Career Strategy Demystified to One Page

Life is too precious not to be thoughtful and deliberate about how you allocate your time, talent and treasure. Managing a career can be a complicated topic with many aspects to coordinate and consider. The path we choose and the decisions we make each day have a significant influence on our health, happiness and prosperity.

Surprisingly, how to approach career strategy effectively is rarely taught in schools at any level. Organizations are not in the best position to offer a comprehensive curriculum given that career strategy starts with understanding who you are at a deeply, personal level. The topic we all struggle with had to be demystified.

In 2008, I authored a framework of seven connected strategies to give professionals a process for answering critical questions and shaping their mindset. I continue to evolve it as I learn new ideas and experiences in a new phase of my life.

Download the Career Strategy Framework one-pager for a seven step roadmap.

Even in the light of daily chaos and uncertainty that surrounds our life, there is a sense of calmness and confidence when you have a deliberate and strategic career direction. Start the journey to reach your full potential – we only get one shot.

How do you feel about your answers to the seven questions?

How To Become An Apprentice In Human Nature – A Must Read

For most of my life I have relied on the laws of physics, mathematics and strategy to explain phenomena and influence how I engage with the world. These laws, theorems and concepts influence our thoughts and decisions. Once internalized, the physical and technology worlds can most often be explained simply and logically. Our studies of first order principles establish the foundation for clear, true and rational thinking.

But, success and fulfillment in life requires relationships and collaboration with people both personally and professionally. Every human is unique, often irrational, making it challenging to explain behavior or how best to engage with someone for mutual success. It is well documented that social intelligence is as important or even more important than intelligence quotient (IQ) in life. Just as the laws of science are explained in physics books, we would all benefit to learn the laws that explain human nature.

Robert Greene’s latest book, The Laws of Human Nature, is a masterpiece for helping you become a better person and learning strategies for engaging with the right people while avoiding others. From the opening chapters on irrationality and narcissism to meditating your mortality, it’s a book that will change your life. It will likely provide frameworks and answers to aspects of your life you could not explain. I highly recommend this book for anyone that can relate to the five value propositions outlined on the back cover above. Understanding these laws, are an essential complement to the expertise that you have developed in your specific field of study.

Ryan Holiday interviews Robert Greene on the background and writing of his latest book.

In the interview, Robert Greene highlights that many people don’t know who they are. Ten years ago when I began running career strategy workshops at Microsoft, it became clear that this indeed was the case for most of the people I worked with. I too was challenged with an identity crisis at various stages of my life. People lacked an inner understanding of who they were now, why they behaved in a certain manner and how to collaborate with the wide range of personalities and cultures.

This intent of the “Know” part of the career strategy model is exploring deep into “knowing” as much as we can about ourselves. It’s a never-ending journey as we navigate through different phases of our life. The “Connect” part of the career strategy model outlines principles and virtues for interacting with people to achieve success and fulfillment.

The Laws of Human Nature has been added to the recommended reading list that aligns with the Know and Connect domains. Just as a new pair of glasses sharpens vision, internalizing these laws will adjust your mental model on how you carry yourself and see the world.

Final words that will last a lifetime


Sundays were always the day that I would talk to my Dad on the phone and every weekend is reminder how much I miss his voice and guidance.  He passed away two years ago and I can still vividly remember the last few days we spent together prior to his passing.  My father successfully battled cancer eight different times but I knew this time was different.

We reminisced about old times and the stories he told about his company that stood the test of time for 56 years.  I was always admired his entrepreneurship and competitive spirit.   On that last day I told him stories about the qualities of a father and leader that I always admired:

  • A Competitor – a man that would compete hard at whatever he did whether it was playing tennis, running his business or fighting cancer eight times over 20+ years.
  • A Connector – no matter where we were around town everybody knew him and he made it a point to get to know people. That was just his way of doing business and making people feel special.  He was a celebrity in my eyes.
  • A Giver – a man with a big heart that gave to others unconditionally even when they did not expect it. His funeral only reinforced this by the many people who remarked the special and touching things he did for them.
  • Do it in style – a man who do everything first class with an attention to extreme detail.

My father smiled and laughed as I talked about those qualities but I knew he appreciated hearing those words of how I saw him.

On this last day I asked him about his secrets to business success and he shared the following:

  • I didn’t need to be smart, I just need to have smart people around me”.  My father never went to college but he was a learner and would find out everything possible about something he was interested in.
  • Pay your employees great and look after them“.  He cared for the financial and well-being of his employees which explained the deep loyalty and commitment they had for so many years.
  • Use other people’s money, have great credit“.   Running a profitable business and taking advantage of cash flow and great credit are important during the tough times.
  • Take care of your customers, go out for lunch and get to know their business“.  My father’s business and personal connections were truly remarkable and he invested in developing relationships with a charismatic way.
  • Do it right or don’t do it at all even if it cost you some money“.  There is something to be said about giving it your all no matter what you do in life and doing it right was perhaps his most memorable hallmark.
  • Be a hustler“.  I always remembered him saying you need to work hard and be scrappy to get ahead in life.
  • Don’t screw people“.  Business can be a small world and he spoke about playing by the rules and respecting your competitors.

The afternoon turned into early evening and my Dad was getting tired.  He turned to me and asked if we could call it day.  I thought this may be the last time I would talk with my Dad. The last two days were full of memories and stories but yet there was something I still wanted to hear before I left.

My Dad cherished our relationship and loved me but it was those three simple words I never actually heard him say to me. Over the years I would often say “I love you Dad” in the hopes of making it easy for him to reply with similar words but it never happened.   I knew it was just his upbringing that made it feel awkward for him.   This would be the last opportunity to hear those words.

I turned to my father one last time and said “I love you Dad”. He looked at me and replied, “I love you son”.  I kissed my father on the forehead and said that I would talk to him soon.  I felt emotions of both sorrow and happiness as I left the nursing home. These were the three simple words I was waiting a lifetime to hear.  I cried in the car after hearing those words but I also knew this was probably the last time I would see him alive.

My Dad’s condition accelerated and a few days later he would no longer talk again.  I will always cherish that last day and the stories were shared.  Perhaps it was the lesson I learned on that day that will last a lifetime.

Life is unpredictable and we may lose the chance to tell somebody something important. It’s easier to avoid a challenging conversation, avoid saying you are sorry or putting something big out there when you don’t know how somebody will respond.

Go for it – it may be the greatest thing you ever tell someone.

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