Why I’m Leaving Microsoft

Why I’m Leaving Microsoft
19 Flares Twitter 8 Facebook 9 Google+ 2 LinkedIn 0 19 Flares ×

Looks like it’s about that time… after 7 years, I’m leaving Microsoft!  This may come as a shock to people who I’ve met over the years, so I’d like to give you all some insight.

This past year was a transformational year for me.  I had completed my responsibilities to launch the closest thing to a startup Microsoft had to offer.  My co-workers were leaving Microsoft in droves.  My product team was primarily based in Shanghai and, after the exodus, I was the only person left in Seattle.  Almost all of my closest friends had left the Seattle area.  My girlfriend and I broke up.  To top it all off, I was diagnosed with some random health issues.

In short: my very stable and predictable life had become incredibly uncertain and unfamiliar in a short amount of time.

Time to Reassess

This was a wakeup call.  I certainly had a lot of internal issues to work out.  I had been living by a set of implicit assumptions that I hadn’t questioned in a long time.  After much reflection, I listed them out and started reassessing them one-by-one.

Assumption: I want to live in Seattle

The unfamiliarity caused by all of these changes was surprisingly unsettling. For the first time in six years, nothing I did was status quo.  My Redmond teammates were gone.  I no longer had a guaranteed lunch crew or anybody to hang out with during the day.  Sure, there were hundreds of Microsofties in my building, but I couldn’t bounce ideas off of any of them during the day because none of them had the context of my project.  The Shanghai team wouldn’t be easily accessible until about 7pm.  I would leave the office and go home only to realize there was no girlfriend to invite over for dinner.  I had spent so much time with her for the previous one and a half years that I didn’t continue to cultivate friendships (amateur mistake). In turn, I lost touch with a lot of previously important people in my life and no longer had countless social options each night of the week.  I was effectively alone: I had no team; I had no girlfriend; I had very few friends.  It’s like I had just moved to Seattle but without the excitement and optimism fueling my desire to explore a new city.  I had battled the Seattle Freeze for years upon first moving here and was not looking forward to trying that again.

Do I want to live in Seattle? No

Assumption: I want to run a company some day

In my initial interviews with Microsoft back in 2004, they asked me what I wanted to do.  I told them I was happy to learn for now, but ultimately I wanted to run a company.  They refined their question and asked me what I wanted to do at Microsoft.  I said, “I want to run this company”.  I made a lot of people smile that day.

Do I still want to run a company some day? Yes

Assumption: I want to have a family some day

Do I still want a family some day? Yes

Is some day imminently close? No, but hopefully in the next 5 years

Assumption: Working at Microsoft is helping me achieve what’s important to me

I had been advised by a former Microsoft executive to live a principled life.  He suggested that I write down the four or five most important principles and use those as the compass to guide my life.  I took the assumptions from above and distilled them into what’s important.  Here are three of them:

Long-term wealth potential

I was raised as a very risk-averse person so financial security has always been important to me.  Getting a job at a big stable company was the end goal.

Just accepted my Microsoft offer in 2005

Me and my parents after accepting my Microsoft offer in 2005. I spent my entire signing bonus on that jacket. #WorthIt

Though, the more I thought about it, the more I realized that I shouldn’t care about money now because I have no need to spend a lot of money now.  I don’t live an extravagant lifestyle.  I have no wife, no kids, no home, no debt.  Aside from rent, food, and the occasional trip I don’t need much money now.  I have a rainy day fund and can live ~12 months on cash savings.

What I should care about is long-term wealth potential and the freedom associated with not having to work.  I like to work (read: I like having interesting things to do that most people would consider work).  I am someone who never plans on fully retiring because I will be bored out of my mind.  I see retirement as the freedom to work on my terms.  Even though I made more money at Microsoft than my family ever had growing up, I would still have to work for decades to provide for my future family and save enough for a comfortable “retirement” where I could finally work on whatever I want indefinitely.

