The Obstacle is the Way (book review)

A medium-deep dive into philosophy - specifically, stoicism - this book was recommended by Kielyn Marrone, who I follow on social media after watching her on the TV show "Alone" (where contestants are dropped off in the middle of nowhere and have to survive longer than other participants in order to win a big $$ prize). In Season 7, Kielyn stayed 80 days in the near-Arctic (shores of Great Slave Lake from mid-September through December). Watching her catch her first fish from the frozen lake was one of the most enjoyable moments on TV ever. She was the third last participant, and everything about her was intriguing and inspirational, including her frequent mentions of stoicism. On her Facebook page, she recommends this book; coincidentally, one of my current mentees is reading this book series by Ryan Holiday, and mentioned it during one of our earliest sessions. I took that as a sign.

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At first, I just dipped in a toe. I have previously attempted to read Marcus Aurelius' Meditations, never making it very far. This started for me back in high school, after reading a quote from him in The World According to Garp.

“In the life of a man,” Marcus Aurelius wrote, “his time is but a moment, his being an incessant flux, his sense a dim rushlight, his body a prey of worms, his soul an unquiet eddy, his fortune dark, his fame doubtful. In short, all that is body is as coursing waters, all that is of the soul as dreams and vapors.” Garp somehow thought that Marcus Aurelius must have lived in Vienna when he wrote that.

So, for more than 30 years I've had a copy of Meditations in one form or another waiting to be read, but with very little actual progress. For Obstacle, I started with an audiobook version, to see if that would help get me into the work. It certainly did. I enjoyed it so much that, after just half of the book I pulled out my hard-copy and dove in, reading it from start to finish in just a few days (being on vacation helped a lot). 

Obstacle begins with Aurelius as the sort of compilation or zenith of stoic philosophical writing but includes many other ancient and more modern philosophers and figures who personify elements of stoicism. Some are familiar stories and people (Lincoln, Edison, Thatcher), others less familiar but still inspiring, embodying the principle at the heart of the book: the things that are in your way are exactly the things you need to be tackling to move forward, and the lessons you learn from each attempt to move or surmount or submit your obstacle become lessons for your life. In other words, what doesn't kill you makes you stronger, but also: to strive, to seek, to find, and not to yield.

Throughout the stories and philosophies you can see elements of currently trendy approaches:

• Minimalism – many of our problems come from having too much and being paralyzed by choice
• Mindfulness – we don't get to choose what happens to us, just how we feel about it
• Personal responsibility – no one else is to blame when we throw in the towel
• Humility – the obstacle doesn't care about you
• Equality – you can always try, but success is never guaranteed or owed
• Persistence – the goal should be progress, not perfection.

I think like self-help or other similar books, the text includes many tru-isms and statements that, when you first read them, seem statements of the obvious. But this is not a self-help book in the sense that it gives no specific directions – no “try this” or “5 steps to a better you”. Instead, it presents, in bite-size pieces - short, focused chapters - stories and messages that cannot help but drive introspection and personal challenge to do and be better. 

As a leader, I was challenged to reflect on situations and obstacles I have encountered – and those I’m currently dealing with – and consider my own role and approach in those. I was reminded several times of my own mini-philosophies: be hard on the issue and soft on the person; don’t ascribe intent; be firm but fair; consider the story I’m telling myself and test it for truth. I saw quickly that many of the most difficult situations, especially those where I feel angry or powerless, could not be overcome by anger or power (few situations can). Calm, creative, and considerate thinking and action, and bringing solutions to the problem, are way to move around, over, or through those obstacles. We also need to be sure that we’re solving the right problem – tackling the right obstacle. If the road ahead is blocked, make sure you’re on the right road before working on how to get through.

Having trouble getting that document you need from a collaborator? Maybe write a draft for the person to edit instead of asking them to write it from scratch. A new policy disrupts your workflow? Get to the root cause and formulate a solution within that new framework. Someone is just not getting your message? Consider what you’re saying and how and change that – saying the same thing again and louder doesn’t make it clearer, it just makes everyone angry.

We don’t need to seek out obstacles – enough will find us on their own – but we should not fear them either. We should welcome the opportunity to problem-solve our way through, learn through that journey, and enjoy the rewards of work well done when we at last succeed. As leaders, we should model that to our teams, show them that, like them, we have our share of obstacles and challenges and we can deal with them rationally, fairly, and successfully.
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I found this book to be meaningful, insightful, challenging, and delightful, and so am adding it to my small but growing library on leadership. I'm looking forward to reading the remaining books in the series (Ego is the Enemy, Stillness is the Key). And I will take another stab at Aurelius (perhaps I'll start with audio again and see what happens).