On Planning, Getting Things Done, and Other Bad Habits

I know, right?  Can you believe it?  Me, the guy who spent two or three weeks doing a blog series on Life Design, and a title like that?  I mean, I’m in favor of weekly reviews, annual plans, written goals, and everything else that can possibly be tracked and measured.

This may be a bit of a contrarian post.  Perhaps even something of a “Devil’s Advocate”-type look at the other side of the coin I’ve so often recommended.  As usual, I’m writing to figure something out on my own, and taking you, Loyal Reader, along for the ride.  Not necessarily a long ride, or maybe even that interesting to you, but a ride none the less.

This is why I tell you not to worry about everyday life – whether you have enough food and drink, or enough clothes to wear.  Isn’t life more than food and your body more than clothing?

– Matthew 6.25

I’ve been reading The Freedom Manifesto by Tom Hodgkinson.  Not sure I agree with everything he says, and it’s certainly a book that’s sparse on actionable material.  However, in light of my recent fascination with understanding just what it means to “tell a good Story” with your life, I have to admit it’s brought up some challenging points.

I would rather have torn sheets and a larder full of beer than be a teetotaller with new bedlinen.

p.69, The Freedom Manifesto

What he’s saying in the larger context of the book is that some people are so concerned with having everything in its proper place that they become confined by their choices.  If you’re constantly worried about whether you’ve got all the “essentials” in place, but never take the time to define what’s “essential” for you, then you may need to reconsider.

If you’re keeping up appearances simply based on society or some external motivating force, then you should probably worry less about what other people think, and spend more time finding out which possessions and activities really add value to your life.  Along the same lines, if you regiment everything you do to the point of inflexibility, you may miss some opportunities to have some spontaneous fun.

So, of course, my question is this:  where’s the line?  How can you determine when to plan, and when to go with the flow?

I’ll be the first to admit I’m a Nervous Nellie when it comes to issues pertaining to the future.  I’m a planner, and I prefer to have contingency scenarios thought out prior to executing anything.  But, when can those types of tendencies be a detriment to truly living life?  Is there ever a time a person should just quit their job, sell all their possessions, and head off to some far away place to start weaving baskets to sell on the web?

And how does one know when that time comes in his or her life?

I’m really at a loss here.  I honestly don’t have an answer, because I think it’s something that is probably different for everyone.  Some of us could stand to loosen up a bit, and more than a few could probably do with a little buckling down every now and then.  How do you determine this for yourself?

Please, share any thoughts you might have in the comments.

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