I love Tabletop Inquirer (@tabletopinq on Twitter) even if they focus on 40k, and refer to people like me on TMP as old fuddy-duddies and dinosaurs.
I've been doing this thing long enough to deal with dozens of these people face-to-face, much less the apathetic legions of keyboard Karens. I've also seen enough people (myself included) who claim they can run things better, or in a completely different direction, only to have everything blow up in completely disastrous ways (not me). My Curriculum Vitae isn't vast, but does reach a number of areas.
Convention Director: CoveCon, close to 100 people in rural Pennsylvania. More importantly, it broke even.
Convention Staff: Lehicon 6-7, Lehigh Valley Game Day 1, Mepacon 1, Numerous Bogglecon and Gobblecons in various capacities (@10-15 cons). Cold Wars 2020 (Education Program)
Dealer: Mountain Top '99, CoveCon, Bogglecon/Gobblecons 97-98, Mepacon 2, Cold Wars '97.
GameMaster: Dozens of conventions, ranging from Lehicon 3 (1990) through Cold Wars 2020, including appearances at Origins, Dexcon, UBCon, Fall-In, and Historicon, not to mention the other conventions referenced above. Ran role-playing, miniature wargames, board/card games, collectible card game demos and tournaments, and even a LARP!
Volunteer: Origins '96, UBCon, Dexcon
Convention Demo Team: Global Games ('94-97), Hackmaster ('01-02)
What did I learn from dipping my toes in various parts of the gaming event?
Running an event isn't particularly hard. Running an event WELL is exhausting.
Finding the processes that work for you, building a team that's willing to sip the proverbial Kool-Aid for an event's success, and going through the steps to make outreach with the gaming community? Mind numbing at best, impossible, for some, and simply soul-crushing for those with delusions of grandeur.
My suggestions for someone who wants to volunteer or even GM events?
1. Attend a con as a participant more than once The classic "If I ran a con/tournament/event/game, I would do..." comes from a 50% experience/50% ignorance. Many times there were instances where things need to be down a certain way to meet contractual standards with the site, any sponsors or event support regs, and in some situations, local/state/even Federal laws.
2. Start small. Even if one event or four-hour volunteer slot doesn't grant you certain benefits, like free admission, it's a good look into the way things operate, the good, the bad, and the nitty gritty details.
3. Don't assume any fringe benefits. The first con event I ran got me into a 3-day con absolutely free. Nowadays multiple events are required for free admission, sometimes 12+ hours for a weekend pass.
4. Grin and bear most of it. As a member of the convention staff (yes, volunteers and GMs are "faces" of the event, for better or for worse), you are the front-line of contact with any issues that may come up. Know where to find higher ranking convention staff to help resolve conflicts. Unless you are in the midst of a critical situation where someone's well-being is at stake, do not escalate any situations without additional con help nearby.
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