Try something like this:
class User < ActiveRecord::Base
has_many :things
end
class Things <ActiveRecord::Base
belongs_to :user
validate :thing_count_within_limit, :on => :create
def thing_count_within_limit
if self.user.things(:reload).count >= 5
errors.add(:base, "Exceeded thing limit")
end
end
end
Edit: updated for Rails 3