Back in ‘96, I had the opportunity to attend my first (and only) development conference (The C++ Developer’s conference). This was an amazing experience, where I got to attend workshops by Robert Martin, John Lakos and others. I even met Dr. Bjarne Stroustrup.

I mentioned to one of my fellow attendee that it would be amazing to work with Dr. Stroustrup. He told me that one of his friend actually worked at Bell Labs. It was great to work such luminaries as Stroustrup, Kernigan and Richie. However, his friend could not help but feel that he couldn’t measure up. Being around such greatness, he simply felt inadequate. Back then, in my mid-twenties, I didn’t get it. I simply thought it would be fantastic to work with such pioneers. Now, with a few more years under my belt, I think I get it.
I wonder how I would feel if I were to work with Larry O’Brien (Magazine editor at 25, someone who did a $100M/year transaction engine in SmallTalk, and uses genetic algorithms to tune C++ compiler settings).

How about Robert Martin and the crew at Object Mentor? The man is a prolific author and everyone at OM seems to be a deep thinker: Tim Ottinger, Michael Feathers and the rest of the gang.

Let’s not forget Scott Hanselman, who can whip out a program to embed images in an MP3 file over lunch (he used a library, but still!), wrote a Tiny OS in C# and puts out a weekly podcast.

I could go on: Roy Osherove, Mark Miller (good lord, he’s got a blog!), Guido van Rossum, etc…
I suspect working with any of them could bring out insecurities. But interestingly, the reason why I sometimes experience self-doubt doesn’t have to do with colleagues, but with the fact that most of our company product portfolio rests on my shoulders. As we’re in the middle of a large product introduction, with multiple deliverable devices, a delay in delivery has a direct and very measurable impact. I don’t own the company, yet the self-imposed pressure to produce is there. That is not a fun place to be. Sometimes I long for the anonymity of a large organization. Luckily, we’re getting a new engineer to take on some of the load.