deliberately on process (aka routines, habits, structure) to increase your ability to focus more intently on completing the small tasks that lead to big successes? Commit to the process of finishing the small tasks well and success will find you!

Holiday acknowledges that life isn’t always a bowl of cherries yet simultaneously challenges his readers to make lemonade out of the lemons that inevitably find their way into one’s life. He shares what he has learned from the experiences of many teachers (past and present) in a thought-provoking and conversational tone. It turns out victory can be ours if we discipline ourselves to practice three critical steps: managing our perceptions, taking small actions and persevering no matter what befalls us. Simple steps yet not always easy ones.

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Ryan Holiday

Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians. He served as director of marketing at American Apparel for many years, where his work was internationally known. His campaigns have been used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, Gawker and Fast Company. His first book, Trust Me I’m Lying: Confessions of a Media Manipulator–which the Financial Times called an “astonishing, disturbing book” was a debut bestseller and is now taught in colleges around the world. His subsequent books, Growth Hacker Marketing and The Obstacle is the Way were both published by Penguin/Portfolio.

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