I think it's not immodest to say that the recent German retreat went well, but nonetheless there things that went wrong and other things that nearly went wrong. Many of these happened simply because I'd never tried to organize a group of people before, others because of misunderstandings and false ideas that I had.
I'm posting these notes so that future organizers can avoid my mistakes, and so make newer and better mistakes of their own. However, this is not "my private page," I encourage everyone who has lead — or even attended — a retreat to add whatever tips they may have.
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Don't plan too much.
Your reponsibility starts when the visitors deliver themselves into your hands at the front door of the retreat centre*. You may of course meet people at the airport, and you may of course advise them on spending a pleasant week as a tourist before or after, but that is not the core of your duties.
* That sentence needs unpacking. I spent far too much time and energy on working out how people would travel to Germany for the retreat, when this is actually none of my business. It is perfectly acceptable to say "You need to be at [this airport] on [that day], I'll meet you there" as Arabella did in Malta.
Don't assume that you know how people will get there.
I made the mistake of assuming that the majority of attendees would be flying directly to the retreat, and therefore booked an in-transit night away from the retreat centre (near a major airport) before and after the session. In the end, only one person actually flew, and he could just as well have taken the train from Frankfurt airport directly to Rineck.
How people get to and from the retreat centre is not your responsibility (unless they specifically ask you for help and you specifically agree to provide it).
Know the territory.
Even if you won't be picking people up from the airport or train/Greyhound bus station, you should look up the times and cost of getting to and from such places, so you can tell people when they ask.
If you do plan local travel (e.g. meeting at the airport) then you must do it properly. Have a printed timetable for the route you'll be travelling, and buy the tickets in advance.
Print out the retreat centre details and the name and phone number of your contact there, and keep those with you. Send this information as a PDF by mail to anyone who is travelling alone. (This sounds really obvious, but I forgot to do it.)
Don't split the time.
Decide what kind of retreat you want to offer, and reject every idea — no matter how good — which contradicts that. My assumption that we needed two in-transit nights in Stuttgart was a perfect bad example of splitting the time.
If you really want a five-day retreat, then it has to start on the evening of the zero'th day. I planned for us to travel to Rineck on day 1, and to travel back on day 5. In effect, I planned a three-and-two-halves-day retreat. If you want to be on retreat from Monday to Friday, then people should arrive on Sunday and leave on Saturday (or Friday evening).
Publish your plans very early, and update them regularly.
Make the dates and the name of the retreat centre known as soon as possible. I would recommend to do this even before you make a booking, to see whether anyone has had bad experiences there or knows of a better place. Take these counter-recommendations with a pinch of salt, though: this is your retreat, and people will hold you to account for what happens. You must be able to stand up confidently for the choices that you make.
Book as early as possible.
Make a firm booking at the retreat centre far earlier than you think you need to. My first choice was already booked over a year in advance for our chosen week. (This actually turned out to be a good thing because Rineck was a much nicer place, but the point remains.)
One reason for booking really early is this: If you take my advice and plan seven days for a five-day retreat, then from the retreat centre's point of view you will be there for three slots: weekend, week, weekend. This may be fine, but the more notice you can give them, the better and cheaper it will be.
The number and names of attendees will change, but that's fine too: hotels and retreat centres are used to this happening, and as long as you keep them informed they will be agreeable.
Don't count your attendees too soon.
People are naturally optimistic and wish to be friendly and helpful, and this will cause them to mislead you — and themselves — with the best of intentions. Immediately make a spreadsheet that only you can see (you'll need several spreadsheets) with the list of possible attendees, and give each one a rating from "committed" to "unlikely." Revise this regularly based on what you hear directly or indirectly.
Very important: drop your attachment to being a successful and well-loved retreat organizer. Try to see that spreadsheet as a flexible set of possibilities, and don't take either commitment or cancellation personally!
Do get firm commitments as soon as possible.
Start asking for commitment as soon as the dates are known. Anyone who does not say "yes" and then close their mouths when asked, is to be noted as "possible" at best. People who reply with "oh, that sounds good, I might come" are to be noted as "very unlikely."
Inform the retreat centre if the number of attendees changes significantly; but don't call them every hour either.
Know your deadlines and plan out your time in advance of them.
It will take far longer than you think for people to reply to your questions, so don't let a deadline sneak up on you. Many people don't read e-mail daily, and others aren't in SL every day. Start asking important questions three weeks before the day on which you must have a firm answer.
Be cautious and conservative about prices.
Try to get firm offers from the retreat centre and wherever else, and be prepared for them to want a deposit.
Make a budget spreadsheet, and include everything you can think of — and then add 15% for bad luck.
Price is significant for most possible atttendees, so publish the total — but make sure that it's clearly marked as "provisional." Update this regularly; as time progresses and the number of things you might have forgotten shrinks (hopefully!) you can reduce the bad-luck factor from 15% to 10% and then to 5%.
Please add a reasonable amount to your price as a strategic reserve for future retreats! We (Kira and Play as Being) do not believe in charging people more than the price we posted for the retreat, so if the costs turn out higher than expected, Kira makes up the difference out of its own funds. Talk to the Retreat Coordinator (currently Eos) about this.