As for luck, I've always believed that “Luck is what happens when preparation meets opportunity”

I don't think what happened to Clear is either Lucky or Unlucky… Unless you want to look at it as “it's quite unlucky that Clear didn't have a Product Manager who could see the product from the users POV or steer the product when the circumstances/opportunities changed.”

The hypothesized outcome imply an experiment. Maybe it will take many experiments. Maybe you have hypothesized more than one outcome.

Outcomes need not be binary. They might be a position specified by a collection of forces where you best outcome happens when all the forces cancel out. Or, it might be the range of outcomes where movement along some axis of force isn't particularly or accutely sensitive. Where the forces are sensitive to movement, you will have to invest in management and systems. Where the forces are insensitive, apply some slack. Make sure your managers can cope with slack. Push elsewhere.

Outcomes may also be scaled, but the transition from risk, where you know nothing, to success is a serialized collection of transitions from conscious unknowing where you will be surprised; to conscious unknowing where you know what you do not know; to conscious knowing where you deal with it, but still lose sleep over it; to unconscious unknowing, where the past is embedded in your systems–something you might want to undo. There is a terrain, a geography, a spatio-temporal experience that couples many dimensions. Strategy is the intent to build the roads, bridges, paint the stripes and the speed limits, open the toll road, and provide wreaker services within your firm.

Having a collection of strategies makes a mess of strategy alignment tools that assume a single strategy. Seek emergence. Seek emergence in leadership. Strategy should enable, rather than extol those that construct it. Leaders do the same.