Cool People
The word “cool” is thrown around in tech rather loosely (“anyone cool you think I should meet?”, “they seem like they’re building cool stuff”, et cetera). But what does that really stand for?
The general understanding while reaching out to people is that you’re going to them with a specific ask. However, I often find myself reaching out to people, I find myself wishing to talk to someone because I stumbled across their profile on LinkedIn/ Twitter/ … and I had a feeling of being impressed with what they’ve been able to achieve, or think that there’s a common interest we share or something they’ve spent a lot of time thinking about which I’d be curious on their take of.
Approaching conversations transactionally, while allowing someone to identify which KPI the conversation leading to, leads them to not develop deep relationships. I find the superficiality of going into a meeting thinking “what can I get out of this person”. To me, that shifts the focus from understanding who you are as a person to moving focus to exploiting the value you bring to the table.
While skeptical of the people who have the word in their LinkedIn bios, I’ve found myself attracted to the idea of serendipity - you'll find impressive and interesting people when you allow yourself the freedom to just meet people who pique your interest. And I don't think that philosophy has failed me yet, in fact, a lot of this was reinforced when I had a remarkable streak meeting some interesting people at the airport.
My current optimization is to find incredibly high impact people and surround myself with them.
Another optimization for my social circles was to find people with a prowess in orthogonal spheres. My underline intention was to find people who really enjoyed being incredibly good at what they did and I stopped distinguishing what game we were focusing on. What that effectively looked like was my social circle comprised of some incredibly impressive pianist, investors, chess players, authors - basically people who were in the top 5-10% of some field. This leads to not only more growth in the friend group but refreshing changes of conversations.
I also aim to get some perspectives external to the echo chambers that I sometimes need to box myself into to get good work done - in order to build products that you're proud of, I often have to spend hours diving into the deep technical nitty-gritties of niche areas. It is obviously not surprising that the biggest downside of that is that you end up dealing with people who work on similar things in similar environments (and thus live similar lives and think similar ways). An optimization (or more accurately, a correctional push) is to also make sure I'm getting out of my echo chamber of Silicon Valley and it's Climbing Gym doesn't feel like I'm winning on understanding or picking up perspectives which I wouldn't usually.
Previously, I used to silo the people in my life into people I knew in a work capacity and the people I knew in a personal context and a professional context and while that was advantageous because it allowed me to be very specific about silo-ing and time-boxing how specific time in my day went, I also ended up realizing down the line that it made my relationship with quite a lot of my friends rather one dimensional (I would exclusive talk shop or work with them). Another interesting thing I realized was that there were number of people I’d consider impressive who were also people I enjoyed hanging out with was a lot greater than the people I enjoyed hanging out with who were impressive - therefore I embarked on a conscious journey to try and integrate these social circles.
A functional question I like to think about is "if I wasn't doing what I'm doing in 5 years, would this be someone I surround myself with"
I stumbled across this piece which I think is thought-provoking read (though, I wouldn't find myself agreeing with all the sentiments echoed in the writing).