One of my startup philosophies is to always plan for two or three things going wrong, all the time. New businesses are chaotic enterprises, operating on limited information in new domains, constantly adapting. You have to set an expectation for the unexpected. If your baseline is a couple surprises every month or so, they’ll feel less like threats and more like business as usual.
That sort of attitude shift goes a long way toward coping with challenges as you build a company. No more “oh my, what are we going to do?”, just a calm, rational “ok, we thought something might happen, lets figure out what to do about it”.
And if nothing goes haywire? Great, you had a good month.
Next week I’ll be kicking off a multi-part company postmortem on Knockabout Games, the development studio I founded in 2002 to build games for mobile phones (during the first wave of mobile, i.e. pre-iOS).