Learn skills that will be relevant for the next 15 years

When I started a software business when I was 15, I knew nothing.  I just assumed that every problem was solvable and that I would learn whatever was necessary to solve it along the way.  After working at Microsoft as a Program Manager, I stopped building things on my own and started relying on developers to make the call of what’s possible and how something can be done.  I also had to rely on marketing teams to come up with business models and go-to-market campaigns.  I had an influence in what was going on, but I wasn’t really doing any of it myself.

Over the last year, I realized that I like building stuff without anybody telling me no. It would only be limited by my passion and conviction.  I built a bunch of random stuff to see what I could do. I built a Facebook data scraper/analytics engine, a mobile phone game, a Sad Trombone site (I know you want to invest in me now).  I did some SEO, analytics, and conversion funnel consulting gigs.  With each item I built, I renewed my excitement for software.

I was shocked that I was able to leverage a foundation of skills and knowledge that I had taught myself when I was 15.  Looking forward, I want to be very cognizant of where I’m spending my time.  What I choose to immerse myself in for the next 2-3 years, I expect to be transferable or relevant 15 years from now.  The more I talk to startups, the more I worry that the longer I spend at Microsoft, the less relevant I will be for anything outside of Microsoft.  Also, by leaving the company, I will grow and gain perspectives that I would have been shielded from for another 5-10 years.  On top of that, should I choose to return to Microsoft, I would have learned and grown far more on my own that I would be even more valuable to the company than if I had never left.

Great people

This has been a huge learning for me, but it’s obvious at the same time.  It’s not necessarily about what I build, it’s about who I build it with.  I need to be around people I trust.  I am far more engaged when I’m around people who I have fun with and can learn from.  I have worked on some interesting projects with not so interesting people and it was a chore.  I have also worked on some not-so-interesting projects with interesting people and it became fun and I learned about topics that I had previously not cared about.

The challenge at Microsoft is getting a uniformly good experience.  Microsoft is a huge company and there are certainly some great people and (to channel Steve Jobs) some bozos.  There are good people, who have great potential, but aren’t applying themselves and are unmotivated to go the extra mile.  There is a lot of “us vs. them” mentality where people care about covering their own ass instead of doing the right thing to get the project out the door.  C’mon guys, we’re all on the same team!  For these reasons and many more, a lot of people at Microsoft don’t tap into their greatness and produce garbage.  I, too, have lowered my quality bar for what is acceptable from software.  My new mentality is to experiment quickly and do fewer things, better.

So is working at Microsoft helping me achieve what’s important to me? Yes and no. I certainly can give each of these areas partial credit, but I would be hard-pressed to say that Microsoft is the BEST place to achieve what’s important to me.

What’s Next?

I must push myself to pursue a startup now.  There’s significant time-pressure.  Never again in my life will I have the risk-profile that I have now.  I have no wife, no kids, no home, no debt.  I am healthy and nothing is holding me back from pursuing a startup aside from being risk-averse and my fear of trying something and failing.  If I were ever in the position to be able to recover from failure, now would be the time.  Each month that goes by, I will be closer to having a wife and kids.  And, unless I marry a sugar mama, that means I need to take a risk now or I’ll be guaranteed to have to work for decades just because I never tried.

I’ve had a great time at Microsoft over the last seven years, but I will be moving to L.A. to cofound Mythly with one of my best friends.  We’re not releasing many details at the moment, but if you go to our signup page and put in your email address, we’ll email you when we have something to show.  We are a couple months away from releasing some early experiments and would love your feedback.

Thank you all for making my time at Microsoft so memorable.

[If you've read this far, thank you... and you should probably follow me on Twitter: @PaulMest.]

19 Flares Twitter 8 Facebook 9 Google+ 2 LinkedIn 0 19 Flares ×

About Paul Mestemaker

Paul Mestemaker is a former full stack engineer and now Product guy based in San Francisco. He helps startups launch their MVPs and gather feedback through usability tests and live site metrics. In his former life, Paul was a co-founder of Mythly Studios and System Center Advisor. He co-authored a book on SQL Server performance tuning. He has been rated as a top speaker at conferences (TechEd, PASS, Connections, et al). He is also a guest lecturer at Colleges and Universities across the U.S. He was the co-host of a weekly tech news show with over 6 million views. Paul's proudest accomplishments is unlocking the "World Champ" achievement on Wordament.

