Chapter and Lesson #5


One of the things I am best at is riding coattails.  Behind every successful man is me, smiling and taking partial credit.  

Tom Haverfod (Parks & Rec)   

As it turned out, my job in Product Support set me up to grab my next pretty cool job at Microsoft.  The Windows Team at Microsoft was looking to hire somebody into Product Management who had some experience with our Support organization.   At that time Microsoft was spending a TON of money supporting retail and small business customers who were calling in to get phone support on all kinds of different issues they were having with their PC’s.  Sometimes it was a Windows problem, sometimes it was the PC Manufacturer, and sometimes it was a problem with a software or hardware program the customers had added to the PC.

Whatever the problem, a big percentage of people would call Microsoft first for help, and this was taking a big bite out of the profits of Windows.  The Product Management team was interested in finding new and less expensive ways to deal with all of these calls.   So they opened up a new position to hire somebody who could help figure out what should be done to drive down those high customer costs.    

Interestingly, the hiring manager for this role was Suzan Fine – Who is now Suzan DelBene, who has gone on to be a U.S. Congresswoman for Washington State’s first Congressional district.    I loved working for and with Suzan. Suzan had a great way about her, she had an infectious smile, positive attitude and get it done personality.  She was wicked smart, and I think at times overlooked at Microsoft for bigger roles that she likely deserved to have.    

Soon after Suzan hired me, I started working for Lora Shiner who was a group manager on Suzan’s team.  Lora was one of my favorite people I ever had the pleasure of working with and for.  She was an incredibly talented marketing mind and had a common-sense approach combined with a fearless attitude where she could stand up to any Microsoft Executive on any issue.

I remember one meeting we had with Bill Gates where Lora was one of the key presenters.  I can’t recall the issue we were discussing at the time.  But for whatever reason Bill was in a particularly foul mood that day.  He took a shot at Lora and said something to the effect that “you must be the dumbest person I have ever met”.   To which Lora replied with a big smile.  “Bill, while I understand you don’t like my idea, I can assure you that I am not the dumbest person you have ever met, not by a long shot”  That comment shut Bill up for a few seconds, he paused, the room gasped and everyone started to laugh, Bill took the comment with good intent and humor and got quickly  back onto a productive track.    

Lora was outstanding because of her confidence, her intellect and her very honest and direct style of communication.   She would mentor, support and get out of the way.  She expected the best from people, and when they didn’t deliver she had this magical ability to help them realize they had let her and the organization down.    Lora could fire a person and have them love her all the way through the process until they were out the door.  Sadly, Lora died of cancer at age 47 just before 9/11 attacks.   I was devastated to not be able to make it to her funeral as I got stuck on the East Coast after the attacks of 9/11 and could not get back in time to make her services.   She was a great friend, a mentor, and a great boss.  I still miss her to this day. 

I was very fortunate to have quite a few fantastic bosses at Microsoft.   Lora Shiner was my favorite boss.  Others included  Yusuf Mehdi a long time senior marketing executive for Microsoft.  Bob Kelly the leader of Server and Tools Marketing and now at Ignition Partners, Jeff Price another longtime leader in Windows and Windows Server Marketing now at VP at Oracle, Danielle Tiedt who was the lead marketer for Bing and went on to be the CMO at YouTube,  all great bosses, each was different and each helped me grow and become more successful in my career at Microsoft.

I had my share of bad bosses too, I will talk about some of them later in the book (without naming names).  Most of the bad bosses were bad because they lacked confidence in themselves, they were insecure in their abilities, and they lacked the ability to truly lead and inspire others.   In my experience, bad bosses tend to blame the people around them for their problems.  They have  a tendency to throw up a lot of roadblocks for the people who work for them and around them.   They tend to take away the energy of people in their groups, rather than create energy.   A great boss creates energy and knocks down roadblocks, they want their lowest level employee to have great success, and they never fear the success of their underlings, they embrace it and support it.

