Roads less travelled, the pain involved & the reasons to persevere #gov20 #opengov #wiunion

The Road Less Travelled in Worth It!

With my wife, I am constantly trying to raise two daughters to be prepared for life in a sometimes turbulent world. The daily conversations are primarily mundane (Spongebob or Disney), but from time to time, more often lately, the topics turn to deeper philosophy and how to best orient them to be able to not just survive, but thrive.

This weekend, they piled in our car and arrived at a public protest in support of our friends and family in Wisconsin who fight for their right to collectively bargain. It is understatement to say that this is a difficult concept to communicate to a five year old, but she got it. And in doing so, she made me realize some very important things about myself and why I fight so hard for things like revolutionizing the use of technology in government and protecting the rights of workers.

You see, I have put my daughters on a road, and they have accepted the manifest journey, less travelled. It always sounded romantic to me as a youth and going through University. The road less travelled apparently casts you as the hero, clearly with all the fanfare and glory associated with it, at least when we talk about it at the age of 18. But at 40, the reality of that road less travelled is obvious. Less travelled mean filled with thorns and distractions, the first cuts may make you feel brave, but the hundreds that pile up after 20+ years of travel make you wonder about your sanity. The scars make you wonder if you were selfish in forcing your family down this route, the pain you see as your friends travel along side you make you concerned for their well being as well.

And when you look into the eyes of your 11 and 5 year old daughters, you wonder aloud whether it is your job now to protect them from the pain of a contemplative life or is it your duty to challenge them to always question common wisdom, constantly question authority and never stop asking “why not”.

A bit of background. While I am most recently a corporate executive (most recently at Microsoft and Salesforce.com) and a trained lawyer (educated at the University of Wisconsin Law School), that was most certainly not the road laid out before me as a child. I was born in the great city of Milwaukee and had solidly working class parents. My father was first a construction worker (Sheet Metal) and eventually worked his way up through the Sheet Metal Workers International Association to work for the Union full time. My mother was a registered nurse for years in West Allis, Wisconsin, where she worked the night shift from 3PM to 11PM every day, to ensure my brother and I could have food, housing and healthcare. It was expected in my neighborhood that you would be raised and grow up to work hard for a living in plants, mills and factories. It was not heard of to go to college, much less law school. My mother and father taught me, there was nothing I couldn’t do, if I worked hard and stayed committed to my principles. I believed them.

I worked my way through Marquette University (three jobs @ IBM, Congressman Jerry Kleczka’s office and running student government) and found a way to get into and pay for Law School @ the University of Wisconsin. My father and I had heated discussion about this road less travelled as it would be hard to explain to his union friends why I couldn’t get a real job. The negotiated settlement was that I would become a Labor Lawyer which I did. I became a named partner quickly in Milwaukee, representing AFSCME and SEIU. Eventually I became the political director for SEIU and eventually branched off to another road less travelled, I started my own business. I challenged the recording industry to embrace digital music in the days of Napster and the RIAA. It was an incredible fight and one I cherish. This experience, coupled with my political work led to a call from the Governor of Wisconsin (the old one not the current one) to become his Chief Information Officer (eventually I also took on the Presidency of the National Association of State CIOs). Those years were some of the most memorable in my life, filled with pitched battles and conflict and resulting in stronger employees, leaders and support staff.

I was honored to be invited to work as an executive at Microsoft after that, talking with global political and civil servant leaders throughout the world. Travelling to China, Singapore, Australia, London, Barcelona, Dublin, Belfast, Berlin, Mexico and more to preach about the power of technology in government. My work at Salesforce is still being settled but I am certain that it will be exhilarating and enlightening and will continue to blaze down the road less travelled.

Revolution, challenge and less travelled roads are not just part of me, it is, in fact, who I am.

But it is no longer the romantic version, it is the very real version. I not only have scars to prove the battles, but open wounds. My wife and I have had conversations about whether it ever gets easier. The travel has been difficult and at times downright terrifying. The battles have sometimes been respectful and at times have certainly and patently been unfair. The wounds have been deep and the tears have taken tolls. To say it has been hard would be an understatement.

And when my daughters looked up at me this weekend, to see why we fight, after much reflection, I let them know they should proudly stand and fight. I know it will be difficult and put them on a more challenging footing. I know they will cry more than I would like and feel like they are sometimes very alone. But, when I look back on a life of challenge, from a position of current trepidation, and I ask myself if I would live that life again…I can only say, yes. And I pray that my children accept the challenge openly and embrace the road less travelled as one filled with true honor. I pray the same for citizens throughout the world, yearning for their own better world.

You see, my friends in Wisconsin proved the effort is worth it. My friends in Bahrain and Egypt have proved the effort worth it. MLK, Gandhi, Mandela all proved incredible sacrifice worthwhile. My friends at Apple who successfully changed the face of music proved it worthwhile. My friends at RedHat who have helped power an Internet that has helped to fuel active dissent and freedom in dark places throughout the world have proved it. The champions of true cloud computing are on the cusp of proving it each and every day. Amazon took on publishing, Apple took on music, Egypt took on power, Vivek Kundra took on the status quo in the USA, John Suffolk took on data-centers in the UK, Jeremy Godfrey took on paper based government in China, Chris Vein took on proprietary software in San Francisco, Lt. Governor Gavin Newsom took on Government 1.0 and pushed us to 2.0 in California. George Meany took on Industry, Ceaser Chavez took on migrant workers travails, Andy Stern challenged the dominant paradigm. Marc Benioff took on everyone.

All of them have the scars of a road less travelled. All of them have spent nights wondering. As will all of you reading this. And I hope this small bit of writing will help convince you, and my beautiful girls, to travel the unmarked road, to fight through the resistance to change, to shoulder the challenge of impossible missions and to fight on through the pain because regular people, somewhere in the world, depend upon you doing so.

Fight. It matters.