My First Week In Startup World

It was 5PM on a Friday and my first week at my first startup was over. Our small office was clearing out hitting a local bar for happy hour. I slumped in my seat, exhausted.

“What a week, it’s so frantic here,” I muttered under my breath as the CEO walked by.

He chuckled and said, “Well Tom, you asked for it. This is what you wanted.” He put in his coat and headed to the elevator.

Poof! Bad Tom whispered, “Fuck that you party pooper…

When I finally pulled myself up, I closed my laptop and packed up. I walked over to the elevator and thought about what I was going to do tonight. My Acela train was scheduled for Saturday morning and my Best Western hotel room had a lumpy bed.

At 43 years old I was debating just going to my hotel room to recover but the devil in me wanted to go hang out with the “youngsters.”

Poof! Good Tom whispered in my ear, “Just go get some take-out and chill out in your room. You’re too old.

Poof! Bad Tom whispered, “Fuck that you party pooper, go out and have fun with your team. It’s what you do in the startup world, you sissy!

There I sat pondering my dilemma. It didn’t take long, maybe 5 nanoseconds of thinking but Bad Tom won.

The waitress places a beer in front of me, I watch the foam spill over the sides.

Fast forward an Uber ride to a “hip” bar in Porter Square where I meet up with my coworkers.

“Hey!” The scream from across a table, the new AE raises his beer glass so I can see him.

I grab a chair at the end of the table as the appetizers arrive. I look at one of the beer menu cards and motion for the waitress to come over to take my order.

The AE looks over to me, catches my eye.

“Hey! I hate to tell you this but we’re going in a new direction for that account as of 3 PM today.”

The waitress places a beer in front of me, I watch the foam spill over the sides. He’s speaking words but they’re not registering in my mind right now.

“So all the stuff I worked on for the account is toast?”

He nods, “Let’s circle up Monday morning. Great job though, you wowed them at the presentation!” He slaps me on my back and goes back to a smaller group of guys.

All guys, a lot of young ones, and only a few old fucks like me.

I note it’s all salesmen and no saleswomen.

I take a long pull from my beer and munched on a quesadilla. We’re in a standard Boston bar, kind of darkish but modern with an open floor plan. It’s cool enough to attract the hipsters but too loud to have a good conversation.

I realize I’m that old, I’m more interested in having a conversation at a quieter bar. This place was built for one thing, to get you and your buddies stone-faced drunk, Boston style.

Things get loud throughout the evening as two distinct groups form. One is a group of introverted software developer types and the other is a small group of loud extroverted salesmen types.

I note it’s all salesmen and no saleswomen.

I sit there lost in thought, taking in the moment. Just over a week ago I was saying goodbye to my coworkers. They all thought I was nuts to quit my 20-year career as a civil engineer. To quit and join a startup that they didn’t understand. Machine learning? What is that? Is that like the Terminator?

…did I make the right choice?

I made one of the largest leaps in my entire life, I switched careers midstream in what would make a normal person faint.

I take another drink from my beer. I think about my partner, how she encouraged me to take the risk. She was my support, the one person who believed in my dreams and helped sail the ship when I couldn’t.

But this all made sense. I knew I was destined to break out of the chains that held me down. I knew I had to shed my anchor and get out of a job I hated.

Now I was a freshly minted Sales Engineer and a Data Scientist. A whatever you want me to be guy to help close a sale. I was always a nerd, an Engineer, a tinkerer.

I would’ve never in a million years thought that I would end up in Sales.

Never.

I looked around the table at my coworkers laughing and drinking the night away and I could help but wonder, did I make the right choice?


A lot of events have been changed to protect the “innocent”, even if they deserved it.

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