Great post. Specifically on the "I can tell in five minutes whether I'll like someone or not part," getting into local maxima is definitely possible but it's not a bad place to be. The folks at that level are great folks and one is able to discern them with less work. I've found, though, that some folks that I initially got a negative impression from turned out to be really great people, outside of the "5 minute" criteria, though it took some work to get there.
So as with any case of potential local maxima, my approach is to spend more time with some of the folks that fall outside this "5 minute" criteria, to a) meet a more diverse group of people and b) improve my "5 minute" criteria so that there are fewer false negatives.
It's a good catch to realize that the main downside to this approach is an inevitable lack of diversity in your friend group. That feeling you are basing it on is a general sense of cultural similarity and worldview similarity. Some of those similarities you want but many you don't.
>'While efficient, I’m not sure how I feel about this revelation. At first glance, it seems great, but as I’ve thought more about it, I’m worried that in this initial judgement I’m likely biased towards certain types of people.'
I'm glad the author is thinking this one over. Without exception, I've found people who are unquestioningly confident in their quick judgments to be horrible judges.
I'm guessing it's some sort of loop of confirmation bias latched with confidence in the initial judgement.
>'Finding a balance here is something I’m working on now.'
For me, I've found it helps to try and change perspectives. To go from trying to classify how I feel to considering how 'they' might feel.
It's going to sound cheesy and possibly really abstract, but I try to think of people less as a classification problem - sorting marbles into bins and more like legos - considering a fit for each piece.
While it's really interesting and insightful overall, the "$40,000/year is enough" part bothers me. I see it doesn't include health insurance, and while it includes "savings" I have to question how much of a safety net he's actually building himself.
It looks like a classic case of "I'm young and nothing bad's happened to me so why get insurance?".
Actually he said he _doesn't_ save anything -- he had some savings going in to it. Furthermore, if he had an extra $800 per month "savings" would be at the bottom of his list.
I dread the "what do you do?" question so much; lately I just deflect with "I'm one of the assholes ruining San Francisco, what about you?"
Granted that's in the context of hanging out with people other than startup people. At meetups and whatnot I usually give them some of the highs and the lows, it lets the other person know they can open up too. We don't all have to be fronting positivity 24/7.
The socially accepted response is a one sentence description which then allows the person to enquire more if they are interested, or move on to other topics if not.
In general society "I'm a web developer" works for me. At a startup meet, I'd be more specific: "I'm developing an online petting zoo".
The key is to listen for prompts before you go deeper. If someone responded to "what do you do?" with a five minute exposition of either their successes or challenges without further prompting from me, I'd be a bit taken aback. After all, I only asked so they'd ask me back and I could tell them how exciting/challenging my job is.
I love these essays. Particularly the "what do you do", "living on $40,000", and "value of writing".
This year I lived on around $30,000 from my start-up and probably another $10,000 in help from parents on plane tickets and other non-essentials. It's been a very comfortable year with travel and probably too many toys.
The scary thing about only having 30k/yr is the lack of a real safety net should disaster strike. I've been there and it's perfectly doable, but I'm quite envious of the people I know with a few million in assets. Hopefully I'll be there soon. :)
So as with any case of potential local maxima, my approach is to spend more time with some of the folks that fall outside this "5 minute" criteria, to a) meet a more diverse group of people and b) improve my "5 minute" criteria so that there are fewer false negatives.