I remember I had one boss, who I will not name, I called him the “wife beater”.   This boss would come into my office totally by surprise and just start berating me over some minute detail he was upset about.  He would swear at me, personally insult me, tell me that I was worthless.  It was disgusting, I was still early in my career and in my twenties, and I was afraid to really stand up to him directly.   After his tirades, he would always come back to my office and apologize for losing it.  He would tell me how badly he felt, and that I didn’t deserve to be treated like that.  He would offer to take me out to lunch, which was the last thing in the world I wanted to do.  It was awful, it made going to work a terrible experience.  Luckily there was a reorganization just about every 8-12 months in those days at Microsoft, so I knew I would not be with him long, and sure enough, the nightmare of working for that guy lasted less than a year.  

The point of this is you need a great boss and there is no shame in riding coattails when they are available.

Learning Lesson #5 Picking a Great Boss is MORE important than Picking a Great Job.   This may be obvious to some people, but it took me some time to figure it out.   Having a great boss who can and will support you is so much more important than the job or the content of whatever job you might be considering.   You could have dream job, but if you have a horrible boss, it will ruin anything good about the job.   Bad bosses kill careers, they kill your spirit, and they can make every day a living hell.   Bad jobs, with a great boss, can actually be somewhat fun and satisfying.  Great bosses are extremely rare.  If you have a boss that is supporting you, helping you grow, eliminating problems and allowing you to do good work, you are in a winning situation.   Even if you don’t love the content of the everyday work you are doing, if you have a great boss stick with her or him as long as feasible.   Specific jobs and the work content comes and goes, bad bosses can be forever!  Or at least they can torpedo your career forever.   If you have to make a choice between Great Boss + Bad Job vs. Bad Boss + Great Job.  Pick Great Boss every time.  

Chapter and Lesson #4


“It is not the employer who pays the wages. Employers only handle the money… It is the customer who pays the wages.”- 

Henry Ford, Ford Motor Company 


When I landed the 2nd time at Microsoft, it was first as a contractor.  I had made up my mind that I wanted to work for the company fulltime, and I was going to do everything I could to land what they called a “blue badge” job with the company.   This terminology originates from the different types of employees who had different color badges depending on their employment status with the company.   Blue badges were for fulltime employees.   Microsoft has always had different color badges for temps, contractors, service jobs etc.    Blue was the gold standard, it meant that you were a full-time employee of Microsoft, with benefits, stock and all the nice, and some not so nice, things that go with it.    It took me about a year of hard work, keeping my nose to the grindstone and ears on the phone headset, and kissing a fair amount of ass to finally land my first full-time job.      

I came up from the bottom, so I had a chance to see the pros and cons of the perma-temps at Microsoft, and the ever-growing legions of contractors the company employs.  Microsoft employs temps and contractors for a few different reasons.  Mostly they want the flexibility in their workforce, it is more efficient for them than hiring fulltime people and having to deal with adjusting that workforce up and down.   For many of the contracted employees, this works pretty well, you can get a pretty decent paying job working as a contractor for Microsoft, and you can have a lot more flexible schedule.   As a contractor you typically can just focus on doing your work, you also don’t have to go to all the bullshit meetings Microsoft has all the time.   

A note about meetings and Microsoft. Microsoft is infamous for holding way too many meetings for just about everything, they have team meetings, group meetings, manager meetings, divisional all hands, pre-meetings, post meetings, meetings to plan more meetings and on and on.  It is an insane “meeting” culture, I don’t know if this has changed since I left.   I can only say that generally if you can’t stand meetings, don’t go to work at Microsoft.  You will have far too many of them and more than 50% of them are total and complete waste of time.   I regularly sat through meetings where there were 100’s sometimes 1000’s of people.  Almost all of them were totally useless and could have been done via a quick email or send a video around.   

