Organising events can be frustrating but is an asymmetric opportunity
Things I’ve learnt organising events
One thing I’m trying to do more of this year is organise more events. Just as I believe that meeting new people is asymmetric , I also believe that bringing people together has disproportionate returns over time. It’s like playing the social lottery, and for free.
I arrange regular cocktail nights, restaurant dinner meetups, and the occasional exhibition visit. These are some things I’ve come to believe over time:
Be liberal with who you invite initially, and then conservative with them after.
- Some people are bad with faces. Some people are bad with names. I’m bad with both. I barely remember anyone I meet for the first time, so having a chance to meet them again soon after is helpful for me. Hence I’m easygoing when inviting people to my events for the first time. At worst we have to deal with a few awkward people for a few hours.
- I also like it when people from different worlds get to interact (e.g. finance and food), so I’m biased towards inviting more people the first time round
- However, I’m stricter when inviting people for the second time onwards. I usually have a better gauge of their personality then, who they’re more likely to get along with, and whether they’re likely to reply in the first place . Which brings me to my next point:
Not replying is different from saying no.
- I’m unsure if Facebook was the one that started the trend, and it’s frustrating how flaky people have become. I understand why people don’t reply - uninterested, unsure, afraid of offending etc. However, the implication of not replying is different from replying no. The latter implies I was at least worth the time to click a button; the former implies I wasn’t.
- You might think your one response doesn’t matter, but imagine what happens when half the group thinks that way. That happens more often than you’d think, and it’s annoying.
- It’s great if you can give a reason, since that helps me know whether you’re uninterested in that kind of event, or just unable to make it that one time. When you don’t reply, I don’t know which I should assume. I’ve historically assumed people were just busy, but have lately switched over to assuming people are uninterested. That implies I don’t need to invite them next time
- However, you don’t even have to give a reason if you don’t want to. Just responding alone is helpful. Within reason, most people will understand when you can’t make an event.
Let people go.
- I’ve hosted 10-15 cocktail nights at my place since moving to NYC 2 years ago. Throughout this time, there’s been a small group of people that I’ve always invited, but never show. I’m always amused when I meet up with them and they express regret at not being able to come 
- I’ve found that many people will say they’re interested in something out of politeness, and then flake after. Going back to point 1, I’ll invite these people a few times, and then stop doing so
- This is fine, and it’s part of life. I can’t and won’t ever be close to some people, and that’s ok. Worry about the people that would worry about you, and care less about the rest. Relationships are always a two way thing
- Partly because I’m actually making the drinks at my events, I’ve noticed they become less manageable past 20 people. I spend more time doing host duties and less time socialising and introducing people to each other
- I’ve found ideal sizes to be 8-10. Larger than that, people start getting left out of conversations and sitting alone
Encourage interaction between multiple people
- I always want to make people feel welcome, whether they’re there the first time or tenth. One way I do so is by introducing people along with an interesting fact about them, such as how she might be an expert on chocolate or he might be an expert on wine. It’s easier for me to brag about knowing interesting people than it is for people to brag about themselves, and gives people something to start off conversations with
- I agree with the quote on how large parties are intimate and there’s no privacy at small parties , but that applies to the guest as an individual. As the host you want that lack of privacy and multiple interactions, rather than a guest just sticking to one other person the entire time.
- As a host, it’s your responsibility to make people feel included. If you notice someone alone, check in with them or try to find someone for them to talk to
If you haven’t put together an event before, I think it’s worth trying. Whether you do it for close friends or acquaintances that you want to get to know better is up to you. Hopefully my experience above is a helpful reference. As always, let me know if you disagree on any of the above.
- If you haven’t seen me mention this before, I’m always down to meet in person; email me
- Not to mention I now know who they are.
- This doesn’t contradict point 2. After not hearing or hearing ‘no’ from people multiple times, you’ve got to take a hint
- Bonus points if you know where this is from
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