“Would you like to meet on February 17th?”

I had to do a bit of a double take. Certainly this meeting, which was being scheduled earlier this week, was meant for December 17th and not February 17th. But I was wrong, we were scheduling eight weeks out, presumably due to the usual combo of travel, vacation, and general busyness.

Over the past few months, I have increasingly instituted a rule that I won’t schedule any form of catch-up meeting, source meeting, dinner meeting, fundraise advice meeting, or what have you more than 48 hours in advance. While I haven’t made this a religious conviction and maintain some flexibility, it frankly has been one of the most liberating decisions I have ever made.

The general premise underlying this model of course is spontaneity. Startups, innovation, and the news cycle happen in real-time, and are never aligned with your agenda planned eight weeks ago. The more you plan your weeks out in advance, the less you are able to take advantage of opportunities in the moment, and that’s a huge compromise — or at least, it has been in my own experience.

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