Working for someone else

This week marks two full years of my employment at Automattic. I was fortunate to celebrate in person with a number of my colleagues as we hosted a workshop for our clients and partners in beautiful Napa, California.

People who know that I co-founded and built my own tech business before joining Automattic often ask me what it's like to work for someone else. My short answer is usually:

  • I miss some of the joys and challenges that go with being ultimately responsible for the success of a business venture...
  • ...but Automattic is a place where I am trusted with a level of autonomy that I'd be hard pressed to find in many other employment situations, and
  • I am mostly just enjoying discovering new ways of doing things and being a part of a bigger team with greater resources available for innovation.

This post is my longer answer. While working at another company it has been useful and interesting to notice what it's like to have a change in my professional identity, not be "the boss," enthusiastically support something I didn't create, and try to balance the joys of "employment" with the inner itch to again be a "founder."

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The Trump we asked for

As an Indiana resident and voter, it's tempting to be embarrassed at the headlines of "Trump wins Indiana" blanketing the national news today. Indeed, I find almost everything about his candidacy, personality and public statements to be deeply problematic on numerous levels. But Mr. Trump's success in the primary and his win here in Indiana are just more symptoms of a brokenness in U.S. politics that goes far beyond this state or this election year.

When I was growing up, a career in politics mostly seemed like something boring, unglamorous and yet perhaps ultimately noble that certain kinds of people would necessarily take on in service of their town, state or country. Many kids wanted "to be President some day," but most would redirect their attention to other more practical and personally rewarding pursuits when they realized the amount of mundane policy details they'd have to immerse themselves in, or the long road of statespersonship that only just began with a law degree or military service. In this way the bar was set somewhat high for entering a life in politics, and while somewhat contrary to the promise that anyone with a good idea can make a difference in a government of the people, maybe in some ways it was a good thing.

As the lapel pin-wearing political class has emerged, the idea of just anyone being able to make a difference in politics seems more myth than anything. In a country of hundreds of millions of people, the same small circles of people are held up as the only realistic candidates. If you're not willing to amass gobs of money (or friends with gobs they can share), compromise your values and public persona to fit with the room you're in, make promises you can't keep and bow to the primacy of the so-called military-industrial complex, it's unlikely that you can succeed as a politician. Those of us who have in the past held out hope for a candidateperson who can transcend those constraints to restore a principled, dignified approach to government leadership have now mostly learned to know better.

So if we can't relate to or become a part of the political class, we at least expect them to entertain us. Between the 24-hour cable network rehashing of Every Little Unimportant Detail, tell-all insider memoirs, the salacious political affairs and scandals of the last two decades and the fear-mongering around U.S. national security, our appetite for political theater that distracts us from any substantive discussion of issues or outcomes has grown each year. Congressional gridlock, court decisions around corporations as people and money as free speech, and a media generally unwilling or unable to do anything other than chase the story of the day means the founding structures of U.S. government that once required a boring but otherwise accountable and productive national conversation have been all but undone.

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