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. about this document

In its current state, this document is very much in ‘if I had more time, I would have written a shorter letter’ mode. With no regards to relative importance, I’ve listed most of everything I know that works (and a few things that don’t work) for casual event planning.

I’ve had some really formative conversations with friends about this topic and have grown to become rather passionate about figuring all of this out. Some of the most meaningful memories from my recent years were born out of fantastically-organized gatherings, and I’m a strong believer that the world would be a better place if we had more of them!

This is my attempt at building a framework for understanding what works well (and what doesn’t) when hosting events.

I’m still not fully sold on the generalizability of my findings and hope to gain more confidence on them over time. As far as I know, it works surprisingly well for my specific circumstances and the specific people I spend time around. Let me know what works and what doesn’t work for you!

II. introduction

If you grew up in the American public school system, you’ve probably had your fair share of 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 (!!)
• 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 my 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.
• 1 day long or shorter: For information pertinent to longer trips involving booking flights, housing, etc., see Trip planning tips.

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

• Board 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 mildly 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)!

III. 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 share some 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.

Typically, plan a very loose agenda. Expect many attendees to show up late, things to take longer than anticipated, etc.

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

IV. 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.
• Be very explicit about hard deadlines and timelines. The unwritten assumption is that most times are loose, and that most people are going to show up fashionably late.
  • For deadlines to RSVP: it’s on you as the organizer to send out regular reminders (minimum of 1 nudge ~1 day prior is appreciated), but there’s no need to be pushy. If someone ‘forgets’ to register they likely didn’t care too much to come in the first place.
  • For strict arrival times, I usually say something like “the train leaves at 6:30. be there at 6:15 at the very latest so we can take time to register and distribute tickets.” (The ‘register and distribute tickets’ can be replaced with any reasonable excuse for people to come early and not feel awkward about it.) Chances are, most people will attempt to arrive at 6:15 and actually arrive closer to 6:30, but everything will still work out!

V. crafting group dynamics

I like to think that all of my friends are rather prosocial, and generally trust them to also invite/hang out with other prosocial people. But it’s inevitable that our vibe checks mess up once in a while. It’s good to be prepared for it.

Additionally, even if everyone is prosocial, your friends probably don’t vibe with 100% of your other friends— I’m sure you can think of certain pairings that would surely end in disaster…

Here are a few specific scenarios for tricky group-dynamic situations and how to address them.

(This section is the most TBD of all, and will be updated as more issues start generalizing.)

odd-on-out problems

If most of your attendee list knows each other from another context (work, school, the gym…), be careful when inviting someone who doesn’t share that context with the rest of the group. When done well, adding someone new to an established group dynamic can be exciting and mix things up— but you also risk putting the odd-one-out in lots of awkward situations.

• At the bare minimum, make sure they’re briefed, know the basics of your shared context, and are mentally prepared to meet a large group of strangers who already know each other.
• Introduce them formally when they arrive— what their name is, how you know each other, and why you think they’d be a great addition to the group. While it may be overwhelming for them to remember everyone else, one new face for the rest of your group shouldn’t be a problem + they now have an excuse, plus a small bit of initial information, to engage further.
• Keep an eye out for when your odd-one-out is feeling left out of a conversation or situation. For example, if you’re with work friends and they start gossiping about your competitor, either fill in your non-work friend with the current tea or try to steer the conversation to something more general (like “do you have any crazy stories from your job?” etc.)

limited seats

Let’s say you’re making a reservation at a famous popular restaurant and they only have a table of 6 left. But, you have more than 5 other friends who’d be interested in joining if they knew about it… what do you do??

• At the minimum, ensure you have strong, defensible reasoning for inviting that specific set of people and no-one else. Maybe you’re holding a get-together with just your college friends, or you’re specifically trying to meet with people you haven’t seen in a long time. It should not be a hasty excuse for excluding someone who didn’t make the cut, constructed at the moment of when they ask why they can’t come.
• A good litmus test is whether you’d be proud of sharing that you hosted this event with all of your non-attendee friends. If you think it’d be awkward if your presence got out to someone, you need to be mentally prepared to deal with it if they found out.

Some possible mitigations for this conflict include:

• Running multiple rounds with different sets of people. Try to convert the problem from “can I fit this person in?” to “when can I fit this person in?”
  • This is most effective for recurring events that have a very obvious justification for having limited seats (like a round of golf, or a 4-person board game). Gaining the intuition of constructing these groups is a separate and difficult skill to acquire, but once you get some practice in you’ll hopefully start building your attendees’ trust in that you’re including them in a way that makes sense for everyone.
• Deliberately outline your decision of who is the buy-in crew vs. who’d be considered an attendee. “A is flying in and can only specifically do this weekend; let’s hang out another time” or “B helped a lot in planning this; they should definitely be included” are both reasonable excuses for explaining why someone is considered part of the buy-in or not.
• Involve those affected by space-limiting in other, independent plans that would be equally or more desirable to them. Do this proactively (i.e. before the event), so they can feel included in your mental space.
• Significantly downsize the event (to 2-3 people) so it becomes a manageable set of 1-on-1 dynamics rather than a messy group dynamic.

This can also apply to softer-limited situations (like the # of people you can fit in your small apartment for housewarming, or even just a limit on how many people you can mentally deal with at one time…)

getting flooded with +1’s

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 outing 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! This is the kind of thing that should happen once and never again when you invite a particular person.
• It is perfectly ok to say no to, or turn down last-minute +1’s, assuming you got notified of them before they show up in person.
• You have no obligation to host unannounced a large quantity of +1’s. If their presence will make your life difficult, they should be expected to self-organize (i.e. arrange their own food/transportation, buy their own tickets, etc., even if they’re in the same physical locations)

slackers and party poopers

Sometimes, you’ll get an attendee that is straight up not having a good time (and is rather loud about expressing this sentiment to you and others).

• first off: please, please try to not do this if you can!! if you’re an attendee and on the fence about whether you’ll enjoy partaking in something, make sure you give yourself plenty of opportunities and excuses to leave early.
• one of the most effective ways to drown out loud negativity is with even louder positivity. if you’re very convicted in the belief that you are personally having the time of your life, your energy can be contagious and bring others out of a rut.
• sometimes, even the best of plans get foiled for reasons beyond your control, and that’s ok!! the best way to mitigate grumblings from things like bad weather or getting lost is to let your attendees know what the risks are beforehand, and to make sure your future plans are resilient to the same types of failures.

VI. Staying in touch

The most successful events aren’t one-offs; rather, they’re a catalyst for recurring friendships/relationships.

• Help new attendees feel welcome by greeting them / introducing yourself sometime during the event, and ask for their socials/contact info at the end of the event. (I personally need to improve at this. being extroverted is hard)
• Although you (as someone who presumable enjoys organizing) will likely host more events than you attend, you shouldn’t be the only person running things! If there’s a natural opportunity to do so, communicate your personal interests for things you enjoy doing/attending so your attendees will keep you in mind if they ever host something they know you’ll have a good time at / say yes to.
• Consider spinning off longer-lived group chats that are not tied one event based on shared interests or recurring series of events. (probably use discord, messenger, whatsapp, signal, etc.)