I just sent this to ChatGPT:

Wrapping up this fantastic ski trip. Had a really good time. But I feel like I’m getting in my own head about people liking me or thinking I can hold a decent convo. Definitely felt like I talked to people who were interested in chatting, but it tapered off as we talked.

Don’t get me wrong:

  1. I’m one of the new guys on this trip
  2. I became friendly with basically everyone
  3. Two friends, also new, didn’t do the same as me
  4. This is a perfectly normal thing, to have a convo with someone and not be completely enamored with them the whole time

But:

  1. I remember a time in my life where I was the center of things, talked with everyone, and felt really respected by everyone
  2. I have had times in my life where I felt on: I could talk to everyone and anyone, and be funny, interesting, etc

So I don’t know. There are tons of people here who’ve been going on these trips for years, and all know each other. And there are groups of friends who just became close. And I came with two close friends who I really enjoyed my time with and I know they enjoyed time with me.

But I wish I could be better. I wish I could be the person who jumps into convos and makes everyone excited. Not just someone who’s there, and might say something stupid or off or not interesting and derail everything.

Part 3: What to do

Nothing? Maybe you’re just not with the right people. Average age here is 44. Most are finance people. Most know each other from other stuff.

Sleep more: I know that’ll work. But I’m shit at it.

Know when to tap out: If you’re tired, not feeling it, just say no. This is based on a theory where I think people don’t care how much — they really care how good. If you’re always on when you’re there, much better than 100% for three nights + 65% for two.

Expectation management: Be reasonable. Don’t expect everyone to love you, just be there.

Be hot: Be groomed, dress well, maybe don’t be exhausted. That stuff shows.

Get some authority: Be involved. Run the thing. Be important. People notice everything — if you’re part of the core and respected, they’ll follow.

Focus on a small group: Be fun for them. People will notice and want to join that fun, or expect you to translate.

Takeaways I don’t like:

Just be yourself. What do you mean. We are not one monolithic person — we are energized, tired, passionate, annoyed, excited, angry, hurt, happy, complicated people. Everything we do is written on our tapestry. You can mold yourself to be better.

Just go for it: Lies. Tired drunk mumbling me just goes for it? And says something really stupid? Nah.

Socializing is a key skill. Really really important. And it is something you can get good at.

It’s hard to get good at without falling into the social hacking pickup artist trap. I should find real research on what makes someone respected, fun, sociable. People throughout history who were this. And why. And if they did it everywhere. Simple things that affect how you act, which affect how you’re seen.

Chat says people read your warmth, competence, and energy. So coming to the function tired, speaking poorly, but with good intentions is 1/3.

And I’m right about quality. No one cares about how much you clock in.

Two things I’m flat out bad at:

  1. Getting sleep
  2. Leaving

I can’t fix those. What can I fix?

Humor: Don’t always be joking. You are super sarcastic. It can come off as making fun of people. Tone it way down — bad humor kills likeability. Reads cringe.

I don’t have a good conclusion. Just have to be better.

Or maybe I just get some sleep.

-Matt

Update: Absolutely killed it at the airport lounge today.