Almost every estimator I have ever visited with has considered what it would be like to start up and run a professional cost estimating consultancy. A lot of contractor employed estimators do some amount of kitchen-table style moonlighting for a couple of clients as a way of picking up spending money. But rightfully, they may be hesitant to give up a sure thing and leave a safe haven for an uncertain business future. You, the professional cost estimator, must have an almost innate sense of how to access risk to do your job correctly in the first place. So how can you determine if the reward is commensurate with the risk?