The first problem is that planning can be a way to avoid doing.  I’m in the little cocoon of my plans – nothing can go wrong at this point.  So the more time I spend in creating and refining plans, there’s no risk.  Unfortunately, delaying is usually the risk I’m taking – but that’s not apparent.

The second problem is that not everything can be planned.  Especially when you’re doing something new, something creative:  Any plans are based on a poor understanding.  A house of cards.

The third problem is that planning can take away the joy of experience and surprise.  The best vacations I’ve had were where we had entire days which were unplanned, and therefore could be spent on … anything!  If we want to go sit on the beach for an afternoon, that’s just fine, because there’s no plans.  Want to eat dinner at 10:00?  No problem.

Of course, I’m not comfortable with jumping past the planning stages in much of my work.  The challenge is to find the right balance.

The most powerful example came when I joined up with Small Fish at the end of 2010.  We were warned that there would be a certain comfort in creating lists, in planning activities, and in writing blog posts.  But because our task was to get out there and sell our services, there was nothing to compare with getting out there and having actual conversations with potential clients.

And it’s made a world of difference:  I now have clients.

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