For me, it turned out that the little bit of experience I had gained in Aerospace doing sales was useful for landing my first “blue badge” fulltime Microsoft job.  The group I was working for at Microsoft was looking for somebody who had some sales experience, but also some experience working in the Product Support Services group – which was the group I was doing the contracting job in.   That combination of experience landed me in a group that was ramping up a new team to sell a new “paid support” product from Microsoft that they were going to call “Premier Support” at that time.   The “premier” part meant that Microsoft was going to charge significant money to the customer to support their products. 

As more and more big corporations were installing more of Microsoft’s products, quite a few companies were starting to run important parts of their business on Microsoft, and they wanted Microsoft to have more “skin in the game” when selling their software to them.   Believe it or not, back in those days, Microsoft was considered more of a consumer software company, and big enterprise customers did not trust that Microsoft was truly committed to supporting big companies IBM for example was.

Microsoft had previously tried to avoid going deep into servicing customers.   It was expensive to service enterprise customers to the level they expected, and it was not considered a core competency of Microsoft.   IBM, HP, and a few others were considered more credible players in the service business in those days.

Microsoft was a disrupter offering a lower price more flexible PC solution, while others were offering expensive mainframe solutions with very high priced service contracts.   IBM had people inside of all these big fortune 500 companies, and anytime something went wrong they would take the bullet for the CIO who might be in trouble.   It made CIO’s very nervous to have a big deployment of Microsoft software and not have somebody at Microsoft who they could choke when things went wrong.    These dynamics made for the advent of the TAM – or Technical Account Manager at Microsoft.  The TAM was a named technical support expert assigned specifically to a company, or even to a specific department of a larger company.  If for example, a big bank had some sort of serious problem happening with any Microsoft product, they could call on their assigned TAM to make sure their problem was solved, even if that meant the problem required an engineering fix from one of Microsoft’s core development teams.  And a company could ONLY get access to a TAM if they had paid for a Premier Support contract.   It was a brilliant way for Microsoft to charge money to support their products, and customers actually jumped at the chance to get some individualized attention from the fast-growing software company based in the obscure NW corner of the United States.  

For me, this meant a new job was born!   My job was to sell these Premier Support contracts to some of Microsoft’s largest and most important customers.   I was happy and lucky to have a Fulltime spot with the company, many of the young people in the division I was being hired into were already “retiring” as they had enough money in stock options to cash in!  They could “call in rich” as they would say.   I figured if these lucky bastards could be retiring before they were 30 years old, I would be able to knock out enough stock options to be done before I was 30 as well! 

Microsoft was fortunate to have a lot of talent in their support group, they did a good job of working with customers and finding solutions to whatever problems they had.   Microsoft acted like an underdog in those earlier days, it tried to continually go above and beyond to make sure customers were getting good service and were happy and satisfied.   It was a fun group to be part of, and in that work, I learned a lot about what customers wanted from our products and services.  I would hear it first hand from the IT Pros who were doing the actual deployments of Microsoft Software in their environments.   These were the people whose jobs were on the line to make our software work at their companies, you learn a TON from these folks. 

Learning Lesson #4  When starting out in a big company, get a job where you are working directly with customers.   The experience you gain working directly with customers is invaluable for your entire career.  You will get more respect from future bosses, co-workers, customers, and partners if you live in the trenches with customers for a decent period of time.  It may not be glamorous or even all that fun at times, but the experience is the best thing you can do for your career.  I recommend getting the experience as early in your career as possible and stick with it as long as you are progressing in a direction you like.   There are TONS of jobs at big companies where you never actually talk directly to customers at all.  Avoid these jobs early in career.  Jobs that don’t directly touch customers are normally easily replaceable, outsourced, automated and early to be eliminated when times get tough, and they won’t give you the credibility needed to accelerate your career.   Companies are nothing without paying customers, every CEO and senior executive knows that.   Senior Executives have more trust and rely more on people in their organizations who have had a strong direct connection with customers.   And most Senior Executives get their positions because of their focus on customers throughout their careers.  

