What do I work on first?

In both my consulting business and from friends, I get a lot of questions similar to this one…
“I came up with a list of 14 possible projects to work on yesterday but now I need to narrow them down to ones that will, well, work.  When you have a list of projects, is there some equation you use to determine the priority?”
Although the process of prioritization comes naturally to some, it can still be a time waster for many.   We can get so wrapped up in setting priorities and writing lists that we fail to take action and move forward with completing the things on the list.  Since I can be as guilty of this as anyone, I work with a simple structure to prioritize those things on my to-do list. 
1) Deadlines – obviously the soonest deadline gets the first attention
But for those items when deadlines are not a factor –
2) Try to alternate easy/short projects with a longer/harder projects. By allowing yourself time to do projects that you can complete in a shorter period of time you are consistently rewarding yourself with the feeling of finishing something.  This feeling of accomplishment and completion are crucial to maintaining motivation when your to-do list is long and/or complex.
3) Try and determine which of the 2 or 4 projects you will enjoy doing the most. Put 1 or 2 of them at the top of the list and 1 or 2 of them at the bottom.  You get to start with something you enjoy and have something else you will enjoy towards the end.   It is the ages old carrot – stick method of motivation.  Start with something you enjoy to motivate you and get your creative juices flowing and then accomplish other things by knowing there is a fun reward at the end.
So those are my tips on how to prioritize.  How do you prioritize that never-ending to-do list?

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