Confidence > Comfort

IT FIRST HIT ME while sitting on a plane.

Shortly after my 40th birthday, I was flying to Florida on a private jet for a weekend of boating and relaxation with friends. By most standards, I had earned the right to enjoy my life and take it easy. I owned a growing company with competent partners and customers. I was well-connected, having launched the Detroit Chapter of the Young Entrepreneurs Organization and served in several other influential business organizations. Many of my friends were entrepreneurs, so I was associated with high-achieving people. I was earning substantial income and could afford the material objects I wanted. I golfed at an elite country club, drove an expensive car, and flew on private jets for weekend getaways like this one. In short, I was living the good life, and I was ready to settle down and enjoy it.

Or was I? Sitting on that plane, I suddenly realized that I was not satisfied. I was “comfortable,” but ironically, that made me uncomfortable. I was missing something in my life of material success. I had reached my destination, only to find that it was the journey I craved. Life was good, but I felt empty. I wanted to feel alive again.

I know I’m not the only one who has felt this way. Many successful people dream, risk, and work hard to get there, but once they reach a certain point, they tend to coast. They stop reaching, and consequently, they and their organizations wither to insignificance. We all know people who retired to the “good life” and died shortly thereafter. Whether literal or figurative, we begin to die when we stop pushing for excellence. A target standing still will get shot.

Remember how, as a child, you would drive yourself crazy waiting for Christmas to come? When you actually opened your gifts, you realized that the anticipation was the best part of the gift. In many ways, our lives are similar. The goal of a “comfortable life” may drive us, but it’s the process of getting there that is most exhilarating – so exhilarating, in fact, one might wonder if he ever wants to “get there” in the first place.

“Security and comfort are desirable byproducts of goal achievement,” writes Dan Sullivan, “but when they become the goal itself, they quickly stop lifetime growth.” Mountain climbers don’t quit after reaching the first plateau. Sure, they might stop to enjoy the scenery, take a few pictures, eat some food, or even camp for the night, but then they set their sights higher and begin climbing again. It’s as if they’re saying, “That was great, but I know I can do better,” and they continue pushing for higher levels, not because they have to achieve, but because they find fulfillment in the journey.

To keep climbing, to keep pushing, to be productive, one must continually push oneself to greater heights than he has gone before. We all like being in our “comfort zone,” but growth occurs outside the comfort zone, so we must discipline ourselves to step out of it. Inside, there’s no incentive to move.

Think about the people you admire most. Whether they’re statesmen, military heroes, professional athletes, religious figures, business leaders, or anyone else, they probably exhibit a unique internal drive that seems to give them joy and peace regardless of external rewards. They are not sitting still. They are always pushing to make themselves better, not because they need to, but because they want to. They are comfortable being uncomfortable, and it’s from that state that true greatness arises.

Such comfort with discomfort can only be realized in a genuine state of humility. The truly great leaders never know how great they are, and not coincidentally, their organizations never concede their greatness, either. They’re always trying to push to greater heights, to get better at doing what they do, enjoying the journey all the way.

Finding Greatness Outside the Comfort Zone
Stand before a classroom of organizational leaders and ask to see, by a show of hands, those who think they’re great. Those who actually raise their hands are deceived, because the truly great leaders never realize they are. How can we make ourselves genuinely humble? By stepping out of our comfort zones. If you think you’re great, then you’re too comfortable. Step out of your comfort zone far enough and you’ll quickly realize how weak or unprepared you truly are, which is the first step to greatness.

Humility in leadership is perhaps best characterized by complete transparency. Scot McNealy, co-founder and former CEO of Sun Microsystems, once commented that when you occupy highly paid, highly visible leadership roles, you must live “beyond yourself.” In other words, a leader must willingly set aside individual desires and motives and act with transparent integrity – in public and in private.

Key to this transparency is a willingness to be vulnerable before those who you lead. You’re never going to get there if you have to be the smartest guy in the room. You must freely admit that you don’t have all the answers and be willing to ask for help. You must also be able to stay quiet and let others speak up. These disciplines may feel unnatural, but that’s right where you want to be. The discomfort will engender genuine humility that might not otherwise be there.

This is so important because organizational greatness must start with greatness in leadership. In his book, My Grandfather’s Son, Supreme Court Justice Clarence Thomas tells how his grandfather, who reared him beginning at nine years old, instructed him to do not just what he said, but as he did. In doing so, Thomas’s grandfather held himself to a high standard and level of accountability. Looking back, Thomas says, “… example is worth a thousand lectures.”

If more CEOs would hold themselves to this standard, we would have more great companies. “I believe there is no more powerful leadership tool than your own personal example,” wrote John Wooden in Wooden on Leadership. “In almost every way, the team ultimately becomes the reflection of their leader.” This makes sense, so why don’t more leaders do it? Because it’s uncomfortable looking in the mirror. Unless they train themselves to be comfortable outside of their comfort zones, they and their organizations will die from mediocrity.

Have you ever noticed how great leaders tend to be physically fit? To meet intense expectations, physical and mental fitness is a necessity. However, it is also a reflection of their desire to be uncomfortable. I think that people who regularly exercise do it for more than external reasons. They like the feeling of pushing their body to new limits and the feeling of health and confidence that comes with that. The discomfort of exercise actually feels good, and so does the result.

Getting Comfortable with Discomfort
So how does one get comfortable being uncomfortable? First, he must be willing to have a long-term view and act accordingly. This is difficult because it often means making decisions that seem unpopular at the time. Great leaders are rarely considered heroes in the short-term. The most important decisions take the longest to play out, so it’s only after some time has passed that history heaps accolades on those who make them. The leader draws confidence from making the right decision rather than the popular decision. Popularity may offer external rewards, but greatness is measured in internal rewards, and this is where true comfort resides. Internal comfort coincides with external discomfort when one is comfortable being uncomfortable.

Second, start with a purpose. In Built to Last, Jim Collins defines purpose as the answer to the question, “Why do you exist beyond making money?” One might also ask, “Why do I get out of bed each morning?” Answer these questions, write down your answers, and take ownership of them, regardless of how uncomfortable it may feel at first. In fact, do it because you don’t feel comfortable doing it! If you want to achieve things you’ve never achieved, you’ve got to do things you’ve never done.

Sullivan writes, “Treat any increase of comfort in your life as only a temporary stage for establishing bigger goals…and your confidence will always be greater than your comfort.”

That’s a great place to be.

John D. Anderson is a licensed CEO Advantage advisor and former co-owner and President of Gorman’s Business Interiors. He has built, led, and advised companies in a wide range of public and private industries. He can be contacted at


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