Chapter & Lesson # 3


Chapter 3 

“Good business leaders create a vision, articulate the vision, passionately own the vision, and relentlessly drive it to completion.”  

Jack Welch 

I decided that when I got my second shot at working at Microsoft I was going to treat that opportunity very differently.  I had a little bit of experience in the real world now.  Even I could now see how PC’s were going to completely transform the workplace.   I was not visionary enough to fully understand how much PC’s were going to change the home, but it was pretty obvious that PC’s were going to be important in many homes very soon.   Of course, Bill Gates had the powerful vision of a PC on every desktop in every home, but that seemed like a distant pipe dream back in 1994.  But when Bill spoke, people listened, and he had a way of making the un-seeable seeable.  For all that has been said and written about Bill Gates, to me at least, he exemplified a bold and strong leadership combined with an amazing vision unlike I had ever seen.  

Gates in my very limited interactions with him, was the real deal, just an absolutely incredible person.  Bill’s vision, intelligence, drive, his massive depth and breadth of so many different areas was just unbelievable to witness. I was amazed and impressed whenever I was fortunate enough to have a meeting with him or hear him speak.  It was just an incredible privilege to be around him.  Whatever you think about Microsoft, its products, its business practices, you can never take away the incredible person that is Bill Gates, and the lasting impact he has had and will continue to have on our planet.   He has made a big dent in the universe. 

So much has been written about Bill Gates that it is hard to come up with anything particularly novel or new to say about the man.  One of the things I always appreciated about Bill was his unique ability to take extremely complex and technically difficult problems and simplify them so that anybody could understand them.    

A meeting with Bill was something that could take weeks to prepare for.  Most of the meetings with Bill were to seek strategic direction, either for a product specifically, or for some kind of directional or strategic advice on the business.  Bill was always amazingly deep on both topics, so much so that you would fear he might ask a question that you had not thought of, and he often would!   When particularly difficult decisions needed to be made, Bill had an incredibly elegant way of weaving his deep technical product knowledge with his insanely good business acumen to come up with what would often be an obvious solution, where he would plainly explain the answer.   

It was amazing to watch Bill lord over meetings with his superior intellect combined with his reputation as the great founder of Microsoft; with his jabbing quick smarts, and his sometimes wicked tongue, he was the only person I have ever seen who could command the respect of Microsoft’s biggest egos and bring them quickly inline.  His leadership was simply unmatched. 

Learning Lesson #3  –  Only work at a company where you truly admire the leadership.   When you truly admire the leadership of the company you work at, the hard times and the difficult things you encounter each day are much easier to deal with.     There were plenty of hard times, bad days, and screwed up things happening at Microsoft during the 20 years I was there.   When you are lucky enough to have great leadership at the top, you end up trusting that good decisions will ultimately be made about the big things that really matter.   This makes it infinitely easier to deal with all the little stupid things that happen in big organizations all day long.   After Bill left the company, it was clear that Steve Ballmer didn’t have anywhere where near the intellect, vision or leadership qualities that Bill did.   You could never be sure if Steve would make a good decision on the big things that mattered, he was way more random, insecure and for my taste a more difficult personality to deal with.    The longer Steve was in power, the more you could watch the company lose its way.   When a company feels lost at the top, the stupid things that happen every day at all companies seem to feel much worse.  You can put up with a TON of bullshit if you feel like you are heading in a great direction overall.  

Chapter 2

“Winners quit all the time.  They just quit the right stuff at the right time”  

Seth Godin  


In 1994 I finally woke up and realized what the birth lottery had gifted to me!  I lived in the Seattle area, in the midst of the PC revolution, and we just happened to have the leader and the most profitable company of that revolution right under my nose called Microsoft!! So, when I finally clued in and figured out that PCs were going to be big, really big!  I thought, what the hell, I better find a way to join Microsoft again.   While I was incredibly stupid, at least I was smart enough to see that this PC thing was really starting to catch on!     Add to that, my young beautiful wife had already started working at Microsoft in sales, where she had run into an old High School friend of mine who was working there as a manager in Product Support, and one thing led to another I was hired back to Microsoft 2 years after my first contract job with the company had ended.  

