The Journey From Attorney to Entrepreneur

I took a deep breath, and stepped for the very first time into my new office. I had to admit, it was breathtaking.  Its floor area was nearly as large as my entire Manhattan apartment. The walls were crisply painted, the carpet freshly shampooed,and even the doorknob looked like it had just been spit-polished. When I stood in the doorway, right in front of me was a couch, with a stunning cherry coffee table separating it from solid wood chairs which had perfect leather padding on their backs and seats. Lavish coffee table books sat on top of it, and, for a government office, the impact was stunningly stately. I took off my overcoat and turned to the left.  My personal closet was there, complete with beautiful wood and brass hangers. I hung the topcoat and my suit jacket inside, shut the door, and turned to the facilities person next to me. 

“Get rid of the couch,” I said. “We’re here to work, and I want this office to show it.” I’d seen a regal, outsized, and nuclear bomb-graded heavy oak conference room elsewhere in the office, and wanted it placed there instead, so that my team of executives could regularly meet, brainstorm, and get stuff done. My words carried weight, and so I knew that, before long, the conference table and chairs would be exactly where I wanted them.

I looked to my right. There was the desk: august and imposing, with matching cabinets, shelves, and chairs of the most baronial designs, ready for attention. My chair felt magisterial, even for a or 6’1”, full-bodied man such as myself. I sat in it for a minute, fingers in a steeple under my chin, thinking of all the work that would be completed atop the desk, then stood up to look at the wall opposite the door.  

It actually was not a true wall at all. From my waistline up, for the entire length of the room, it was a massive window, overlooking Battery Park City and the Hudson River. The sun was setting on what had been a glorious summer day. The Park’s towers reflected scarlet, clementine, and boysenberry light, the light rippling on the water’s waves was a nearly blinding white, and the sky was a stunningly dusky diaspora of the entire rainbow.  I could see a massive cruise ship trudging along between the buildings, its windows twinkling even more light against the darkening firmament. I sipped from my mug of coffee and took a minute to feel some disbelief that this boy from faraway Kansas was the one getting to see this unbelievable sight.

The office, the view, the conference table: these were the things I focused on that day, and, looking back, it was for a reason. For years, my dream had been to be a top executive at a government agency, to be in a position of authority over the direction of an entity doing something good for the world, to be able to positively impact public policy, to really make a name for myself and do something that mattered. And so the boy from the Midwest had worked and worked, and pushed and pushed, and taken the steps he needed to get there.  And against the odds, I had made it. I was the second in command of an entire government agency, and a prestigious one at that. My dream seemed like it had come true. But that day, my mind couldn’t focus on the substance of what I had achieved. All my mind dared to think about was the furniture. My victory was an empty shell.

Year 2:  2017

I stood in front of a loading dock, surrounded by faceless brick blocks called “buildings,” and began to walk up a ramp to the door. I opened it and looked at the bare-boned industrial interior. Two thick metal doors stood in front of me, iron gray with only the words “The Brooklyn Press” on an attached sign breaking the industrial feel.  And then I opened the door to my new workplace.

Floor-to-ceiling, a multitude of brilliant ink colors covered an entire side of the room. Posters of images that were radiant, whimsical, humorous, or just plain cool covered the walls. A carousel-like printing press, with screens blindingly bright from their ink coatings, seemed ready to spin like a merry-go-round; I could almost hear the kids laughing. A tin-foil effigy of The Predator’s monster sat next to a plastic Godzilla on top of the ink curing unit; a Bill O’Reilly dartboard decorated a wall behind. The sound of high energy rock music filled the air.  Hip t-shirts sat on the tables, ready to be boxed up and sent to folks who would be ecstatic to see their vision come to life, ready to wear. 

I took off my motorcycle jacket, hung it up, and looked at my business partner. His beanie-covered head was fronted with a broad smile, his slim physique was open and ready to give a hug, and his simple word rang through the shop: “Welcome!” Our apprentice turned around, looked at me, and broke into a smile, too. “Let’s go into our new office,” my partner said. And we walked into a little nook under some stairs that would become our ground zero for creating something new together, something full of joy, something that was ours.

That little nook had a desk that my business partner had made from scratch, and a desktop that the two of us shared until we could afford something new. The roof was the underside of a staircase, and the wall opposite the door was part concrete wall, part steel back door. I had no view of of skyscrapers or of sparkling river fronts. But when I opened that door, as I often did, and still do, I had something even better.  I had the outside, fresh air, real sunshine and a breeze that came in and filled the whole room. I had something better than a fancy title, oak desks and a sumptuous view. I had joy, I had warmth, I had a life.

The man who had worked his way up the government ladder was long since gone. He had entered that world because he wanted to do work that would make a difference, to somehow have his visions weave into the world’s fabric of ideas and have those visions someday, in some small way, take on a life of their own. But the large, institutional, and All About Eve-esque world of government bureaucracy was a place where one only lived others’ dreams (or none at all), where joy was an unknown, and where the concept of fun went to die. Without my dreams, without joy, without fun, is it any surprise that all I could care about were the reflections of a setting sun?


The change in my life has been radical. The nice suits and cushy couches have been replaced with something far less glamorous, but far more substantial: color, passion, and my own vision becoming a reality. That is the true power of this entrepreneurial life.

Scott Mason
About Scott Mason 1 Article
I am a business owner, entrepreneur, accomplished senior executive, and attorney with 25+ years of public, nonprofit, and private sector leadership.

Be the first to comment

Leave a Reply