I love living in a time, in a country, and with a mindset of learning. Not everyone who has lived past the half-century mark embraces the magnificence of continual learning. Many opt for being good at what they know and focus on a future in which learning is no longer required. Who made up what it means to retire anyway? I personally want to do what is progressively next until what’s next is death. Maybe it’s just me. After all, I am past the half-century mark and you know how those types of people are…

So, everything thus far has been beside the point. You see, recently I made a monumental discovery about the value of pessimism. I lived most of my life believing people want to be friends with, work with, hire, and follow people with positive attitudes (true statement by the way). I never realized how the hyper-positive attitude expressed by my words was a barrier to being taken seriously. I remember being interviewed by an executive search firm for a CEO position. At the end of what seemed like an awesome conversation the recruit told me about how nice of a guy I was. He went on to tell me he did not think I was ready to lead his client’s company. I spent the better part of the next couple of years reflecting and trying to figure out why that successful, but misguided recruiter made such an inaccurate assessment. Without even giving me the chance to meet his client, “you’re not ready” was the response. It was very clear I was passionate about the mission of the company, had the educational credentials, previous experience, compensation expectations, and availability to do the job. What was unclear, to me at least, was what in the world could make me seem not ready? I recently discovered the most probable answer was a lack of realistic pessimism.

I spent the interview answering questions with a great deal of positivity and enthusiasm. I spoke of success as if it was all there was. Don’t get me wrong, I was not being arrogant. I spoke of the value of teamwork and collaboration. I spoke of the fact none of the successful things I’d been involved in were due to my knowledge and know-how, but of the team’s. I clearly expressed the successes as being the ability to play to my strengths and team up or hire to my weaknesses. Having a good understanding of what the job entailed, I knew the successes I highlighted were exactly what the job description and recruiter by explanation of the issues were looking for. So, how could it be I was not ready!? The answer is, my one hundred percent glory story made me sound naïve and unbelievable. My responses made me sound like one of two things were true. Number one, I had not experienced enough or done enough to reach a point of failure, or I missed the failures, risk, and difficulties faced by others under my watch. If either case were true, I was not ready to assume the position in question. Blasted HINDSIGHT!!!! (grateful).

Any of us would be leery of a doctor who planned to do surgery on us or one of our loved ones, but failed to mention the risks. We would be skeptical about an investment opportunity being sold to us as a “sure thing.” Too good to be true is too good to be true. If we as leaders, express ideas about vision and the future, but fail to express the risks, potential difficulties, or potential costs, we seem less believable, ill-equipped, and untrustworthy. Someone who expresses the hopefulness for the future without communicating a pessimistic ode to the risk of potential missteps comes off like person who is ill-prepared to lead in a world of uncertainty. People want to follow and invest in leaders who have been battle tested. Leaders who will not blindly lead into the minefield of the marketplace without the metal detector of risk awareness. Credibility comes with an understanding of risks.

As you strive to demonstrate positivity by putting your best foot forward, don’t be afraid to mention the times you stepped in dung along the way. The conversation about how you overcame could prove invaluable.

Remember, nothing said is everything, but everything said is something…

Charles Pulliam… Until next time…

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