money talk - should I cut my hair?

Here are the details
* Software industry, I train sales reps on how to effectively engage with customers using iPads
* Hair is roughly chin length, will not neatly fit in a ponytail
* Culture for a software company is pretty uptight but remember its much less uptight than most other industries
* The boss is trying to change the culture to be edgier
* Due to some HR things unrelated to my hair or my ability to do my job, its basically impossible for me to get a promotion and/or raise at the company without first taking a major paycut
* 3 big meetings in Jan where I will be training >1000 sales reps on using the iPad including main stage presentations
* The only person who has commented on my hair being long (it takes 18 months to get chin length) is the boss that is trying to change the culture. He made a few remarks on the topic but when I pushed on him, he dropped it.
* I am already a well known odd ball within the company. I am generally well liked within the company.
* Other than the 3 events in Jan, I won't have any other event where my hair would matter until June and by then it will neatly fit into a ponytail

Here is what my hair roughly looks like


I am very torn on this. I like my hair. My wife likes my hair, all of my friends love my hair, strangers comment on my hair. At the same time I don't want to make my work harder, of course its basically impossible for me to get a raise and or a promotion so why should IGAF?