20 Lessons Learned From 20 Years Working @ Microsoft

I have written a short online book on my career experiences working at Microsoft.   I call it “20 Lessons Learned From 20 Years Working @ Microsoft ” The “book” is really more of a long blog post, or a set of stories and lessons learned working in corporate America.    The focus of this blog is really about building long-term financial freedom, and paths that can help you get there.  Every path is unique- and for most people, working a day job will be one of the most significant components for building and sustaining your financial future.  I hope that my lessons learned and experiences can be helpful to young people as they move throughout their own lives and careers.

I plan to post a chapter or so each week.  Today I start with the Prologue.


You could write a book about this place.  That is what we would always say while we sat around a conference room laughing at what an incredibly bizarre world it was living and working at Microsoft’s headquarters.   Microsoft, based in the small Seattle suburb town of Redmond Washington was definitely a strange world all onto its own, even for Seattle, a fast-growing tech-driven city, Microsoft revolves around its own inward universe.  With an oddball culture, designed and driven by hyper-aggressive overachieving nerds in what was a rapid growth company in a blazing hot sector.  Microsoft was a one of kind place.    

I worked at Microsoft for a little more than 22 years.  The first couple years as a contractor with a break in between, and just shy of 20 Years – as a Fulltime or FTE, or Blue Badge, as they call it.  I left Microsoft in October of 2014.  I was one of those people who was lucky enough to retire early and start enjoying a new life outside of the daily grind.     

Just about a year after leaving Microsoft, I started thinking about that book idea we would always joke about.   I wondered if there was enough interesting material to really create a book about my experience.  I thought maybe a decent web blog post would be interesting to a few people.   I know that I didn’t want to write a memoir, as frankly, my career was really not that unusual or special.   I figured there was probably a good amount of learning that would be worth sharing, even if it was only pertinent to people who cared about moving up the company ladder.  I was fortunate enough to move up to a fairly high level inside of Microsoft, particularly for a guy with no fancy pedigree, no Ivy league school, no MBA or computer science degree, just a state college degree in Liberal Arts, and the willingness to learn, work hard, grow and climb the company ladder as best I could figure out how to do.   My journey took me from starting out as the lowest level call center employee the company had, to being the General Manager of Microsoft’s largest Internet Media Business MSN, where I led a business that had more than 400 Million users, and drove nearly a Billion dollars of revenue for the company.   

My hope is that this online book can help people who are trying to navigate their own way through the corporate world.  Or those who are considering a career at Microsoft or some other big tech company.   My path for sure was unique and fairly lucky, I was at the right place at the right time.  I do believe that you make a lot of your own luck, but luck itself is a big part of my story.  Of course, some had much better and luckier timing with their Microsoft careers, but I for sure have nothing to complain about and had many very good years at the company as it was growing and expanding. 

There were some funny moments I will try to share and a little bit of an inside glimpse of some of the nuttier things I saw and did at the company.     Most of my facts are straight, at least as much as I can remember them, some dates are likely to be slightly off as I was not great a keeping a daily journal.  The exact dates and even some of the details are not really the most important part of this online book.  For a young person who is looking to join a new company, figure out if they should leave what they are doing today, and want some advice from somebody who has been there, the general examples and learning lessons are really what I hope makes this book useful and interesting.   

Some of the people’s names in the book have been changed, to protect the privacy of individuals, and to protect me from getting sued by them.    My hope is that by sharing some of the things I learned the hard way, the people who read this book may avoid many of my mistakes, and may be able to take advantage of some of the things that I learned while clawing my way through the jungle of Microsoft.    And if no learning can be had, maybe a few can get some amusement and laughs from some of the stories.   As it turned out, after I got about halfway through what was going to be just a long blog post, I decided there was at least enough here for a short online book.  The book is structured as a sequence of stories & experiences with my reflection on those experiences, which I have called “learning lessons”.   It took some time and true reflection to develop the learning lessons most of them I only understood in hindsight.   So here it is, my online book on my Microsoft experience.     

  1. Chapter & Lesson One 
  2. Chapter & Lesson  Two
  3. Chapter & Lesson Three
  4. Chapter & Lesson Four
  5. Chapter & Lesson Five
  6. Chapter & Lesson Six
  7. Chapter & Lesson Seven
  8. Chapter & Lesson Eight
  9. Chapter & Lesson Nine 
  10. Chapter & Lesson Ten 
  11. Chapter & Lesson Eleven
  12. Chapter & Lesson Twelve
  13. Chapter & Lesson Thriteen 
  14. Chapter & Lesson Fourteen