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I recently had a conversation with a financial executive who we’ll call Dan. At one point the conversation shifted to personal matters, such as where he lives and details about his family. Dan told me that he lives in Central Long Island (NY) and is the proud father of four children. I asked Dan if he had a boat and he responded that he once did and that the kids used to love going out on it. But the two best days of boat ownership for Dan were the bookends, the first day that he got it and the day when he got rid of it. The time in between was full of more anguish, between lack of function and reliability, as well as maintenance and care, than he ever would have signed up for.

I asked Dan what happened to the boat during Hurricane Sandy. A big smile spread across his face as he thought back to that event from 5 years ago, not because of the general impact, but due to its specific effect on his boat. Dan was really hoping that Sandy would put him out of his marine misery but carving the boat into countless pieces. This would have gotten him an insurance check without having to go through the trouble of selling his erstwhile vessel. But when Dan went out to inspect his boat at the docking harbor after the storm had passed, he found that while all of the other nearby boats were in ruins, his was ironically untouched, as if God was playing (not so) funny games with him. And so he was forced to stay in this unwanted relationship a little bit longer, until he finally moved forward with a sale.

As I pondered Dan’s maritime tale, I thought about just how many of us do the same thing all the time. We encounter a problem, whether it’s a foul relationship (with a boss, coworker, spouse, etc.), a product (car, boat, home, etc.) that we regret purchasing, a program that we wished we had never signed up for, or some other issue in our lives, and hope that somehow we will be miraculously saved without having to put in any effort of our own.

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One of the best insights that I have heard about complaining was shared by Jack Canfield, author of the “Chicken Soup for the Soul” series. Canfield said that all complainers have to have “a reference point of something that they want that they are not willing to risk creating.”

An analysis of this definition reveals two key elements. The first is the idea that we complain when we have reference points that we think we want more than what we have. An example of this would be your car. When there exists a nicer, better, faster, etc. car than the one that you drive (which there does), any problem or deficit with your vehicle (real or imagined) may lead someone to complain about the one that he has. In contrast, something that is rare (such as a tattered keepsake from an event or icon), will not cause us to complain even if it is in far from perfect condition.

Another example of this idea would be a spouse or child. When that person fails to live up to our expectations, whatever they might be, it is likely that we will complain or at the least harbor some form of resentment. But, if our spouse were to happen to be the only person of the opposite gender in the world, or if our children were the only ones available, then our perspective would change immediately.

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In today’s fast-changing marketplace, it can be difficult to achieve mastery in even one professional field. To taste success in multiple areas is quite the challenge, especially when that includes industries – such as real estate, land development and high-tech – that have witnessed such a remarkable range of highs and lows in the pre-recession, recession and post-recession periods that have marked the past dozen years.

Recently, I had the opportunity to sit down with such as individual who has. Dustin Bogue serves as President and Chief Executive Officer of San Jose-based publicly traded homebuilder and land developer UCP, Inc. (NYSE: UCP). In addition to his extensive experience and success in the area of land acquisition and development, Bogue’s professional experience also includes creating two technology start-ups, despite having received no formal training in that area.

While these accomplishments are impressive, it was the timing of Bogue’s ascent that makes his achievements all the more remarkable.

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Within in a few months my dream will come true. I will have published my first book. This book is the product of three plus years of effort, including settling on a topic (becoming the new boss, a book for new leaders to experience sustained success), identifying a target audience (new leaders, primarily on the front-end of their leadership journey), doing lots and lots of writing, testing my content online through regular leadership posts, finding an editor and publisher, and working through the complex publishing process (even the cover design can be a big, time-consuming and emotionally charged deal).  

Without question, this is an exhilarating feeling. Not only am I proud of what I have achieved, but I am super excited to know that very soon I will be able to share my ideas and experiences with so many others.

I often reflect on how I got here and how difficult it may have been had I tried to achieve this goal as a full time head of school (my previous position). Leaving aside the fact that my experiences in that position provided much of the fodder for my text (something that I likely could not have shared freely while under contract), I think that the rigors of full time employment would have made such an undertaking daunting, to say the least. Without having real control over my time and with the many demands of school leadership, how could I have possibly seen this process through? The likely answer is that I wouldn’t have. And I suspect that many leaders with great content, ideas, anecdotes, experiences and achievements feel similarly.

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Today’s weather up in the northeast (US) was far from ideal, at least if you were hoping to go in to work. After three rounds of shoveling, there’s still no end in sight to the white invasion that has made travel and general life activity a challenge. But the good news is that the time outside has given me opportunity to reflect and ponder how snow-related lessons can have a positive impact on us today and well into the (hopefully warmer) future. These are some of the ideas that came to mind:

1. Be prepared – Nothing spells doom for a day like today than the absence of proper preparation. Knowing that a storm was looming, I made my way out to the shed yesterday to get the snow blower, shovels, etc. We also stocked up on food staples and other necessities. In life we also need to be prepared for what’s to come. Sometimes these challenges are in the “forecast”. Sometimes they arrive will more suddenness. Either way, the better prepared we are, the likelier that we can take life’s challenges in stride.
2. Plan for the worst but expect the best – One never really knows what weather you’re going to get, which is why the weathermen like to cover themselves with a wide range (say, 12”-24”, for example). While we need to prepare for the worst, we should always expect the best, and plan to maximize our days rather than succumbing to the “what can I possibly get done on such a day?” mindset.

