Organizing fun events with friends

Summary

A working theory on how to organize trips, events, and social gatherings with >=3 people.

Request for Comment

This post is in need of your feedback! Please send me any thoughts you have; it would make my day :)

If you reside in the Bay Area and want to chat about this topic irl, I’m happy to buy you a coffee in exchange for your insight (or anything else you’d like to talk about)!

I. introduction

If you grew up in the United States, you’ve probably had the wonderful opportunity to experience the dreaded group project.

“Alright, class! we’ll be spending the next month making (insert busy work)! Get together with the 3 other random people at your table, and you’ll have the next 5 periods to discuss how you’ll divide the work amongst yourselves. Have fun :)”

One revelation I’ve had is that casual event and trip planning falls surprisingly close to the group project archetype:

• Usually, one (or if you’re lucky, two) people become the organizers of the group. Due to one circumstance or another, they end up doing most of the work. They might even enjoy it a little (gasp)!
• The majority of the group serve as attendees. Although they’ll do the bare minimum if they can get away with it, they’re well-intentioned, communicative, and are willing to do their part (assuming they know what it is).
• If you’re unlucky, you’ll get a couple slackers. It would have been less work and stress to have them not be part of the group at all, but you’re stuck with them

This document is written for the organizers (and curious attendees). Your scholastic sacrifices have prepared you for this moment; you have what it takes to pull off the craziest funnest event of your dreams. ️ it’s your time to shine!

disclaimer: these are not professional event-planning tips

I’m not a professional event planner, and don’t intend to ever be one. (Maybe one will read it at some point and roast me constructively??)

The intention of this page is to document the patterns I’ve found while hosting low-to-medium-stakes gatherings with friends. I hope they’ll help, but if you’re torn between trusting my words and your instincts, you should go with your instincts.

What types of events apply?

The event I envision when I’m writing down these ideas share most of the following characteristics:

• Fun and optional: There’s no obligation to attend; it’s assumed that everyone who RSVP’s wants to come!
• Variable size: You probably have a min and max capacity in mind, rather than an exact number or list of people who need to attend.
• Low (monetary) cost: The price tag of the activity isn’t a barrier to anyone’s attendance.
• Might involve +1’s: A rule of thumb I like to follow is “open invite for your friends and their friends”. You can extend one more layer if you really want to (friends of a friend of a friend…) for large house parties and the sort, but this gets really difficult to manage really quickly so I don’t usually recommend it.

A few examples of things I’ve helped plan (or plan regularly) that follow these archetypes include:

• Weekly game nights
• San Francisco Streets, an urban exploration walk/transit through every neighborhood in SF in a day
  • I intend to run this again sometime, but bigger and better!
• Hiking, climbing, skiing/snowboarding, golf, and other outdoorsy things nearby
• LaunchHacks, a 200-person high school hackathon
• Various excursions including Yosemite, Korea, and weekly adventures while I was studying abroad (blog posts coming soon…)

Also refer to Things I want to do or organize for a list of future, aspirational things I hope to do at some point in my life.

Please don’t be a stranger and contact me if you’re interested in joining anything (either as a co-organizer or follower)!

II. the buy-in crew

Solo organizing is really scary. What if no one shows up? Or everyone replies “maybe”? It sucks when you’re the only one putting in the effort to organize, buy tickets, and otherwise take the risks, only for nobody to acknowledge it and carry the weight with you.

This is why I like to follow a rule: I don’t start organizing something until I have at least one (ideally two) other people willing to enthusiastically support it.

I call this group of people the buy-in crew.

Buy-in doesn’t have to require money! (But if money is involved, these are the people who are willing to put some down right now to make it happen.) Typically, the biggest cost is social risk— they’re probably announcing the event and inviting their friends, too; if the event flops miserably, they’re willing to take the blame with me. This event is theirs just as much as it is my own, even if they’re not the main organizer.

The buy-in crew is the minimum set of people needed to make an event happen. Even if nobody else shows up besides them, you know for sure it’ll be a good time!

Pre-planning for your buy-in crew

Even if you’re lucky enough to have people who trust you unequivocally, you should probably have at least some sort of plan in mind before bringing in others.

I tend to like writing things down in a Google doc. This doesn’t need to have finalized plans at this stage (you should be asking your buy-in crew for feedback and availability), but can have sample dates/times, locations, and a list of people you’re planning on inviting. Provide a few options to choose from— you’ll narrow them down together.

(For a more complete example, see the Yosemite trip template)

III. blast the invites

Once your buy-in crew is sorted, the next step is to get your attendees on board.