Now I was starting over at Microsoft, with a job that may have even been worse than the first one I had started with!  At least at this point, I had the good sense to quit the dead-end job I had in Aerospace and move on.  It was sort of a second chance for me to make something of myself.   

This was not the worst path for me to take.  After bumping around in the Aerospace business for a couple years, I saw how difficult it was to grow a career in a mature industry.  I was working for a sales manager who had been in aerospace for more than a decade already and had only moved up far enough to be my boss.  He was a nice guy, but his spirit was waning, and he knew his boss had to quit or die before he was going to get another bump up the old corporate ladder.  The environment was depressing, the old-timers at the company had that glazed look in their eyes, of a life wasted.   

As it turned out, the Aerospace company I was working for was going through a rough patch of their own.  The company had just lost their most important patent while I was working there and was about to lose their largest customer as a result.  Unfortunately, the very day that the company’s most important patent expired, their biggest customer, The Boeing Company, called up the CEO and told him that they were now going to take all the product they had been buying from us in the past and do the work “in-house”.  Boeing told the CEO that they had been waiting for this day a long time and that they had felt they were been being ripped off for the past 20 years!   It was a hard day for everyone at the firm. 

That very same day, the CEO of that small aerospace company called an emergency company meeting, it was just before Christmas and he broke the news to the entire 120-person company.  For many of them, their careers were over, about half of the staff would have to be let go, there would be no end of year bonus, and the Christmas party had been canceled.   It was a grim day for the people who had spent a good part of their life working for the company.  Some were crying, some were mad at the CEO for not steering the company in a brighter more prosperous direction.  It was a wake-up call for me.

I was sort of glad that the company was likely going to lay me off.  I couldn’t stand the job, and I could see that whatever my future was going to hold, this job was not going to make it very bright.  Also, the CEO and founder of the company was a greedy and grouchy old guy.  And I thought to myself,” if this guy is the best that one can aspire to here, I really need to think hard about getting out this place”.  

One of my favorite stories of working at that company was a time when I had gone to the breakroom to cook up some microwave popcorn.   I then brought the popcorn back to my desk to snack on while working.  As soon as I got back to my desk a fellow sales trainer/corporate slave came running up to my cubicle in a bit of a panic.  He told me that the “old man” (that’s what we called the owner and CEO of the place) HATED the smell of microwave popcorn!  He had a strict rule about not bringing it into the offices from the break room area.  This guy was dead serious and seriously worried about me, I could be fired for eating a bag of popcorn at my desk.  I laughed, I sat down and ate the entire bag of popcorn, and I thought to myself, I am not going to last very long at this place.  I quit Friday of that week same week.  I told my boss I planned to start my own company.  But really I did not have a plan.  I just knew that I could not stay at that company any longer, it was never going to go anywhere, and I did not like the work anyway.

This all made me appreciate the Microsoft opportunity so much more than I would have if I had not had this experience.   I think it also motivated me to try to be a much better employee and work harder to impress my superiors when I had a good opportunity.   Yes – I was slow on uptake, but the learning lesson was a valuable one.

Learning Lesson #2 –  If you find yourself in an obvious dead-end situation, QUIT!   Had I not had the good sense to quit what was a decent but dead-end job in Aerospace, I would never have had the chance to have my incredibly fortunate and lucky run at Microsoft.    The old saying “winners never quit” IS WRONG! —winners do quit, and quitters do win.  Quit often and start over when it makes sense to do so.  Timing is important, and so is luck.   If you are having trouble knowing if you should quit.  I recommend reading The Dip by Seth Godin

  Throughout the rest of this book, many of the learning lessons I write about are meant to help you identify if you are in a winning or losing situation.   And to help you find your way to areas and scenarios where you can win.  Believe me, there were a lot of people who were better at timing and getting luckier than I did at Microsoft, even when I was damn lucky to get what I did! 

