Audrey Hepburn in Breakfast at Tiffany's eating a croissant and drinking coffee.

Why I try to be vain

How I look at vanity & why I think its useful in small doses.

tldr: A little bit of conscious vanity has asymmetric upside.

Vanity in small doses is good. Conscious vanity forces you to take pride in your appearance and perception in a self-aware, non-shallow way. Luckily, people who respond to non-shallow and vain people are often your counterparties in professional and social situations.

I've noticed, I get asymmetric upside in these situations. 1) I feel more respected 2) I haven't compromised into believing vanity is actually good, so I don't feel shallow 3) if the counterparty is themselves vain they relate to me 4) there's no downside if they don't notice or value it. I've found if they're indifferent, then they're super substance driven and they're only focused on the content of the situation anyways. So vanity is a great hedge!

It can’t be mindless though. Pride in a suit and tie won’t work everywhere – it’s not the same kind of vanity for every situation. I try and cater to my counterparties. VC meeting? Start-up interview? I have to own the room with that hoodie. Enterprise sales call at their HQ? Button up & sweater all the way.

It feels dumb to invest in vanity because it feels like a pattern you’ve seen dumber people fall into. I think thats the difference though, you can fall into it or choose it and I think people can tell who is who. The key is that vanity has to be self-injected, I have to buy and believe in its value.

PS: here’s me at 16 wearing an overcoat trying to look like the Peaky Blinders. I was trying to be vain but I was just being dumb.

Me at 16 wearing an overcoat trying to look like the Peaky Blinders.