I am in a weird position vis-a-vis Worldcon. "Fan to pro" is a pipeline that's as old as organized fandom itself. It's what a lot of us dream of when we start attending, working, and organizing conventions.
"Someday, it's going to be MY name on the program book, and MY name they put on the T-shirts" is not an uncommon fantasy, and it's part of why we have Fan Guests of Honor, and (in the filk community) Listener Guests of Honor. Because we all want it.
We all WANT to be the person whose birthday party is so big, so cool, so awesome, that people will pay to attend.

When I started volunteering at conventions, I was fourteen. Saying that I was going to be the next Mercedes Lackey got me pats on the head and extra shifts to work.
I attended my first Worldcon that same year. I was staffing bids by the time I was sixteen, and I was still far too young to fully understand what I was getting myself into by the time I was a Worldcon Department head.
Something many people don't realize: I am a fully trained Hugo administrator. I was trained by a woman who was very very good at the job, who wanted me to have a place in fandom if my dreams of literary success didn't pan out.
She wasn't being cruel! Statistically, what I wanted wasn't any different than what everyone around me wanted. The odds were never in my favor.
Putting together a Worldcon is a shit-ton of work, money, time, and yes, love. Because you're paying for the privilege, every step along the way, and if there's no love there, you're not going to reach the finish line.
The bid process is grueling. It involves throwing parties at all the conventions with a large enough membership and history of WSFS involvement to have been deemed "important," paying for all food, drinks, and hotel rooms yourself.
So that's a minimum outlay of X cons, where "X" is a number I don't know, but is at least two memberships, one hotel room, and $1,500-$3,000 USD for party supplies per con. Meaning probably also a rental car to get them to the hotel. And airfare.
I can't do it. I have worked my Worldcon bids, and I'm tired. I know my limits. I will not be putting together a Worldcon bid in the future.
And it's not just the parties, although many people will say the parties will make or break your bid--and they may be right, I don't know. You also need people to staff your table and hand-sell your venue, for hours a day, for the duration of the con.
This is just the visible-to-fans part. You'll also need to find a venue large enough to fit the convention's needs, negotiate with hotels nearby, and keep in mind that the membership of WSFS gets to vote on whether you've spent all that time and money for nothing.
Putting together and running a successful Worldcon bid costs substantially more than I was paid for my first three novels. And there's no guaranteed return. Ever.
I'm seeing a lot of people complaining about the bids for future Worldcons, and I can't blame them, because some of those bids are not for places I would feel safe going. At all. But it is not the place of WSFS to say "no, you're bad people, you can't host a con."
The membership votes. And sometimes, yeah, the membership is going to vote in a way we don't like. I was ecstatic when Nice dropped out, because the French Rivera has a history of anti-Roma racism that would have made that con impossible for me to attend.
And there ARE people who vote on the basis of "is this a place where I want to take a vacation?", so I was honestly concerned I'd have to sit a year out due to racist fuckers and American voters not understanding my concern.
But as of right now, the WSFS constitution gives all power to the voters. There's no grand council that gets to decide if a bid moves forward.
If you want WSFS to have that power--if you honestly believe this wouldn't be used to somehow restrict Worldcon to only American bids for "affordability" reasons, or to invalidate your bid because it's "too remote"--there is a path to that power.
Any member can attend the Business Meeting and put forth a motion. You will need to find one other person who's willing to be an official author on that motion, and you will need to write it as if it's about to be used as a hammer to bash your own head in.
Motions take two years to pass. So you could put forth a motion for consideration at Worldcon in 2021 (the 2020 agenda is already full), to be voted in 2021, and then again in 2022, and if it passes both years, you can give WSFS that power.
It takes this long to keep people from buying themselves a permanent Worldcon. I can't through a hundred grand at a bid to buy myself a Seattle Worldcon, then ram through an amendment that says Worldcon can ONLY happen in Seattle going forward.
WSFS is a fan-run organization that has taken immense steps to limit its own power and keep that power in the hands of the membership. If you want something changed, sometimes you do have to step up, volunteer, and change it.
Does that suck? Sometimes. Is it exhausting? Absolutely. Is Worldcon the property of WSFS, and something we all own a little piece of when we buy our memberships? Yes.

As a community garden, what we grow is what we plant. If you want tomatoes, start digging.
You can follow @seananmcguire.
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