The Obstacles Really Are the Way

I was excited to get my hands on Ryan Holiday’s new book, The Obstacle is the Way, because it focuses on a strategy that some of history’s great men and women used at critical moments in their lives.

This strategy, Holiday writes, can be adopted by anyone, just as it was in times of great adversity by ancient Greek orators, 17th Century writers, Union generals of the American Civil War, 20th Century astronauts and athletes, and Silicon Valley entrepreneurs of the 21st. It’s origins though, can be traced back nearly two thousand years to the private journal of a Roman Emperor:

The impediment to action advances action. What stands in the way becomes the way.

Then I got really excited, because I learned that Ryan was coming to LA at the end of May to give a talk, Q&A, and sign some books. I made plans immediately:

  • I commissioned my younger brother to draw a fun gag gift (a revised version of The Last Supper with Ryan and some of his heroes, including Robert Greene)
  • I worked Memorial Day so I could take the event’s day off and beat rush hour traffic up to LA.
  • I tracked down my copies of Ryan’s books which I’d lent to friends.
  • And on the day of, I brought lots of work to get done before the event, to stay on schedule with my upcoming novel.

I had the whole day planned out and departed for LA, confident everything would go as planned. I found a Starbucks just a few miles away from the event’s venue. Sitting at a back table, I wrote all afternoon, knowing I’d enjoy the night even more if I could hit my day’s page goal. A few hours later I did.

With just 45 minutes until the event, I hastily packed up and left, walking briskly through the parking lot to my car. But when I got to the parking spot, my car was gone.

It was just gone.

Although I probably had a frozen look of shock stuck to my face, my mind raced into panic mode. I called the police to learn if anyone had reported a car break-in at the parking lot. No one had. That’s when I saw it: a parking sign on the other side of the lot.

It read: Parking One Hour Maximum.

Still on the phone with the police, someone tapped me on the shoulder: A parking policeman. He said that he’d towed my car, as I was parked for well over an hour. He gave me the number for the towing company. I called them and they said that it was too late. The only way they’d release it was if I show up and pay. ‘How far away is the garage?’ I asked. ‘About two miles.’

But there was no time to walk twenty minutes. I was supposed to be six miles in the opposite direction in less than 45. I didn’t know anyone in LA to call, even if my phone hadn’t died on me. I felt powerless.

It may not seem like a big deal reading this, but I was angry. I was angry at the LA parking laws, and at the placement of the sign on the other side of the lot. Although I didn’t show it, I was mad at the two strangers I asked for a ride after explaining my situation, who wouldn’t help me. But most of all, I was disappointed with myself. If only I’d seen the sign or parked at a meter, or chosen a different seat in Starbucks, one facing my car to keep an eye on it.

The parking authority gave me directions to the towing garage, and told me that it was open 24/7, so it didn’t matter how long it took to walk there. My car wasn’t going anywhere.

That was the problem — the obstacle keeping me from getting to the event. Taking a deep breath to calm down, I realized that my car wasn’t going anywhere. I could get it after the event.

I hailed a taxi. The driver didn’t know exactly where the store was but I’d recalled the address vaguely. We drove and drove, street light after street light. I was going to make it, but why was my heart still pounding the whole taxi ride? My chest felt squished and I was breathing deeply. I rolled the window down to get some air.

I was worried, I realized, because I didn’t think I was going to be able to enjoy the event. In fact, I was already planning about how I’d get back to the towing garage after it was over. I knew I could grab a taxi back, as I was sitting in one, but I’d slipped into over thinking worry mode. I knew I was in it and I was angry that I couldn’t just turn it off and relax.

The taxi pulled up with 30 minutes to spare, and stepping inside helped. I rushed to the bathroom and splashed cold water on my face. A minute later my breathing had slowed.

That’s when those two lines returned to me:

The impediment to action advances action. What stands in the way becomes the way.

I left the bathroom and picked a seat close to the front, determined to get the most possible out of this event.

The seats soon filled up with fellow fans and Ryan stepped up to the front. He began by reciting that very quote from his preface.
Sitting there, I felt stronger because I suddenly realized just how difficult embracing some obstacles are for me, especially unanticipated ones.

However, I was determined not to let my shyness keep me from asking some questions I’d prepared (I ended up asking the most), nor did I let it keep me from making a new friend (who later gave me a ride to the towing garage). I shook Ryan’s hand after he signed my books, and felt satisfied that it had been worth it.

Driving home, a bit later than planned, I realized that the set back was an opportunity for me to confront an insecurity of mine: panicking in the face of unforeseen problems.

But also, I thought about the surge of genuine appreciation I felt for my girlfriend who offered to come pick me up (I was more than two hours out of the way — and she was just coming off a long shift at the ER). She has that cool-headed approach in emergencies that I don’t.

By confronting this about myself, to first gain awareness of it, and then to act to reverse it — to lean in and have the courage to face it — then correct it, I was able to turn a shitty roadblock into an unforgettable evening.

I hope, as Ryan wrote in my book, that I “face many obstacles in life” like this one. Uncomfortable as they may be, those obstacles really are the way.

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