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I had this problem in the past, always chasing my tail. A few yeas ago I fashioned a grand, sweeping plan to change my situation and decided to carry through with it. The plan was very specific and required a specific order of events to materialize. As the years went by, certain of these criteria collapsed or were no longer viable. It was necessary for me to adapt the plan to new circumstances. I did this many times, as certain parts of the plan would collapse and new methods of compensating had to be found. I must admit that luck played no small role, but it seems that the plan will work, even with all of it modifications. So, rather than optimizing, I merely adapted, and hedged my bets at every new twist.
 

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Some general thoughts on planning:

1) "no plan survives first contact with the enemy" although written from a military perspective Moltke's quote rings true for planning as a whole. What Clausewitz calls the friction of war - stuff just happens - sometimes in your favour, sometimes not. Are you flexible in your approach to adapt without replanning.

2) Are you using planning as an avoidance behaviour? (I notice, curious0610, that you mentioned execution as well so this is general comment not neccessarily directed at you)

3) What part of the plan needs changing? Is it the steps to get to your goal or is it the goal itself.

4) How are you defining your plans? - by outcomes or by detailed next things to do - be clear about separating goals from steps - overall goals should be reasonably fixed - how to get there may change on a daily basis!

5) Self development - are you working on your capabilities to reach your goals as well as your tasks? This is often not really considered.

6) sorry to disappoint you but there is no such thing as a plan that remains elegant during execution (see point 1) Life simply doesn't happen that way - I know this sounds harsh but an elegant plan is not a plan (a plan by definition is capable of being carried out and takes into account messyness)

7) Keep your overall goals in mind and flex to find routes to meet them.

8) Do you use SMART Goals (Specific, Measurable, Acheivable, Relevant, Time bound) For INFJs I would also add that goals should resonate emotionally as well. i.e. it fits your values and just feels right (you lot know what I mean! other types don't seem to get this!)

9) Use your intuition as well as logic - planning often ends up very logical - allow both to come into play
Excellent advice!
 
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