Making the transition from corporate to startup

Published by Ryan Paugh on November 20th, 2007 in Entrepreneurship, Work/Life | 13 Comments

There's a great coffee shop in downtown Madison that I go to called Fair Trade with a collection of regulars I've never talked to.

But I feel like I know their life stories because I've spent so much time examining the way they go about their day.

One of the most interesting regulars is a middle-aged blind man.

His cane speaks to the room as if it were giving him an introduction. Everyone looks to see what the unusually rhythmic beat is all about. Then they nestle their heads back into their books, laptops, diaries and that's that.

He taps his way over to the table next to me and takes off his jacket. He struggles to get his bearings, so I give his chair a little nudge to steer him in the right direction.

"Thank you," he says.

He then strides his way up to the cashier – a journey he must have made hundreds of times before—orders a cup of joe, and returns to his table, mug in hand. People watch, wondering if he's going to position his coffee flat on the table surface. I watch too.

I wonder to what extent he feels the ogling eyes around him. Even I can sense when someone is drilling away at me with curious stares. What's it like when you can't stare back?

While I'm working, and he is eating, I look up and notice the blind man is "looking" around the room. I wonder what he is looking for.

It only takes about five minutes before he stops looking. Whatever it is he wanted enough was enough. With the same amount of ease it took for him to take off his jacket and sit down, he put it back on, stood up and headed for the door: Tap, tap, tap…

I couldn't work anymore. I began to feel sick. Because right before he exited the shop, I realized exactly what he wanted.

You see, there's a reason I try to do work on State Street in the midst of University of Wisconsin's college community. It offers me a better chance of connecting with people and easing a portion of the loneliness of living in a new city.

I get a window seat at Fair Trade every day so I can be close to the bustle on State Street. I used to think that watching it makes me feel like I'm a part of the action. But in fact, watching it only serves to remind me that I'm an outsider.

I used to think that doing a startup would be so cool and that I'd be happy doing it anywhere. But moving to a new city with no friends is hard – even if you have the best job in the world.

I read that the life of a startup is essentially a lonely task, but I didn't believe it until I lived it for myself, here in Madison. And I know I'm learning a lot about business right now, but I wonder if I'm losing some part of myself as well.

So back to that guy. He wanted exactly what I did – an opportunity to connect when you feel like a complete outsider.

One thing that I always pride myself on is my willingness to talk to anyone. And I barely said a word to him.