The Obstacle Is the Way

"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

Problems. Challenges. Roadblocks. Obstacles. Small irritations. Big thorny dilemmas. Inconvenient tangents. No matter their size and what you call them, we all face them. Like taxes and weeds, they are inevitable; clear one away and more appear!

So my curiosity was piqued when I came across Ryan Holiday’s book, The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph. He promised to reveal a formula for success that would help readers “get unstuck, unf**ked, and unleashed” (his words not mine). A way to turn “every obstacle into an advantage.” Was this book the long sought after Holy Grail for over-achievers or under-performers?

The answer appears to be both! Holiday took it upon himself to collect, understand and publish lessons learned from ancient philosophers (also referred to as Stoics) in true actionable books style. The book is divided into three sections, one for each step in the journey that will help you turn your obstacles into advantages: perception, action and will. The chapters read like our The Big Ideas and Insights – each one named to inspire action and nurture positive results — recognize your power, think differently, channel your energy, love everything that happens. And the book is chock full of relevant quotes, captivating stories and good old common sense which make it a very enjoyable read.

The Big Idea

The Big Idea: The biggest takeaway from the book

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

An actionable way to implement the Big Idea into your life

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!

Insight #2

An actionable way to implement the Big Idea into your life

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.

The reality is the road to success is full of potholes and can only be paved through hard work. Rather than asking yourself if you are up for the challenge, ponder a different question: What would be possible if you simply focused on what you can change? Today. Right now. In this very moment. Shift your focus and you will see a myriad of possibilities where once you saw only obstacles.

Tell us about a time when you encountered one or more potholes on the road to success and how you eventually managed to navigate your way safely to your destination. How did you recognize the opportunity disguised as an obstacle?

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Dianne Coppola

ABOUT Dianne Coppola

I am passionate about leadership development, change management, community collaboration and…reading! I’ve been writing for the Actionable Book Club since 2014 and love to share my book insights with folks like you...
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