That sounds like a really cool job, but at the same time seems pretty stressful. You have to make judgement calls all the time and whatever you call, someone will not be happy with you.
I wonder how the nature of the employment works? Are you employed by the league or do you take contracts? Also, how do you move up to bigger higher level leagues?
We are independent contractors, unless you're working professional baseball under the MLB flag then you're employed by the league even if you're only working minor league baseball. So, I am a member of an umpire association in my area that assigns me games. The association is contracted by travel tournament directors, HS/college athletic directors, ect to get them umpires for a tournament/games. They then assign to members of the association based on experience and more importantly your skill level.
It's also about who you know for sure. I wouldn't be where I am today or assigned the games I get if I didn't know someone who knew someone who knew someone. It's a lot of networking and politics too, which is why we have some older umpires in our association still getting high level assignments that they shouldn't be getting.
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