Junto Convenes on The Good Life: The Pursuit of Happiness in Silicon Valley

Two days, two provocative lunches as part of the Silicon Valley Junto Q2 conversations in San Francisco and Palo Alto on The Good Life: The Pursuit of Happiness in Silicon Valley.

Check out the notes from the meeting. Tim Taylor blogs the lunch, too. "Man’s mind stretched to a new idea never goes back to its original dimensions," Oliver Wendell Holmes once said. That’s what I’m feeling right now.

Coming out of the conversations I feel reinvigorated to lead, to live, and to pursue happiness with a vigor unaffected by the ultimate outcome. It is, after all, about the pursuit. It is, I would argue, the most important pursuit of all.

This I Believe: Life, Liberty, and the Pursuit of Happiness

NPR has a great series called This I Believe where people — famous and not famous — write and read essays about their personal convictions. It’s moving, it’s inspiring.

Andrew Sullivan, the public intellectual whose blog I read for its ceaseless intelligent commentary, has a truly wonderful "This I Believe" essay. Listen to the audio for full effect (British accent) and then read it in text and parse his words carefully. I love it.

When I have time I will try to record my own This I Believe piece.

Book Review: Consider the Lobster by David Foster Wallace

From time to time I wrote formal book reviews on works I particularly like. Previous formal book reviews have been on affirmative action, national security, the CIA and Afghanistan, and atheism. This review is on Consider the Lobster (And Other Essays) by David Foster Wallace. Thanks to Jesse Berrett for reading a draft of this.

It’s always been about David Foster Wallace. From his three-part name to his anything-but-New York-intellectual author photo, his authorial presence looms large. Consider the Lobster is no departure from what’s worked in the past for Wallace: essays, on everything under the sun, that can only be described as brilliantly hilarious, in part because of Wallace’s self-consciousness. An essay about Senator John McCain is as much about a failed presidential run as it is about Wallace’s first foray into political journalism. An essay about English grammar subsumes the ivory-tower debates on bias in dictionaries in favor of Wallace’s own travails teaching writing to college students. And then there’s the trademark Wallace deep immersion: he goes somewhere mildly interesting (in this collection, a lobster festival) and somehow captures a rainbow of details, described with such vigor and thoroughness that the only thing we’re convinced of by the end is that only David Foster Wallace could stuff so many random moments with such perfect adjectives.

Wallace’s trademark footnotes and sub-footnotes are here, partly to add accompanying information, partly to reflect Wallace’s racing mind, and predominantly to twist the conventional relationship between body and notes: many of the gems – when he reflects on the adult video conference and its effects on young women, for example – lie in at the bottom of the page. A reader usually can choose whether or not to pursue a point more deeply in the footnote, but with Wallace you have no choice. Skip footnotes at your own risk.

Some of Wallace’s essays run awfully long. “Big Red Son,” on the video porn conference, is extremely tiring by the last page. The quirkiness which makes Wallace so fun to read can also be crippling; at points you say “enough, already” and plea for linear assertions. Wallace proves elsewhere he can find the balance. “How Tracy Austin Broke My Heart” packs just the right amount of personal interjection with hard interpretation to provide insight about why we buy dull sports memoirs even though once-famous athletes let us down time after time with banal prose.

So Wallace succeeds when he complicates the environment he finds himself in just enough. When he tips this balance, though – for example, his random and unrelated interpolation explaining his view on abortion – Wallace becomes too self-interested, too amused at his own wondrous ability to be entertaining and mostly right.

By the end of this collection, I craved one last essay: a deeply immersed profile of David Foster Wallace himself. We are convinced of his larger than average personality and brain, and naturally have some questions: What is he like? How does he do his reporting? How does it feel to be him? There are no easy answers mainly because Wallace plays hard-to-get in the press. He did no interviews for this book. He lives an elusive life in Claremont, CA where he teaches part-time at Pomona College. There is a sense that Wallace is totally aware of this, too. It’s what makes him attractive, it’s what frustrates his readers in a delicious way: the only person who could do a just profile of David Foster Wallace is David Foster Wallace himself. And since such a piece (besides being weird) would erode the very mystique that makes Wallace interesting, readers must, somehow, find solace in the footnotes, and watch his mind work from a distance.

Transparency Takes You Off Autopilot

When I meet with people who read my blog regularly, auto-pilot is not an option.

You know auto-pilot — it’s reciting your stock lines, fun facts, or personal biography in the way you’ve always done it. Maybe someone asks you a question about X and, when you’re in auto-pilot, you search your mental drawers for some stock answer that most closely matches the question and then respond. Auto-pilot is lazy. I try to avoid it, but since most strangers ask me the same 5 questions it’s seductively easy to slip into.

Except when that person’s been reading my blog. They know my one-liners. They know my interests. They know when I’m bullshitting. A few weeks ago I had a smoothie with my friend Jason and along the way I reverted to auto-pilot. I brought up my theory about how in tense situations the best perform even better and the worst perform even worse.  He said, "Dude, you wrote about that on your blog a month ago!"

This is how transparency is beautiful. It keeps me on my toes. It forces me to really focus to what someone’s saying and to construct new ideas based on what I take in, instead of reverting to my theories of yesterday.

On the Road in Arizona, Illinois, Colorado

I’ve lived in San Francisco for 18 years. I’ve spent far too little time in other interesting cities. The past couple weeks I’ve hung out in Phoenix, Scottsdale, Chicago, Boulder, and Denver with friends and family. I head to LA this week (I’ve been there plenty). I love all these places. (Don’t you have school classes? Yes, but between spring break and "sick days," I get by.)

Wednesday morning I saw Dick Costolo in Chicago, CEO of FeedBurner, who’s a nice and sharp guy. The FeedBurner physical office reflects their market (RSS and blogs): it’s totally open, transparent, and equal. In other words, no offices, no cubes, just desks. After our chat Eric Olson of VentureWeek and new FeedBurner employee introduced himself to me — it’s always great to put faces to voices! Chicago is an awesome city, especially the people who were all super friendly.

I spent the rest of the afternoon, night, and morning taking care of some personal business which I will write about later.

Next I flew to Denver and taxi’d to Boulder where I caught a panel on how screwed up the patent system is, especially for start-ups. My pal Brad Feld was on it and afterwards I had sushi with him and his wife Amy. I pondered rolling out my sleeping bag on a Boulder sidewalk, but decided instead to follow my gracious hosts home and crashed in their guest room. Good call. The bed was 100x better than a busted futon I slept on a night earlier, and I got to wake up to an amazing sight:
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The next morning I hung out at the Mobius VC office, got briefed on global warming, neuroscience, applied psych in business, and libertarianism by Dave Jilk, and cried myself 14 tissues in the bathroom since Seth Levine rejected me in favor of frozen rain. (It’s ok Seth, I still love you, but no outbound link for you this time.)

My last stop was Denver, where I visited an old friend who I have done a poor job of keeping up with. He’s had a tough four years of high school (three different schools, three different cities). It was good to see him, check out his public school, and hear what he’s thinking for college.

I returned home happy, grateful for the mentors in my life, energized, and with much work.