My first job out of college required me to wear dress pants, a button-down shirt, and a tie to work each day. I was working at the front desk of a Comfort Suites for $5.50 an hour.
The next job had a more standardized uniform of khaki pants and a blue button-down shirt. I was on the way up the corporate ladder as I landed an Assistant Manager gig at Blockbuster Video at $7.00 an hour.
Subsequent positions had similar dress codes and increasing compensation, but these weren’t jobs I wanted.
The work uniforms became sort of symbolic to me. I could work hard and share lots of ideas, but at the end of the day I was constrained by a certain paradigm of what I could and should do.
In the mid-90’s, I worked with a variety of computer magazines at Miller Freeman and ZiffDavis on the business side.
These were sort of old school environments, and I was expected to wear a suit.
I still cringe at the memories of walking across town in New York City on humid August days in my 2 for $79 suits, and how I’d be as sweaty as a college basketball coach by the time I reached my office.
In 1997, I left the magazine world for my first dot com startup job at a place called Medsite.com. This was also my first affiliate manager position. It was one of those open lofts where employees were encouraged to be creative in their marketing efforts.
That was good, because I had never had a marketing job, or even a class, before then. The dress code was more relaxed than I was used to at previous jobs. We could wear jeans every day. Every day!
That might not seem exciting to many affiliate marketers, but it was a fashion revolution for me. Gone were the cheap suits in favor of a closet of jeans and collared shirts.
This sort of dress code continued with my next affiliate marketing jobs at Refer-it.com and ClubMom.com. But even that started feeling restrictive.
I used to get a weird thrill on work days when I would be heading to a Yankees game at the end of the day. After work, I’d switch from my jeans and collared shirt to shorts and a Yankees jersey. It felt forbidden and magical to walk among the corporate cubicles and show a little leg.
I finally went out on my own in 2004, and dressed comfortably, I never looked back.
My wife, Vicky, asked me recently why I wear shorts and a t-shirt to work every day. The answer was simple… because I can.
You know the old saying about dressing for the job you want? I guess I want to always have this job.