Everyday I leave my home, bike to the East Norwalk train station, ride the train to grand central, and then walk to the office. The majority of the time, it is uneventful. I simply continue listening to my podcasts that I start at 5 AM, put on a movie on the train, do some writing, then listen to my audio book on the walk into the office.

That is the routine.

You want to know what really mucks up the routine?

When you see your boss and make direct eye contact with him at grand central.

I was walking out of track 13 where my train always comes in. I use the restroom, check my watch, and head up the couple of floors. I am priming my watch to track my walk (yes, I am that wierdo) when I see something I did not expect.

I see my boss in is khaki pants, dad sneakers, blue button button down shirt and iconic black aviators walking directing toward the same thicket of doors I am. As I am traversing up the ramp, I note that he has headphones in, as do I. Perhaps this is a wonderful chance to not acknowledge this is a thing at all and I can just move forward with my day.

I deliberately slow down so to give him some breathing room. Don’t want to chance a fender bender. That would not be good.

It is a this point I should say that I do very much like my boss. He is a very good man. He is a great boss. He has very fair and he works his fucking ass off. I have been on trips with him before and it is perfectly enjoyable experience.

However, at 8 AM in the morning, talking is not high on the list of my priorities, or his.

So I slow down. Bracing myself for the traffic that is about to be jammed up by my slowing of the pace. As I shuffle my feet, a cold sweat pours over my soul.

He saw me. I saw him. He looked right at me, and I looked right at him.

We make the eye contact, even if he has his shades on.

Now it is at this point we exchange pleasantries…and by that I mean we just nodded at each other in acknowledgement. Alright, so far, so good.

However, an issue arises. We both exit the same door from grand central. We both take the same crosswalk from across from grand central. We walk together for about two blocks. Me, just in front of him. This is what we describe in the business as awkward. What the hell am I supposed to do now? Do I just continue on my way? Do I let him pass me as a sign of respect? Do I buy him a cup of coffee?

Swimming in my own thoughts, the answer put right in front of me. As I am pacing in my mind but walking forward on the sidewalk. As I am staring down at the concrete sidewalk, I see a crosswalk ahead of me. I look up and the red hand is blinking. Now is my chance. I quicken my pace (as subtly as possible) and scamper across crosswalk onto the other side of the street. I turn left up the avenue and I peak to my left.


This is how I felt. This is what I thought of

So now that I am no longer feeling the nagging breath of my own thoughts on my neck, I raise another question.

Who gets to the office first? Who walks through the doors and has the bragging rights of being first into HQ? Is there going to be a checkered flag when one of us taps that keycard to the front door?

I decide it is best not to care. I go about my meandering, weaving through the streets wherever the crosswalk signs take me. I walk, hating the morning bustle and smell, and get to the office. I put my backpack down. I do my normal thing and the antsy nature of my own brain starts to finally simmer. I am whack-a-moling the creeping thoughts of whether or not my boss and I acknowledge that we saw each other in the office. Worrying about such things is not useful with my boss, seeing how he is a robot of efficiency, punchy one-liners and embracer of simplicity in conversation. There was never a chance our eye contact and tango on the sidewalk would be talked about ever again.

In case you are wondering…yes, these are the random thoughts that float through my brain on a day-to-day basis. It is both enticing because I am always doing hypotheticals, but also exhausting because sometimes turning your brain off is a good thing.

I hope none of you random readers have this type of encounter.

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