28 Comments


  • Good, honest post. Things are not this clear to most people. I think you will do something significant. Would love to hear about it.

    Reply

  • I wish you and your business partner all the success…and definitely would like to stay abreast of your success. You may have felt that most of your friends left Seattle, but there are still plenty of us remaining–you’ll be missed man! K-

    Reply

  • I really like your style Paul. And you leave an impact on those you have spent any amount of time with. Thanks for the opportunity to follow along on your adventure and see what’s next.

    Reply

  • you just made your table tennis training partner really happy ;)

    Reply

  • Proud of ya cuz. It takes guts to take the next steps in life, scary and unpredictble as they may be at times. Now I’m keeping my fingers crossed that your handsome mug will show up at my wedding next may :) love ya.

    Reply

  • Wow! Huge decision…time to do it! I know you will succeed…it’s what you do.
    I couldn”t be prouder. Love and good luck with your new life chapter.

    Reply

  • Life is a journey and you are about to embark on a new adventure that I hope will be exciting, challenging, successful, and just as important FUN!

    Reply

  • Good luck, Paul :) Stay Positive and Positivity will find you <3

    Reply

  • Paul, you have certainly given this much thought and have done nothing in haste. I think you are absolutely right…that this is the best time to make a major move such as you describe. I have no doubt that you will be successful and happy! Good luck and lots of love!

    Reply

  • Good luck Paul! It is good to see that people with the same risk aversion as me still dare to take bold steps.

    Reply

  • Good Luck Paul and glad to have met and partied a little with you. Cheers mate!

    Reply

  • Your honest words made me think… Thank you!

    Reply

  • Very inspiring post. I was/am feeling very similar to you with slightly different inputs. I am going for it too.

    Reply

  • Good luck Paul. Ping won’t be the same! I’m looking forward to seeing Mythly!

    Reply

  • Good for you, Paul! You were the one who helped me realize my dream of working at Microsoft was possible, and then helped to make it happen. It was great and I wouldn’t trade it, but I too left to pursue goals similar to yours, and am learning a ton. Thanks for your generosity toward me, and congrats for continuing to dream big! Cheers, Scott

    Reply

  • Well done Paul, you certainly answered the only question I asked about that product and its really good to see people like you motivated to go forth and maketh. Power to your elbow, the world needs start-ups and start-ups need good people.

    - Ronnie

    Reply

  • When will your startup start?

    Reply

    • @Pit: We’re in startup mode now. Not sure when we’ll have something to show. We have shown our prototypes to ~150 people. I imagine that we will solidify a few partnerships to get the ball rolling in the next month. Though, I think it will be a while before we have a scalable product. I look forward to blogging here about it. Stay tuned!


  • Made me think about my own priorities a bit – excellent post. Thank you. BTW, I am also in the LA area, whereabouts are you?

    Reply

    • @Swanand: We’re in downtown L.A.


  • Good for you, Paul! I hope it works out great.

    Reply

  • Excellent post and certainly commend your spirit. Will be missed at Ping

    Reply

  • Excellent post and all the best.

    Reply

  • Where is the like button for this post? It needs one. :)

    Reply

    • Glad you liked the post. There should be a like button at the top of the page. Let me know if it doesn’t work for you!


  • Hey Paul — great post. Very thoughtful.

    Although you say you’ve grown up financially risk-averse, you’ve taken a bold step by becoming an entrepreneur.

    It’ll be cool to see how it pans out. Looking fwd to keeping in touch as things move fwd!

    Reply

    • Thanks, Aki! Let me know next time you’re on the west coast.


  • [...] wrote a whole post on leaving Microsoft.  The gist of it is that I enjoyed what I was doing, but now was the time for me to try to go out [...]

    Reply

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>

19 Flares Twitter 8 Facebook 9 Google+ 2 LinkedIn 0 19 Flares ×