On Fear, Pants, and Vocational Destiny

Theodore Roosevelt once said this:

If you could kick the person in the pants responsible for most of your trouble, you wouldn’t sit for a month.

It’s so true it hurts (get it… get it?!? Okay… too early…).

By the time I left college I had worked for some really large companies and I was looking to continue that trend because it’s really all I knew. The startup world wasn’t even part of the equation nor would it be part of my life for a little while longer.

One of the most significant jobs that I had was at Dell, Inc. I joined their Enterprise organization and hacked on their core eCommerce technology that powered, at the time, the largest eCommerce website on the planet.

It was a total clusterfuck with an estimated number of individual web pages in the ~11-12 million range. The fact that this was “estimated” was because we didn’t even really know how many sites were out there.

Consequently, we had an entire “clean up” team that was tasked with finding and removing out-of-date pages. What a colossal waste of time and money. I felt bad for that team because it was a really rough role to play and I especially felt bad because I was creating new pages daily with almost no process to track them.


But during that particular time I learned a ton about what it meant to build products and engineer software in a large environment.

Mostly, though, I learned the ins-and-outs of corporate politics, bureaucracy, and organizational jockeying for position, power, and presence. I was unimaginably-terrible at this.

What I didn’t understand (but came to understand over time) was that the slightest investment in the areas of organizational management and social psychology “in the field” of my work environment could pay great dividends.

Most of my issues were truly self-inflicted per Roosevelt’s thoughts (and some of this too) because I didn’t want to spend the time learning what it meant to be part of a team and navigate the relational dynamics that were so key to my own survival. I also had my first real experience managing a team and wow did I totally suck at that.

One of the most important (life) lessons I took away from my time at Dell was understanding how fear was a significant (if not the most significant) factor in doing work. It was everywhere I looked. You could taste it in the food, smell it in the air, and feel it as you typed into your monitored notebook computers.

It was this never-ending sense that your job could be eliminated at any point in time and that you were definitely not in charge of your future or livelihood. This “out of control” feeling clearly created anxiety and even panic when “Corporate All Staff” emails hit our inboxes once a month about “Corporate Restructuring.”

I came to the hurried conclusion that this feeling was something that I could not live with. It was unhealthy for me. It was causing me significant health issues. I just didn’t know what my alternatives or choices really were. I felt helpless.

Almost as therapy I started building my own stuff at home, nights and weekends. Side projects, essentially. I grappled for a small amount of control that I could and hoped that I could just make it through the next organizational restructuring. Keep my head down, don’t make too much noise, stay “under the radar” as best as I could. I wasn’t living but at least I was surviving I guess.

And so I was kicking myself for wanting to do something but not knowing what to do and teetering between apathy and disgust and a ton of self-hatred and self-loathing.

Much later I came to the conclusion that this wasn’t Dell’s fault (or any corporate entity for that matter) but my own. I was more in charge of my own vocational destiny than I had allowed myself to believe.

And that has made all the difference. I could have quit. I could have stood up for myself. I could have made a bigger difference. I just lacked the mental wherewithal, the courage, and perhaps even the heart to do what I knew was right.

I think of Roosevelt’s quote often… and it might be the reason why I choose standing desks now.

Just kidding… kinda.