Others I knew at Microsoft were even more amazing at timing.  Those who left to join Google, as an example, just as Microsoft’s hypergrowth was ending, were particularly impressive to me.  It’s hard to know just when the right time is to jump to a new opportunity, but if you really watch for the signals and ACT on them, you will be better off for having left a job that is dead or dying and take that jump toward moving to a better future.   

Chapter One

Chapter One


“The first duty of a human being is to assume the right functional relationship to society – more briefly, to find your real job, and do it.”

Charlotte Perkins Gilman


My first Microsoft Job:

My very first job at Microsoft was as a temporary worker or what they had called a “contractor position” it was the year I graduated from College, 1991; I landed a job on the DOS 5.0 sales hotline.  The only reason I got the job was my brother’s x-girlfriend had taken a job at a temporary staffing agency that was placing lots of bodies inside of Microsoft.   Microsoft was growing very fast in those days and frankly could hardly hire people fast enough.  If you had a college degree, a pulse, and could work on the telephone for 8 hours a day, you were pretty much qualified “enough” and you were in.  There may have been a basic typing test involved as well, I have a hard time remembering it all now.  I knew quite a few people who got their start at Microsoft this way over the years.   Many of whom went on to have very successful careers inside the company and out.

It was not a glamorous start.  The specific job I was assigned was taking telephone orders for a new version of DOS, which is short for Disk Operating System.   This particular release of DOS had some new stuff- or “features” as they say in the software business.   The release was notable as it was the first time that Microsoft made an effort to sell an Operating System to retail customers as an upgrade.    So, DOS 5.0 kicked off a big business for Microsoft, selling upgrades of computer operating systems to their installed base of somewhere around 60 Million users at that time.   The installed base of Windows PC’s is in the billions now.

The office park where they set up this temporary sales order desk I was working in was not on the main campus of Microsoft. It was about 3 miles away near downtown Bellevue in a nondescript office park called “Ridgeway Campus”. Microsoft had taken a lease there and occupied 3 of the buildings.   Pretty much all of the employees in these outpost buildings were temporary or contract employees.   They did not officially work for Microsoft.   It was mostly a bunch of young kids in their early 20’s getting a start in the job market.   The only “benefits” offered with the job were free soda and a pretty nicely stocked kitchen with decent snacks.   I remember that pretty well because I was coming off of being a starving student, and while I was only making about $5.50 an hour with no “benefits”, I thought it was great that I could drink a lot of free soda and eat a LOT of free snacks.   For the temps, it was always clear that you were a 2nd class citizen of Microsoft, there were no health benefits, stock options, gym memberships or any of the respect shown to full-time employees, but you did get the free soda and snacks, and the people were generally nice enough.

It was a good place to get some experience in the business world when you were fresh out of college with no real prospects.  The job market in 1990 was not very strong, and it was particularly slow in the Seattle market.  I was just happy to have a job.

My days consisted of sitting in a very small cubicle all day for my 8-hour daily shift. The workspace was really too small to even call it a cube; it was more like one of those long row desks that you see at a library with little privacy walls in-between each sitting area spaced out at about every 3 feet or so.   It was adequate space to get the job done.   And for the most part, it was all young kids who were just out of school and it was not all the different than studying in a crowded library.  Everyone there was just looking to make some money, get some experience and move on.

I, and the group I worked with actually had a lot of fun doing that job.   I remember that we had a script which we had to follow when we answered prospective callers.  We were told to answer the phone saying.  “MS-DOS 5, No PC should be without it!  My name is “Bob” how I can help you!”    To entertain ourselves during the day we would make up fake names and accents when we answered the phone.  The guy sitting next to me was hilarious, he would do an entire call with a very deep southern accent.  He would answer the phone using this long drawn out southern hillbilly sounding accent, “M…S…..D-O-S ..FIVE…, No dang PC should go without it, this is Alligator, how the heck can I help ya!   He would keep it up for several calls in a row.  His hijinks encouraged us all to come up with our own characters.  You would never know who was going to use what character next, it was like a zoo at times.    It was fun having a job where you could have some laughs and goof off a bit.

