Seth's post today on the tradeoff between risk and reward is spot on. I'm especially in agreement when it comes to that first jump (from point A to point B) - that's the risk you should be focusing on. The way I see it, by committing to that first jump - developing a plan, managing the plan, analyzing the plan, resetting the plan, etc. - then understanding it's reward, the second jump (point B to point C) becomes less risky.
Yeah, there will be new minor risks along the path to point C but since you've already gone through this process and can reference previous actions and effects - see plan, above - the risk is reduced, while the reward remains the same.
And taking that first step is rewarding in so many different ways. You'll become more efficient. You'll understand your internal operations better. You'll get to know your staff and their strengths intimately. You'll even get to know your industry in finite detail (including customers, competitors, vendors, etc.).
As Seth closes:
Riskless is hardly worth your effort.