Why I left Microsoft

By Scott Berkun, May 2005

My reasons for leaving Microsoft were the opposite of why I went to work there. I arrived at Microsoft a scared kid just out of college. I was desperate to start my life, and get out of debt. During my senior year I interviewed with every software company I could find and was rejected by every one. When graduation came, I had nowhere to go so I moved into my girlfriend’s apartment. My friends left for new cities and the start of their adult lives or swallowed more of their pride than I could, and moved back in with the parents. Soon my girlfriend left for the summer, studying half a planet away in Australia. My only companion was my dog Butch. We lived cheap together: ramen noodles and dog bones. I paid the bills writing chapters for technical books, and essays for magazines. At night I’d escape by poking at a novel that would never see the light of day.

Oakland/PittsburghFor years I’d been following the plan given to me: go to high school, go to college, get a job. From day one of kindergarten onward there was always a next step waiting. The choices were easy and safe: which classes, which activities, which universities. But an hour after my college graduation, sitting alone in an empty apartment on Beeler street in Pittsburgh, there were no more choices laid out for me. I confronted my future as a kind of void for the first time and was terrified. I’d never understood that emptiness, despite seeing its effect on older friends and my older brother. Until I was sitting alone surrounded by it, without the defense of a plan or a friend, I had no idea how frightening it was.

So that July, when I was invited to Seattle for a second chance at Microsoft (I’d been rejected the first time), it was a godsend. No one else was calling. The night before my interview, too nervous to sleep, I drove my rented Geo Metro all over Seattle. The long stretches of tall pine trees and the wide clean streets looked to me, a boy raised in Queens, like a foreign country. Everything in Seattle was neat and safe, and so quiet. I drove slowly through the night, afraid of getting in trouble just for being there. Before heading to my hotel, I went to the Microsoft campus, a long stretch of 3 story buildings on shallow green hills, laid out between forests and sports fields. I stopped by one of the basketball courts and stepped out of the car, taking it in. I doubted I’d ever see that place again.

ID photo, taken 9/94After a year at Microsoft, around 1995, I became a program manager on the Internet Explorer web browser project. I was paid well to lead smart people in the making of software used by millions of people. Some of the dreams I had as a computer science student, the idea of designing something many people would use, had come true. Before I knew it I was in my mid-twenties, was promoted to a team leader, and was rewarded for being as smart and creative as I could be. Soon I managed others, and years later would have the role of teaching other teams of engineers what I’d learned.

But when my ten year mark at Microsoft wasn’t far away, I felt the return of the emptiness I’d felt on graduation day. This time the void wasn’t about what was outside me, it was about what was going on inside. I questioned what I was doing with my time on the planet. Dreams of my college years had been fulfilled, and if I didn’t make big changes soon, I knew I’d be repeating myself.

There were other challenges I wanted and I feared spending my life like a sad, confused bird of prey, circling the same territory over and over again, never understanding why there was nothing new to find. I needed a new situation to jump into and despite what my managers and peers said, I knew I couldn’t do that while working in the same place. I had to move on. I was surprised to find that even though I was ten years older, my fears about the big unknowns were just as scary as before. But when I measured my fears about staying, I found they were stronger than those about leaving, so I left.

David's photo from my last lecture as a Microsoft employeeSo I chose to leave Microsoft less for reasons of escaping a particular place or group of people, but more to seek out a new set of circumstances to live in. Just like I sought out Microsoft to escape my fears of the post-college emptiness, I looked to leave Microsoft to create not a void, but a new space to grow in. One of my own choosing. I ran to Microsoft to escape my fears of failure. I left Microsoft to define my own idea of success. I pulled out the beaten up novel, and the half written essays, and planned a life around writing, the deepest, scariest, truest dream I had. How long I’ll last, I don’t know. Success with a writing life, even on my own terms, is harder to come by than with software. But its been over a year now and I haven’t looked back.

46 Responses to “Why I left Microsoft”

  1. Ali

    i just read the myths of innovation. you have done a awsome jobs. this is now one of the best book i ever read
    keep up the good work

  2. Niko

    Great essay! Your books are ones of my favorites… can’t wait for a new one.

  3. claymm

    You lived in Seattle for 10 years without learning the difference between pine and cedar and Douglas-fir. Them trees ain’t pines.

  4. Mackenzie

    Hello Scott :)

    Sorry I do not know much about your previous blog posts. This one caught my attention through Twitter.

