Chief Pessimism Officer: Annoying, Yet Necessary?

The other day, I was telling a friend about the progress that we have made helping businesses find office space online at TheSquareFoot. He commented on how exciting and fortunate we were to be seeing such great growth. I did what I normally do and tempered their enthusiasm. He said he understood the modesty, but from someone who only hears updates every six months, it seemed pretty incredible to him.

I commented that I am content with our progress, but in no way satisfied. Although we were just about to complete our best quarter ever, I had already moved onto to being concerned about the next quarter. I quickly understood how public companies typically worry about future quarters' growth, even in the midst of a banner quarter. If you want a view into how my mind words, having our best quarter ever only means we have to worry about sustaining that progress and continuing to gain momentum.

Courtesy of the Library of Congress, LC-DIG-FSA-8D24901

My friend's retort, "Well, wouldn't it be pretty beneficial to enjoy how far you have come for at least a few minutes? Man, that has to be annoying to your co-founders."

While I wholeheartedly agree that it doesn't make sense to ignore your accomplishments and not relish in the excitement of hitting company milestones (otherwise, what's the point?), I also think having someone on the team constantly scanning the potential minefield of future issues is a necessary evil.

After all, as Yoda said, "A company, one quarter does not make". Well something like that, I just wanted to relate to Jedi saving the galaxy.

I think a team should be built with a bunch of unrelenting optimists, but there are certainly benefits to having at least one pessimist in the mix as well. It is impossible to succeed in the startup world without having a rosy outlook and without the belief that anything is possible, but at the same time, you need someone who can be realistic and point out all the potential risks in front of you so that the the team is able solve for the best way to mitigate them. There is a point in time when all startups that achieve some early success start to believe their own hype and I believe having a pessimist on the team helps to ensure hubris will not be a downfall.

Although dealing with a pessimist (especially during boom times) may be taxing, I think--well, I hope--that my co-founders would say it has been very beneficial in the growth and maturity of our company over the past few years.