The new issue of Harvard Business Review has a good article about how strategy-making should feel. Usually I am wary of applying business lessons to military operations, but I do think that the business world knows a lot about strategy because its leaders have to think about it every day, while a military leader can slide by for decades without having to think seriously about it -- or to have his lack of thinking tested by reality.
Basically, making strategy should not feel good, avers Roger L. Martin. (The article is titled "The Big Lie of Strategic Planning," but I don't think that really captures what it is really about.)
"Fear and discomfort are an essential part of strategy making," he writes. "In fact, if you are entirely comfortable with your strategy, there's a strong chance it isn't very good.... You need to be uncomfortable and apprehensive: True strategy is about placing bets and making hard choices. The objective is not to eliminate risk but to increase the odds of success." Indeed, if there is not much risk, there probably isn't much strategy, he emphasizes: "Strategy involves a bet."
But, you say, you've written strategy documents, and you felt just fine? Martin suggests that you probably were actually mistaking planning for strategy. "A common trap," he soothes.
Another insight: The better your strategy, the shorter it likely will be. "There is no reason why a company's strategy choices can't be summarized in one page with simple words and concepts." (Indeed, U.S. strategy in World War II didn't even take up a page.)
The article reminded me a bit of Michael Porter's classic admonition that, "The essence of strategy is choosing what not to do." Speaking of that approach, there is a good essay to be written by someone applying that thought to President Obama's foreign policy: The essence of his administration may be in what it chose not to do. That's not a bad thing -- I think the same was true of President Eisenhower's administration. For example, Ike's rejection of the recommendation of the majority of the Joint Chiefs that he nuke Vietnam. He wasn't against using nukes, he just thought that ground forces would inevitably follow, and he was determined not to get involved in another land war on the periphery of the Communist bloc.