Tennis, Psychadelics, and Entrepreneurship

I’ve always thought of tennis as perhaps the most difficult of sports.  It’s like hitting a baseball, but while you’re running, and with 90% of the addressable target area out of bounds (in the net, outside the lines, etc).  To top that off, you’re a team of one, battling yourself, inside your head.  So it’s… Continue reading

Automating your way out of bad behavior

As I write this, I’m sitting on the platform at the Back Bay Amtrak station in Boston, waiting for the train to New York. At 9am (6 minutes ago), I got a text message prompting me to write a blog post today. It said “Get your blog on!  It’s a good thing”.  The text message,… Continue reading

Investing vs. getting in debt

I’ve been thinking a lot about what it means to invest lately.  I’m not just talking about investing money, in savings or stocks or whatever; I mean investing in a broader sense, in yourself and in everything you do. I am without question an urgency addict — as a general rule, I procrastinate, let things build… Continue reading

Something to aspire to

Today I spent some time with Brad Burnham from Union Square Ventures.  Among other things, we were talking about what’s going on at Code for America and Civic Commons, as well as the latest in the fight to save the Internet. Separately, during the day today, the USV team was interviewing candidates for their new associate position.  It’s sweet job, by pretty… Continue reading

Ritual and Tradition

Last week, I mentioned an article called The Making of the Corporate Athlete (originally published in 2001 in the Harvard Business Review).  If you haven’t read it, you should — it’s a short read.  Long story short: successful athletes take a “whole body” approach to optimizing their performance, and other kinds of professionals could benefit… Continue reading

Speaking from the Heart

Last month, I attended the Massachusetts Technology Leadership Council’s annual unconference.  My favorite session, by far, was Bill Warner‘s “Building a Startup from the Heart”. I found Bill’s approach to be inspiring, and immediately went home to incorporate his ideas into some OpenPlans materials that I’d been working on (e.g., a new page on our… Continue reading

Writing to your future self

I love seeing people write to their future selves. Here’s a note I came across in my very own inbox today, no doubt jotted down on my iPhone while I was half-drunk at a party. Drake. Neon Indian Groove shark – friends playlist    Darius.  Radius radius Brother “Radius radius” is my favorite part.  I… Continue reading

Unplugging (sort of)

This week, we’re on vacation in Cape Cod with my wife’s family.  They’ve been renting the same tiny cabin by the beach for the past 35 years, and coming here is pretty much the highlight of our summer each year.  Last summer, we brought Theo here when he was just three weeks old.  This morning,… Continue reading

The optimism of the traveler

This morning, I drove from Boston to Cape Cod, alone with my thoughts except for Theo sleeping in the back seat.  Once we were out of the city and smoothly on the highway, I got to thinking about work, and things really started clicking.  I found myself reaching for my iPhone to record voice memos… Continue reading


I’ve been thinking a lot about fitness lately, mostly spurred on by the great stuff coming out of Clay Johnson’s new blog, InfoVegan. Clay has been drawing a parallel between physical obesity and information obesity, and has been diving deep on what it means to have a “healthy information diet.”  It’s inspiring stuff, and definitely… Continue reading


I spend a fair amount of time thinking about LifeHacking.  Getting my inbox filters just right so I can get to “inbox double-zero,” syncing my iPhone and my Google Calendar, setting up ssh keys in all the right places, etc. But something I’m still not that good at is “LifePruning,” that is, the continual process… Continue reading

Knowing the tone of the room

One of the toughest things I’ve encountered, as I attend meetings, speak on panels, do interviews, and go to conferences, is that you never quite know what the tone of the room will be like until you get there.  In other words, there are always a ton of different approaches you can take to a… Continue reading

Is _____ for you?

I get way too much spam in my inbox, even just counting things I’ve signed up for myself.  Most of it I delete, but today’s email from CoTweet stood out, and is worth mentioning. A while back I signed up for CoTweet, just to check it out — nutshell: CoTweet lets you collaboratively monitor and… Continue reading

Changing behavior, one bag at a time

Yesterday, American Airlines announced that it’s going to start charging a fee for checked baggage. Of course, this will draw the ire of frequent and not-so-frequent flyers everywhere. But, perhaps it makes some sense. What’s making flying expensive right now is the cost of fuel. So, if people pack less, planes will be lighter and… Continue reading