Last week, I had occasion to return to Chicago, which was my stomping grounds for nearly a decade in the 1990s and early 2000s. While I was there, I spent time with a former colleague, reminiscing about the good old days. We were both still in our 20s when we began working together nearly 20 years ago.
I was amazed at how quickly the two of us were able to catch up talking about our respective families and careers. Here’s a guy I’ve only seen a handful of times in the past decade, yet it was like I had seen him just yesterday. With the formalities of families and jobs behind us, our discussion turned to storytelling about our time together at a company that shall go unnamed.
You see, when we started working together, we were in a company filled with 20-somethings ready to take over the world. We were, as they say, young and dumb. We didn’t know what we didn’t know, but somehow it worked. We worked together and we played together. And we broke every conceivable rule of business (especially those pesky HR laws).
At times, the place looked more like a cross between the TV sitcoms Friends and Cheers than a place of business. We had our favorite watering hole, an Irish pub called the Brehon, where the owner’s American Express card routinely covered the damages. They were fun and chaotic times!
As we reminisced about our time together, we told story upon story — each a little more outlandish than the one before. Some of the people I work with today were there as the storytelling escalated and looked on with skepticism. They just couldn’t believe we actually had done some of the things we were claiming. Scout’s honor, every one of the stories was true. In fact, we left out a few of the racier stories to protect innocent — or not so innocent.
Here’s what I can tell you about my time reminiscing with my friend and former colleague, it was fun. Not as much fun as some of the things we did back then, but just plain fun to remember an incredible time in our lives. As a group of young kids, we just didn’t know any better. We made our fair share of mistakes, but we also accomplished a lot because we were just too dumb to know what we shouldn’t have been capable of. Maybe they’re right, ignorance is bliss.
There were times when employees pulled all-nighters to finish a project that should have taken a week under normal circumstances. We were just too dumb to know that it couldn’t be done in a night. There were times when we tried things that had no business working, but ended up as tremendous successes. We were too dumb to know that we shouldn’t have even attempted them. There were times when we made pitches that we should have been embarrassed to even consider, yet closed the deal. We were just too dumb to know that we shouldn’t have asked.
So what’s the lesson in all of this? Is it that being dumb pays off? Probably not, but it did in this case. I guess the lesson is that sometimes we’re all constrained by our own thinking. It becomes very easy to conform with the business norms. You fall into a pattern of “this is how the world conducts business” and this is how you must think and act in a business setting. You become “corporate” instead of entrepreneurial. And when you begin to think like everyone else and act like everyone else, you lose that edge that can set you apart from the crowd. You lose your swagger.
I read this morning that Apple has the largest market cap of any company in the history of the U.S. Now, there’s a company that breaks all the rules and has achieved tremendous success because of the way it conducts itself. It has a very unique culture that it works hard to maintain, but it’s anything but “corporate.” Say what you want about the company Steve Jobs created, but it works.
As I think back to those times with my young colleagues in Chicago, I do so with fondness. It was a fun and energizing time for all of us. I wish I could bottle what we had so that others could infuse it into their companies — it would be worth millions. Instead, I’m faced with figuring out how I can grab the best of what we had and make sure it’s a part of our company today.