    As a 15 year old Sydney school student heading into grade 10 this in the coming few weeks I have decided that when I leave school I want to move to Seattle and work for Microsoft. I m not sure what position I want inside the company though.

    My question is, what is Microsoft like to work for? Do you think that the company has a long future ahead of it and would you work for them again? Also anything else useful you can think of :)

    You are probably thinking ‘Why is a 15 year old boy thinking about what he wants to do hen he leaves school? He should be out with friends!’ I am really passionate about the future of technology, epically the future of the Windows operating system and I want to be a apart of it.

    If you are unable to answer these questions that is fine, I just thought I would try.

    Thank you for your time,


    1. Shiggity

      I think he’d probably tell you you’re missing the point

  5. Scott Barstow

    Scott —

    I have just stumbled onto your blog via YCombinator Twitter feed. I really enjoyed this article, and it hits very close to my personal position at this time.

    I have spent a lot of time thinking about why I made the decisions I made in the past regarding career, and they were very much along the lines of what you articulated here. It was the expected thing to do, for the most part.

    Even though your post is 5 years old, it was really timely for me personally.

  6. Omkar dash

    Very Very moved by this piece of writing. Bookmarked you! I can related myself, somehow.

    A Fresh engineering graduate who just started working at Asia’s largest IT company.
    Twitter: @OmkarDash

  7. Omkar dash

    Very Very moved by this piece of writing. Bookmarked you! I can relate myself, somehow.

    A Fresh engineering graduate who just started working at Asia’s largest IT company.
    Twitter: @OmkarDash

    1. Scott Berkun

      To Shadow14l: Interesting. I’ve actually never been fired. I suppose that has more to do with the good fortune of never working for a company that was falling apart, or for managers who were unfair, but every single job I’ve left in my life, so far, was by choice.

  8. Eddi Hughes

    I feel inspired to look down the path of the future.

    The last part about taking on writing reminded me of Californication.

  9. Maintenance Man

    This seems strange. I thought it was very hard for developers to get a job at Microsoft. To think that they were the only one who offered you a job back then.

    As an aside, did you make any money off Microsoft stock options. I know their stock has been stagnant recently. But if you had some old options priced low…

  10. Stephen Lloyd Webber

    Way to go. I’m a similar kind of guy. Goodbye to the University – hello to living in Italy and teaching online!

  11. Pankaj

    hi scott,
    nice explanation of the various phases of life & inspirational too that u had gone through. I just wish and pray that you scale new heights while doing something new and creational in your life.
    Your New Friend.

  12. Scott Berkun

    Sachin: No. Although I would like to write a book about my time at Microsoft, I doubt I’d make it fictional.

  13. Sachit Gupta

    Scott, really like this post. About to graduate from college, this is exactly how I feel.

  14. Leann

    Love it! That’s why I left Microsoft ;-) Good for you for living with courage and conviction (even when it was scary) and thanks for your MS contributions!

  15. Mita


    Reading this today, seven days before I am going for most probably the most important interview of my life, gives me great hope and comfort.

    Its nice to read about your amazing journey, your courage to write about your feelings, and for being able to leave a place like MS for chasing your dream…

    Great work and I know you are a survivor, so all is well…

    – Mita –

  16. Doug Thomas

    I have no doubt you will find that “success” isn’t what you seek, but when you find it- whatever “it” is for you- you will know it, and you will smile! For me it was retiring over a year before I turned 62, using after tax funds to pay for the first year and a third of a frugal but satisfying life of blogging, volunteering in my community, and rescuing a pound cat I call Louie. I type this as I smile. “It” for me was removing myself from the poisoned world of office politics and change programs that each promised to be am improvement over the one before. Yeah.

  17. vivek

    Great! There is always two kind of voices one come from heart and another come from mind. When you passed out of college you listened your mind but at last by leaving Microsoft you listened to your heart, and that gives us peace.

  18. Deepak Surti

    Hi Scott,

    I would love to know 2 things:

    Why were you rejected by every software company that you interviewed for?

    Why were you accepted the second time while being rejected
    the first time @ Microsoft?

    I am an avid reader of yours and Paul Graham’s essays. The simplicity and honesty in your writing always strike a chord.

    Thanks for all the great fun I have while reading your essays.

