Obstacle to Opportunity: A Book, a Blog, a Parable, and a Podcast to Help Get Unstuck


I’m working on a new book, and despite all of the summer distractions (I’m a sucker for distractions) the first draft is about 75% complete. Of course, 75% done with the first draft means I have about 90% of the work left. But hey, progress.

The book is a manifesto meant to help first year lawyers get off to a fast start in their careers. Working on the book has dredged up lots of memories of my own time as a young lawyer. It was an exciting time, although difficult. My legal career was marked by fits and starts. I practiced at big firms, started my own small one, had success, but ultimately determined it wasn’t for me. I’ll never go back (and this time I mean it).

Recently Heather and I found ourselves reflecting on the following question: Would life have been easier if I had just kept practicing law instead of pursuing other things?

The most significant change that this choice would have forced (or better put, enabled) is that Heather would not work as much as she does. Whether by happenstance, or more likely as a result of my flitting back and forth between different business ideas and pursuits, today the core responsibility for managing our marketing business falls on Heather’s shoulders. She’s the general of this army.

And it is with that perspective that, at times, I think things would have been easier on all of us if I had just put my head down and pushed to make partner at the law firm I joined out of law school. I imagine that we would not have faced some of the obstacles that we’ve grappled with over the years that have arisen due to working together as entrepreneurs.

But then I consider the alternative. All that I love, and that we love, about our life together may never have materialized had we chosen a different path. The decisions we made then would almost certainly have had a butterfly effect, leading to a much different life now. And who is to say that what was easier then would have led to a better outcome? What if the obstacles we faced in life are, in fact, responsible for everything – our family, our friends, our interests, our dreams – that we cherish about our lives today?

What Stands in the Way Becomes the Way

The butterfly effect is, of course, a theory – one can never know the inverse impact of a decision. But one thing that we all know, intuitively and from life experience, is that the easy way is not always the right way. That’s an ancient truth that’s been passed down for millennia.

Thousands of years ago Roman emperor Marcus Aurelius wrote: “The impediment to action advances action. What stands in the way becomes the way.” This is a core tenet of Stoicism, the philosophy that derives from the collected works of Roman thinkers.

We all get stuck. And when we do, the tendency is to look for the easy way out. That’s human nature at its core. It’s an instinct baked into our genes.

But the easy way is usually the wrong way. The way forward is typically through the obstacle, not back or around. {tweet that}

I get stuck all the time. And more often than not I take the easy way out. Sometimes, though, I face the fear – and, yes, the obstacle is almost always rooted in fear – head on, and that’s when good things happen.

Because it’s not instinctual, tackling the obstacle requires inspiration and motivation. When you’re stuck, a bit of lubrication is required to get unstuck. Whether I’m grappling with writer’s block, avoidance of a difficult conversation, or the desire to quit on a tough workout, there are a number of resources I turn to overcome procrastination induced by fear. Here are a few of my favorites.

A Book 

At the age of 27, Ryan Holiday had his third book published, and it’s a must-read for anyone who’s ever faced an obstacle in life. In other words, it’s for everyone. The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph examines the trials and tribulations of significant historical figures, and details the methods and mindsets that allowed them to overcome life’s challenges. It draws heavily on the principles of Stoicism. It’s a lesson in the power of grit.

A Blog

Maria Popova is one of my favorite bloggers. She is a voracious reader and prolific writer. She shares her insights about the world and our place in it on her blog Brain Pickings. Popova describes Brain Pickings as: “My one-woman labor of love – a subjective lens on what matters in the world and why. Mostly, it’s a record of my own becoming as a person – intellectually, creatively, spiritually – and an inquiry into how to live and what it means to lead a good life.” Her blog posts unearth wisdom, and connect dots, from books – mostly old ones – in a way that helps readers gain new perspectives on enduring challenges.

A Parable 

Parables are ancient truths that stand the test of time. Their power lies in the simplicity of storytelling. One of my favorites is “The Two Wolves.” It’s a lesson in the power of positive thinking.

An old Cherokee is teaching his grandson about life. “A fight is going on inside me,” he said to the boy.

“It is a terrible fight and it is between two wolves. One is evil – he is anger, envy, sorrow, regret, greed, arrogance, self-pity, guilt, resentment, inferiority, lies, false pride, superiority, and ego.” 

He continued, “The other is good – he is joy, peace, love, hope, serenity, humility, kindness, benevolence, empathy, generosity, truth, compassion, and faith. The same fight is going on inside you – and inside every other person, too.”

The grandson thought about it for a minute and then asked his grandfather, “Which wolf will win?”

The old Cherokee simply replied, “The one you feed.”

When it comes to overcoming obstacles, we are often our own worst enemy. If we “feed” our negative thoughts, our outcomes will be negative. If we feed our positive self, we can achieve anything. {tweet that}

A Podcast 

I listen to a bunch of different podcasts during “margin” time – in the car, on a run, while grocery shopping. A new favorite podcast of mine is by one of my favorite authors, Malcolm Gladwell, who has written a number of bestsellers including Outliers and David and Goliath. Gladwell is a curious contrarian who thinks and writes about the unexpected implications of the decisions we make and actions we take. He has a new podcast called Revisionist History that is excellent – as entertaining as it is interesting and informative. In typical Gladwell fashion, it leverages storytelling to “examine the way the passage of time changes and enlightens our understanding of the world around us.” Gladwell uses his podcast platform to “go back and reinterpret something from the past: an event, a person, an idea. Something overlooked. Something misunderstood.”

What I like most about Revisionist History is that it inspires me to look at issues from multiple angles. If the answer is not obvious, if the obstacle looms large, there’s almost always a solution. Sometimes you just need to look at it differently.

Parting Thoughts 

The past few years have presented a few obstacles for Heather and I. Most of them have been constructed of our own choosing, and neither of us wish to undo a single flap of the butterfly’s wings. Nonetheless, having twins, moving to a new place and giving up the security of one of our businesses (my law firm) to put all of our eggs in one basket have all posed challenges. And the burdens resulting from those decisions have fallen primarily on Heather’s shoulders. Let’s face it, no matter how carefully and thoughtfully a husband and wife plan for the delegation of duties, the weight of responsibility for the children and household falls to the mother. Throw a business into the mix, and that’s a recipe for stress.

It’s not that Heather took on this role grudgingly. Just the opposite, in fact. She encouraged me to follow a different path with my career not because it was easy for her, but rather out of a desire to allow me to pursue a passion. While I sometimes overlook her generosity, I’ll never forget it. And, when we both step back and look at the big picture, we realize that, indeed, what stands in the way is the way.

Through the smoke and fog of the day-to-day, we both see clearly that the obstacles we’ve overcome have helped us to build a bridge to a life we cherish – not in spite of the ups and downs, but because of them.

Hopefully the resources we’ve shared help you address some of the challenges you face in your own life. Are there any book, blogs, parables or podcasts that you find helpful? If so, let us know by leaving a comment below. We’re always interested in adding to our own portfolio of inspiration.

LifeJay Harrington