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Date: 2013-06-03 07:35 pm (UTC)
Biggest challenges in putting together a convention for the first time:

Identifying your goals (small, big, medium; weekend-long party, academic track, passionate discussion among like-minded people, guests of honor/no guests, video program, art show, competitive masquerade, games)
Figure out how many people are needed to achieve each goal
Figure out how many people you have available to work on the con
Recruit those people, making sure they have the same vision you do
Identify a date and facility
Create a realistic budget with a known break-even point (number of memberships sold at a particular rate to be able to cover all expected expenses)

There is a lot of useful info in the Conrunners' Wiki (http://www.conrunner.net/wiki/index.php?title=Main_Page). The most useful thing you can do for yourself before organizing a new convention is work on an existing one, which will give you an idea of the work involved and help you get in touch with people who know how to do the work.
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