About half the time the customers calling in had absolutely no clue why they needed or wanted this newfangled DOS 5.0 operating system.  Luckily, we had a script that had some basic features and selling points we could read to persuade these eager callers.   In those days memory constraints were a big deal with PCs.   PCs were not the awesome multifunction devices we think of today, where you can play games, socialize with friends, buy anything on earth etc. etc.  PCs were for serious stuff like watching a green blinking cursor and trying to figure out what bizarre command you could input to make the PC do something interesting.  There were, of course, some programs out there like Word Perfect, Lotus 123, and lots of different business apps for the PC, a big problem people had back in the early PC days was literally running out of RAM memory and the program you were using would just stop working.  So, DOS 5 had a memory saving feature, it also had an undelete feature for the first time, and was the first time that DOS was sold as an upgrade.   This dorky video was made for training salespeople and the retail sales channel.   Watch it for a good laugh…

Funny enough, none of us in this sales group actually had a PC at our desk and almost nobody really had a PC at home in those days.  So, we had pretty limited knowledge of what it was we were actually selling.   Microsoft did provide PC rooms where you could go and learn more about PC’s and the various programs.   That would prove to be very valuable to me as I would spend my break time and time after work playing around with the PC and with various programs, as I was naturally curious about how things worked and figured it would be useful for me to actually know what it was I was trying to sell.   I learned some pretty decent PC skills in those labs, and it turned out to be very valuable later on as my career started to blossom.

Oddly, none of us had PC’s at our workstations, PC’s were still very expensive, and networking them together in a meaningful way was just starting to take off.  So, while we were on the phones we used paper forms to fill out orders as they came in, and we read our sales scripts straight off of good old-fashioned paper.   At the end of the day, we would pile up all the orders we had taken and put them into a big bin, where somebody would plug them into a PC and I never knew what happened after that… To me, the day was done, there was no homework, no stress thinking about the next day, no worries, I just clocked out, and went home to have fun, play a game of tennis, or do something fun with friends.  There was no evening email to check, and there was no sense of things “piling” up at the office while you were away.  It was a nice way to live.  Even if I was still living like a poor college student.

The DOS 5 job was a short-term assignment, it lasted just a few months my first summer out of college.  I was offered a fulltime job at the end of that contract to work at Microsoft’s inside sales call center.  Incredibly and stupidly, I declined the offer, for two reasons.  First, I thought the work was pretty damn boring, so signing up to do inside sales of whatever the next version of DOS was going to have seemed like a great way to kill myself with boredom, even if it was relatively fun and easy, I could not imagine signing up for 2-3 years of that kind of work.  Second, I had another offer on the table for a couple thousand dollars more, and I wanted to buy a car!  Microsoft offered stock options, but I thought those things sounded like total bullshit!  J  In my idiotic view, I needed some cash now for a new ride!  So, I took a competing job at a small airplane parts manufacturer in South Seattle and proceeded to waste about 2 years of my life selling specialized plane tools to airplane manufactures and airline repair shops.    It was a bad move, of which there were others to follow…

Learning Lesson #1 – For those who are early in career – Always think long-term when making a job choice!   The best thing you can do is find an early stage growing dynamic company, start anywhere they will have you, & create your own luck by working hard & being at the right place at the right time.    For my part, I could have listened to the many people who gave me this same advice, but I first chose a less than mediocre company that was going nowhere so I could make a few extra bucks in the short term.  THAT WAS A DUMBASS MOVE!  And it probably cost me several hundred thousand dollars in lost opportunity and stock options!!  Uhgg!