To See if You Can Fly, You Must Escape the Cage
May 2, 2019

I dropped my luggage into the overhead space above and slid into my seat. The train was only half crowded and I’d have a window seat in a row all to myself. I stretched out and checked the time. It was 12:15 PM. If everything ran to schedule, I’d be in Boston in four hours with an hour to spare before my meeting with my client. I smiled out the window as the Manhattan skyline slowly faded from view.

Just two years ago, none of this seemed possible. Back then I would’ve been in a cubicle in a Boston office building making cold calls with another 5 hours to burn. There were no daytime train rides between cities and business trips were few and far between. In those times, I couldn’t see a path to this life where I could control my own schedule and help clients on my terms. It seemed like this farfetched dream that was out of my grasp.

If only I could’ve told myself, back then, what I know now. This life was there for me all along. All I had to do was go out into the unknown and find it.


I flipped open my MacBook and went into my client’s file. Tonight would be our fourth coaching session together and we were making progress, but I knew that we had yet to make a major breakthrough. Similar to the situation I had found myself in two years ago, this client was in a job that had become just a paycheck to him. He wanted to do something more inspiring with his life and wanted to do it on his terms.

He and I both knew what he wanted, but it had been hard up to this point figuring out a way to bridge from the comfortable life of a salaried employee to a more risky venture. How could he be sure it would be worth it? How could he be sure he wasn’t making a big mistake?

I pondered these questions as the train zipped passed Stamford and onto the Connecticut coastline. What had I told myself back then that gave me reassurance that everything would be OK? It was so long ago now that I was having trouble remembering how I made the mental shift from fear to possibility. How could I share with my client the power that I discovered years ago?


The train moved steadily along the bay, as I drifted in and out of a light sleep, passing Mystic, CT and on into Rhode Island. We approached Providence and I blinked my eyes open to the sight of billboards and puffing chimneys. The New England coast had been swallowed up by urban sprawl and 19th-century factories. One of the billboards had an advertisement for Roger Williams Zoo which I had visited a few times as a kid. The sign had colorful parrots peaking their heads out from behind the text.

I thought back to my client as the sign passed me by and remembered an experience I had had when I was still trapped in my 9 – 5 office job. It was a Sunday in late April and I had been biking through Boston’s Jamaica Plain neighborhood when I remembered Franklin Park Zoo was nearby. I hadn’t been to a zoo since childhood and decided to make a quick stop in. Inside the zoo I saw tortoises, monkeys, and giant lions. Each exhibit was more crowded than the one before it. I checked my map and saw there was a bird sanctuary towards the back of the zoo and, hoping it was less crowded, I decided to check it out.


I walked into a tiny dark cave-like room that the map had pointed me to. There was no one else in there. I looked around and saw there were three suspended cages hanging from the ceiling. Each contained parrots and other tropical birds that dripped in vibrant colors. They waddled across small branches and fluttered their wings, staring at me all the time. The two birds on the left calmly walked from side-to-side in their cage, but the one on the far right was restless. He was chirping and flying about the cage tirelessly. One thing was clear: he wanted out.

I left the zoo sometime later and began to mount my bike for the ride home. It was then that I heard tweeting as a flock of birds soared above. They must’ve been returning from the south after the long Boston winter had ended. I thought back to the parrot in the cage and realized how much he would’ve liked to have joined them.

At that moment I realized that I was the parrot in the cage that was restlessly trying to get out. Like the birds that flew above me, I wanted to fly freely and take on the world in my own way. In fact, I saw that if I didn’t escape the cage, then all the opportunity this world had to offer would never become available to me. Was I sure I could fly? No. But I’d rather try to fly than live in a cage the rest of my life. 


I came back out of my daydream and into the train as we shot up past Route 128 and into Boston. I now had the message I had to deliver to my client. In order to see if a bird can fly, he first has to escape the cage.





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