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One of the most widely watched TED talks on education was delivered by Rita Pierson. In a moving talk entitled, “Every Kid Needs a Champion”, Pierson, a second-generation educator, emphasized the importance of building relationships with students. She details her experience working with some of the hardest challenges in the system: kids who haven’t tasted academic success and often lack strong adult relationships that can provide guidance and inspiration and also strengthen resolve. Her successes, she says, were to a large degree the result of believing in her charges and giving them a vision of a better tomorrow.

Ironically, having a champion can have its downsides for kids as well. In a recent parenting post by Kathy Caprino, the author cites leadership expert Dr. Tim Elmore, who shared a list of ways in which parents today are failing their children by coddling and crippling them. Such behavior, says Elmore, prevents children from becoming the strong, independent leaders and balanced adults that they are destined to be. According to Elmore, current parental failures include:

1. Not letting our children experience risk – We live in a dangerous world that is full of risk. But instead of allowing our kids to get out there, we seek to provide a strong layer of protection. For kids to succeed, they need to fall a few times to learn it’s normal. Parents who remove risk from their children’s lives will promote low self-esteem and greater insularity in our children.
2. Rescuing kids too quickly – Today’s adults have a propensity to swoop in and take care of problems for them. When we rescue too quickly and over-indulge our children with “assistance,” we remove the need for them to navigate hardships and solve problems on their own.

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Ask the average person what it takes to be a great leader and you will surely hear a bevy of characteristics and qualities, such as visionary, communicator, motivator, and charismatic. Perhaps you will also hear such idealistic qualities as humble, possessor of strong character, and servant of others. All of these relate to how a leader is perceived by others and how he relates to them. While these attributes unquestionably assist leaders in their work with their people, they will still under-deliver if they lack one critical but often overlooked internal quality: self-esteem.

Self-esteem is defined as the degree to which individuals feel comfortable with who they are, believe that they have inherent value as people, have the ability to demonstrate that value, and are confident in their ability to successfully achieve their own measure of success. It isn’t about being boastful, self-centered, or domineering. Rather, it’s about representing ourselves with quiet confidence, as an equal among equals, and leading others from a position of internal strength.

Self-esteem is vital for leaders because it’s what gives them the courage to lead, to pursue success, to and be decisive. A leader with high self-esteem does not feel threatened by others’ ideas, nor will they have a problem with hiring great people and empowering them to accomplish incredible things. Strong self-assurance makes the leader want to see the best in others and help them succeed, knowing that others’ success is ultimately their own. He puts the organization first and is the most committed person in the building. A self-confident leader is more concerned about being part of something great and accomplishing the task than worrying over who will get what position or what recognition.

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One of the greatest challenges that confronted me when I assumed the role of head of school was the contrast in personalities between my predecessor and me. In many ways we were polar opposites, including our general affect, how we interacted with others and in the amount of quiet, private time (with the door closed) that we wanted or needed to function effectively in our jobs.

At the time, I really didn’t appreciate this issue. To me, I was who I was and I assumed that everyone else would simply get used to dealing with a new boss. In hindsight, I feel that I could and should have taken more time to understand my personality and, by extension, leadership profile and how that may impact those around me, especially when they were used to something very different. While personality differences between leaders are to be expected, when they represent a major shift then there can be a difficulty in adjustment for everyone involved. And that difficulty became apparent soon enough in my situation.

One of my favorite leadership training sessions is based on the True Colors Personality Assessment. In this system, people generally identify as being one of four colors: blue, green, gold or orange.

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A story is told about a reporter who was interviewing a successful bank president. He wanted to know the secret of the man’s success. "Two words”, he was told, “right decisions.” “And how do you make right decisions?” asked the reporter. The reply: “One word: experience.” The reporter pressed on. “And how do you get experience?” he asked. To which the banker replied, “Two words: wrong decisions.”

We all recognize the importance of job and life experience, especially for leaders. Experience gives leaders context for important decisions that they must make and insight into how best to lead, motivate and respond to their people. Experienced leaders have been through the wringer before and can use their past learning and decisions to guide them moving forward.

Yet, for many new leaders, experience can be hard to come by. And in today’s fast-changing, competitive environment in which more and more young people are assuming leadership roles, it can be critical for them to find ways to gain experience quickly in order to ensure that they make as few “wrong decisions” as possible, for their own sake as well as for those that they lead.

What can new and aspiring leaders do to gain the benefits of experience when they simply don’t have much on-the-job learning under their belts?

1. Go for training – Identify educational programs that are reputable, respected, and, more importantly offer cutting-edge instruction and hands-on learning that translates well into real-life situations. 
2. Volunteer – See if volunteer opportunities exist for such things as such as managing a project for an overworked leader. (If they presently don’t, go ahead and pitch an idea. Someone is bound to take you up on it if they think that you can help.) Use the opportunity to engage in meaningful work as well as reflective conversations about the leadership task. In this way you can learn much about leadership and how to plan for it in a low stakes environment where there is less pressure to perform and risk of backlash.

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