Today, 9/9/09, is my 35th birthday. Some thoughts:

Twitter pushes “less is more” (a principle I usually agree with) way past the point of absurdity and is adored by lots of smart people.

Wired asks “Why Craigslist Is Such a Mess” and concludes “the public is a motherfucker” (their word choice!).

You can’t make sense of the world as rational place. Public discourse is mostly righteous indignation masking self-interest or fear of change, not reasoned debate.

You can only see the edges. Facebook and Youtube show us how things really are. A Youtube video going viral on network news does not, however.

The world is big. Really big. It used to seem smaller, through an accident of history, when, in the 20th century, the flow of limited petroleum temporarily exceeded the infinite flow of information. You will never know most people. You will never go most places.

The “tip of the iceberg” is a bad metaphor. A better truth may be that 80% of reality is nothing like the 20% you see. If almost everyone you know is doing or thinking something, 99.9999% of the world quite possibly isn’t.

There are ambivalent choices. There is not one right answer. But you have to pick!

At a small company someone is the guru and he reads or listens to the industry guru and you think you have mastered your craft, that you know the right way to do it. Then I went to a large, heterogeneous organization and had to relearn: there is always another way to do it. I thought I knew that, but there are so many completely different ways to do it. If I thought the debate was between C# vs. Java, it was really between C# and Java vs. things you’ve never heard of.

If there are eight levels of programmers (of course not really) I am somewhere in the middle: I have a good job; I do important but not sexy work. I could get another job with my skills, but maybe not a better job right now. 50% of software developers don’t want to be managers—which leaves the remaining 50% of us hoping we are the 1% that gets to be CTO some day. In the meantime, how do you stay ambitious while staying where you’re at?

Which brings me back to the first point, which is a paradox. My job is to bring order to things, to make them not broken and behave in predictable ways. But engineer things too well, and they don’t work, either. Adam Bosworth says it better than me: “It is an ironic truth that those who seek to create systems which most assume the perfectibility of humans end up building the systems which are most soul destroying and most rigid…. Conversely, those systems which best take into account the complex, frail, brilliance of human nature and build in flexibility, checks and balances, and tolerance tend to survive beyond all hopes.”

I’d like to think there are connections in the above, but it’s a human trait to see patterns where none exists – the “Triumph of the Random.”

Also, Hannah starts kindergarten today. I remember liking kindergarten at Laurel School. It’s a new feeling to be a parent when I can remember my being my child’s age myself. Good luck, Hannah!

*In Douglas Adams’ The Hitchhiker’s Guide to the Galaxy the “Answer to the Ultimate Question of Life, the Universe, and Everything” is 42. That is also my house number and significant street in New York, but now I’m really seeing patterns…

Here is my recurring nightmare version of the American Dream:

1. Have an idea for the next .com, Web 2.0, etc. success story.

2. Decide I need to leave my job and start my own company to develop the idea properly.

3. Hire Cheryl on to manage the business.

4. The company grows successfully yet organically, remains a small family-friendly concern, and we are able to offer our employees health insurance.

5. One of our employees, or worse, someone in the family gets cancer, it metastasizes and requires intensive chemotherapy.

6. Our insurance company, directly through rescission or effectively by raising our rates, drops our coverage.

7. I die homeless wandering the streets of Boston.

At step 3 I am taking on extra risk by putting all the family’s financial eggs in one basket (but that’s why it’s a dream). And thankfully, things could turn out better in Massachusetts thanks to an individual mandate and non-profit institutions committed to their mission (but it’s a nightmare, too). Admittedly, I might never start my own company, but small companies like this really do exist–I’ve worked for a couple of them before my current large-organization job.

Republicans say health care reform is bad for small business. But doesn’t the current system penalize small businesses that actually provide health benefits?

Don’t we get insurance to protect against just this sort of bad luck in the first place? How can anyone (unless they’re on Medicare, and selfishly care for no one but themselves) not wish for change–and not expect their representatives to be working constructively toward it?