An attendee is different from the buy-in crew in the following ways:

1. The event will still be successful whether or not they show up.
2. There’s no expectation for attendees to contribute to organizing. You’ll tell them where and when to show up, what’s going on, and (optionally) how much they should pay you; in exchange for their presence and payment, you’ll take care of the rest.

Here are a few things that have worked well for me:

• Attendees are much more receptive to events with a specific time, date, and location.
  • As an attendee, getting hit with the “hey u free on fri” text is the worst. I might be free, but if I say yes I won’t have any excuse to get out of something I don’t want to attend!!
• Plan around your buy-in crew’s availability, but be hesitant to reschedule for attendees outside of that group.
  • If someone really wants to join, they’ll work around your schedule.
  • If they don’t, they’re probably better off going to the other thing they have that’s conflicting.
  • If you want them to come badly enough that you’ll move everything to get them in, they belong in the buy-in crew!!
• Attendees usually want to know who’s coming before they RSVP.
  • Give them this information at invite-time (or use a platform like Partiful)!
  • Invite the rare attendees who don’t care about this first. That way, you can start building up a list to give to the people who do care.
  • For smaller/more casual gatherings, a simple mention of ‘Alice is coming so far, Bob is a maybe’ are very appreciated.
  • Make sure your non-buy-in attendees know the event will happen even if they no-show. (often as easy as starting invites with ‘Charlie and I are organizing…‘) This reduces the burden of choice for them, and ensures they won’t feel peer-pressured to say yes against their will.
• Stagger your invites.
  • Invite attendees you think are most likely to say yes first, then go through your maybe list as the no’s come in. Doing so ensures you’ll have a better sense of how many people are coming earlier on, while still allowing your event to fill up if a few people can’t make it.
• Be ready to accept the uncertainty of blasting in group chats. Before you announce something in a GC, make sure you’re ok with anywhere from nobody in that chat to everybody in that chat showing up.
  • If you’re not ok with everyone showing up, you should invite people individually instead.

IV. Slackers and pitfalls to avoid

Just like in group projects, you’ll most likely get attendees that make your life harder as an organizer (most likely +1’s and friend-of-friends that you haven’t met before). Attempting to completely close off your event to them is futile and can get in the way of ensuring the event feels welcoming to well-intentioned attendees.

Slackers are welcome exactly once. More verbosely: I try to ensure everyone has a good time regardless of their behavior, and go out of my way to accommodate slackers so they don’t disrupt everyone else; but I will never invite them to anything again.

Here are a few types of slackers you’ll run into in the wild, and some tips to deal with them:

• People who never pay: You’ll take the bill for something they bought, and they’ll never offer to pay you back / ignore you when you ask. (This can be a difficult conversation if they genuinely can’t afford it, but most ppl in this category definitely can.)
  • Ask yourself: is this relationship worth burning for $N dollars (how much they owe you)? Sometimes it is, and you’d rather angrily demand them to pay up rather than keep them in your life. More often than not, though, some introspection will reveal that it’s worth eating the cost.
  • Organizers almost always pay more than the average attendee when money is involved (after nonpayers, unaccounted-for taxes, etc). You have the authority to round up bills and cook the books a little to make sure you can recoup your costs ;) most of your attendees will be more than happy to accommodate since they know how much work you’ve put into making the event happen. Just make sure to be transparent about it.
    • As an attendee, I often round up a few dollars to the asking price since I’m aware of what goes on behind the scenes. I encourage you to get in the habit of doing the same if you can afford it; just a few dollars here and there goes a long way towards strengthening friendships!
• People who invite way too many +1’s without telling you: Organizing is already an uncertain sport when you have all of your yes/no/maybe’s accounted for; someone bringing 5 of their friends unannounced to a 10-person reservation can easily be day-ruining.
  • Unless you explicitly mention “open invite” or “please bring a +1”, it should be assumed that attendees ask for permission before bringing someone else to an event they aren’t hosting. Don’t be shy on telling someone about this etiquette if they’re genuinely unaware!
• Chronic complainers: if they’re not into it, they should just leave and organize their own instead of loudly ruining it for everyone else
  • If you’re running an event and it’s a total disaster and everything is your fault… it’s ok. Rain comes; places get double-booked; you oversleep. it happens. I cri for you. It still doesn’t make it OK for people to make you feel even more miserable.
    • Give attendees a way to gracefully dip without making it feel awkward if something unexpected happens.
    • It’s usually not your responsibility as an organizer to cover cancellation fees or unplanned costs! Don’t be afraid to split these evenly.