As the author Edward Abbey once said, “A pessimist is simply an optimist in full possession of the facts.”
In reality, good leaders are three parts optimism and one part pessimism. In the words of legendary investor Charlie Munger, this makes them cheerful pessimists.
A cheerful pessimist believes getting things done is never easy, and the worst-case scenario is lying right around the corner, ready to trip up success.
So, they fret about the details and guard against what can go wrong, not expecting it but presuming it is more than likely.
This makes them good planners and strategic thinkers as long as they balance this pessimism with an optimistic view of people, opportunities, and future events.
We could actually call such leaders “negative optimists,” but the label “cheerful pessimist” actually sounds more uplifting and probably does a better job of highlighting this critical recipe for leadership success.
Great leaders believe in people. So much so that they are hugely positive and optimistic about what they are capable of.
They project this optimism with their words and actions, giving others encouragement and challenging assignments where they can grow and develop their skills.
Such leaders also see the hidden opportunity in a challenge, looking to recast what is a problem into an advantage. This optimistic lens doesn’t deny the risks inherent in a challenging issue but focuses primarily on what can be done about it to everyone’s benefit.
Exceptional leaders are also confident about the future. They insist on taking a positive view about events and future outcomes.
They understand the power of this optimism for motivating others and lifting morale up so that everyone is geared for success and the hard work it will take to achieve it.
While not every forecast they make is rosy, they prefer to emphasize the positive to boost everyone’s confidence, including their own.
However, great leaders are also tremendously pessimistic about accomplishing tasks.
Their experience gives them grave doubts that completing tasks will occur without hitches or setbacks. Therefore, they plan, set deadlines, check in on progress quite frequently, and focus on completing each step and detail with the highest degree of quality.
They recognize that it is this pessimism that enables them to be optimistic about everything else.
As the New Year approaches, consider becoming a more cheerful pessimist. Your team will benefit greatly from this ideal mix of three parts positive and one part negative.
Cheerful pessimism may sound like an oxymoron, but it is actually the recipe for great leadership.
A Daily Dispatch from the Front Lines of Leadership.