  19. doh

    you actually scanned your badge? lol, funny. i only worked as a blue badge for 4 years and like a yellow badge for 2 before that. i left for less eloquent reasons. i was planning to stay for at least 10 years but didn’t make it that far for no fault of my own. left the state and everything. i was in the Army and ETS’d from Ft Lewis eventually making my way to MS Redmond at the bequest of another. lived in WA for a total of 10 years. i really wish i would have scanned my badge now that i think of it. i did find an old cisco script of mine stuffed way down in my duffle bag several years after leaving. it was actually used in a production Internet facing network, and i was in awe as i reviewed my work that i had done for the big MS. i cracked that cd like a{n} USAF bird crash landing in N.Korea. i forgot i had it. anyhoot, cheers! and i guess you wrote a book, will go hunt for it. – former fellow employee

  20. jason

    After reading this it seems crazy that you would leave your job, but such are the luxuries of living in the land of opportunity. I’m Irish, living in Ireland and I spend my days currently watching a once proud nation hobble aboard the train of economic uncertainty bound for jobs that promise no definite future. I am unemployed, with a family and 2 kids to look after. I have started writing, it gives me strength. I admire your drive and strength. it has worked for you I know it will for me. Best wishes for the future.


  21. Julianna

    Thanks for your post, although written 6 years ago, but it is very relevant for me at the moment. I am about to graduate business school, and is accepted into law school… the natural thing to do would be to go to law school. But, I’m not sure about that anymore. I never wanted to become a lawyer, neither am I interested to spend 3 years in law school trying to just get the “legal background” for business. I want to work in the business field. In fact, I don’t understand why I studied for the LSAT, apply for law school in the first place. Well… if I am being completely honest with myself, I think I know why… it’s because at the time I was both scared to the “real world”, scared to start a career, plus law school would be a prestigious thing to have. If not law school, my alternatives would be to look for a job or teach English in France for one year, to discover a new country, earn money and improve my French. While many people I know are doing finance, consulting, accounting, you know, one of those professional careers… should I really be teaching English? I know I have to let go of my ego on this one… but somehow it’s just really hard.

    The truth is all of these options seem interesting and promising… but the thing is that I don’t know what will come out of them… if I take option A, where will I end up in 10 years?… That factor of uncertainty about each option is essentially what is stopping me from making a decision. It’s been a month and half since I have felt this way… I used to be very happy person, who smiles and laughs a lot. But these days, nothing seems to cheer me up.

    With school, if you put in hard work, you know exactly what you will get out of it. But with career… no matter which option you pick, you just NEVER know where you will end up. I think I might start contacting some organizations in France to see if I can teach English there for one year and just take a year off from school, career and everything else that a new grad is “suppose” to do.

    Actually I’m still feeling incredibly lost. If anyone has any suggestions, I’d really appreciate it.

  22. Tamara Gerber

    Dear Scott,

    Your story pauses at the basketball court on Microsoft Campus. Not a word about your interview, what you did better the second time around,…

    I realize it is an old essay and you probably don’t want to go back there. Just curious.

    Did I mention I work in HR ;-)

  23. Anitha

    This is such an inspiring article. Good one!

  24. sanousy

    God! a similar story happened with me … with huge companies too …

    let me rephrase it … all success I did … I left behind for them! and finally I discovered that they used me …

    in the same time … I could not do anything alone!

    Now … although I do not find a job at the most of the time … but I feel none trying to control my life …

    I think you made the right choice … for now I tried several times and several ideas to work alone … but I feel they’ve stolen my potential to do anything!

    Being so dynamic and creative means others with “static” ideas to control your way of thinking …

    after 17 years of work … I found myself just like a horse running in the horse racing lane for the sake of my owners!

    so I decided to break the lane fence and go to the wild..

    Currently I am happier ( may be less money, if >=0 only :P) but I believe that still I have a chance to live as a simple human instead of creative robot!!

  25. Zorba

    What ever you do, do not go work for Microsoft. I was there for many years they DO NOT STAND behind their values. Putting together a blog about the experiance there in hope it will help others make the right choice.

    1. Scott

      I play guitar badly, but I love it. In that photo I sang a song about being a PM at the end of my last presentation at Microsoft.

  26. kannan

    What is so romantic about leaving a highly respected technical job for writing self-help books and giving boring lectures that one can anyway figure out by himself if he thinks enough? As said in the movie ‘School for scounderels’ an idiot cannot help himself by reading a self-help book, because he is an idiot.

  27. wicked

    I feel inspired to look down the path of the future.



  1. […] My story with software is simpler. I was smart. My dad got us a computer when I was 12 or 13. I liked it and it made sense to me so I’d be on it hours every day. I majored in Computer Science because I found it interesting and it made sense. I liked designing things, and got very lucky – I got hired at Microsoft to lead teams and design stuff.

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